my friend is a terrible employee — should I tell her what I really think or just give her sympathy?

by Alison Green on July 16, 2020

It’s the Thursday “ask the readers” question. A reader writes:

I have a friend who I have never worked with. I want to start by saying she’s an amazing friend: supportive, smart, funny, kind, all the qualities you want in a friend … but I suspect she is a terrible employee.

We are professionals in our late 30s, and I’m not sure she’s ever left a job on truly good terms. We have graduate degrees in similar areas and work in parallel fields, so I understand the kind of work she does even if we do not directly overlap. As her friend, I hear over and over again about the toxic bosses, the problematic comments, etc. As a manager, I hear many of her stories and think, “Oh, you played that really wrong,” but rarely say that to her directly as it just makes her upset — and fair enough, she’s come to me as a friend, not a coach. I’ve heard the stories of her firings and kept to myself the general sense that, yeah, the boss did the best thing for the company even though it stinks for my friend.

Now she has taken a job that seemed like a really good fit on paper, but it is already falling apart a few months in. She has called a few times to complain about the unfair treatment she has received, how everyone hates her, how she’ll have to quit within six months, and so forth. Because we have never worked together, I have always been extremely careful not to make assumptions, to listen and to just be her friend, offering sympathy and a shoulder to cry on. But now I feel like saying, “We are middle-aged and there is a pandemic. You need to put up and shut up and just do the job or you are going to be completely screwed.”

I know this is more of a friendship question than a manager question, but do you think I should redraw those lines? Do I owe it to her to give her my professional opinion, as opposed to my friend one?

Readers, what say you?

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  1. Kate*

    Pose this as a question to your friend. Ask if she wants true career/professional advice, or is just coming to you for sympathy. She’s best positioned to answer that question. Frame it as, “I’m in a similar field, I am managing teams, maybe I can offer some tips.” If she says no, she says no. If she says yes, set up a clear time to talk ONLY about that, keeping a space separate from your friendship.

    1. Matilda Jefferies*

      I was going to say the same – ask her if she’s looking for advice or just sympathy, and go from there.

      I would also try to draw some boundaries around work talk, because it’s going to be hard for you not to get involved either way. And you certainly don’t need to take on anyone else’s work stress, especially now! See if you can find things to talk about other than just listening to her venting about work. You could use some of the advice from yesterday’s thread “My coworkers’ constant talk about stress is stressing me out.” Good luck!

    2. AdAgencyChick*

      I wish I were better at this myself, but I think if the friend’s answer is “sympathy only,” then OP would also be within her rights to say, “there’s only so much of this I can listen to.” Or at least, when it’s getting to be too much, “Can we make today a day where we talk about anything but our jobs?” Emotional vampirism and all that.

      1. Eillah*

        As someone who is putting a lot of work into moving away from being an (unintentional!) emotional vampire, I really appreciate that the term now exists and that there are comprehesive, non-judgemental ways of both acknowledging its existence and having ideas for how to grow and become less blood-sucky. Hooray for honesty!

      2. RestroomTimeExtraordinaire*

        this is a very good point, about the emotional drain of being sympathetic and to be the sounding post for another person’s job stress. If the friend is ONLY looking for somewhat industry-knowledgeable ears, but isn’t open to any feedback, that’s a big ask of the LW (and ongoing for a decade). the LW didn’t explicitly ask for advice on that topic, but if I were in her shoes, I’d evaluate how much energy to invest (for future), should the friend reject any advice or feedback.

      3. Code Monkey, the SQL*

        Let me tell you my very best strategy for that – I had a friend whose relationship with me was almost completely “she complains, I offer sympathy/advice.” When I realized I wanted out, I framed it as “Look, I love you, but I realize I’ve got my nose in a lot of your business, and I need to back up. You deserve space without me offering my input on every single thing, so I’m going to stop myself if I start to do that.” And then I would go “whoops, I’m getting up in your business again, let me back up,” and then change the subject.

        1. MasterOfBears*

          I LOVE this and I am stealing it. I have a friendship that can go the same way, and as this language points out, I think it’s on me as her. (Not to say that’s always the case, but I could definitely use the reminder to step back)

          1. Code Monkey, the SQL*

            It was definitely a draining interaction pattern, but I realized I contributed to because, well, who doesn’t like to be The Wise One Who Has The Answers? But it was all the time, and it made me tired, and even when I did give The Answers, I didn’t get listened to, so I stopped the part that I could, and the relationship naturally ramped down some.

      4. Mama Bear*

        Agreed with the above. Sometimes people only want to vent and don’t want advice. However, you don’t have to be her perpetual dumping ground for work complaints. I’d redirect long gripe fests and focus more on other things of value to your friendship.

        1. Gail*

          “perpetual dumping ground”

          Ask yourself, “Do I really want to be someone’s trash can?”

      5. Turtle Candle*

        Ooooh, yeah. I had to do this with my husband, who I love very much and who I always want to support, but he was in a bad spot at a former job and was just spinning and spinning and spinning on the same topics, eternally. They weren’t things he could fix and they were going to stay bad until he switched jobs (which he did), and he was genuinely that stressed about it, and in that case I don’t think he was “the problem” (unlike LW’s friend, he hasn’t had those issues anywhere else), but nothing was going to end about it until he got a new job.

        So I started to say “Ok, you have ten minutes (fifteen minutes, half an hour, whatever made sense)” and then we’re going to talk about something else.” Or “the house is a no-work-zone this weekend.” Not “you may never talk about it again,” but just, we can’t keep rehashing the same thing or we’ll both go bonkers.

      6. Washi*

        Agreed. I had a friend who wanted to vent to me a lot about a legitimately difficult situation, but did not want anything from me but pure, unadulterated sympathy. No opinions, no questions from me, just a lot of “I’m sorry that sucks.” And when it went on a long time, I started to feel almost…dehumanized? Like I was no longer her human friend with unique thoughts and feelings but a coffee machine where she could press a button and hold out her cup and a stream of warm validation would come out. And I don’t judge her for wanting the coffee – she deserved a nice hot cup of coffee! But I could not be the perpetual coffee maker.

        I like your scripts, and have used them for close friends where I want to be really honest about my limits. For a softer/less close version, I’ve said things like “well, I don’t think I have anything super helpful to offer on this” or “I don’t think I can say anything you haven’t already thought of” and change the subject.

        1. Turtle Candle*

          Oh my goodness, I was stumbling toward this, but you’re right–when all someone wants is affirmation and sympathy, it’s not a conversation really. There’s no mutual engagement. And if it goes one way for a long time, and the balance of mutuality does not reflect both ways, you really do start to feel like a machine for dispensing temporary goodfeels and not a person.

        2. Taniwha Girl*

          This is why people loved Eliza, the early computer that just spun the question back at you. “I hate my mom.” “Why do you hate your mom?” etc

      7. Diahann Carroll*

        Agree with all of this, and I had to draw similar boundaries in the past with a friend (not related to work, but to a guy who was utter trash to her). I’m the type of person that if you keep whining about something and make no effort to change the situation, I am going to say something even if you don’t want advice because now you’re making it my problem.

    3. Kramerica Industries*

      I feel like for someone who constantly vents to OP, asking “do you want some tips/advice” is going to feel like OP isn’t taking her side. I think I’d layer in advice with the venting. “I also hate when people do X. I find it gets easier when I do Y” or “that sucks and it sounds stressful, but I’d be even more stressed without a job right now”. This way, it’s clear that OP is still sympathizing with the friend.

      1. Insert Clever Name Here*

        It could come across that way, but layering advice in with the commiseration would be really irritating to me if I was just trying to vent to my friend. It’s good relationship hygiene to ask “do you want advice or sympathy” when you realize you’re in one of these loops.

        1. The Supreme Troll*

          Unfortunately, I think that with The Friend’s (friend), even asking a question like that would offend her. As if there is some strange, crazy idea that she could actually be doing something wrong.

          What AdAgencyChick above and Lygeia below said are probably the only safe way to walk around this.

      2. Gazebo Slayer*

        I don’t like “that sounds stressful, but I’d be even more stressed without a job right now.” I don’t want to feed into the idea that, if a lot of people are unemployed, no one has a right to complain about their job.

    4. UrbanChic*

      This. I find “How can I best support you – do you want a listening ear or can I help problem-solve?” is a good question.

      1. Phouka*

        This is a strategy that my husband and I use — “Do you want me to help you solve the problem or do you just want to vent?” has saved us from a lot of arguments. Once you start saying that, it’s out in the open and you can act accordingly. PLus, it tends to defuse the situation quite a bit and no one feels like they aren’t being heard.

        1. Amaranth*

          I find this works really well, and with one friend I then tell her ‘okay, you get five minutes only, and then you have to step away from the negativity’ — if I frame it as a no-brainer that her attitude is just feeding on itself it seems to curtail hours of woe. Also, there is enough stress in our world these days without diving into it without purpose.

    5. MK*

      Hmm. Here’s a thing I learned by reading fanfiction: many people say they want constructive criticism, they even sincerely believe they want constructive criticism, but in fact only want praise and get defensive and even offended when offered even the mildest not-completely-positive feedback.

      Which is to say that the OP’s friend may answer that she would like advice, probably sincerely believing it, but not be ready to hear that she might be the problem.

      I think the OP should consider if she can offer “put up and shut up” advice, but frame it as expediency only. As in “That must be horrible for you, but, given the job market right now, don’t you think it would be better to try to tolerate this aweful company than risk long-term unemployment?”.

      1. Caliente*

        I concur – I have been explicitly asked for advice and then people get mad at you for giving your opinion. I find that its just not worth it.

        1. Tardis4Life*

          Same. I’m currently dealing with this with a long-time friend. She specifically says she’s asking for advice and not venting, but then gets pissed off that I’m not agreeing with her and “judging” her. She’s miserable where she is, and keeps asking for the same advice over and over again, but won’t actually do anything to help herself (like apply for a new job). There’s always something else that’s more important and everyone is out to get her. It’s honestly exhausting. It’s been 2+ years of her constant complaints about her job and her horrible pay, but she hasn’t applied for one job and is now on her 3rd move into a new apartment instead of dealing with her main issue. But she’s annoyed at me for not being more supportive of her issues ‍♀️!

          1. Mad Harry Crewe*

            My answer for that is “you know my advice hasn’t changed. What are you hoping I’ll say here?” or similar. You don’t have to stay stuck in the same loop with her. Sometimes it’s even worth pointing out the stuck-ness – “You know my advice hasn’t changed. It seems like you’re really stuck on something, because we keep having this conversation every few months. [What’s really keeping you in this job / Do you think it would be worth working with a therapist and digging into it]?”

          2. Amanda*

            I dealt with this with a friend but regarding a personal issue, not a professional one (regarding a terrible guy she kept getting back together with). Finally, I used a script similar to Mad Harry Crewe’s — “You already know what my opinion is on this, and it hasn’t changed.” I also at one point, when it kept persisting asked gently, “You keep asking for my advice but you don’t seem to want to follow it. Is there something else happening or something that you’re hoping I’ll say?”

            Either way, I would change the subject because frankly, my friendship cannot be entirely based on the emotional labor of being the sponge for a friend’s bad feelings or advice-seeking or complaining all the time. There needs to be some give and take. I have been the friend on both sides of this, as I think many of us have, and I’ve appreciated when someone can gently let me know that I need to dial it back.

        2. Mr. Shark*

          I get your point, but it seems the LW is frustrated with the situation as is, and either it’s going to end because the LW no longer wants to listen to the complaining, or maybe it will end because the LW does give advice and the friend isn’t receptive.
          Either way, the LW may need to get out of the situation. So taking the approach of just asking, “do you want my advice or are you just venting” is the right approach.
          If the friend just wants to vent, the LW can then decide if she wants to keep hearing it or not, or move on from that friendship.

      2. Turquoisecow*

        Yeah I could be wrong but I’m betting even if the friend says she wants advice, she doesn’t want to hear that she’s part of the problem, and she definitely doesn’t want to hear that from a friend.

        If there’s a way OP can kind of gently point out one or two things that should probably have been done differently, great, but the friend is probably not going to react positively to too much criticism, especially from someone she sees as a friend.

      1. TallTeapot*

        FWIW-Captain Awkward has a lot of really great scripts for dealing with this sort of friend!

        1. Insert Clever Name Here*

          +1 to checking out Captain Awkward. Her advice is a great companion to the advice AAM provides.

    8. Jules the 3rd*

      +1 Ask her. Be kind, specific, and solution-oriented.
      – Limit it to 1 or 2 repeated patterns.
      – Don’t try to talk through all her defenses and reasons, just say, “I have heard you talk about Thing X, with examples A, B, C. Response Y is how I’ve seen people get the results they want in those situations. Do you want to hear more about why Y is more effective, or think up some Y scripts, or role play a response Y?”

      eg:
      Gross boss / co-workers is making gross comments and Friend seethes quietly or yells at them. Y might be “repeating ‘why would you say that / why is that funny, I don’t get it’ until they get stuck trying to explain it without being openly sexist / racist.”
      or
      Boss points out error. Friend’s normal response is defensive in some way, looking for blame. Y might be “Tell boss, ‘thanks for pointing that out, I will work on it’, then going away to think about the feedback:
      1) Is there a view where Boss is not wrong? (ie, is it a style difference, a preference?) If Boss is not wrong, change it and cheerfully hand it back – Boss may see things that Friend does not, that drives different decisions.
      2) Is it something that needs a process fix or clarification? (ie, a style guide so everyone’s clear, or writing down who cleans the test tubes): If yes, go back to Boss with a solution.
      3) If Boss is actually wrong, how important is it, and how would Friend want to address that? (ie, a pattern of having women clean their test tubes but not men might be pretty important, stealing the women’s time. But Oxford commas outside of legal documents aren’t critical. Don’t shoot me…)

      Good luck to Friend, this can be really tough. If she says no to you, you might recommend she try a therapist or career coach with a specific ‘how can I respond to X in a constructive manner’ question.

    9. Smj*

      Agree. I have a friend like this. We work in the same field, though not all of her jobs have been doing that work. She has had a hard time getting past entry level type positions and this is why. Very creative but lack of attention to detail, little follow through, lots of excuses. There was a point where she asked me several times to help her with her resume, which I did. I feel like I have a pretty strong grasp of resume/cover letter writing and spent a fair amount of time with it over a few drafts, but she didn’t even take my most basic suggestions regarding formatting. Things I suggested knowing that people like my own boss do take them into account when reviewing. I decided after that that I wasn’t going to interfere. I was congratulatory when she got something, listened when she wanted to vent and the time her contract wasn’t renewed. Right now she’s going on a couple years of unemployment. She’s married and her husband can support them, so it’s been ok for her, but I just don’t bring up the subject of work at all when we talk or hang out.

    10. Never Sleeping Beauty*

      Exactly what I would say. I have a personal policy to not give advice unless it’s asked for, but in the case of this kind of thing happening repeatedly, I might try to clarify, and make it clear that either option is okay with me.

    12. Penny*

      Ditto! The best relationship advice I ever received (friends or romantic) was to ask if the other person is looking for a sympathetic ear or if they would prefer advice/suggestions when they come to you with a problem.

      1. Alex (UK)*

        Yes! And when the shoe’s on the other foot and I’m the one with a problem, I try to be clear with the listener upfront and say whether I’m looking for advice, or if I’m just wanting to vent.

        I’ve also started practicing it to myself – just clearing it up in my own mind as to whether
        I want advice on a situation, or if I just need to let off steam. And I’ve found that by doing that internally, it can help with the proceeding conversation with a friend – I’ll have more of an idea of what advice I want, or it’ll lower the intensity of the rant. Win win all round.

    13. LGC*

      Yeah, that’s probably the thing – ask her to choose which hat she wants you to put on!

      That said…honestly, if this is a repeat occurrence, maybe both hats are the same. Sometimes, being a good friend is being honest, even if she gets mad about it. I’m not saying that she should give full-on career advice, but pointing out, “Karen, I love you, but your colleagues had some good points” might be the kindest thing to say to her. (Although, it sounds like LW has said that and Karen pitched a fit.)

    14. JSPA*

      Yup! Especially if you’re even slightly overlapping with the sort of job that her managers do, as well as the sort of job your friend does. If she doesn’t want advice, you could offer to do the sort of role-play where each person does “air quotes” to explain what’s going on in their head.

      Hearing, “Hunh. That’s an unusually personal and reactive response to feedback” and “I’m in a bind here; I need the work to be performed a certain way, I need the worker to feel supported, and there seems to be no way to give feedback that’ll make that happen’ as the interior monologue (rather than, “What a B—-, and she dresses like a slob, too” or “I knew it was a mistake to hire her”) may help.

      You can even frame it as, “it doesn’t matter what the boss is really thinking. What matters is that you answer AS IF this is what your boss is thinking. It helps the boss live up to that best option, instead of both of you racing for the bottom.”

    15. Beth*

      Very much this. Ask her if she wants advice, then let her answer guide you. If she does, say what you think and then move on with your friendship from there; don’t keep rehashing it once you’ve said your piece. If she keeps asking, unless something has seriously changed since last time you talked and your advice would be materially different as a result, tell her “you already know what I think” and change the topic; you don’t want advising her on her work to become the main focus of your relationship.

      If you think she needs help but wouldn’t be open to hearing it from a friend (or wouldn’t let you keep it limited to an occasional topic!), consider pointing her to other resources instead of giving advice directly. Link her to this blog. If there’s a blog or book or podcast or twitter or etc. by someone in your field that you like, send her that way. Suggest talking to a career coach, if you think that might work.

      And if she just wants sympathy and isn’t open to advice at all, remember that friendship doesn’t obligate you to be a bottomless pit of endless listening to the same stuff. Listen and offer sympathy when you have space and time, but if it’s too much, it’s OK to say “Let’s make today a no-work-talk day, I need a day off from thinking about our field!”

  2. JokeyJules*

    i can’t speak on how to frame that conversation, but as a friend i would absolutely say something, just like if my friend was in a slew of bad relationships. that might start with just pointing out that she hasn’t ever left a job on good terms, always thinks where she works is toxic, and then trying to get to the root of what exactly the problem. i trust that my friends would tell me explicitly if i was in the wrong about these things, and i know that they trust me to do the same. if it seems like she is in denial of her part in this, thats to be expected. just keep asking for the facts to get to the bottom of it all, and hope she figures it out on the way.

    also i refer them to AAM articles about whatever theyre dealing with. it helps.

    2. Jaybeetee*

      I’d caution getting too “therapist” about this, which “getting to the root of the issue” sounds like. Saying this as someone who had a rough period for jobs (that eventually got better) *and* has a poor relationship history (work in progress), my very supportive and well-intentioned friends are not equipped to unpack all that.

      That said, if “getting to the root of it” means just asking a few questions to get the friend thinking about how they can approach things differently, that’s a bit different.

      1. Fiona the Baby Hippo*

        Agreed! I think even if the LW suspects that the friend might be more to blame than she puts on, there’s just so many unknowns. I think any help should be from the perspective of brainstorming solutions or options rather than trying to be a wake up call on someone’s entire percieved reality.

      2. That Girl from Quinn's House*

        I would 100% recommend a therapist though.

        My backhanded way of suggesting a therapist is, “Wow, Person sounds really challenging! Maybe a therapist would be able to help you find some strategies to handle them better.” It gets them in the therapist’s office, and the therapist can sort them out from there.

    3. SarahDances*

      Agreed. If you can’t be honest with a friend, then in my opinion it’s not a real friendship at all. When telling a friend something I think they may not want to hear, my tactic is to preface it with “I’m going to say this because I’m your friend and I wouldn’t feel right staying silent, but you’re an adult whose judgment I trust so I won’t ever bring it up again unless you ask me to.” That way the truth has been said and they can let it marinate as much or as little as they choose, while knowing I’m not going to keep harping on it forever.

      1. JokeyJules*

        i’ve definitely had the tim gunn “I like you and i want you to succeed and so here is some feedback” moment with friends, both giving and receiving.

        2. TootsNYC*

          The times I’ve done that, I drop the clearest, most succinct summation, trying to keep it short, and then I stop talking.
          I have a horror of lecturing people, mostly because I hate being lectured. So I make a serious effort to NOT lecture people (as a boss, as a parent, and as a friend).
          (as a parent, I do sometimes have to elaborate, and I try really hard to make it an informational tone, much the way I might explain it to a young person I was mentoring–hey…)

          I’m always torn; I don’t think a person is being a good friend by not pointing out the “spinach on their teeth,” and just being sympathetic is not helping them. So I might say, “That’s actually not particularly wise.” or “I’m not surprised he reacted that way–I think I would too.”

          I was bitching about my co-op president to a friend who was herself on a co-op board, and she pointed out one of the flaws in my logic. And said, “That doesn’t sound particularly fair.” She didn’t dwell on it, but it really did impact my thinking. Later.

      2. Caliente*

        I mean…you’d think, but I’ll tell you I have had more than one friend explicitly ask my opinion on something and then get quite mad with the results. I’ve even said I’d prefer not to give advice, I don’t know,everyone is different and try to get out of giving advice and they’ll still insist on hearing it yadda yadda and then get mad.
        Everything pointed out is then battled about so its like well why bother if you’re going to defend your position. Why are we in an argument not NOT of my making? Its no good.
        As an example, last time this happened – I have a friend in a (non physically) abusive relationship, the guy is just a tool and she was just complaining about every move he made for a year(we’d spend AT LEAST an hour a week on the phone about him), usual declarations of being done on a Monday, back in the saddle by Thursday. Agrees to everything I say about him, points I make but then again, back in with him again. Finally after about a year I very kindly said “You know, you’re a great person, you can manage your own relationship, we don’t need to continually talk about this guy and no matter who you see I will always be your friend, like our relationship has nothing to do with whatever guy you’re seeing. Go out with him no problem but I just do not want have these kinds of conversations about him anymore.” Well, she completely stopped talking to me right after that and we’d been friends for about 15 years.
        As an aside I recently reached out to her since we’re in this strange times and she’s a single mom with a kids so I wanted to be sure they were ok and she did respond.

        1. cmcinnyc*

          That’s the risk, right there. I’ve had these convos (giver and receiver) and the risk is always the friendship itself, no getting around it. I’ve only had it come to that once, and it was also pretty abrupt. We’ve been in touch a very little since, on her terms, when she wants to reach out, but it’s clear we’ll never be friends again. In her case, my best guess is that she’s ashamed of the mess she’s always in. This friend was one to make a big, entertaining drama. It was always funny, she was always self-deprecating, but the fact was she was, and remains, frighteningly self-destructive. I kind of broke the terms of our friendship when I stopped laughing along and told her I was concerned about her. She’s a person with a lot to give, but nope, she couldn’t hear it. I don’t regret saying something. Maybe somewhere down the line she’ll hear it again from someone else and get herself off the ledge.

        2. MK*

          If a person stopped talking to me because I refused to function as an unpaid therapist, frankly I would question our whole friendship.

          2. Not So NewReader*

            Therapist or enabler? There’s a mighty fine line. Caliente’s friend had a repeating cycle going on:

            Friend got fed up with SO and dumped off on Caliente. “Oh I am so done here.”

            Later, friend felt lighter and decided to try again with SO. And again, the friend collected the next load of problems (remarkably similar to the last load) and went to Caliente again. And so the cycle kept repeating.

            If we do as we always then did we will get what we always got. So the question becomes, “Friend, what parts of this would you like to change so you get different results?”

        3. JSPA*

          If what friend wants from the friendship is primarily to process the drama of the One Important Relationship, or especially, to create the emotional tension of “do I stay or do I go,” the friendship (as usually understood, and as understood by you) apparently petered out a while before that point.

      3. Kiki*

        Yes, I like this phrasing and I like saying that you’re only going to bring it up once unless they ask for more. I have the same stance with friends’ significant other issues: I will tell you if your new significant other is terrible one time because I care and want the best for my friends, but I know it will hurt and create distance in our friendship if I say it more than that unsolicited.

    4. RedinSC*

      This. Years ago my sister, who had been in a slew of bad relationships finally told me that she’d been doing a lot of thinking. She finally asked herself “what is the common denominator here” and realized it was her. I’ve used this also in professional settings when talking with friends and employees about issues that keep emerging.

      OP, I’d ask your friend to think about the common denominator here (her) and if there’s anything she sees that she’s repeating that she could potentially work on.

      1. katiekaboom*

        This reminds me of my favorite saying:
        “if you meet an asshole in the morning, you met an asshole. If you meet assholes all day, maybe *you’re* the asshole”.

        1. Dagny*

          Eh, yes and no.

          I know lovely people who have had slews of bad relationships because they have terrible character judgement. I know lovely people who seem to be magnets for a-holes because they were mistreated as children, and, sadly, predators can sense these things. There are people who become so accustomed to a toxic workplace that they cannot function normally in a healthy workplace. There are people who were just never taught how to do ‘intermediate pushback,’ i.e. not just diverting the conversation, not going nuclear, somewhere in between, and end up being picked on and picked on and picked on until they explode.

          Those people do not benefit from being told they are a-holes; they are not. They benefit from learning in their adult life what they did not learn as children.

          1. Natalie*

            Sure; they may not be a-holes themselves, but the underlying point still holds true. They are the common denominator here, and in order for things to get better, they need to change something.

            (And that is WAY easier to type than to actually do…!)

          2. JokeyJules*

            i’ve always felt that phrase is pointing towards introspection, rather than just settling with “everyone else sucks!”

            1. Washi*

              Yeah, I think it’s about “what actions can I take to make things better instead of wishing other people would be different.”

          3. Gazebo Slayer*

            +100

            There certainly are people who think everyone else is an asshole because that’s what they are, but some people do get trapped in genuinely bad cycles.

          4. Dagny*

            To all above: if you tell someone they are an a-hole, that is not code for ‘be introspective and fix your problems because you’re a good person who should live a better life.’

            1. Washi*

              I don’t think katiekaboom was saying that you should literally tell someone that exact saying (at least I would never cheerfully call a friend an asshole!) but that the general principle can be applied to other situations.

        2. TootsNYC*

          or you could be choosing the assholes, and it’s time to re-evaluate how you’re making decisions; maybe there’s something skewed in your evaluation process.

    5. Dagny*

      “At my company, if someone does X, it would be interpreted as Y, because of Z.”

      Alternatively, if she’s smart, kind, and hard-working, but clueless about workplace norms, research executive coaches (or whatever is appropriate for her position) in your location and offer suggestions.

    1. Oxford Comma*

      Be prepared to back down if the answer is sympathy.

      If she says feedback, I would start gently because she may really only want sympathy.

      1. EddieSherbert*

        +10 – even if she says feedback, you may find she only want feedback that says she’s right (so actually sympathy!)

      2. fposte*

        Though I also think it’s fair for the OP to decide what’s best for her, not just the friend. It seems like she’s starting to consider that but hasn’t really been clear with herself on it. Does she feel it’s important to make the point? Does she not want to hear more about Friend’s exploits in projecting her problems on those around her? Those count too, not just what Friend might like to have happen.

        1. Turtle Candle*

          I agree. If she wants to vent, that’s an allowable want, but it’s really, really, truly okay to not be the person she vents to, especially as you already sound frustrated and this has been going on for… what, years? Over a decade? (Understandably frustrated. You have more patience than me, LW!)

          Being a sympathetic ear all the time is draining even without the frustrating element of ‘the common denominator of your problem is you.’

          I think one thing that often gets overlooked with the ‘do you want advice or do you just want to vent?’ is that venting is one-sided in a way that advice isn’t. When venting is mutual in about the same amount (whatever that amount is) that’s not a problem, but it can rapidly get out of whack with one person unloading and the other person being… loaded… upon.

          And if you don’t think you’re going to be able to be the vent-ee, it might be kinder not to ask the question (because then if she says ‘vent’ you’re stuck saying ‘well, too bad’ or else resenting her) and instead saying something like ‘hey I realized that the work venting is putting me in a bad mental space so I can’t be the person you talk to about this for a while.’ (Or ‘limit it’ or something, but you can legitimately cut it all off if you want.)

    2. SierraSkiing*

      You can also soften that ask a bit- “That sounds rough. You know, I manage a team, and I do have some thoughts on what might help. Would you like advice, or just to vent?”

      1. Formerly Ella Vader*

        And I might make it even softer by saying “You know, if you ever wanted to hear some tips that I could give you from the situations I’ve encountered, we could talk about that sometime, just let me know.” Then I’m not expecting them to answer yes or no on the spot, just leaving an opening for them to bring it up later.

        I also like the way TootsNYC put it about making a succinct statement and then dropping it. When someone comments on my decisions and expects that they need to keep elaborating the point until I tell them they are right or I agree, that’s unlikely to change me. I’m stubborn and proud, and it’s very hard for me to change my beliefs during a conversation. If they say it once and drop it, not acting like they have any right to know how/whether I use the information, then I’m more likely to think it over later and perhaps come to change my mind.

    4. Neosmom*

      Exactly. I have had direct reports come to me clearly upset. I have prefaced the conversation with, “Are you venting or looking for help solving a problem?” The speaker gets to set a very clear boundary and then should not be upset at the listener’s responses.

  4. Hills to Die on*

    I have someone in my life who is really great at presenting things to people in such a way that doesn’t leave them feeling defensive. Mentions how another person did X, and how it’s limiting them. I also just happen to be doing X, and so then I have a side-entrance to bring it up and (or not) and correct it or ask for help with it. Very supportive, non-judgmental. That’s what I would try to do.

    1. Anonys*

      I might find it a little backhanded if someone told stories about other people that related to something I was doing wrong but without telling me directly. I feel like it’s sometimes hard to pick up on these cues and I would hate to wonder whether or not this “story” was actually a comment on my own behavior. That’s something which WOULD leave me feeling extremely defensive. It would make me want to respond: “if you have something to say to me, just say it directly”.

      Maybe I’m misunderstanding how your friend does this, but I think being direct (before making sure the other person actually wants to hear your opinion) or asking questions like “Do you think you could have handled this better, do you think you doing x contributed to escalating this conflict” is the better option. Besides, someone like OPs friend might not have reflected on their own behavior enough to relate the “story” to their own shortcomings.

      1. The Friend*

        Right – I worry this approach would come off as passive agressive. But thank you for the suggestion! I will think about whether there’s a way to work it in.

        1. Lisa H*

          I dont know if anyone has mentioned it but therapy! My husband has been fired at so many jobs and it was always due to bad bosses or they just didn’t understand that he was trying to do what was right for the company. One day when he was complaining I just said I’ve had enough and refused to talk about it anymore. I recommened that this is one topic I cant deal with and if he wants to vent he needs to make an appt with a therapist. He did and is now happily self employed and still goes to therapy as he still needs help dealing with and maintaining professional relationships with his employees and vendors etc..
          This issue with your friend is above your pay grade! Nicely and diplomatically advise her to get a therapist.

        2. Smithy*

          It’s 100% a passive approach – but in my experience it’s a very unique friendship where truly critical professional advice is sought.

          I’ve been in my current field for over 10 years, worked at three places. The first two places had different mixes of toxic environments, bad individual actors, etc. Over the years and in different ways, my friends certainly heard enough about both. After I left for my current role, I don’t know what I was talking about but vividly remember my friend’s husband saying something to the effect of “the thing in common with your bad workplaces is you”.

          I can list 101 reasons why I reasonably assessed the problems at both places, and 101 reasons why I wouldn’t listen to my friend’s husband – but my immediate emotional response also made it very clear to me that this was not a setting where I was seeking hard truths and growth. If this friend is truly in a place where she’s open to that, giving her a passive door to walk through would be my suggestion. If otherwise she’s a wonderful friend, then I’d see this more as seeking not just sympathy but also validation. It’s a unique and specific friendship that is easily build for feedback.

          1. TootsNYC*

            my immediate emotional response also made it very clear to me that this was not a setting where I was seeking hard truths and growth.

            I remember talking about decluttering with a friend who had just spent a week helping her mother pack up the multigenerational family home in order to move. And I started off by trying to say, “What I need is some time and the cooperation of everyone else,” and she interrupted me after “what I need is…” to forcefully interject,
            “What YOU need is a DUMPSTER!”

            I too had an immediate reaction like the one you describe. Mine was: “We do not have the kind of friendship where you can tell me some good, hard truths.”
            And: “The WAY you delivered that comment is exactly WHY you are not the kind of friend who can tell me some good, hard truths.”
            And I absolutely dropped all effort on that friendship for years. We’ve started back up again, but it’s not as close.

          2. Allie*

            I have friends who I get professional feedback from, but met most of them at work or in grad school so they are in a very similar professional position to me. It’s actually very valuable to be able to ask someone “based on how I was when we worked together what do you think of X situation”

      2. Hills to Die on*

        I may not be describing it very well. It doesn’t come across that way to me, but I can see where someone who is otherwise a direct, open person would wonder at the technique. I suppose it depends on the friend’s personality and the relationship with the OP.

        1. Web Crawler*

          I feel like when it’s done well, this technique is more like: “Here’s some related situations you can learn from. I don’t know what you have in common with these situations, and you know yours better than I do, so pick what’s helpful and ignore the rest”.

          If it’s done badly, then it’s like “once upon a time, I had a friend who’s totally not you, and she messed up her career until she tried this one easy trick.”

          1. Something Something Whomp Whomp*

            I agree with that framing, Web Crawler. Hills to Die on, does your friend preamble their advice in any way that flips that “oh, I’m gonna get some advice” switch for you?

        2. Nopenopenope*

          I know exactly what you’re talking about! I use this technique regularly with personal- and business-related discussions. I’ve found it to be an excellent tool to get people to consider their situation from a third party perspective if you frame it right, which can really cut through the defensiveness they may not even be aware of exhibiting/feeling when the topic is specifically them and specifically their situation and “solutions” feel like “judgment”. If it’s someone else and someone else’s problem, you can often way more easily break out of the “everything is bad and I don’t deserve bad things” mindset (which we all share to one degree or another) and get their focus redirected onto the problem solving aspect.

      4. Rosie M. Banks*

        This has absolutely happened to me. I had to make a major presentation in a situation that was not really part of my usual work context. A few days later, someone who was there sat down with me and just happened to randomly start a conversation about all of the ways that kind of presentation can go wrong. (“I’ve seen people make mistake A, and mistake B, and of course, other people make mistake C . . .”) I was left thinking that something had gone horribly wrong with my presentation, but I didn’t have any idea what. It would have been far kinder to say, “The people in the back couldn’t hear you” or “You used too much jargon,” or whatever the problem was. I’ve also become extremely wary around the person in question: you’re going to judge me harshly on my performance but not give me any idea what went wrong? No.

    3. Gamer Girl*

      As a non-confrontational person who’s originally from the Midwest, I would be cool with this approach. It’s an approach I would understand and, to me, is very face-saving for the other person! I don’t think everyone will agree (as in the comments above already), but it’s very much a know-your-audience type of situation.

      1. Alice906*

        Agreed! I love this approach. I don’t particularly care for the very direct, “do you want to vent or do you want advice?” strategy, because if I just want to vent, I then feel like the person is just thinking about all the advice they’d like to give me while I’m venting and I become self-conscious. The question can almost make me feel like I really *should* be asking for advice instead of just venting, which I realize isn’t necessarily the intention, but I would worry about it anyway. I’m firmly in the camp of: direct advice should only be given when one is directly asked for it (and even then it’s reasonable to be a bit circumspect about it!). On the other hand, sharing a story from your own life or a friend’s can be helpful without coming across as advice. “Here are some things that have happened to me. I don’t know whether this is helpful or not, but maybe it’s something to think about.”

        1. Alice906*

          I should add that I am exceedingly careful not to abuse a listening ear, and obviously, people vary widely in terms of which approaches they prefer . . .

        2. NotAnotherManager!*

          I think this demonstrates that it’s just important that OP know her friend and how she’d react. I’d much prefer a direct question over hinting around and innuendo. When I say to my husband, “I’m just annoyed and want to vent for a few minutes.”, I can trust that he’s going to keep his problem-solving hat in the closet and nod at the right places. For me, the question is a good check on where I am mentally and what I really want from the conversation. I come from a family of hinters, and they drive me crazy. Just say it already!

      2. Something Something Whomp Whomp*

        You’re right in that it’s a face-saving approach, which is a bigger priority in some cultures than in others. I wonder if part of the challenge in deploying it well is about how critical the advice giver is in general. If someone tends to express an opinion on everything it can be more challenging to place passive advice into a healthy context.

    4. NotAnotherManager!*

      This reminds me of a college roommate I had whose mom would always call with some cautionary tale of some kid two towns over when she suspected my roommate was doing something she didn’t want them to do. Roommate was wise to it and used to play with her mom a bit to see how far she’d take the story.

    5. Not So NewReader*

      I agree with you, Hills.

      I don’t do well with venting. Part of the reason is I ended up with a bunch of family who vent. I am talking DECADES of venting about the same problems and doing nothing.
      I. am. so. tired.
      So I realized that I was being used as a dump. Dump off a bunch of frustration with me and then keep doing the same thing that causes the frustration.

      Using a third party or even drawing on one’s own life experience can be a solid way to help the person listen along and face their concern. Stories can be easier to listen to when it’s not about the listener in particular.

      Tone matters. This is important, tone really matters.
      It’s also important to show empathy- “Gee that sucks!” or “Dang, you deserve better than that!”.

      [It’s amazing how many people get relief by hearing someone else thinks what they have going on sucks. Additionally, it’s amazing how many people have never once been told they deserve better than the crappy thing that happened. The latter problem sometimes puts a lump in my throat. “You are how old and NO ONE in your life has told you that you DO deserve better???” I don’t say that part out loud, of course.]

      As to people feeling it’s passive-aggressive to tell a story in such instances, I guess it matters how the story is done; if the listener sincerely believes that the speaker has actually heard what the listener said is the problem; and a bunch of other factors.

      Laying the groundwork before launching into the story is important. And that can be as simple as, “Oh man, that is awful. I am sorry this happened to you.” Or it can be a longer set-up for the story.

      It’s also good for the story teller to “hang loose”, let the story mean whatever it means to the listener. I have had it happen where the listener actually picks up on a finer point that I missed and that point helps them somehow. Ha! It wasn’t the point I was aiming for, but does that matter? Not really. Most situations have several positive and strong responses that are very useful. Usually there is not just one EXACT way of responding to difficulty.

      My wise friend used to say that it is really helpful to trust that people almost intuitively go toward the correct response for their setting. Yeah, sometimes they don’t and that does happen. But it can be very helpful to realize that many times people already know the answer for what is going on they just need to drag their answer to the forefront of their thinking.

  5. Lygeia*

    I think you can ask your friend some version of “hey, do you want my opinion on the situation as a professional or are you just venting?” and go from there. You are also within you friend rights to set boundaries about how much work talk you want to put up with. “Hey, work is a stressful subject right now. Can we talk about something else? Did you see the latest episode of TV show we both like?”

  6. Anonymous Educator*

    It sounds as if you’ve done a ton of listening, which is good. Usually, I would say you should just listen and not try to offer any advice, but since you have done a whole lot of listening already, I don’t think it’s out of line to say “Is it okay if I offer you some advice?” then see how receptive she is. If she says, “No, I can handle it,” she clearly just wants to vent (and then it’s up to you how much venting you want to deal with). If she says, “Okay,” give her some advice that one time.

    1. Diahann Carroll*

      So do I. Letting her walk around living in the delusion that everyone sucks but her does not help her in her life or career.

    2. Batgirl*

      I agree. A real friend tells it like it is; you don’t have to let that take over the friendship. State it once and maintain your position without being a nag. You say “Look, I’m seeing a pattern across your last x jobs, and I think that not only is this pattern going to get you fired, its been causing you misery and is going to make you miserable in your next job. I think there are some easy things you can do to improve matters. Do you want to hear them or do you just want unconditional support no matter what I think?”
      Because the past is an indicator of the future we can rely on her getting upset with you to silence you again before resetting the relationship to complaints mode. If she ever tries to bring it up again I would say “You know what I think about that and we don’t agree. How about (subject change)”.
      I say that because I couldn’t participate in the justifying part of her destructive cycle, but maybe you can.
      You do risk losing the friendship with my advice, because she clearly wants things on her terms which is an entirely blind, uncritical, supportive set of noises for whatever bonehead thing she does (She expects that support at work too, I would guess). However I told myself ages ago that I wanted my friendships to add something positive to my friends’ lives and I won’t actively join in with supporting a friend’s destruction, I owe them that even if I lose them. I’ll still be standing by.

  8. Falling Diphthong*

    I like Kate’s framing, and will add that because you have never given her professional advice before and are instead sympathetic and supportive, she might be open to hearing it as a one-off in a way that she wouldn’t if you were always trying to explain her errors.

    1. Coder von Frankenstein*

      One detail to keep in mind – LW *has* tried giving professional advice before, and it made the friend upset, which is why LW no longer does it.

      “As a manager, I hear many of her stories and think, ‘Oh, you played that really wrong,’ but rarely say that to her directly as it just makes her upset.”

      2. Batgirl*

        Yeah, the typical response to hearing an uncritical friend tell you that you effed up is to hear them out and see if their read matches your experience. My response would be “Shit, do you think I can still recover this then?” OP’s friend may not be able to hear any kind of criticism; on duty or off.

  9. 'nother prof*

    I don’t think it’s a matter of friend opinion vs. professional opinion. You care because you’re her friend, and what you propose saying to her – that she’s screwed if she gets fired right now – has nothing to do with managerial judgment. I can see saying that to her with only a bit of elaboration: “We are middle-aged and there is a pandemic. The unemployment rate is horrific, so you are going to be completely screwed if you lose this job. Why don’t you say to yourself that you’re going to ignore/accept with grace X, Y, and Z-type things for the next six months/year? It won’t be perfect, but no one is getting perfect right now.” You might come up with X, Y, and Z based on your own professional experience, but you’re really only saying anything because you’re her friend.

    1. 867-5309*

      I like this. It takes the focus away from her behavior directly, which could be read as judgmental if she’s not interested in that kind of feedback.

    2. Eillah*

      I don’t agree that late 30’s = middle aged! I would not recommend including that in a proposed script.

      1. Mazzy*

        I was researching recently if I am middle aged. 40 used to be the cutoff, now I’m seeing 45 as the cutoff? It seems like there is no longer a set age range anymore.

        However, if someone called a 38 year old “middle aged” I wouldn’t correct them. The point is “no longer very young and prospective and able to perpetually job hunt without a proven track record” not “officially meets a census definition of an age range with a vague border to begin with.”

        1. Diahann Carroll*

          now I’m seeing 45 as the cutoff?

          Yup. My city’s Chamber of Commerce hosts many young professional networking events and has a dedicated group with a cutoff of 40.

        2. allathian*

          Middle-aged is not bad. It’s the age group with all the privileges and much of the power, after all. Being 40 is much more fun than being 20 ever was for me. I know myself and my limits much better and I’m much better at stating and keeping my boundaries. It’s great to just not GAF!

          I once read a definition that said that middle-age is not a physical age, but a state of mind. It’s whenever you hit the point when comfort and convenience are more important to you than adventure. If that’s the case, I’ve been middle-aged from about the age of 28. Some never hit middle-age, but go from young adult to senior citizen.

      2. Alianora*

        I agree. Regardless of where you draw the “middle-aged” line, I don’t think it helps make your point. Maybe the implication is that they aren’t just starting out their careers, but in that case it would be better to say that specifically.

      4. Jaybeetee*

        I have a friend who frequently refers to himself/us as “middle-aged” at 33! I finally talked to him about it, and he’d read the average life expectancy is “60-80”, putting anyone over 30 in the “middle-aged” zone. Now I have no idea where he read that – every stat I’ve read puts life expectancy in our country well into the 80s for all genders – but he’s stopped saying it in front of me anyway.

        1. MK*

          Even if the life expectancy is 90, you have entered the middle part of your life at 30. I wish people would stop treating this word as if it were dirty; growing older is not offensive or hateful and we don’t have to pretend it’s not happening to us yet.

          1. Amy Sly*

            For all people complain about growing older, you meet surprisingly few people interested in the alternative.

            1. Mizzle*

              *high-five*
              I say that all the time! Usually, people look at me all puzzled and say “growing… younger?” and I get to explain to them that that doesn’t appear to be an option yet, it’s either ‘grow old’ or ‘die’.

          2. fposte*

            Yes, totally agree. Our continuing cultural blindness to ageism is weird and interesting to me when we’re moving toward such thoughtfulness in other areas.

          3. allathian*

            Yes, this. Sure, I’d like to have my 20s looks and physique back, but not at the cost of losing the life experience I’ve gained in the 20 years since. I’m in a much better headspace in my 40s than I ever was in my 20s or even 30s.

            Most of the authority and power in the world is wielded by people in their 40s, 50s and 60s.

        2. Lovely Day in the Pandemic*

          The average life expectancy is not 60 for any group in the US. I’m 65, never heard such a thing, guess I should be dead. My DD is 35 and I don’t consider her middle-aged. We Americans put way too much emphasis on putting ourselves and others into little boxes. Growing older has not been offensive or hateful but I hate folks feeling over the hill at 30, especially since there is no hill. Aging is fine but does not need tobe accelerated.

          1. The Friend*

            I think my main take away here is that most people think being middle aged is a bad thing! I … do not.

          2. Not So NewReader*

            It was a while ago but I read an article that said doctors believe at age 34 we start our down turn, we start to exhibit the symptoms that will eventually kill us.

            I have to wonder how widely believed this is and how much it shapes our collective thinking.

            Additionally, a lawyer explained to me that the charts used for estimating life span for living estates clearly show that if a person lives beyond 75 the probability of them living to be 90 or 100 goes way UP.
            (This is important for estimating how much usage an older person will get from a house that is being purchased by adult child or other person. And it impacts the price paid for the house.)

            So if these types of things are accurate, then it’s not just a “public opinion” problem. Various arenas are buoying up this type of thinking that 30 is middle age and that it’s near the half way point in our life expectancy.

            I do agree that there is no hill. I know young people who have faced battles that I have never faced and I am not sure if I would handle it as well as they did. OTOH, I have an 80 something friend, if I call her up- “Hey let’s go do X!”, she’s ready and running. I forget she’s 80 plus.

            Putting people in little pre-defined boxes does not serve them well, but it also does not serve us well, either.

          1. allathian*

            That’s odd, given that you have at least 30 years left in the workforce, provided you don’t get a debilitating illness. And given the way the world is going, more and more people will be forced to work until they no longer can, as they can’t afford to retire.

      6. Werd Nerd*

        Agree! I am commenting only to address that portion. I just turned 50 and only now consider myself “middle-aged”. Plus it has no relevance here.

      7. The Friend*

        LOL, I’m the OP and I said it mostly as a joke. I would certainly never call anyone else middle aged unless I knew it’s how they self-identified.
        But the framing I’ve heard that makes sense is to take how long you expect to live, divide it in three, what section are you in? Even if I plan to live to 100, late 30’s is in the middle!

        1. irritable vowel*

          You and your friend definitely aren’t middle-aged in your late 30s, and I don’t think you’re doing yourselves any favors by over-aging yourselves. You have at least another 10 years ahead of you before you may start to feel and look physically middle-aged – enjoy your relative youth while you still have it, because it isn’t going to come back. And being in your late 30s is a fine time to still be figuring out your career and what you’re willing to tolerate in the workplace – so, better that your friend does it now, before she’s truly middle-aged and may have a boatload of other responsibilities that limit her options.

        2. Jules the 3rd*

          Meh. Identify how you want – it’s your life.

          Critiquing the use of a common, nebulously defined term like ‘middle-aged’ doesn’t move the conversation forward.

          2. Turtle Candle*

            Yeah, especially given that the LW has clarified that they had no intention of using the word in a script, this feels like serious word nitpickery. Unless you see “middle-aged” as a slur, I guess, but then nobody should use it, vs. reserving it for people over an vague line.

        3. Solitary Daughter*

          The Friend, I get you. I’m 40 now, and I guess I’m looking right at middle age. I would not like to be this age and acting like your friend at work. I’ve certainly had roles and positions where I’ve probably acted like her at times, but with age and experience, you would like to think she’s gotten a little calmer and wiser about work. I feel like that’s why you said “middle aged” — you are grown up and you should know a little bit better about the root of the problem, or at least make better choices about situations. I personally feel like a dose of honesty isn’t bad at this point in your friendship. The honesty could come in the form of a sit down where you say, “I’ve known you for a while now, and I can’t but help see a pattern that maybe you can’t. It might be worth thinking about X, Y, Z.” Or the honesty could just be telling the truth when you have the opportunity. She complains about something that sounds like her own doing? Tell a kind truth: “To be honest, if somebody I manage said that to me, I might react in the same way + why”. You don’t have to have a state-of-the-union talk. You can just acknowledge a reality beyond hers. She reacts how she reacts.

          1. The Friend*

            Exactly. Whether or not we are, in fact, middle-aged, we have been in the workforce for over 15 years. We are more than 10 years out of grad school. We are past the time in our careers when we can make the same mistakes over and over, or whine about every perceived slight – we have accrued enough knowledge and experience to do better than we did at 23. That was basically my point – I would, as I said, never be literally that blunt about age.

            Though I certainly feel middle aged, and not as a bad thing! I manage a team at work and raise children at home. I have earned my grey hairs and am really glad not to be young and naive any more. I enjoy being in vibrant, happy, middle-age — self aware of where I’ve been, where I want to go, and what I need to work. Which is very different from when I was 23. So I see middle aged as a badge of honor, not a denigration, and apologize to those who thought I was being a downer with that.

            1. Solitary Daughter*

              I hear you. I was chatting with our neighbor’s son the other day — college kid, young, bright, enthusiastic. Such a great kid, with so much in front of him. And I was thinking after our conversation: would I want to be young again? I would not. I have loved everything about getting older other than having to say the number, because it reminds me how fast time is passing! Part of growing older is growing smarter, and knowing yourself. It’s almost like your friend is missing out because of that.

            2. allathian*

              Thank you. I was trying to say something like this upthread, but you put it so much better.

        4. Lovely Day in the Pandemic*

          I never heard this, but actuarial tables are a far more accurate source for life expectancy data.

    3. Sam.*

      I would likely do something like this, but I’d lead in with a question, like, “Considering the pandemic and the current dismal job market, have you thought about what you will do if this job doesn’t work out?” Depending on the response, I might follow up with, “I know you’re not happy with these situations at work, but given everything, I’m wondering if it would be smart to ignore/accept X, Y, and Z for now, or at least until things are a bit less uncertain and you have more options if you want to leave. And if you want to talk through specific strategies to use, I’m happy to do that.”

      2. Fiona the Baby Hippo*

        upvoting this! You may not make your friend able to realize she’s the problem you imagine she is, but you may be able to help her see ways she can make things better, which I think is the end goal of wanting to give a friend advice.

      3. NotAnotherManager!*

        I was going to make a similar suggestion – framing it something she has to suck up for right now and providing advice on how to get by versus focusing on the larger issue might help. If she can make a shift in this situation, it may be give her some pause to reflect on past bad jobs and see that it may have been the same thing.

    4. Tyche*

      I agree with this general idea. You could then segue into tips for how to deal with the situations at work to ease stress. This might be a situation where a little white lie of, “I’ve been in this situation before and I handled it by…” might be appropriate. Sometimes framing it this way can take out some of the bite and it’s more personalized and relevant. I only suggest this because OP indicated her friend doesn’t seem to receive these messages well. Being straightforward is ideal but doesn’t seem like it gets through here.

    5. Quinalla*

      Yup, I think this is a moment for “real talk” with your friend. Normally I’m of the “do you want advice or just a sympathetic ear?” kind of person, but for something like this in this situation I wouldn’t feel right unless I gave her one quick real talk about it and then ended it by saying “I won’t give advice on this further unless you ask me for it, but I didn’t feel right not saying something because I want my friend to have a job during this uncertain time!”

      1. Willis*

        I agree with this. I think this is a situation where you can say it clearly once and, if the person isn’t receptive, move on.

        I have a friend who had a series of jobs where he quickly got frustrated with coworkers and managers and always thought he was getting screwed somehow or not correctly recognized for his expertise. So he was always unsettled and looking for a new job. On the one hand, it didn’t impact me if he changed jobs frequently or had personality conflicts. But, on the other hand, there’s only so many times you can listen to the same repetitive complaints and, of course, you don’t want to see your friend unhappy. Eventually I think I and another friend kind of pointed out that maybe his expectations were too high and everyone has to compromise with folks at work, etc. and I think it did sink in a bit (or at least spurred him to get more help).

        So, I do think there’s times in life where you see someone you care about repeating negative patterns where it can make sense to say “hey, I can see this happening as an observer that cares about you, it seems to bringing you down, does it make sense to look at ways you can change things?” But if the person isn’t receptive after that, I probably wouldn’t keep pushing.

    6. Ellie*

      Another agreement here: I like the framing of focusing on helping her keep this job in during this current uncertain job market.

      It feels less like “I have been holding back criticism all this time but can’t hold back anymore” and more focused on immediate changes she could try. If she sees positive results, it gives you something to build on in the future. E.g., “Have you considered doing X again? You really made it work last time!”

      It also gives her room to accept advice gracefully as opposed to “I’ve been wrong all along about so many things”

  10. GG GG GG*

    I would ask her directly if she wants advice. If she does, tread carefully but give her the advice based on your experience. If she doesn’t, just let her vent.

  11. Sola Lingua Bona Lingua Mortua Est*

    My ¢¢:
    When she asks for help, put on your manager’s blazer and advise her as a supervisor. Until she does, I would just let her vent and sympathize. She’s not going to change/improve until she wants to; trying to speed that process up is just going to strain your friendship.

    2. Caliente*

      Yes – I think this is the way to go, wait until asked! And even then, be prepared for her to get mad.

    3. Khlovia*

      Salve fellow Latin fan. In high school, I turned the old saying your moniker is partly derived from into a song, to the tune of Wabash Cannonball. Latina lingua mortua est, quam mortua quam potest esse, Romanos totos mortavit, et nunc mortandest me! (A little trouble with the meter in the second clause there.)
      Second verse is the translation, still to the tune of Wabash Cannonball. Latin is a dead tongue, as dead as it can be; it killed off all the Romans, and now it’s killing me!

  12. Serafina*

    LW could try to broach it as “do you want me to put on my professional-in-the-industry hat rather than my friend hat and see if that can help you improve things?” ONLY if Friend says yes, then (very delicately) say things like, “Well, thinking from a workplace perspective in my experience, it does seem like you could…” and focus on different ways Friend can approach her workplace rather than saying “you’re doing this wrong,” etc etc.

    Friend still might not accept the advice or take umbrage, but at least LW will have tried, and LW does have the right to say, “I’m not up for job venting anymore, let’s talk about other stuff.” If Friend is a real friend, she’ll be happy to.

    There’s also the possibility of recommending a career coach/counselor to her friend.

    1. Alexander Graham Yell*

      An old friend and I had a habit of saying, “You know, you’ve brought up this issue a few times before. Maybe it’s time to start problem solving so it doesn’t keep bugging you?” We were always there for each other for sympathy, but sometimes the best thing to do is to really solve the problem.

      That said, I have another friend who will constantly complain about every job she’s ever had, and I was sympathetic until she was complaining about unfairly being put on a PIP and then let go. “I mean, okay, fine, I struggled with meeting deadlines. But when I did turn things in, it was always perfect!” (She was in marketing. Deadlines were serious.) She’s not going to listen to anything except, “Oh, that sounds awful, I’m sorry you’re dealing with that,” so that’s all I ever say before changing the subject.

      1. Sola Lingua Bona Lingua Mortua Est*

        “I mean, okay, fine, I struggled with meeting deadlines. But when I did turn things in, it was always perfect!”

        It would be so hard for me to not point out that “on-time” is part of “perfect.”

        1. Alexander Graham Yell*

          This was in the middle of her telling me how she was going to HR to tell them she was being unfairly targeted because after her boss put her on a PIP (unfairly, due to irrelevant details like missed deadlines as she explained later) and now that she was on it, he was tracking *every mistake* and reporting them to HR. It was harassment, she said, and then dropped that line.

          1. Diahann Carroll*

            Wow, lol. I couldn’t have sat there and listened to this with a straight face. You’re a good friend.

          2. Not So NewReader*

            A friend who was over 50, missed an important deadline at work.
            “Well management has to understand, blah, blah, blah.”

            Management did NOT understand and wrote her for it.

            She went to the union AND she lawyered up.

            They went to court. (!!!)

            She got off the hook somehow. But as they exited the court house the lawyer said, “You can not miss deadlines PERIOD. You won. THIS TIME. If you do this again, DO NOT call me. I will NOT help you. They are correct. You are WRONG.”

            After she finished telling me all this, my friend expressed total shock that she actually had to meet deadlines. She was incredulous that she had to follow the rules.

            I was so in awe of watching this total disconnect, that I did not even respond to her story. Later, I decided the lawyer had told her everything she needed to know and I was not going to make out any better than the lawyer did.

            With some people we can only hope/pray they make it to retirement so this story line can be over.

            1. Serafina*

              Nice! I’m a lawyer myself, and I would’ve done the exact same thing. I will often tell people “this is not an attorney/client relatonship, blah blah disclaimer, but let me put on my lawyer hat for a moment and tell you what I *would* say in this situation” to deliver constructive criticism (only if someone has asked me about my legal opinion).

              I’ve had clients get upset with me time and time again for telling them what they don’t want to hear and what I think the other side will do in a dispute. “Who’s side are you on?! Who do you represent?!” they often say. And I respond, “You, but part of my job is to WARN you about the weaknesses of our position and anticipate how the other side will respond.”

      2. 2 Cents*

        I’m laughing because I can just imagine her boss. “I turned that work in!” “But the campaign ran 3 months ago.” “Yeah, but now if we run it again, we’re ready!” (I’m also in marketing, so know that the deadline is the deadline.)

  13. Colette*

    I think you have 3 choices.
    1) Do nothing; her career is hers to manage
    2) Comment in the moment. “Did you really? Wow, that would go poorly at my job.”
    3) Have one (and only one) big picture conversation with her. “Friend, I’m concerned about you. Your last few jobs haven’t worked out, and from what you’ve said, it sounds like you are doing X, Y, and Z. In our industry, employers expect A, B, and C, and will react badly to X, Y, and Z. I’m worried that you’re going down the same path now. I’m afraid that if you keep doing X, Y, and Z, you are going to end up unemployed in a pandemic.”

    I would probably do #3; there’s a 75% chance we would no longer be friends as a result.

    1. Specks*

      Exactly… it seems from the letter like the friend takes feedback poorly, and there’s no reason to think she will suddenly do a 180 on that. I would tread carefully, or, more likely, not say anything at all, unless she specifically asks because she’s ready to listen. Otherwise your advice will land on deaf ears and you’ll lose this person (and a chance to help her in the future, when she’s ready).

      1. Colette*

        Personally, I’m of the opinion that part of being someone’s friend is that you have to speak up when there’s an issue consistently holding them back. Maybe it’ll end the friendship, but … friendships end sometimes, and maybe it’ll help them down the road. My conditions for bringing something up: it has to be an ongoing issue where they consistently make choices that are harmful to themselves or others.

    2. Anon for this*

      I have a friend who is supported by her partner but keeps trying to work, and it’s come out like this:

      2008: I had to quit. My boss was abusive.
      2010: I had to quit. My boss was abusive.
      2011: I had to quit. My boss was abusive.
      2013 (conversation with her partner): She had to quit. Her boss was abusive.
      2014: I had to quit. My boss was abusive.
      2016: I had to quit. My boss was abusive.

      I figure it’s either obliviousness – in which case my perspective isn’t going to be helpful – or it’s a cover story for something she knows she’s struggling with – in which case my perspective is going to embarrass her. I’ve said nothing.

      1. Sabina*

        I had a friend with a similar pattern. Turned out she was hiding her alcohol addiction. She never dealt with it directly, went on to get on permanent disability (I don’t know how) and we are no longer friends. It is sad.

      2. Rusty Shackelford*

        I have a relative who was either fired or “harassed into resigning” from every job she’s ever had because her superiors “didn’t like her.” Every job. Spanning decades. And you’re right, there’s nothing I can say that will help, so I just don’t say anything.

        1. Batgirl*

          This is a thing you see in schools. Student won’t do well unless there’s an ah-may-zing rapport with the teacher. It’s something they’re supposed to grow out of.

      3. EddieSherbert*

        It’s amazing to see these kind of patterns – I actually have a younger relative who started this in… what, elementary school? ANY subject they did poorly in was because the teacher hates them and is out to get them! (even worse, their parents *totally* supported it, interfered with the schools, and repeated that message to everyone who would listen.) What a strange coincidence that every single French teacher they ever had hated them – clearly they’re only bad at French because the purposefully teacher set them up to fail! And it’s the same thing now that they’re an adult…. Every job ends because “someone hates them and was out to get them” so they got fired or laid off first or ‘had’ to quit.

        IMO, when people have a long track record like this and can’t see the one thing every situation has in common (them!) or understand what that likely means (they’re the problem)…. it’s probably not worth trying to point out the pattern unless you want to end the relationship.

      4. That Girl from Quinn's House*

        I agree, because I work in a field that is laden with toxic workplaces. Some of the stories could be their own TV series. If I’d kept a diary I could probably have optioned it and I’d be rich right now.

        The only people who know all the gory details are my husband and a few close friends, because I am well aware that once you have more than one outlandish story people assume you are the problem. Usually I’ll just say, “Oh I found a new job with better hours/better commute/more room for growth!” or “I actually wasn’t interested in that promotion, it’s too time consuming,” even though I applied for it and my boss said flat out they need a man in that job then proceeded to hire one with half my experience and made me do his work for my lower pay rate, that sort of thing.

    3. cleo*

      +100

      This is really good advice. Especially have only ONE conversation about the big picture issue.

    4. Not So NewReader*

      I especially like #2.
      “Oh man, I’d get buried UNDER the building for that one!”

      But I do think there is a 4th choice. And that could be she is in the wrong arena or picking the wrong types of employers. Some areas are much harsher than others, for some people. OP might be able to work with, “I noticed you always pick employers with X characteristic. That’s a tough nut to crack. Perhaps choosing employers withOUT X characteristic would help you somehow.”

  14. AnonACanada*

    “Would you like advice or do you need to just vent?” is always a good question. If she says she just needs to vent, tell yourself “not my circus, not my monkeys”

  15. Watry*

    With my friends, I’m able to just come out and ask “Are you looking for advice or sympathy?”, but for this to work you have to be able to trust that the friend will a)be honest if they don’t want advice and b)not be angry about what you say.

  16. Dream Jobbed*

    This is a tough spot to be in. My first response would be – have you ever had to tell her anything about herself before that she did not like? And if so, how did she take it?

    If you’ve been able to offer critical analysis in the past and she was fairly receptive, I would have a gentle but honest conversation about the patterns you keep seeing in her career. Maybe start in small bits.

    But if she has responded negatively to past critiques, or has “punished” you in some way, you’re probably better off letting it go and letting her run her own life.

    Most of us can’t see some negatives/poor behavior/bad patterns in ourselves. This is true professionally, but also in life partner choices, personal dress codes, spending habits. Some people can accepted guidance from others, others can’t stand anything messing with their world view. You help the ones that will take it, but you avoid the consequences from those who can’t because it’s just not worth it.

    Unfortunately, you are the only one who knows if your friend will allow someone to look at herself honestly or not.

  17. Littorally*

    This is going to hugely depend on whether she wants advice or not.

    The next time it comes up, or when work-related stuff in general is going on, you could gently broach that topic by asking something along the lines of, “Hey, I hear your frustrations with a lot of your jobs. I think I could give you some advice based on my experience. Is that something you’re interested in? Or would you prefer I just be a listening ear?”

  18. ThisColumnMakesMeGratefulForMyBoss*

    Unless she would be receptive to any work advice you could provide, I would just continue to listen to her complaints. You said if you provide insight she gets upset, which leads me to believe that even if you gave your 2 cents didn’t end your friendship, it would change it. If she does ask for your opinion, maybe try asking questions that lead her to draw the conclusion herself, but outside of that I would stay away from work advice.

    On a sort of related non-work topic, I have a friend who was persuaded by another friend to have a chat to convince the other’s friend’s sister not to get married to her first husband. They tried talking to her and the friend got married anyway, and it while they remained friends, it has never been the same.

    So I follow a rule that unless I think my friend is in a dangerous situation, I keep my nose out of it and listen.

  19. AnonEMoose*

    It’s tricky. But I think, as a friend, you could maybe point out the pattern? Something like “We’ve known each other for a long time, and you’re an amazing friend. So I’m going to tell you something I’ve seen. It seems like I’ve heard X, Y, and Z from you in most of your jobs, and I’m thinking that if you meet one jerk in a day, you’ve met a jerk. But if all you meet are jerks, it might be good to think about some stuff yourself.”

    Using your own phrasing , of course – she’s your friend and you have a better idea what she may respond positively to. The basic idea is to try to get her to think about the pattern, not just the individual instances. I kind of had to do that in my own professional life, and it wasn’t easy. And it required a lot of biting my lip and smiling and nodding, and rephrasing things or not saying them. But it also led to a lot less frustration and job hunting.

    1. Mbarr*

      I like this. If they ask for an opinion, then offer the recognition of pattern.

      I tend to not offer opinions about my friends’ jobs, because while we both work in similar industries, our companies have vastly different cultures. I hear things happening in their jobs that I think is inappropriate… But I tend to err on the side of more standard office professional behaviours.

      I also suspect that when people fall into these bouts of negativity, it’s probably not job related, but also about their personality/mental health. I’ve had friends who always think, “I’ll be happier at this new job” when it’s not the job’s fault.

    2. juliebulie*

      I was specifically going to recommend pointing out the pattern, but AnonEMoose beat me to it.

      Whatever you do, keep your work-related observations/advice brief and seldom, because every tiny thing you say will feel like a ton of bricks to her.

    3. PJ*

      This is what I was thinking. I would try to gently say “it seems that you have the same issues in every job. Do you think there’s something on your end? Are you coming off wrong to people?”

    4. Washi*

      This is kind of what I do with friends, and what I appreciate being done with me. A truly nonjudgmental “this is what I’m seeing – do I have that right? Is there something I’m missing? What do you think is going on here?” And I don’t mean nonjudgmental like you can’t have an opinion, more like if you went to a friend’s house and she had what appeared to be a giant nude cubist self-portrait, you’d be like “is that what I think it is? where did you get it? why is it here?” You don’t have to pretend you love it and want to take it home, but you can inquire curiously without saying “that’s terrible, what a horrible choice you have made.”

      1. Not So NewReader*

        I love these thought provoking questions. Since I don’t do well with venting I have used thought provoking questions to try to get the person to think a little bit about what is going on and what they can change.

        If nothing else, the people who just want to complain stop complaining to me.

  20. Caroline Bowman*

    I would ask if she wanted advice or just wants to blow off steam and ask really seriously.

    If she said she wanted feedback I’d ask her about her jobs over the last 5 years and to have a think about any patterns she might see (because sure, it’s quite possible that there may have genuinely been bad bosses and problems outside of her control – many of us have had bad luck from time to time), chat about that and then talk about how you might personally handle things differently or how, as a manager, you might feel or what might improve things for her, giving personal examples.

    If the conversation starts getting prickly, then say that you absolutely don’t want to be intrusive or unkind, but those are your honest thoughts and you are happy to be her sounding board and good friend because she’s a great friend and a wonderful person.

  21. PromotionalKittenBasket*

    I like the question “What do you want to happen in this situation?” and then “would you care for some advice?” If yes, then “Having been in a similar position, what I’m hearing is X and it might be worth trying strategy Y,” or “What I’m hearing from your story is X. In the past, I’ve found strategy Y to work really well.”

    A friend of mine who is generally great at her job but was looking at changing roles into another field in the organization was frustrated that they wanted someone with formal training, and walking with her through the thought process of “Why might they want that? Would I learn that by taking a class or two? Am I interested in taking that class?” and she eventually realized she just wanted a different boss who wasn’t micromanaging her actual work, not to switch fields.

    There’s no telling if it will work, and you know your friend best, but I’m a big fan of open ended questions that might prompt someone to look at a situation from another perspective.

    2. drpuma*

      Oooh, I like “What do you want to happen in this situation?” I’ve set *myself* on the straight and narrow a couple of times just by thinking through the end result I want. I wonder if having the friend articulate her “perfect job” would surface some unrealistic expectations or aspirations.

      1. General von Klinkerhoffen*

        I love that question, because it cuts to the heart of even nebulous problems. I tend to frame it along the lines of “if we could wave a magic wand” so it doesn’t get too heavy, they’re under no obligation to be realistic and I’m under no obligation to meet the request.

        1. PromotionalKittenBasket*

          Yes! That works too :) I also like it because it reminds me that I’m not the person who can fix the problem, so it gives me a degree of emotional distance

      2. PromotionalKittenBasket*

        Same! Most of my advice techniques are just recontextualized from years of CBT (which is why one of my party tricks is telling everyone to see a therapist for a checkup)

      3. LKW*

        I like this phrasing /question too. I suspect that there are unrealistic expectations like no timelines, no grunt work or more responsibility without having demonstrated capability. The next question could then be “if you were your boss, how would you change this? Do you think your boss can/would/should do that?”

        But really it sounds like she just wants to vent.

        1. allathian*

          Yeah, it does. And it’s perfectly OK for LW to put her foot down and say that she doesn’t want to listen to the same venting over and over. If the friend doesn’t want to change the subject, then there’s a serious problem in the friendship, and frankly it may not be salvageable.

  22. Purt's Peas*

    If you want to maintain the friendship, I think you’ve got to cut out work talk and cut out being her emotional support after yet another firing. It seems like you can’t keep just nodding in sympathy when you have no sympathy for the latest way she’s messing up–but you also shouldn’t become her work coach.

    You already know that she isn’t receptive to your advice; in the times when you’ve told her that she’s in the wrong, she’s gotten upset. Attempting to provide more advice, or attempting to shift the dynamic so you’re an authority on her working life, will be poisonous and possibly deadly to the friendship.

    3. Cedrus Libani*

      I’ve had to do that to a dear friend re: relationship advice. I have said my piece, he’s a grown adult who gets to choose his choices, further discussion is only going to annoy us both. (He’s gone on 2-3 first dates a week for over a decade, and he hasn’t found a “perfect match”.)

    4. The German Chick*

      This. I would ask her if she wants advice or if she wants to blow off steam. “If it’s the latter, I am sorry but I don’t want to listen to it anymore without trying to help.

      1. Not So NewReader*

        Yep. I have my own steam that I deal with, processing yours is too much for me.

        Ya know, sometimes when people are left alone to solve their problem they actually solve their problem….

  23. MissGirl*

    Are you willing to continue to listen to her vent or are you over that since it’s clear she isn’t going to change? If you’re done listening, say something along the lines of, “I love you, but your self-sabotaging all of your jobs, and it’s clear you’re looking to complain and not actually fix this. I can’t be the one you come to with work complaints anymore.”

    Then change the subject every time it comes up.

    1. Sen*

      I agree with this.

      I had one of my old bosses offer me some good advice about how to deal with girlfriends in horrible relationships. Tell them that you love them, you support them, but you can no longer talk about their relationship (on in this case, work) because you’ve seen and heard the same story repeatedly. Harsh? Maybe. But often times, it removes the primary way they react to a problem (venting to you), and encourages them to deal with the problem differently (hopefully, in this case, it’s getting her act together).

      Not saying it’s fool-proof. But it might be something you want to think about.

      1. Diahann Carroll*

        In my experience, they just go and vent to somebody else who will co-sign their foolishness, smh.

        I’m done giving people advice.

    2. Dust Bunny*

      I had to do this with a friend who got in the habit of complaining to me about her boyfriend-then-husband. She’d already pretty much admitted to me that she was punishing him for her previous husband’s issues. I finally had to tell her that I thought XYZ of this situation and if she wasn’t willing to consider couples counseling/reevaluate her approach to the poor man/etc., I had nothing to offer her as a sounding board. I think we’ve pretty much downgraded the friendship to “FB friends” but I’m fine with that.

    3. Uranus Wars*

      Ehile this approach might strain things in the short term, it will likely be the best for the friendship in the long run. And I feel it’s the best suggestion of the ones so far. It doesn’t force advice but it also says “hey, I can’t be your sounding board anymore, I have my own crud to deal with.”

      I had to have this conversation with my father a couple years ago about a personal thing. Our relationship was strained for quite a while because (it seems) without that thing for him to talk about he had nothing else to share with me. It seems sad and harsh, but we’ve gotten back on track in the past few months and I think our relationship is probably stronger in the long haul. I’m not longer dreading picking up the phone or visiting, and my stress levels when waaaaaaaaaaaaayyyyyy down by not having to listen to it so much.

  24. Lora*

    I don’t even know but will be watching this thread. Have two friends who are nice enough people but I would consider them a nightmare to manage, and I completely understand why they’re always at the top of someone’s layoff list.

    One screws around on her phone all. The. Time. Constantly. Taking selfies in sensitive areas where there should be no photographs. Never looks up from Facebook, for hours, spends nearly every waking moment on some kind of social media. And worse, cannot take the slightest hint of constructive criticism – any hint that perhaps she might have handled something just a liiiiiittle bit differently, she LOSES IT. Nothing is her fault, ever, and how DARE you imply such a thing. Fine person to sit at a dinner party with, horrible to manage that attitude.

    The other is just flaky like you wouldn’t believe, but apparently her whole field is made of flaky people to some extent so in comparison only delivering about 50-75% of the time is okay? It would drive me nuts for someone to need constant reminders to show up to work (as a grown adult nearly 50 years old with a graduate degree – we’re not talking a kid new to work) and then to do the flippin job she was scheduled to do and reminded of a task list without leaving the lab a complete mess for the techs to clean up after.

    1. Former Young Lady*

      I’ll also be watching this with interest. A have a good friend who is one of these people. She’s constantly miserable at work, and it’s because she’s a bull who insists she was born to work in china shops. (She’s also significantly older than her management, and assumes this means she understands china better than they do.)

    2. Morning reader*

      I like much of the advice suggested so far in comments. But I’ve known a couple of people like this, and from the perspective of Old Person, I have to say, don’t expect them to change. I’ve never known one to change, anyway. Advise them, don’t advise them, recommend therapy, pass along resources like this one, continue to commiserate, draw a boundary on discussing work, whatever works best for you. Just don’t expect friend to change.

  25. Escaped a Work Cult*

    I don’t know how to open it but I think if you frame it as a concerned friend of “pandemic ruining job prospects” she’ll probably be more receptive.

  26. The Grey Lady*

    I have a friend just like this. Most of the time, she just wants to vent to me and doesn’t care about the advice I give her. I have tried to point out some things she may be doing wrong in the past, but she never listens. She insists that it’s everyone else’s problem and she is the only one doing things right. In my experience, these people never change.

  27. Mazzy*

    You can 100% offer feedback, it’s just how you provide it. I think the feedback versus sympathy is a false dichotomy, because you can offer sympathy precisely by offering very low-grade feedback in the form of “maybe” type questions.

    I would frame it as:

    “you said the same thing about your coworkers at the last place. Are you sure that isn’t just the way things are?”

    “You’re complaining about your coworkers not knowing anything about ABC, but that’s your expertise, so why do you think they should know it as well as you? Maybe you just have to suffer through their stupid questions. That’s why we get paid the big bucks to be there!”

    “The things you’re labelling as toxic seem somewhat normal. Unless your boss is yelling at you or expecting you to work 12 hour days with no overtime or something, I don’t think you can call it toxic. I definitely would arrange a sit down with your boss to discuss why you both have different visions for the role and different expectations. Even if you have to leave, at least you’ll both understand what went wrong.”

    Now with the last one, the hope is, your friend listens to the boss and hears a thing or two where they might be expecting too much, and decide to change

    1. Mazzy*

      I forgot one I think is important:

      “You called me about being treated unfairly in that other situation. I agree it was unfair. But that doesn’t mean they are unfair in general, or that those other situations you described are in the same boat.

      I had some situations where I was treated “unfairly” in the beginning of most new jobs, but after you build your reputation and get credibility, or they just understand what it is you even do all day, alot of those situations stop happening. Meaning, people agree with me more, I get more leniency to come in late if I need to, people don’t forget to invite me to meetings, etc.”

  28. Keymaster of Gozer*

    I’m of the ‘my best friend is the one I can trust to tell me plainly when I’m doing something wrong’ opinion with regards my own friendships. I mean, if I was constantly making the same errors, then whining about the consequences to my friend she’d definitely say “look, you keep messing these things up but not doing anything to fix it and I don’t want to hear another x years of venting about an unsolved issue, I don’t have the resources”.

    She’s done it twice. Both times I was being a total arse. Both times I got upset for a little bit. Both times I realised that yeah, she was right, I needed to DO something. Both times we got past the upset feelings.

    I personally prefer a slightly different approach if a friend/family member is constantly complaining about the same situation: I tell them that what’s going on is bad, yes, and I’ll provide all the support if they want to change/get out of it, but I don’t want to keep hearing about it.

    1. Red Reader the Adulting Fairy*

      Your last paragraph, 100%. I’m a fixer, and I know that. I’m working on waiting to be asked to help fix, rather than just throwing myself into fixing, but oh my god, if you just vent and vent and vent and vent and vent about the same thing all the time and still don’t actually want fixing, my ability to resist the urge to fix ended about six vents ago and now you’re just torturing us both by repeating it ad nauseam.

      1. Double A*

        YES. Come to me if you want to solve the problem. If you want to vent, you get to vent about a thing once and I’ll be patient. Next time, I’m gonna start problem solving.

      3. Batgirl*

        I’m fine with venting in some situations; like it’s just a generally unfixable thing, or it’s too many spoons to fix it to be worthwhile.. But when someone’s being an arse, or self destructive? I’m going to say something. Some exceptions for “This is their path they need to see it for themselves” but not when its the same mistake every time.

  29. KayEss*

    What’s the outcome you want here? If it’s “Friend shapes up and doesn’t get fired”… well, you can’t really control that. If you think the friendship can handle it, you could try ONE time offering to give her a candid opinion/advice. Don’t launch straight into it, especially since you’ve been a sympathetic ear for so long. You could also try adding a “what do you think you’ll do about that?” component to your usual sympathetic responses, though her response may still be “I’m gonna blow this popsicle stand, consequences be darned, because it’s cramping my style.”

    If the goal is actually “Friend stops getting on your last nerve with work drama venting” (I may be projecting a bit), there are strategies you can employ to shift the conversation. The best is probably Captain Awkward’s “make it boring”: don’t reward poor-me whining with long shows of sympathy or attention, just respond “hm, that sounds tough” and immediately shift the subject to something enjoyable for both of you. It may feel cruel to cut off the sympathy, but it’s far crueler and more likely to damage the friendship if you just seethe in silence about her as she blithely continues on and then eventually explode.

    1. The Friend*

      Oh. Thank you for pointing that out.
      I think it’s a little bit of both? I really don’t want her to get fired, because I think losing her job right now would be ruinous and I would worry about her as a human I care about. But, also, of course there is some of “friend stops getting on your last nerve with work drama venting” because … yeah.

    2. JessicaTate*

      I agree with this. I find myself asking myself, “Is she really such a great friend if this is how she is?” In my experience, this kind of disconnect can be one of the steps toward a friendship drifting apart in your late 20s and 30s. For me, “I cannot listen to this immature, self-destructive cycle when you are taking no active steps to improve” is a thing I would think, but probably not say, as I let us drift apart. That’s not advice, just experience.

      So my exasperation level leads me to think about the advice they give when a friend is in an abusive relationship, but won’t leave. Basically have one conversation where you lay it out. “I think this is bad. I want the best for you. I’m sincerely worried that you are going to quit this job during a pandemic, which could be financially ruinous because it is so hard to get a job now. But you keep repeating the same patterns over and over and haven’t been interested in any ways you could adjust. So, whenever you decide to break this cycle, I am HERE for you 100% to help. But until you are ready to do something about it, I can’t listen to you vent about it anymore. I love you, but we have to talk about other things when we’re together.” And you follow-through. You shut her down every time she starts to vent. “I told you, I can’t listen to that until you’re ready to do something productive about it.” I don’t know if it it as directly translates to a self-inflicted job-related cycle, but it’s an option to tackle it head-on. It’s not subtle, so could cause a big rift abruptly. But being blunt might be the only way she hears it, and if it’s getting super-annoying anyway… maybe it’s worth the risk?? (Only you can judge that.) Good luck.

    3. Not So NewReader*

      This might sound harsh, OP, but for myself I find that the friendships that go the best are those friends whose work ethic is similar to mine. I mean within a range similar to mine. For example, people who say, “I overslept for the 15th time this morning and they fired me.” I am just not going to be able to relate to that very well. Much younger me had a huge fear of oversleeping and I did things to make sure I was up on time. One of those things was a dual alarm clock. It buzzes and I set it to turn on the radio 15 minutes later. If the alarm does not annoy me enough to get up, then the alarm combined with the radio will annoy the crap out of me and I will get up. (The clock is on the far side of the room. I have to get up to turn it off.)

      I just can’t relate to being late 15 times. I really think that deciding to be on time is something one finds for themselves. I am not going to be able to help my friend to decide to be on time if they are chronically late.
      The best I can come up with here is to suggest a second shift or third shift job so they can sleep in. After that suggestion I am pretty much out of ideas.

      It could be that you find you need to step back a bit and use a space cushion here for interacting with your friend. Sometimes I tell myself, “This is who this person is, period. I can either love them as they are or I can grant them space in fairness to them. But changing them or even hoping life gets better for them is not realistic.”

  30. Annony*

    I think it is time to redraw the lines, but not in the way you are thinking. It sounds like you are tired of offering sympathy when she is self-destructing. Especially now when everyone is really stressed, it is understandable that you do not have the emotional energy to be her sounding board. Tell her that. “I’m really sorry you are having a tough time at your job, but I cannot be the person you vent to anymore. I am emotionally drained right now and cannot handle it. If you ever want someone to give you advice about navigating the situation, I’m here for you but I just cannot listen to you vent about your job anymore.”

    1. Not So NewReader*

      My wise friend used to say this is not as cruel as it seems. Sometimes we have to get out of the way so REAL help can get in.
      OP, you could suggest that you have not been real help for her and she should find other sources.

    2. RebelwithMouseyHair*

      I had a friend say that to me. I was falling apart at the time and needed professional help and she was just overwhelmed by the extent of my falling apart. She told me she couldn’t handle it, I started doing hypnotherapy and various other things, and somehow I muddled through. We are still in constant touch even if it’s limited to FB because she moved to Sweden.

  31. bananab*

    This sounds like one of those frictions where the relief is less likely to come from your friend changing, which frankly is not likely to happen, and more from establishing at least a cursory boundary around work talk. If firings and other disciplinary action at over the years didn’t spur change here, pearls of wisdom from a buddy won’t either. IMO of course.

    1. Person from the Resume*

      Ha! That also stuck out at me, but that’s not the point.

      But I do agree that by mid-30s, you are hopefully settled into a stable career path. You’re not longer in the post-college career exploration stage.

      1. Carroll*

        It depends really. I went back to study again and finished at 31. I’ve been in my current career for 3 years now and am still happily exploring.

        1. Former Young Lady*

          Late thirties, and I sometimes call myself middle-aged, but this might be skewed by the distribution of life expectancy among my relatives.

          I also know a lot of sixtysomethings who also consider themselves “middle-aged,” and it always struck me a tad optimistic.

          But I agree it’s much more about career stage. My same-age BFF is in a similar situation to the OP’s friend; she’s also still working retail. Her managers are ten or fifteen years younger; there’s a lot of kvetching about maturity levels. Having once been a late-teens/twentysomething supervisor, I remember questioning the maturity of my thirty- and fortysomething reports as well. Like, if they were really too good to answer to me, what were they doing in frontline customer service?

          1. Carroll*

            Seems like a bit of a weird generalisation about people who have younger managers. It hasn’t been a problem for me, I have a very good ongoing relationship with my last manager who is quite a bit younger than me. I still turn to her sometimes when I need advice because I respect her impressive competence that has allowed quick and well deserved progression. She respects me too and helped me to get my last promotion.

            I haven’t really seen it as a problem among my colleagues either. And my work place has quite a lot of people who stop progressing past a certain point for whatever reason, but stay in the job due to its pay, conditions and the fact it’s the major sector in my area, and are managed by younger people as a result.

        1. allathian*

          Yeah, some people are in denial. Middle-aged is not an insult. I’d much rather be solidly middle-aged than an insecure, self-doubting, naive twentysomething. YMMV, of course.

  33. Detective Amy Santiago*

    I have cultivated the reputation among my friends of the person who will tell you what you need to hear even if it’s not what you necessarily want to hear, so I lean towards being honest. Like others have said, ask her if she wants honest feedback first. Some people are open to it and some aren’t.

    If you wanted to be a little less direct, you could just start linking her to letters on this blog.

    1. Malty*

      Genuinely came here to say direct her to ask a manager! If she’s repeatedly getting fired it’s warranted.
      Also Amy I can’t decide if you being the one to tell it straight makes you more like your namesake or less..

  34. 2 Cents*

    When a longtime friend and I are venting about life and either of us brings up something (and especially if it’s repeatedly), the one will ask the other “do you want some advice or problem solving?” If either says no, we know it’s just a venting session rather than a “solve my life problem” session. Sometimes you have to get it out! (Wine helps.)

  35. Fiona the Baby Hippo*

    I also think it’s worth considering what advice is most helpful, esp mid-pandemic, and think if there’s ways to give advice w/o sticking up for or justifying the behavior of bosses or coworkers, even if you might think it’s warranted. It’s obviously hard to give advice w/o knowing the specifics, but I wonder if there’s a midway point between “shoulder to cry on” and “work coach” where you could say things like, “Since your boss isn’t likely to change soon, and you don’t want to be out of work mid-pandemic, are there ways you can do xyz differently to make things easier on yourself?”

    I imagine it will be REALLY hard to have a big picture “You repeat the same mistakes at every job” conversation but it might be helpful to just nudge her to think about ways she can adjust her behavior and instead of framing it as who is right/wrong make it more about how she can best function in an environment that, for whatever reason, isn’t ideal for her.

  36. Notthemomma*

    Upvoting the ask if she wants advice, with a Strom suggestion that you have a conversation that this does not reflect what you think of as her friend, and before ANY advice is shared, have a serious conversation with her that you do it from love and concern and what the boundaries are, as well as let her know some things may be difficult to hear.

    Also, perhaps an incremental approach, where you suggest she change one thing for a week and document for herself the outcome, and build on that the next week.

  37. hbc*

    Are you at a point where you have a hard time being sympathetic and supportive without lying? That’s where I’d be now, and it might make sense to make work an off-limit topic for the two of you. You can go really diplomatically and indirect (“Talking about work is stressing me out, I’m sorry, I can’t be your outlet here for the foreseeable future”) or you can be more specific about why you’re backing away, which gives her the options of grumbling acceptance or actually seeking advice.

    I’m thinking along the lines of: “I’m sorry, I can’t be your supportive ear on this anymore. Every time we talk about work, I’m practically bursting with wanting to give you advice that you probably don’t want. Heck, I wouldn’t want it in your position. So let’s put a moratorium on work talk and talk about anything else less loaded, like finances or religion or something.” If she pulls for advice, great. If not, you’ll need to enforce the ban–literally cutting her off mid-sentence when she starts complaining about work.

  38. Esme*

    I think you’re protecting her feelings at the expense of your own. I would tell her it’s hard to hear her talk about what is basically self sabotage.

    1. Uranus Wars*

      I think you’re protecting her feelings at the expense of your own.

      I think a lot of us do this and it takes someone else pointing it out to get it. Sometimes it’s unrecognizable, but when you realize it – and stop doing it – it’s so freeing.

    2. Not So NewReader*

      Hard agree. OP, if you are at the point of writing Alison, you are probably pretty close to the hard, final line.

      I remember trying to help my parents. I went to counseling because I wanted to help my parents so much.
      After many months, the counselor said, “Your parents don’t want help. You need to just move on with your life.”

      My heart broke into pieces. I picked up the pieces as best I could and I moved on with my life. The only take-away I have is that I tried.

      And this might be your only take-away also, OP, you tried.
      We don’t get to pick who accepts our help and who does not. And this is super interesting to watch, because I found out that I guess wrong too often.

      One place I worked we had a large group of people we supervised. My boss and I had running commentary on this, as we never knew who would accept advice and who would not. Many times we were hit with surprises. I would think to myself, “Oh, I can help Sue with her productivity levels.” yeah, right. Sue wasn’t hearing it. Bye, Sue.
      Then I’d decide to talk to Bob about his lateness. Of the two, I would have picked Bob as being the one who would NOT listen. And what happened next was Bob listened and wasn’t late again. I guessed the wrong outcome, again.

      Life relationships run in a similar pattern. No way to predict who will do what. Oddly, i have seen too many people surprised when *I* used their advice. I guess people generally are used to having their advice ignored.

      A good thing to look at when offering help is to see how much the person is trying to help themselves. Don’t put more effort in than they are for a long period of time. (People in crisis may initially need more help than they can actually give themselves, but this is what having a crisis is. So in these instances you want to look at it over time and then decide what to do.)

    3. Batgirl*

      But the friend is going to be really unhappy at work until she figures this out. So no one feels good.

  39. Hey Karma, Over Here*

    I understand that you are concerned, OP. I would be, too. A lot of people are suggesting tactful ways to ask if friend wants advice. Do you think she wants advice? Has she ever asked for advice? Does she ever ask what you think about these situations she puts before you?
    Before you invest anymore time in this person is on a track that seems to be doomed, determine if you care more than she does.
    And if she is happy with her chaotic career style, you need to decide how much of the effects you are going to take in.
    You cannot be more invested in her career than she is. You are writing for advice. She is not. Step back figuratively and literally. Limit your role as therapist/confessor and see how much better you feel.

  40. TL -*

    I am pretty honest with my friends, so this is definitely from my own perspective, but I would have a one-time conversation with her, in “you seem to have this pattern repeating a lot in your life, where every job is toxic and, honestly, I’m not always sure I agree with your perspective. I think rather than venting to me endlessly, this is something you should work out with a professional/in therapy. It’s really hard for me to hear about this over and over again; I worry about your professional and financial stability when you go through jobs so quickly, especially now with pandemic and the uncertainty of the future.”

    I’d also say that this was a one-time conversation and a difficult conversation to have, and I understand that this is difficult to hear and it was also really hard for me to bring up.

  41. Aaron Poehler*

    Your friend sucks and she isn’t a good friend any more than she’s a good employee.

  42. employment lawyah*

    Not if you want to keep the friendship.

    What people say they want (honesty) is rarely what they want in relationships*, and transitioning to a claim-of-objectivity friend-analyst will probably not help yours.

    If you want to help your friend, you can always say something like “it sounds like you’re having a lot of trouble; you should talk to a career counselor.”

    *See, e.g., “does this haircut make me look bald;” “does this shirt make me look fat;” etc etc

    1. June*

      I agree – at this point she needs to seek assistance/tools with someone who can help her move forward (AKA counselor or career advisor).
      I think I would say – “Hey friend, as much as I can listen or provide advice if that is what you want, it would be a smart idea to seek assistance from a career counselor. They will be able to give you tools on how to manage your boss, speak and be heard, etc. Would you like me to help you look for one?”

  43. Maybe*

    If (that’s a big IF) your friend says she is open to feedback, you can try framing it in terms of:

    “I can tell you what the situation may very well LOOK like to your manager/coworker, from their point of view. They might be wrong to see it that way, and you might be right about everything! And maybe it shouldn’t be that way, but ‘should’ doesn’t matter–you can’t control what is in their head! All you can do is deal with what IS. And what IS, is, that you may get better results for yourself if you [do x, think differently about y, whatever].
    “Do you want to have a good working environment and keep your job in a pandemic, or do you want everyone to understand that you feel you are right about XYZ? Right now, you can’t have both. It may not seem fair, but maybe the way to be kindest to yourself right now is to do what you have to in order to get your most important needs met.”

  44. Jem*

    > I have a friend who I have never worked with. … but I suspect she is a terrible employee.

    I would just stop and shut up. If you haven’t worked with them directly then there’s a good chance you don’t have valid insight into how they work. Just because they’ve confided in you in that things are difficult for them doesn’t mean they’re actually a terrible worker.

    My first thought also: is the person writing in white, asking about their “black friend”? Or is it a man talking about the work habits of his woman friend? There are so many real world examples of marginalized folks facing unfair critiques that my first thought is “what makes you think you’re qualified to share any feedback”?

    1. The Friend*

      I’m the OP. We are both white women who went to college together and come from the same socio-economic background. Part of her problem at her current job is that she is being accused of microagressions.

      1. Littorally*

        Ohhh, well, that’s a different complexion.

        Does she relate these microaggressions to you? In that case, it could be a chance for you to address that issue without tying it to employment.

        Her: “I said XYZ and they called it a microaggression!”
        You: Hmm. That’s… really not a great thing to say, for ABC reasons. I can understand why someone would be upset about it.

        1. The Friend*

          Yes, it’s separate from the longer-term problem (AFAIK), but I’ve called it out when she’s brought up things that I think could be offensive. In basically exaclty that “I can understand why someone would be upset about it” way. It has gone ok, but not in a way that makes me think all discussions would.

          1. Not So NewReader*

            Uh, seemingly unrelated but maybe not?
            I know I can get cranky when I am tired. People could say microaggressions, cranky or whatever. Since i know I am tired and getting cranky, I organize my work so that I am off by myself yet still working away.
            Is she getting enough rest? Does she seem tired to you? Does she seem to regret what she said once you talk about it?

            It’s amazing how proper rest can change a personality. Once I had a set bed time each day, I found that it was easier to be the person I wanted to be. I wonder if she wants to be a better person.

          2. Batgirl*

            I don’t know that I could have patience with that. Its one thing to be defensive of your own mistakes and feelings… But to not care about how you’re making more marginalised people feel because what? White fragility? So, assuming it was unknowingly done; now she knows, because she was told, how that makes someone feel. At that point whose feelings are more important? Hers or the other persons?

      2. Em Dub*

        Yikes! That sounds like something you should have a conversation with her about! Have you seen signs of this behaviour in her non-work life?

      3. Half-Caf Latte*

        I am having trouble reconciling “supportive, smart, funny [and] kind” with “everyone hates me” and “being accused of microagressions.” Maybe I just run in liberal circles, but I genuinely cannot think of anyone who I would describe as supportive and kind reacting to being called out for microagressions with blaming others. I’d expect them to be able to grasp why treating colleagues with respect is important.

        I’m not sure this is a “professional advice conversation” as much as an “let’s talk about racism and social justice conversation.”

        1. Diahann Carroll*

          “Liberals” are some of the biggest culprits of microaggressions in the workplace. And no, many of them don’t take kindly to being called on it, either.

      4. Foila*

        Ooooohhh, that….potentially changes a lot here.
        From my limited perspective, there are roughly two situations where a group makes life difficult for an individual over microaggression accusations. The first is a very homogeneous group, where the combination of having very little variation in experience and being overwoke can lead to these virtue-signaling cascades.

        The second is when the behavior of the accused is so bad that it can’t be ignored. Normally getting people to recognize bias-driven misbehavior is just a nightmare, so when it suddenly becomes an issue, it’s because you’ve got a real problem. And given your observations about her past work issues, I’m suspicious that it’s this second case. And what they’re calling “microaggressions” is actually “a pervasive pattern of bigotry”.

      5. RebelwithMouseyHair*

        Have you ever noticed that kind of behaviour in a social setting? I mean you are who you are and I find it hard to square your description of her as a friend with the kind of person who could do that kind of thing. Although of course there are people who are nice to friends and not to their reports. It might show up in her treatment of the waiter when you eat out together though? I suppose it’s possible to be accused of such a thing by a manipulative person with a chip on their shoulder who delights in playing the victim, but it’s a charge that needs to be investigated (not by LW). Mostly the micro-aggressor is not even aware that their victim might feel like they’ve been aggressed.

    2. Kalros, the mother of all thresher maws*

      It’s possible to gain plenty of insight from being someone’s sounding board, and when that’s the case, it’s reasonable to kindly offer food for thought. OP isn’t judge, jury and executioner of her friend, and I don’t believe she’s trying to be. I think she believes she’s picking up on patterns that her friend may not be self-aware about and wants to help, which is coming from a place of kindness, not judgment.

      1. Rusty Shackelford*

        This. You can tell a lot about how someone works, even if you’ve never worked with them, based on what they complain about.

    3. Batgirl*

      It’s good to watch out for that sort of thing but when someone is flaming out of every job AND a trusted peer from adjacent field is saying to themselves”You did what?!” Then Occams Razor: they probably are just a terrible employee.
      If you don’t think people can make a second hand assessment based on clear evidence, then we should probably all stop trying to in the comments.

  45. Alex*

    It’s so hard to give advice about this kind of thing because it really depends on the dynamics of your friendship. I’d think first about if she is the type to listen to you. Have you ever had success giving her hard-to-hear advice? If not, it may not be worth it to cause tension in your friendship.

    I’d also think about whether or not the stuff you are advising about, if you choose to do so, is advice about what she should do next, or what she should have done. If the latter, I’m not sure you have as much influence and may make her be more defensive than if it is advice about what to do next. Telling someone they handled something wrong in the past can more easily come off as criticism and judgement than advice about what you think they should do going forward. I use this measure to give advice to a similar friend, who is actually also a colleague, but vents to me all the time about our workplace and how awful it is. She is right a lot of the time, but also contributes plenty to the dysfunction herself. She too is a good friend and has a lot of great qualities, but just does extremely poorly with workplace politics and getting along with people she doesn’t agree with. If I see her going down a path that I think will be destructive, I let her know (in as kind a way as I can). If she is telling me about having gone down that path already, I just listen with a sympathetic ear.

  46. yutraswe*

    Maybe not in the moment, but perhaps:
    My sense is that you need someone to commiserate with & I’m happy to be here for you. If you ever want more, I may be able to provide a useful outsiders perspective.

  47. Laura*

    I have that friend. I’ve worked at her job and now work in a related area where I have a lot of face time with managent. My friend has had her job for 15 years but has never been promoted. She was very upset when a manager told her that it would help her to dress more professionally. She has never understood that poor choices she makes in her personal life affect how her coworkers view her. BUT she doesn’t want to hear that being on time and not rolling her eyes on video calls will help her because her work is performed at an acceptable level and other things shouldn’t matter.

    1. Uranus Wars*

      This is a hard conversation as a manager, too! Looking like you just rolled out of bed when you are presenting (on camera or in person) is just not a great look – but when commenting on someone’s appearance it’s hard for them not to get defensive. I would probably be the same way if on the receiving end, so I get it, but MAN!

  48. justheretoosay*

    I’ve run into this situation with a friend of mine before, and in that case, it helped to look at it from the perspective of “That sucks! But, in all honesty, I could see how your behavior *could be seen* as [bad thing],” instead of “That sucks, but I think *you did* [bad thing].”

    Example: My friend was very, very busy at work, and also undergoing a rough patch with regards to her mental health, leading to procrastinating, then staying up until all hours of the night to get work done, then showing up late to work the next day, and while client deadlines were never missed, internal ones certainly were. Eventually, she got talked to at work about her time management.

    At first I just nodded in sympathy (which was genuine: her mental health leads to a lot of struggles), but a week later she was still talking about it, saying stuff like: “I just don’t understand. Why me? [Boss] has also come late on internal deadlines sometimes and I always get my work done eventually.”

    And I was just honest. I said, basically: “Look, I am NOT saying they’re right, but I am saying that when you’re up all hours of the night to get work down, coming into work later as a result, and missing internal deadlines and [other things she’d told me about], these things can lead to an appearance of poor time management. Again, you and I both know that you are swamped with work and I’m not saying your bosses are right that you have poor time management, but again, I’m just telling you what could look like.”

    She took it well, or at least, she stopped bringing up the incident to me. It am sure it does depend on your friend and your relationship with her.

  49. Anonymous at a University*

    I’d continue to listen unless she asks directly for advice. But it’s absolutely your prerogative to set limits around the listening, and to say something like, “Wow, that sounds hard,” then change the subject. I’ve had to do this with someone who kept making very basic mistakes over and over again (like deciding to tell co-workers on the first day that they were “un-Christian” because the workplace played music other than gospel and they were “morally obligated” to change it to a gospel station) and losing jobs as a result. At some point if I’d had to listen to her constant “But why am I losing my jobs???” venting and nothing else for hours on end, I would have made a comment that would have cost me the friendship anyway. Limiting it ultimately did serve both of us, even if my friend didn’t know that.

  50. PharmaCat*

    I have a different perspective. I was not quite like your friend, but I definitely job-hopped in my early years. This was back before the internet and mental health awareness. Statements like “nobody likes me”, slight paranoia, etc, for me were undiagnosed general/social anxiety. I’m not trying to provide a diagnosis, but it is something to consider.

    Also, as someone who has no social awareness, I almost never “play it right.” Fortunately I am in a highly technical position, but it has still damaged my career.

    1. PharmaCat*

      Also to add, I was not quitting jobs, I was running away from anxiety. The next job the anxiety would build up until I had to move on.

    2. Titta*

      Yes, this also! You said it well, PharmaCat.

      Few years ago I had a huge realisation, that MAYBE, just MAYBE not everyone hate me or even think about me that much. I am still the odd one in our office, but I am kind of able to stand that feeling and take reality checks every once in a while. Like “okay, has anyone actually said anything nasty about me? and didn’t I just get more responsibility and a raise? Why yes I did. Would they give a raise to someone they hated? No, no they wouldn’t.” :D

      But anyway, I know listening to this stuff as a friend is frustrating.

    3. Not So NewReader*

      “Nobody likes me.”

      Well that’s not true. Very seldom is a person important enough to be disliked by all. She is just not that important, like the rest of us are not important enough to earn across the board contempt.

      The one thing I’d watch for here with this attitude is that you, OP, can end up being an “idiot” for befriending her, if she is defining herself as not likable.

  51. Treebeardette*

    “Do you want advice or are you venting?”
    Based on your letter, I think you know how to handle it from there. :)

  52. Jaybeetee*

    I feel like by now I probably would have responded in the moment if she was blatantly handling something wrong. Even if not directly to say *she* was handling it wrong. I might say, “When that situation comes up at my workplace, I handle it XYZ way.” Luckily many of my close friends are able to handle feedback, so if that came up with one of them I might do a more blunt, “You did what??” But you need a… certain type of relationship to pull that off.

  53. Rebecca*

    I had a similar friend – very self-sabotaging. She worked on a large corporate campus and would take advantage of that by booking conference rooms in other buildings and sitting in them to watch movies. Or she’d just leave. She’d often take a company laptop home and not report to work for days – once HR had to call her and ask that if she was quitting she at least return the laptop. I believe she eventually lost that job in a RIF but it was a long time coming.

    Anyway…a lot of times these problems are not really “work” problems, they are life problems. I am not close with this person anymore so I don’t know how she has been helping herself, but I do know she’s been at the same job for a while now and has finished her degree. So something must have fallen into place, I’m guessing after a lot of self-examination.

    You might want to ask your friend what else is going on? How’s her family, relationship, etc? (Assuming you don’t already know.) Or she just could be the type of person who is unwilling to accept responsibility, in which case your frustration is warranted.

    I understand what you’re experiencing…in the moment I always felt bad that my friend was unhappy or had lost another job, but she just kept doing it to herself. It was not an energy I wanted to be around and so we are no longer close. It seems as if she is doing great now and I am glad for her, but during the tough times I truly did not understand what she was doing. It was beyond me – both to understand and to fix.

    Good luck, and I hope your friend can get some help.

  54. Frankie Bergstein*

    Coming at it from the friend’s perspective — if I were the friend who was lovely as a friend but likely a very difficult coworker, and someone close to me could provide insight — I’d want that insight! If it were a close enough friend that they’re showing up for me at a lot of important life events and that I go to with problems, I’d expect that. My husband and I do this for each other.

    This feels like a courage, honest, compassionate conversation that close friends could have. It wouldn’t be weird conversation for me. Awkward, difficult, something I’d need to practice – sure, but not something I’d hesitate to do.

    Then again, I’m clearly in the minority in this thread :)

    1. Rusty Shackelford*

      I had a coworker who wasn’t even a close friend tell me that my actions were perceived in a way that I did not realize or intend, and I appreciated it.

  55. Kalros, the mother of all thresher maws*

    Sometimes being a friend means lovingly calling someone on their shit. If it’s painful to see someone you love continue to screw herself over, you don’t have to bite your tongue. Only the parties involved can judge how to frame it within the bounds of the relationship, or guess how well it’s likely to go over, but even if she’s not receptive to constructive feedback, it’s not a friend’s job to be an unconditional sounding board. If your friend isn’t interested in feedback but continues coming to you for sympathy, and you’re not feeling terribly sympathetic, you can and should redirect the conversation.

    1. Diahann Carroll*

      Sometimes being a friend means lovingly calling someone on their shit.

      Quoting because this bears repeating.

      1. allathian*

        This is definitely true. Of course, if the friend isn’t ready to hear this message, it could mean the end of the friendship.

  56. anon for this*

    And maybe don’t call her middle aged to her face when you are noth only in your 30s.

    (Also in general implying that people should be in certain places in their life because of their age isn’t the best look.)

    1. Former Young Lady*

      People in their mid-30s will be at various places in their careers (late bloomers/took time off to start families/education, etc.). None of those places is inherently wrong. Sure.

      But I don’t think the OP is talking about professional achievement. She’s saying there’s a reasonable explanation of emotional maturity once you’re past the “emerging adults” phase of life. If you’re in your mid-thirties, you’re old enough to distinguish between critical feedback and senseless persecution.

      1. Former Young Lady*

        *expectation, not explanation. Not my worst Freudian slip but not my best, either. :)

      2. anon for this*

        That’s the point, if applying it to one person that you know the background of it’s fine, but it’s a terrible generalization. It’s good to keep it in mind, so by using a generalization aay that someone should be something at a certain age doesn’t wind up deeply hurting someone you dont want to hurt or leading you to discriminated against someone.

        1. Former Young Lady*

          OK. I don’t think you understood or are engaging with what I actually said.

  58. ShwaMan*

    “I’m so sorry you’re going through this, it must be difficult. I really like my work, but I’d be beyond frustrated if I kept ending up in jobs that I hate. Why do you think this keeps happening to you?”

  59. Titta*

    Ouch, this is a tough one! I have had these friends that are decent people in general but have some area in their life, that they manage to screw over and over.

    I would try to be kind or kind of joking, depending on the friend, but ultimately say what you thought about saying. And then try to steer the conversation into something else.

    I wouldn’t try to “coach” them or give more spesific advice. Just because personally I would find it irritating coming from a friend.

    But obviously you know your friendship!

  60. Hannah*

    Just be sympathetic. With everything going on in the world, empathy is appreciated from friends. If she needs work advice she can go to a mentor. If she’s mid-30s, that should be a given.

  61. Mid*

    I’m fairly young and new to the career world, but several of my friends are likely bad employees. When they complain about toxic workplaces, I direct them here and hope they read other articles as well, and hopefully learn from them. With some people, I’ll offer a more blunt opinion, but usually I’ll ask if they want to hear it first, unless it’s something unusually dire (like I know that what they’re doing will get them fired and I know they can’t afford to lose that job without risking eviction.)

  62. Nobby Nobbs*

    You’re getting a lot of good advice about asking whether she wants feedback, how to phrase things, etc., but I’d like to add one more step before you do any of that: assess your own emotional state. You’re coming across as really frustrated in your letter, and whether or not that’s justified, it can easily color any attempt to give advice in unhelpful ways. If I were you I’d take a hard, honest look at the likelihood that my advice would come across as more judgemental, accusatory, etc. than I meant simply by virtue of how long I’d been sitting on it. If you think this could be the case , it might be better to take some time to emotionally separate yourself from the situation before trying to help. It’s okay to say “I can’t be your shoulder to cry on for work woes right now, sorry!”

  63. Anne Elliot*

    Hoo boy. Please take this comment with an enormous grain of salt because I will say that I am not friends with this person anymore. I too had a friend who lost or quit job after job for reasons that were pretty obvious to me, even though I only ever heard her side of things. And, as recommended here, I finally did ask “are you looking for advice or commiseration” and although she said “both!”, she never took the advice so I moved to strictly commiserating.

    But even just commiserating was not a long-term solution, because it ended up I do not have an inexhaustible supply of energy to continually sympathize with problems that my friend herself was probably creating but either could not fix or did not want to fix. It got to the point of her being like, “I’ve lost another job! I just do not understand this, it’s so unfair!” and me being like, “Oh no, again? What a big mystery this is!” I never said that last part to her, but that’s what I said in my head. So ultimately I had to say something along the lines of, “we really need to talk about other things more and your employment situations less,” and she found that super unsupportive, and that situation was honestly a big part of why we both let the friendship fade away.

    1. Hey Karma, Over Here*

      This is what I typed and then found did not post, so I will simply second this.
      OP, you are creating game plans, you are writing for advice, you are worrying. Friend is not. Friend is enjoying endless sympathy and attention.
      As for work, you cannot be more invested in her career than she is.
      As for friendship, how much mental space do you typically give your friends? This is not sustainable. You are going to crack. Set some boundaries about how much you will listen to and then turn off the drama llama show.

    2. Former Young Lady*

      Heh! I have an ex-friend who sounds a lot like your ex-friend. Every day job she ever held was fun for a week, and then suddenly it consisted of the most heinous oppression anyone had ever endured. Every manager she ever had was an incompetent dictator. Why were all of them complaining about her attitude and her job performance? “What a big mystery” indeed!

      She was also always cutting a former close friend out of her life for not being supportive enough of her dreams (career, men, what-have-you) or for being too “needy” (…having problems of their own, I guess). Eventually my number inevitably came up. It stung, but it was also a relief.

    3. Batgirl*

      Yeah I think these friendships are destined to end in emotional burnout unless the less sociably able friend is willing to either take some feedback or stop talking about the problem. They tend not to do either because it’s not an ability they have!
      If they are otherwise nice people, I tend to give an honesty memo as kindly as I can when the writing is on the wall that we’re on the way out anyway. It may be just a teaspoon to dig with, but with time maybe they’ll get there.

  64. Aggretsuko*

    This depends on your friend, but if friend is blockheaded on this topic, I don’t think it’s worth bringing up. I have a friend like this and I just keep my mouth shut. I may think she’s being more difficult than she needs to be, but she is absolutely gonna do what she’s gonna do regardless of my opinion. Not worth the drama.

  65. Caliente*

    I concur – I have been explicitly asked for advice and then people get mad at you for giving your opinion. I find that its just not worth it.

  66. SaffyTaffy*

    My mom was like this all through her career. I’ve heard from multiple people that she was excellent at her job and terrible to work with. It created a suspicion that she could never be successful because everyone hates her. And all it took was me being her daughter to internalize that same crap. I wish so much that a friend could have approached her and coached her. Friends coach one another!

  67. Manana*

    Unless she is complaining about not having income or having to job hop, don’t say anything, and even if she is ask if she wants advice. AND EVEN THEN probably soft coat it. Your last line about her being middle aged and putting up/shutting up says to me you have a lot of pent up feelings about this that will very likely come across as mean-spirited. She can both be a bad employee and also be working in toxic offices, these are not mutually exclusive things. Repeatedly working in toxic places (many industries are uniformly crappy to women) makes it very hard to be a good employee.

  68. Lexi Kate*

    Ask privately if they want advice, it sounds like they are more a friendly acquaintance you used to know well. We call everyone a friend now, so I’m not sure how close you all are if you can tell her. My friends attend all my kids parties, they stop by when I’m not home so they don’t have to go to the grocery and take what they need from my house (laundry detergent, eggs, ketchup), they treat my sister like she is their sister and my mom like she is their mom. I can count these people on my hand. I would absolutely call them out on anything that I thought was jeopardizing them, their career, or their children. I have Friendly acquaintances that I used to know well, we meet up for drinks, and talk on Facebook, I invite them to my Annual Halloween party but not my kids parties. I wouldn’t tell them about their bad career choices unless asked, I have offered on one occasion to give advice if they really wanted it (not while we are in a group). They took me up on it and gave excuses for everything, and they were convinced I moved up based on “being liked” and having good managers.

    1. June*

      Hope your friends are restocking your pantry! Or better yet, my friends will restock anything they borrow/use along with beer for hubby and flowers or cookies for me. :)

      1. Lexi Kate*

        It goes both ways, no one wants to go to the store if they only need one thing especially after they work all day. It evens out.

  69. Beth*

    I’ve had several friends — now former friends — who were mysteriously unable to keep jobs, but whose job problems were never their fault. Eventually, each of them turned out not to be much of a friend, either — the intersection of entitlement and terrible attitude made them bad friends as well as bad employees. Some of them turned out to have worse personality elements lurking under the self-sabotage and self-justification.

    Bottom line: you may lose your friend if you try to talk honestly to her. You may lose her anyway. In your position, I might try to say something, but I would first brace myself for terminal blowback. And I would accept that a person who responds with terminal blowback was a friend who would eventually prove too toxic anyway.

  70. 9to4ever*

    Over many years, my friends and I all have vented about work and offered each other advice…it’s been a pretty organic process of sympathy and feedback combined. “Ugh, your boss said what? Well, did you try approaching her with this idea?” etc. etc. (Not in the same field as my friends, but we have all been able to help each other out with navigating various situations over the years.) I would say if this is NOT happening, it could be that you don’t already feel comfortable providing feedback, either because she’s so defensive or because you are worried about offending, or a combination. But for the relationship to be mutually beneficial, you do need to be able to be authentic and not worried that someone will bite your head off.

    1. Elise*

      Can you gift her sessions with a career coach? This will only work if she’s willing to hear you out and recognize that she has problem that she might not be able to solve on her own. But then find a good career coach. Try TheMuse.com or google other sources. And then give it to her as a birthday gift or holiday gift or whatever. A bit like paying for a friend to enter drug rehab, but it could truly help.

  71. Bookworm*

    Agree with many of the other comments: ask if she wants your advice/thoughts as a friend OR as someone who has experience in the field. How she answers will tell you.

    Since you talk about friendship: I had a friend who was somewhat like this (it was in her personal life and our professional ones didn’t overlap). There was always something wrong, something always happened that caused a fallout, someone didn’t like her, etc. Some of it was stuff that wasn’t really her fault. But if it’s a pattern, at some point you (general you) need to realize that YOU are the problem, not everyone else.

    I may be projecting, but this may be a friendship you may want to begin to distance yourself from, for both personal/mental wellness if it’s bothering you and/or professional reasons. Only you can say, though and it’s up to you.

    Good luck.

  72. Eve*

    Folks like this usually have other issues going on. Is there any way for you to suggest counseling/therapy? Once you make that suggestion, back out of any discussions about work that she wants to have.

  73. Good friend or bad friend?*

    I didn’t say anything to my friend when he got offended over every bit of feedback from his new manager, when he said he was going to give an ultimatum that they switch him back to his old manager or he would quit, when he said he had filed for unemployment even though he did quit. I finally said something when he sued his former employer after they contested the unemployment claim. He dumped me as a friend for not being supportive enough.

      1. Good friend or bad friend?*

        He believed that any and all feedback was discriminatory (even including when they repeated the same instruction in more than one individual training session). Therefore he believed that he was forced to quit due to a hostile work environment. And so on.

  74. AnotherLibrarian*

    I have one dear friend who is, let’s be clear, not a very good employee. However, they are a dear friend. I think you have two options which others have highlighted. The difference is that my friend knows it and we are in totally different fields, so I can’t really help her.
    A. Ask if she wants advice and then offer it.
    B. Have one (and only one) moment to tell her your concerns. Don’t rub it in. I have used phrasing like, “I’m only going to say this once and I hope you know it comes from a place of love. But I am concerned about X” And then never bring it up again, unprompted.
    If she’s a true friend, the relationship should survive this.

  75. Virginia*

    If you want to give your friend advice, go for it. Just know you may lose the friendship. I had a friend that I had to set boundaries with and she got upset and we’re no longer friends.

  76. aunt bop*

    Before you say anything, I would suggest checking any of your own biases. Is your friend BIPOC or a member of any other group that experiences microaggressions and marginalization on the regular? Yes, she is the common denominator in these situations, but toxic bosses and problematic comments run rampant in workplaces. Is what you are considering the boss doing the right thing basically silencing a person who is pointing out real issues and suffering from unfair treatment based on her identity?

    This may not apply to this situation at all, but I think it’s worth giving it some thought.

      1. Diahann Carroll*

        Yup, and her friend is the one being accused at this new job of microaggressions.

  77. Safely Retired*

    Ah yes, when the one factor common to all your problems is you.

    I believe that if you lay it on the line with your friend, you will no longer have a friend.
    If you think it is more important to give your friend the chance to see things more clearly than to continue as things are – friendship plus biting your tongue – then give it a try. But my impression is that you have no more chance of getting through than those bosses and managers did.

    Can you maintain the status quo and not have it eat you alive? By writing you have shown that it is getting to you. As yourself how long you can sustain that. If you run out of patience your choices become being blunt to working out way out of the relationship without confrontation.

    Perhaps it is possible to stay short of laying it on the line by making responses that address situations indirectly, based on accepting the importance of the business. Will that sort of thing help? I doubt it. Will it hurt your friendship? Probably. Is it worth a try? That’s up to you.

    Friend complains of the way Boss handled a situation between Friend and Coworker: “Managing staff disputes like that is a thankless job. If one isn’t unhappy, the other is, and often both can go away mad. I’m glad I don’t have that job”

    Friend complains about a deadline that they are expected to meet: “Yeah, it is a PITA when something really has to be done and it requires pulling out all the stops. I’ll do it what it takes when it really matters but they better not expect me to put in overtime like that every week.”

    Friend complains about having to do work over because they were told it was wrong or otherwise unsatisfactory: “Yeah, I had to learn the hard way that being good enough by my standards isn’t always good enough. There was this one time… (insert anecdote, probably imaginary, with moral of I was wrong)”

    Of course your friend is likely to respond “You really don’t get it!” because she is blameless, by definition.

  78. Akcipitrokulo*

    It might help to phrase it as “ah… I think I know what you mean… one way I found of handling that is…”

    Make it a tip to handle a situation, not that they are doing something wrong.

    “Hmm, I knew a llama groomer who used to do that – what I found helped was…”

    1. Some Lady*

      Yeah – if you phrase it as ‘here is something in my own experience that related to that’ – that’s more similar to conversations on any topic. In addition to the example above, you could say something like “I’ve seen so and so handle this really well; what she did was…” so it’s not even about you doing something better. It will probably depend on your friend, your relationship, and your friend’s current mood how receptive they’ll be. For example, if they’re really emotional about something that just happened, they might not be in a place to hear it as much as they might another time. Depending on your friend and relationship, this could come after the ‘do you want to vent or really talk about this’ question so many have suggested.

  79. HarvestKaleSlaw*

    You can’t “fix” people. Someone who has a very well-established pattern like this that they are oblivious to, will need therapy, hard work, and a decent bit of luck to change.

    That said, you don’t have to feed the bad mindset either.

    Example: “My boss is so toxic! Why did I land in another bad job? I’m cursed!”

    Bad: “The problem is not your boss, it is you! Let me explain what’s wrong with you, so you can fix it.” (Not their therapist.)
    Bad: “Ugh, what a rotten boss. That really stinks that this keeps happening to you.” (Don’t validate their f-ed up worldview either.)
    Okay: “Man, you sound really frustrated. Do you want to go to the batting cages together and blow off some steam?” (Their feelings are valid. You can acknowledge and listen. But redirect the pity party after a while.)

  80. LCS*

    The kind of person who keeps running into these issues at work is very rarely someone who is good at taking constructive feedback in a mature manner and then incorporating that into their approach going forward. Even if you specifically ask the “advice vs. support” question, and even if she responds with “advice please”, I’ve got low confidence that this ends up being a constructive discussion that doesn’t impact the friendship. It takes a lot of skillful coaching to help someone (a) first of all realize that ability to take feedback is a valuable skill to develop, and then (b) to actually develop it. It’s not typically a one-and-done situation. As someone wanting to maintain a close friendship, I wouldn’t put myself into that sort of coach territory as a long term prospect, and I’ve got low confidence it would be of value as a one time thing – so better to step back and focus exclusively on the friendship aspect.

  81. beanie gee*

    It’ll be one step to even accepting advice from a friend. It would be another huge, hard step to have her hear the advice in a way that actually gets through. She very likely does not want to change and might see any advice you give as somehow siding with her enemies.

    I think it’ll be really really hard as a friend to get her to see that it’s her own behavior that’s causing her problems. I don’t know who the right person would be, but it’s going to be hard.

  82. The Bill Murray Disagreement*

    I would just leave it alone. You mention in the letter that she’s not taken feedback well before; if she’s not asking for advice, she’s probably going to bristle even at the question “do you want my sympathy or do you want feedback?” because as well-intentioned as that is (and I think it really is), someone who’s prickly at best about feedback is going to (rightly) assume you don’t agree with how they’re approaching the situation. Basically, that question is tantamount to saying, “I think you’re handling this poorly, but if you don’t want me to I won’t give you any details about why I think that.”

    That said, my take on this could be completely off & a couple things might point to that. Has she ever asked for advice from you on this or other topics, and if so, has she taken that advice to heart? Does she seem like she’s genuinely at a loss for why these work situations keep arising around her (as opposed to having a tone of indignation and/or anger which suggests she might think she’s blameless)? If either of these are true, I think saying something like, “I’m really worried that this is happening again; what can I do to help?” and see what she says. It’s far less ‘confrontational’ (which is not the right word here, but it’s as close as I can get) than the ‘do you want sympathy or advice’ question so many folks have suggested.

  83. Epsilon Delta*

    I have a handful of very close friends who I would be pretty direct with, but only once or twice. “It sounds like by doing X you might have caused Y.” But if they continued to make the same mistakes and complain I would not keep offering advice unless it was years later. And even if they ignored my advice I would continue to commiserate.

    The rest of my friends I would just commiserate, or perhaps ask if they wanted my opinion on the situation depending on how I thought they would react to honest feedback.

    In both cases, I would not offer feedback every time. I would do it once or twice then stop. Becoming a job coach is going to make your friendship weird.

    1. Epsilon Delta*

      And I am reminded of something my husband says a lot. “People only change a little bit at a time, and only if they want to.” Even if your friend hears your advice and thinks it’s valid, her actions will probably not change a whole lot, at least not in the short term.

  84. Jean*

    Recommend AAM. Seriously. I have told every single one of my friends who has had professional challenges (and honestly, what working person HASN’T had professional challenges?) about AAM and what a great resource it has been for me. I have been reading AAM for about a year, and it’s been like a grad level course in strategies for professional success.

  85. animaniactoo*

    “Hey Anne,

    I love you and I want only the best for you – and I’m really concerned during this extremely unstable time that it sounds like you’re having major work issues again.

    In the past, I’ve tried to offer you advice where it sounds to me like you’ve contributed to some of the issues you’ve had without realizing it, but that made you really upset and I took that as a sign that you just wanted to vent. But I feel like I wouldn’t really be a friend if I didn’t tell you that there are things that I’m hearing that I think you can do differently that will improve how some of the stuff you’ve talked to me about goes. I’m willing to talk to you about those things, if you’re open to hearing about them – even though they may upset you, all I ask is that you look at them and consider them and decide for yourself if they’re valid for what going through. Please let me know if you’d like to do that.

    If you’re not up for that, I would really like to suggest seeing about doing some therapy to dig through this, because you keep running into it over and over again. Either to help you sort out what you’re missing when interviewing, or maybe to work on some different approach strategies for the work conflicts that could be useful in reducing some of the issues you run into.”

    By e-mail, by instant message, or by phone. If by phone or instant message, you probably won’t get it all out at one shot, but these are the points you want to cover and the kind of tone you want to go for. And if she gets defensive/upset, the answer is “Hey, I’m not saying it’s all your fault. Just that you can work on your end to make sure that you’re absolutely in the clear and have done everything you can, and I have some suggestions for what I think I’m hearing. I’m sure there are many problems that are because of someone else, but that still means you (and I!) have to find ways to survive dealing with them and stay sane.”

  86. Pyjamas*

    Put it in another context: suppose OP were a therapist and their friend was exhibiting symptoms of mental illness. OP would be too close to diagnose/treat the illness.

    In this case, OP’s expertise is that of a manager but, as in the hypothetical case above, they are too close to the friend to give feedback/advice.

    What they could say is, “I’ve noticed this situation is happening over and over again and I am too close to you to help you. You need to talk to an objective professional about this.” And then, OP needs to lovingly refuse to be that sympathetic ear because that is just giving the friend a way to avoid dealing with the problem.

    1. Batgirl*

      I agree that letting a friend treat you as an free therapist can be a bad idea, particularly if you’re starting to get alarmed.

  87. Georgina Fredrika*

    I’m always surprised when my friends DO appreciate my honest advice rather than telling them what to hear. But sometimes they do. Sometimes they even refer to it much later, like “what you said eventually got me thinking.”

    It’s kind of a larger question about what friendship means but I think you should try to steer them right. Not with the hardnosed truth someone else might give, but a gentle shove in the potentially right direction.

    It is absolutely true, also, that we often decide what is normal based on how people react to us. If you start reacting (nicely) as if this is a “her problem” it might allow for some introspection that isn’t happening if everyone nods and agrees to “yes, this is unfair to you”

  88. HV*

    I heard – years ago – that a percentage of the population isn’t capable of/is less receptive to/self-examination. I’ve certainly worked with people like that, and I think earlier in my career was inclined toward that behavior. I then had a boss who wanted to post mortem EVERYTHING. It sucked at the time, but it was great training.

  89. Sen*

    OP, you’re receiving some really great advice here, but something else I want to bring up is whether or not this friendship is worth it to you anymore. I say this with all the kindness in the world, as I’ve also faced similar problems in the past.

    Friendships are a two-way street, and if someone has worn you down to the point of extreme frustration, it’s hard to bounce back from that. I implore you to think about your life without her — Do you think you’d miss her? Would the good outweigh the bad? Or, do you instead feel a sense of relief?

    Best of luck, OP!

  90. Koala dreams*

    I understand that you are afraid of risking the friendship, but the thing is, this kind of venting and negativity can ruin friendships, and from your description, it’s already heading that way. So the alternatives are changing something and maybe save the friendship, or keep on as before and see the friendship slowly erode.

    You have tried giving advice in the past, so maybe it’s time for a ban on work talk and/or venting. “I find it very stressful to talk about work problems all the time. This is a difficult time and I just don’t have the emotional bandwidth for that. Let’s talk about lighter topics instead, such as X or Y.”

  91. Half-Caf Latte*

    I picked up on the fact that friend has a graduate degree and is struggling to keep work.

    One of the ways I think academia sometimes fails to prepare people for the work world is the nature of the schedule. Semesters run 4 months, and then you get a short break, and then come back – to a completely fresh slate – new professors, new syllabus, the smell of new planners and notebooks.* Unless it’s the smallest of graduate programs, you’ll still get new faculty regularly, and classmates. You don’t really have to learn to work with people for long time frames, or sustain projects for years. She may have not encountered those realities of the working world until her late 20s, and never adapted.

    OP: do your fields have any avenues into contract work? I wonder if she could be successful in short-term-by-design roles.

    *good intentions, that’s what they smell like

  92. Goldenrod*

    Personally, I would steer clear of giving her any advice. I don’t think she will want to hear it and it will just ruin the friendship. I would just say, “oh that sucks” and change the subject. :p

  93. fancypance*

    I would start asking non-judgmental and curious questions when she says things about work. It doesn’t have to be confrontational, but maybe it could prompt some self reflection within her.
    “Why do you think they reacted that way?”
    “Oh, I always do X in that situation, how is doing Y working out for you?”
    “If this job doesn’t work out, what will you do?”
    “What are the top performers at the company doing?”
    “Wow, weird, how did that happen?”
    “Did they make their expectations clear?”

  94. Kara S*

    I think you should ask your friend what kind of feedback she wants. You could say that you’ve been in a similar situation and have some advice on how she could improve the situation if she’d like to hear it. If she says no, there’s not much point in offering feedback she will not listen to.

    It would also be fair for you to tell her you aren’t available to hear her complain constantly about her work if it’s a very one-sided, complain-y conversation (I’d word it differently when talking to her though).

  95. Mandie*

    I think I would handle this by asking leading questions that sound sympathetic but encourage her to reflect. Example:

    OP: “It sucks to go to work when you feel like no one likes you. What is making you feel that way?”
    Friend: “The woman in the cube next to me smirks at me all the time.”
    OP: “So it’s just the one woman, then, or does everyone act like that?”

    OP’s friend is probably going to stay on this toxic path until she reflects on her own shortcomings and decides to change. I can’t tell you how many times a question from another person made me discover something important about myself.

  96. RWM*

    In my experience, people take anything other than a really clear “wow, no, I don’t agree with what you are saying here” as agreement/support…so by not saying anything—especially when you’re a manager—you’re probably letting your friend think they are totally in the right when they are very much… not. And I do think if you care about this person, you have a responsibility to speak up and try at least once to not let your friend make a total ass of herself at work.

    I’ve found that a good/gentle way to communicate this is saying something like “I actually think your [manager/coworker/etc] has a point” after your friend does a Big Vent where they are clearly in the wrong. (I think in general it’s good to ask if people want advice, but if she’s venting a LOT over the course of several conversations, you’re allowed to weigh in.) Saying this is not super accusatory, and is a good way to start a conversation about it where you can share your POV and they can hopefully hear you out. And if they get super defensive or don’t take your advice, well…at least you tried, and they know how you feel about this!

  97. Ms Fieryworth*

    There might be space to approach this in a constructive way, and pass on the problem to someone else. You could try something like ‘You’ve had a lot of experiences where you’ve been unhappy in your job, and I wonder if you would benefit from getting a career coach to help you figure out why that is. I think they could help you figure out what the patterns are in places that you have worked, to help you find a better fit in your next job’. There’s lots of great coaches out there, and they can tell your friend their messing up without you being involved. I’ve used this tactic a few times with people in my life, and it’s always worked out well.

  98. memyselfandi*

    Lot’s of good advice here. My personal experience is that I am grateful to the friend(s) who had the hard talk with me when necessary and did it with grace and good humor. And, I’ve done the same for those good friends. It has made my friendships stronger.

  99. Bob*

    If you think she will take it badly (which it sounds like she will, if even from her one sided explanations she looks like the problem) then its likely it would be friendship damaging/ending.
    You might want to take that step, is it worth a lifetime of being her Freudian counselor?
    Thats a question only you can answer?

  100. SJJ*

    I’d say that she seems to have these issues a lot, and offer to help give her some advice.

    But, there does come a point where it’s like “Either take advice or stop talking to me about it.”

  101. MissDisplaced*

    Even if you’re allowing her a place to vent, you can still ask questions much in the manner of a therapist.
    > Why do you think that happened that way?
    > Did you consider X?
    > Have you considered A or B as a factor?

    There is also the case that, as a friend, you suggest she seek professional help from either a career coach or a therapist. Because you, as a friend, have noticed a repeating pattern and are concerned for her and want her to be happy and professionally fulfilled.
    Also, is it possible she is just in the wrong line of work for her temperament or personality?

  102. Xanna*

    I think to some extent this comes back to who both of you are as people. I think we all have people in our lives who give great advice that makes us feel empowered, understood, and valued, as well as people who give advice in a way that feels judgemental, dismissive, or generally unkind. It’s why advice columnists exist! As a rabid consumer of this site, as well as other advice columns, I think we really see this when there’s a columnist we dislike – one of the previous Prudies for Slate was like this for me – despite people writing in and asking for advice, the responses didn’t strike me as empathetic, or likely to actually inspire the writer to make improvements to their situation – and even though it had no impact on me at all, I found myself bristling and slightly defensive on behalf of the letterwriters. Giving great advice is hard, which is why communities like this are so loyal and check daily for Alison’s advice, even on situations that are totally irrelevant to our own lives. (That being said, while I’ve yet to have a Hanukkah balls incident of my very own, I await the day with bated breath!)

    It’s hard to give a script that someone can read out and instantly become an intrinsically good advice giver – it’s a skill, and requires just as much talent in communicating and understanding how humans work as actually understanding the work issue at hand. If Alison or Captain Awkward was this person’s friend, I think they’d definitely give advice that’s compassionate and productive while still honest, and know how to back off if the friend isn’t receptive. I think a lot of people could do the same in LWs situation, but it takes some self awareness to know if that’s you or not.

    If you’re not a historically excellent advice giver – maybe pointing the friend to some resources like this site could be helpful? Personally, I’d probably do it by finding an outrageous letter that’s tangentially similar to your friends complaints, where the response affirms “wait this is insane” but then offers professional solutions to advocating for oneself without blowing up the entire situation – if the friend is interested, this community is such a valuable resource for conducting oneself in the workplace and they can explore it themselves in the dignity of their own home, but if they’re not ready for that type of introspection, at least they can have a laugh at someone else’s dysfunctional workplace.

  103. Former Retail Manager*

    OP, if I were you, I’d talk to her directly and candidly, regardless of whether she asks for advice or not. My reasoning is twofold 1) Part of being an adult (in my opinion) is stepping in and at least saying something when you see someone you care out doing something that is damaging to their life that has the potential to have serious and/or long term consequences, even if they don’t want to hear it and 2) The other part of that, is your friend should be able to hear feedback from a close friend, about an important matter affecting their life, without ending the friendship.

    Most adults will, at some point, receive feedback that may be truthful, but also hurts. Assuming the information is delivered in a kind, but direct and honest way, your friend should take it to heart for what it is….an attempt to send her a wake-up call before she does irreparable damage to her career at a particularly bad point in time that may indeed have long term consequences. Who knows when things will return to “normal?”

    As for how to phrase it, so many great suggestions above.

    I personally had this discussion with a longtime, close friend of mine, although it wasn’t a planned discussion and I was pretty brutally honest, which is my personality. She was upset and didn’t speak to me for a little while. However, she did eventually get over her anger and say she appreciated the conversation and it did cause her to reflect on her own actions and certain personality traits and how all of it has contributed to her repeated job hopping because she always seemed to have conflict with someone at every job. She was the common denominator.

    And honestly, if she hadn’t gotten over it and spoken to me again, I would have been okay with that because I don’t want to have friends that can’t handle the truth and won’t accept any fraction of responsibility for their role in certain situations. Most people who always seem to find themselves being wronged by their employer will eventually exhibit the same behavior in their personal friendships.

  104. Anonymous Hippo*

    I have someone in my close circle that’s the same. I hear stories about work troubles, and almost universally I side against them (in my head). I have tried to make a few suggestions separate from the complaint sessions, but they don’t seem to be effective. I think you have to just divorce yourself from that, because unless they are coming to you directly to help themselves change because they’ve figured out it is warranted, you will just end up losing a relationship over it. They want support, not advice.

  105. Van Wilder*

    I would usually agree with others that you should frame it as “Do you want sympathy or advice?” but you might be at the point where you want to try to help your friend even if she doesn’t want your advice.

    The only thing I can think of is to frame it as a one person intervention. “I need to talk to you about something serious. During this conversation, we’re going to put our friendship on pause. I want to talk to you as a colleague in the same field. And once we finish this conversation, we can go back to being friends. Do you agree?”

    (Loosely based on language my mom recently gave me for arguing with friends.) But ultimately, she just might not want to hear this message from you. She may be aware of her issues on some level but it hurts to hear them from a friend who is successful in the same field. It’s kind of you to try. Good luck!

  106. Elle by the sea*

    She could be the problematic one but it’s also possible that she has been terribly unlucky with jobs. If you have a graduate degree and/or are knowledgeable in the subject, you get bullied at work very often (by colleagues and managers alike), no matter how hard you try to fit in. I’m very lucky with my team and managers at the moment, but the vast majority of my experiences has been like that of OPs friend. They were not at all task-oriented, were mostly interested in social maneuvering, and didn’t care about the quality of your work. Only mediocre people who are good “team players” (=not what I consider to be a team player, but rather someone who is willing to engage in mob behaviour) were appreciated.

    1. Colette*

      That’s never been my experience. (But also, how would people find out what degree you have? If it’s not a requirement to get hired, it’s probably irrelevant to the job.)

      1. Elle by the sea*

        Well, most of the jobs I’ve been in had graduate degree as preferred qualification. Also, even if it was not required, everyone knew everyone’s details (including degrees), most people used to hang out on the weekends and go for drinks on Fridays.

        1. Something Something Whomp Whomp*

          The vast majority of people I’m close with have a graduate or professional degree (ugh, did I really just write that?), and I’ve spent almost all of my career in “graduate degree preferred” jobs in more than one industry. I’m also in a very introvert-friendly field, if that helps put things into perspective. While I’ve not had this issue myself, I know people who have experienced what you have, and it often seems to involve one of a couple things:

          (1) They’ve worked in a series of offices or an entire industry that’s endemically toxic for people like them (i.e. women in certain parts of STEM)
          (2) They have some (often minor) social issues that make them inadvertently seem…well, professorial and presumptive. The example I’ve seen a few times is someone who often comes across as though they’re trying to teach people things they’re contextually likely to already know. When you’ve got an environment of highly-skilled people who are otherwise comfortable sharing knowledge, that kind of thing at best comes across as not reading the room and at worst makes someone seem like they may lack professional respect for their colleagues. You want to give someone the benefit of the doubt when these things happen, but when the person who does this isn’t actively building rapport (see my introvert comment above), it can be difficult not to assume something negative.

          Nothing excuses bullying, and I’m sorry that you’ve had bad workplace experiences. Being smart with takes a different skillset than being smart at, and folks who struggle with the latter sometimes wade into situations where they generate ill-will they don’t mean to. I don’t know if that’s what was going on in your situation, though.

  107. Karia*

    Ok, two sides here. I’ve had a lot of difficulties at work because I work in a volatile industry, and have worked for objectively dysfunctional small companies. So if someone keeps having a bad time I don’t necessarily assume it’s their fault.

    However two things jumped out here; ‘six months’ and ‘fired’.

    One of my very dear friendships basically fell apart because we were both whinging to each other about eminently fixable issues that required therapy, not sympathy.

    Overall my advice would be to gently refuse to be her sounding board any longer. You are not required to be her unpaid therapist or condone her bad choices. Boundaries are great!

  109. GreenDoor*

    Wow. We might have the same friend! I would base it on how she is when you have conflicts within your friendship. Is she open minded when you want to deal with conflicts in your friendship? Does she say she’ll do better going forward….and then improve….or fall right back on bad habits? Or does she turn around and blame all the friendship conflicts on you or others in your circle? If she seems open to honesty and candor when you’re dealing with friendship conflicts, she might be more receptive to hearing your manager-take on her work issues. You can soften it with, “I’m saying this as one friend to another, but here’s what I’m seeing….” or “You know I love you like a sister and I want you to do well, but honestly….”

  110. Aphrodite*

    Say exactly to her what you said in this letter because it’s perfect. Her response will be your answer.

  111. tangerineRose*

    Maybe recommend the friend start reading AAM (maybe give it a few days so this isn’t the article she first reads).

    It might be worth trying to talk through what you think the other person’s point of view, so something like, if I were your manager, I’d be taken aback when you said…

    1. Heidi*

      Or you could do what some others have done and describe the scenario for her last firing in detail and post in on the Friday free-for-all. Then just ask what people think. It might be a way to for her to get advice without you having to be the sledgehammer of truth. You can use a codename so that we know that it’s you.

  112. CouldntPickAUsername*

    I think this is a case where you directly ask her what she wants.
    “do you just want to vent, do you just want some emotional support or do you want to hear me offer some serious advice?” then go from there, she has to be willing to listen.

  113. Picky*

    “I’ve noticed you have a pattern where you start out excited about a job, and then a short while later you are disillusioned with it. I’m worried you may be self-sabotaging by having unrealistic expectations about what the job is going to be and then crashing when it’s not perfect. Have you considered talking this through with a therapist or life coach?”
    That is the sum total of what I would do… don’t go into any detail about thinking she might be the problem, but also don’t fall into the trap of assuring her it’s not her fault. Don’t be her therapist, but refer her to one. (If she wants more details you can shrug and be all, “I don’t know, I just thought talking about it with a professional might help…”)

  114. Jennifer Juniper*

    OP, sounds like you may be tired of listening to her endless whinging while she’s self-sabotaging.

    You may need to put limits on how much complaining you’re willing to listen to. The old standby “What are you going to do about it?” may make her think.

  115. LGC*

    adjfasfkjdashkj if you switched the genders and lowered the ages a bit (I’m mid-30’s and my friend is early 30’s), I might have written this letter.

    Honestly, I’m with the early consensus here. But…I slightly dipped into this in my reply to Kate up top, but I honestly think your friend opinion and your professional opinion should be closer together. (JokeyJules says this more colorfully in the second comment – basically, this is the career equivalent of a string of bad romantic relationships.)

    That said, don’t give “professional” feedback unless she’s specifically asking for it (or if you offer it). But…honestly, dude, like – it sounds like it’s difficult for you to listen to her tales of self-sabotage, so you get to excuse yourself from them. You also get to say that she might not have done the right thing (you can be gentle about it, of course) sometimes. With my friend like this (who just got laid off from his most recent job – so he did leave on good terms), I generally make sympathetic mouth noises, and then…honestly, I’ll let him vent and then mention gently where he might need to improve (or that – you know – there is room for improvement). But also, I’ve accepted that to a large degree he’s not going to listen to what I have to say (despite me actually being his boss for a year and a half – or probably because of it ¯\_(ツ)_/¯), so most times I’m like “mm-hmm yeah that’s awful.” And then excuse myself.

    Which it sounds like you’re doing, to a degree.

  116. LogicalOne*

    Slippery slope. On one hand you don’t want to ruin your friendship with your friend but at the same time you don’t want them to get fired from a job during a pandemic. In my honest opinion, if she is mature enough to handle the truth, you need to give her some tough love. Of course, everyone is different you so may or may not know how they will react if you give them honest advice. I would ask, “Is there anything I can do?” and/or if they ask, “Am I doing anything wrong?”, slowly dip their toes in the water. Don’t be mean about it but maybe ease them into why they are being treated the way they are. I always believed that it’s better to offer harsh criticism than do nothing because harsh criticism comes from a place of love and caring. If your friend really values your friendship with each other, they should understand. Especially at your age, she needs to be mature enough to handle such conversations.

  117. Utility gal*

    As someone who struggles with social etiquette I have to think about these kinds of conversations in advance. I tend to preface the sympathy requests with “I need a reality check to tell me if my reactions are valid”. (With closer friends this sometimes comes out as ” someone is crazy here – is it me or my (boss/parent/lover)?”). Perhaps validating feelings (versus approving actions) is all the LW’s friend is seeking? In contrast, my “oh no what should I do?” Conversations tend to start with “I need a favor can you give me some advice on X?”. I wonder if the LW’s friend sends subtle signals as to exactly what she is seeking?

  118. Lauren*

    Maybe sit down with her and make a physical list of what went wrong at each job and see if you can identify specific patterns and ways to begin creating solutions. Literally write this down. With a pen or on a computer and then highlight patterns with a literal highlighter. Say, “These three incidences show that you have trouble gleaning information from data. Would an online course on statistics help?” Or “You’re losing your cool customers. Here are some strategies you can use to keep your head when a customer is being rude.” Or “maybe switch from sales to marketing?” And let her know that you’re bringing this up now because the economy is crashing and you care about her as a friend. Friends help friends ensure they can pay the rent and put food on the table and this is one way to help with that over the long term. Not easy at all, I know. Good luck!

  119. RebelwithMouseyHair*

    My personal take is that advice is useless, even when specifically asked for. I learned about this when training to work as a volunteer counsellor, but it works for other relationships too. There are four main scenarios, and each come with a problem:
    1. They follow your advice and succeed: this is the best scenario, but carries the risk that they then put you on a pedestal and come to you for advice on absolutely everything, increasing the possibility of 2.
    2. They follow your advice and fail: you lose all credibility. If it comes after a 1. scenario, it hurts all the more.
    3. They don’t follow your advice and succeed: again, you lose all credibility (perhaps your advice did really suck in fact!). This doesn’t matter so much if you’re a friend (far more if you’re a counsellor) but you might get some snark or gloating from them, and they won’t ever listen to your advice again.
    4. They don’t follow your advice and fail: they might avoid you for fear of hearing “I told you so”, or they might come back to you but what can you say that won’t sound like “I told you so”?

    So, rather than dispense advice as a Wise Old Witch, I frame it as a question “have you tried talking to your boss about changing your hours?” or “what might happen if you just said you’re going to groom the llamas before painting the teapot lids?” or “has anyone ever reported that dick to HR?”
    An advantage I feel for myself when asking questions rather than giving advice is that I feel less personally invested in the outcome. If I give advice, I absolutely want it to work. If I ask a seemingly innocent question about a possible solution, there’s no egg on my face if my friend tries to implement it and it all goes tits up.

  120. cncx*

    I think it’s really hard. I had a friend who kept making the same mistakes in full time remote work and even though she was doing a good enough job she wasn’t doing what she needed to do in terms of optics and politics and i tried in so many ways to tell her but she always brushed me off because i don’t work remote even though i work for people who are full time remote. At some point OP has to decide if this is a friendship she can keep. It was really hard for me to see my friend get fired three times for stuff that was essentially preventable (ok maybe one of the jobs it wasn’t her “fault”) and after a while it was hurting me to listen to it, tbh.

  121. Some Lady*

    A wise person I knew would often comment “Does she have no friends?!?” whenever she saw behavior that was embarrassing, wrongheaded, or particularly unhealthy. It distills the idea that friendship is about having people who care enough about you to tell you when you can do better, and valuing people when they do that because they make you a better person. It doesn’t mean everyone you consider a friend is someone who can participate in this type of relationship with you–that depends on the people involved and their dynamic together, so you’d have to determine if your friendship is in this territory or if the value you get from your relationship is something good but not this level.

  122. Stixx-and-String*

    One of my favorite saying is “If you encounter one asshole, you met one asshole. If everyone around you is an asshole, YOU’RE the asshole.”

    It’s really telling when someone has difficulty getting along with everyone, all the time. It says a lot more about that one person than it does about everyone around them.

  123. Emily*

    This vaguely reminds me of one of my friends! She’ll complain about something that happened at work … that is totally reasonable and within the things I would expect from most jobs. I try to frame my responses to her as my general statements or my own preferences rather than “feedback.”

    As a recent example, she complained that she wrote something for internal use and her boss “changed it so much,” even though “only a few people are going to see it.” Having gone to college with this friend, I am 100% sure that the boss’s revisions were necessary. So, I said (truthfully), “Personally, I actually love a harsh editor, because I want my writing to be the absolute best it can be, and I’ve learned a lot from my boss’s edits… If yours is nitpicking, I get why that’s frustrating, but just think of it as a way to learn her style!”

  124. Juanita*

    My best friend in the entire world is exactly the same.I swear she has worked everywhere. She now hates her new job–which is an excellent fit for her–and is planning a career shift. She stays as low levels because she never stays anywhere long enough to get a promotion or the skills she needs. She recently made some poor career choices because she thought some social media accounts (which are essential in our field) were “too much” to keep up. What do I do? I ZIP it. She has never asked for advice. She has unfortunately an attitude about work I can’t change. When it comes to work she is in constant victim mode. Her issues are way beyond what a friendship can fix. If at some time she comes to me for some honest advice I will offer it. But she has to see she has a problem–and that just isn’t going to happen.

  125. Smile Time*

    OP, I think a lot of people have someone like this in their life. I do. Others have provided you with useful framing tools with how to identify if advice or sympathy is being solicited, but I wanted to offer this up:

    I know that it’s natural to want to be the voice of reason for a friend who we are observing self-destruct, but in my experience people who are so deep into these kinds of patterns are really, nearly intractably set in them. You’re not your friend’s therapist, and so it’d be difficult for you to redirect her own attention towards inward reflection – which is ultimately what is needed here – and begin asking herself how her own behaviors and choices have contributed to her situation.

    She’ll probably need to come upon that on her own. What I’m most sad to read is that you mention “her firings” – meaning she has been terminated more than once and still isn’t interrupting her own persecution delusion. Losing your job, or even coming close to it (PIP, etc.) is usually enough create some self-reflection in others. If this has not, she might not be ready to do that internal work yet – and if she isn’t, she might not be ready to hear any advice you’d give her anyway.

    Good luck!

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