I can’t go on vacation because no temp can meet my boss’s demanding expectations

by Alison Green on February 28, 2018

A reader writes:

I work in a rather specialized field and when I was originally hired, it took close to a year to get one of my managers to trust in my abilities. It worked out well and 13 years later, I still love my job. The problem I have is taking time off. For over a decade I’ve taken three days in one week and two or three in the next, to give me the sense of having a whole week off. The problem with that is there isn’t anyone to cover me, so I end up doing 10 days of work in three or four.

Nine years ago, I took three weeks off and I trained a temp for three days before leaving. I had a wonderful vacation, and upon my return to the office I found a Post-It on my monitor asking me to call “Joyce.” I did and she asked if she could come by. She shook my hand and said she had to meet the person who could handle my desk. Apparently she was the third temp to cover while I was away. First temp went home in tears on her third day. Second temp went to lunch on her first day and never came back.

I really, really, really, want to take three weeks off again this year. I don’t want to put another temp (or more) through a similar experience but am unsure how to proceed. My manager told me I’ve set the bar ridiculously high and he gets impatient with those who aren’t as good at the job as I am (I’m paraphrasing his much harsher words). I know this isn’t fair at all, but he isn’t going to change for the once or twice a decade I’m away for more than a couple of days. I would be grateful for some guidance. I don’t want to spend my entire vacation worried about what I’m going to come back to. I can chat with him easily but I need the right words.

I’d tackle this on two fronts: your boss, and the temp agency. You say you have good rapport with your boss, so say something like this: “It’s not possible to get a temp who will do my job as I well as I do, since I’ve been doing it for 13 years and know all the details of how you want things done. In order to stay here in the long-term and continue doing my job the way you want it done, I need to be able to take vacations and not worry about what I’ll come back to. That means that on the rare occasions that I’m away, you need to lower your expectations of the temp covering for me and not drive them off in tears. Otherwise I can’t take vacations, and if I can’t take vacations, this job won’t be sustainable for me in the long-run.” The idea here is that you’re using the fact that he thinks no one can do the job as well as you to scare him into agreeing — since he should see that losing you for three weeks is far preferable to losing you permanently. Maybe you can even agree on a list of things that he will not expect from the temp (although I’d remind him of that list the day before you go; don’t rely on him to remember it).

And talk to the temp agency too. Explain that this is a highly demanding job and you need someone with a thick skin who’s used to dealing with demanding executives. You don’t just want any temp — you want a temp specifically selected for this context, and one who’s been warned ahead of time that your boss is demanding.

Beyond that, you’ve got to give up some control. It’s possible that you’ll do all this and the temp will still leave on day one and not come back. That’s not your problem. You get to take vacations even if no one can cover for you. Your boss will find a way to make do, and you’re not responsible for it if he doesn’t.

The deal with vacations isn’t “you only get them if you can ensure there’s zero impact on anyone else.” In fact, the deal is often that there will be impact, but people survive. Assume that your boss will survive — even if it’s a messy few weeks — and go take some time off.

Read an update to this letter here.

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{ 278 comments }

{ 278 comments… read them below }

  1. Detective Amy Santiago*

    Does your boss ever take vacations? Would it be possible to take yours at the same time, thereby circumventing the need for a temp?

    1. Mona Lisa*

      Or at least it would cut down on the number of days a temp would need to be present or deal with the boss!

    2. Jules the 3rd*

      That’s not actually a reasonable request – the employee should be able to take her vacation when she wants to.

      1. Ask a Manager* Post author

        Yes, in general. But if she wants to take off three weeks, which is more than many places will okay, that might be the way to make it work. Or alternately, if she *chooses* to do that, it might ease the pressure on the OP in a way she welcomes (rather than feeling like a restriction).

          1. OP - I need a vacation!*

            That would be the dream. Unfortunately we have to be extremely cautious about how we spend money as it belongs to the rate-payers. Our board of directors reports to our government. The amount of business justification needed and the many levels of approval required for a temporary body in a seat is somewhat overwhelming.

        2. Chinook*

          I have known quite a few admin. assistants who plan their vacations around their bosses for the simple reason that it makes it easier for them to disconnect. The ones who were most successful at this, though, also had bosses who would leave for a few weeks.

          On the flip side, since my first jobs were as a teacher, I never had an issue with not choosing my vacation dates because it wasn’t a norm in that industry. So, working mine to coincide with someone else’s has never been an issue.

        3. OP - I need a vacation!*

          I actually have 39 paid days off per year, not including all our government holidays (Thanksgiving, Christmas, etc.) Twenty-two of those are vacation days and 17 are personal days to use for whatever we want.
          Due to the specialized nature of our work, time off can be difficult to take as it’s always based on whether or not it’s okay to leave the office understaffed. If an emergency occurs and bodies are needed, people can be called back – and they come.
          For example, in 2011 we had a rather serious event happen that affected close to 80,000 people. Not only did many of the employees return, they worked 22 to 23 hours PER DAY, and even support staff (including me) were at work for 12 days in a row, averaging 14-16 hours per day, until things were resolved.
          For me to be off at the same time my boss is, isn’t feasible really. Someone needs to be able to either be of assistance to employees with questions, or to know who to route those requests to.

          Gosh, sorry to be so wordy but it’s difficult to explain without some detail.

    3. Bea*

      I’ve never had a boss who would go with this idea because then you’re effectively shut down for 3 weeks. The business rarely allows for the wheels to completely screech to a halt like that.

      It would depend on the industry and company of course. When my boss is out an assistant would be there to still field requests and let clients know we didn’t just run off to Bermuda or rolled up shop in the middle of the night (which could be me and my experience with fly by night businesses that do that sort of thing. One day the phones and emails just go unanswered until they disconnect due to failure to pay. Sigh)

      1. J. F.*

        In general I agree, but the LW did it once *nine years ago*. Doing this once a decade is not entirely unreasonable.

        1. Cafe au Lait*

          Yes, and there are some vacations where one week to ten days won’t be sufficient. My husband and I will earn a month’s vacation in five and three years. (The length we’ve been at our jobs). Already we’re discussing the possibility of going to Japan. We’d like to go while my MIL is still alive so she can show us around her home town, etc. Three weeks is just the right amount of time to go there, come back and acclimate before returning to work.

      2. Lily in NYC*

        It really depends on the office – it is incredibly common for people here to take 3 weeks off at once (we have a very generous vacation policy and people use it).

  2. Artemesia*

    So abusive to treat an employee this way and so wrong to buy into it such that you indenture yourself to a demanding boss. If you got hit by a bus they would survive. I’d be insisting on a couple of week vacation every year and what ever other days you have from time to time. No one is indispensable but bosses like this will turn good employees into their slaves if they are allowed to do so.

    1. Amy S*

      To be fair to the employer, LW didn’t say that boss was refusing her vacation requests because the temp wouldn’t be as good. LW has put this expectation on herself that she doesn’t want to put anyone through that again. That’s the part she needs to let go of and just plan a vacation.

      1. Delphine*

        It seems that it’s not just about putting someone through that experience, but returning to work to find out that she needs to now make up for all the things that didn’t happen while she was away.

        1. Amy S*

          But I feel like that’s how it is for most people when they go on vacation. I’ve never been in a job other than retail or food service that had someone cover for me while I was away. You do as much as you can before you go and then catch up when you get back.

          1. OP - I need a vacation!*

            Our work is quite unique and we have government deadlines to meet so it’s not that easy, which is too bad.
            I also lead a team of administrative assistants and I’m doing my best to cross-train wherever possible. I can’t have anyone take on my work on top of their own, or even share my work between them as their own workloads are heavy. We’ve attempted it and it’s just not doable.

            1. Jerry Vandesic*

              Can you have one of the other admins take over your role when you are on vacation, and have a temp replace the other admin in the meantime? Maybe a temp might be more successful in the other admin’s position.

              2. Just Sayin'*

                I think this is a BRILLIANT idea!! OP? Would that work? Maybe that admin could get the blessing from on-high to train on the super secret software too — a good redundancy for the office in case of unexpected dire emergency as well as your well-deserved vacation.

                2. OP - I need a vacation!*

                  I’ve spoken with one of the women on my team about this a few years back but she didn’t feel confident enough. I will revisit this, thanks for mentioning it!
                  Her skill set has sharpened a lot and maybe she will feel like giving it a try. It’s also a 12.5% increase in her salary for the time she’s covering me.

                  LOL at super secret software. Sounds so silly doesn’t it, but it’s accurate.

    2. Becky*

      We had (NOT literally) a “hit by a bus” situation at my work last week–We were doing some stuff with new hardware and it turns out that not everything had been set up properly. There were plenty of people who knew how to correct it-Carl, Matt, Becky (myself), Adam and Larry were all able to do it but all were out that day and David, Janet, Elise and Bob were there but none of them knew how to correct it. We ended up having a meeting this week to figure out how/where to document that knowledge so if we were in that or a similar situation there wouldn’t have to be any bugging of people on their day off.

      1. OP - I need a vacation!*

        That’s a problem for sure. It’s similar for us as well.

        There are two applications I use that no one, not even my boss, knows how to use. It requires in-depth training and special permissions that have to come down from on high with scads of justification required. Again, due to constraints there are no funds to allow for more than the bare minimum of people-with-knowledge.

  3. The Cosmic Avenger*

    In addition to sharing the list of things that the demanding boss will not expect from the temp, I would also leave that list on the OP’s desk FOR the temp. If you get a veteran assistant who can handle them, it’ll prepare them for these unreasonable demands and they might actually be able to meet some of them, but if not, the temp can remind the boss that they can’t be expected to be immediately up to speed and performing at the OP’s level.

    1. Snark*

      I feel like the most one can really expect from a temp standing in for a 13-year veteran is “does the bare minimum to keep the wheels on the bus.”

      1. FunTillSomeoneLoosesAnEye*

        Basically “is the building still standing and not visibly on fire?” is my expectation usually.

        1. Jadelyn*

          100% agreed. Don’t get us in legal trouble, don’t actually murder anyone, don’t let the place burn down while I’m gone. Keep some kind of nominal track of what’s happened while I’m gone so I know what I’m dealing with upon my return. Don’t rearrange my damn files unless I specifically left instructions for you to do so. Everything else, I can handle when I get back.

        2. Alternative Person*

          At this point, I usually prepare a fire extinguisher and just get it over with.

          (I am both writing very specific documents detailing exactly how everything needs to happen and dreading the wreckage of when I get back from my two week training trip)

      2. Hills to Die on*

        Exactly. You can’t expect temps to do the job as well as the full time staff or do every task. It’s okay to have some loose ends when you get back. Perhaps your boss can reduce the scope of the temp work or have a temp there with you for a few days before and after while you work side-by-side for those 3-4 days with 10 days of work in them?

        1. Snark*

          Yeah! Or maybe the temp could take care of the routine aspects of whatever it is, and have you come in and do only the wrap-up and expert input when you’re back. I also like the idea of having the temp support for when OP gets back and is cramming.

        2. JoJo*

          Going by personal experience, yes you can, and often do, expect the temp to slide into the position held by a long term employee, immediately know everything, get everything done exactly the way the long term employee does things, and act as if she’s an incompetent idiot when she doesn’t, in fact, know everything or do everything the exact same way.

            1. Ophelia*

              FWIW, I get the impression that was sarcasm coming from someone who’s been in the shoes of that particular temp, though I realize the tone isn’t necessarily coming across.

              2. Church Lady*

                Oh boy, this post triggered some awful memories and anxiety I experienced temping for Unreasonable Boss when his admin/receptionist took a full month off to go get married in Hawaii. I was given 5 days to shadow her and cross-train, which in any other setting would be more than enough for me to competently keep the wheels turning (I should add I had been temping for a while and I’m a copious note-taker and perfectionist, always got great feedback from temp bosses). However, this guy was angry, aggressive, sneering and just hell-bent on making everyone around him miserable. He was standing next to the front desk when an incoming phone call I had transferred didn’t go through and was rerouted back to me. I apologized to the caller and went through the transfer process again, this time it worked. Once I hung up, he exploded, windmilling his arms, face all red and apoplectic. It was a potential client for his law firm and he proceeded to lecture me on how I was supposed to check that a phone call went through before hanging up…that this was a potential loss of a client…It deteriorated from there and I ended up resigning midway through my assignment. He was nasty to the end and I lost my connection with that particular temp agency, but it just wasn’t worth the emotional turbulence. I was an abused spouse and his constant criticism and rage was triggering. I hope the OP takes her vacation without a moment’s hesitation. Her boss is not reasonable.

                1. LS*

                  Yes, I had a similar experience replacing someone. I was actually in the same organisation (but a different department) and had heard that this boss was very demanding, but that was okay, so was mine. It turned out that the boss was not so much “very demanding” as a giant baby who, when his extremely patient assistant was away (for life-saving surgery!), threw tantrums that “Catelyn” wasn’t here, Catelyn wouldn’t do it that way, Catelyn would know what he wanted without him having to ask. He frequently demanded that I call Catelyn, but she was a smart woman and had turned her phone off and left only an emergency contact number: her husband who knew not to put the call through.

                  Sometimes the position is genuinely demanding, sometimes it’s just the boss being an ass.

                2. cncx*

                  yeah, i was an abused spouse and i had to stop working for lawyers because the explosive rage got to be too much, i couldn’t have it at home and at work. i was constantly anxious and triggered.

                  out of the marriage and that job now so yay.

          2. Princess Consuela Banana Hammock*

            Of course people do behave this way, but it’s ok for OP to point out that this is a ludicrous way to interact with the world (and with temps).

      4. The Cosmic Avenger*

        I was referring to Alison’s tip “Maybe you can even agree on a list of things that he will not expect from the temp (although I’d remind him of that list the day before you go; don’t rely on him to remember it).”

    2. Surrogate Tongue Pop*

      I don’t see where OP indicates they are an assistant, which may or may not be the case (“handling the desk” can mean different things in different industries). If it is, a primer on “how to do the basics for XYZ manager” left on the desk is helpful. If not, the temp cannot be expected to do anything beyond “keep the lights on”. In either case, setting the expectations with boss and agency is sound advice.

      Go forth and enjoy that vacation, OP!

      1. OP - I need a vacation!*

        Technically I am considered an Engineering assistant, but with a whole lot of specialized training and experience.
        I realized I didn’t mention a couple of important things: not only do I work with my boss but also 21 others (specialists in stuff most people have never heard of) who rely on me for guidance and assistance as required. I also lead a small team of admins.

        We are able to use only one specific temp agency and it’s sort of in-house. The temps are all familiar with our basic functions. There are times there are no bodies with experience in our corporation and the agency is forced to go outside. What a kerfuffle that is.

    3. Ama*

      Yeah, I have a tendency to wind up in jobs where I am basically the only person who handles certain tasks. When I go on vacation I make sure my boss and the people who are covering for me have a list of the tasks they are expected to handle (with tips such as the location of certain files), the emergencies that are appropriate to bring to my boss AND the tasks/questions that they can feel free to say “Ama will get back to you when she’s back in the office.”

      It’s hard for people to understand what’s a priority if they aren’t as familiar with the workflow, so this just keeps everyone on the same page.

      1. OP - I need a vacation!*

        Agreed. I can’t seem to stop stepping in and taking responsibility for things I see falling between the cracks. Our corporation can’t have cracks. :) Suddenly it’s part of your job description.

    1. Ask a Manager* Post author

      She says she loves her job! Some people are able to deal well with difficult people, or with certain types of difficult people. If she has a job she loves, I don’t want to guilt her about staying in it. Those are hard to find.

      1. Kyrielle*

        And if she loves it and leaves it, she’s left a job she loved…and left an opening for someone who might not love that job. There’s no responsibility to stay in a job to “save” someone else, but leaving right now sounds like a mostly lose-lose scenario, assuming she can start using her vacation more as she wishes.

      2. Kate*

        Also, this reminds me of that letter the other week “my boss loves me but hates my coworker”. Since the boss is clearly happy with the OP’s work, she’s probably having a completely different experience than the temps who quit. That doesn’t mean she has to think it’s fine that the boss treats others this way, but since she loves her job and seems to be OK with her boss, I wouldn’t guilt her into quitting on principle.

      3. neverjaunty*

        While true, it wouldn’t hurt for the OP to take a hard look at some of the dysfunctional parts of her job that she can fix – like buying into the idea that she is irreplaceable or that it is her job to manage her boss’s expectations, and making sure that she is sharing information and training so that she isn’t “irreplaceable”.

        1. MM*

          I think OP actually rather values feeling–or being–irreplaceable. (I don’t mean this as a cutting comment; I’m basing it on OP’s comments here as well as the letter, and I’ve done the same thing in the past.) Unfortunately that’s kind of the trade-off, in my experience: you can truly make yourself irreplaceable and get the admittedly massive satisfaction of constant problem-solving, making everything go, being valued and relied on, and knowing you’ve improved the working day of everyone around you (not to mention the end user/customer/beneficiary); or you can have decently predictable hours and leisure time. The problem with making yourself truly needed is that it can’t be turned off when so desired. There really is great fulfillment to be found in that for some people, but I don’t see a way out of this for OP (again, based on additional information in the comments) without 1) putting her foot down and insisting that some depth be added on the bench in terms of redundancies, 2) accepting that she will no longer be able to run quite such a smooth ship, or 3) giving up on remotely regular vacations.

      4. Annoyed*

        Still she’s entitled to a vacation. A reall disconnected vacation. She needs to take it, guilt free every single year.

    2. Catalin*

      No guilt intended! But the boss sounds mercurial and potentially volatile. Sometimes those kinds of people are volcanos, erupting out of nowhere even after long periods of rest.

      1. Bea*

        I don’t know where this idea of the boss comes from. He could be so many things. I’ve seen temps walk off from jobs over so many things and cry over nothing what so ever.

        We’re hinging our opinions on Joyce, who is so ridiculous as to approach the OP after the fact because she had a bad experience with a person in a temp gig. She sounds like the real treat here more than a pissy boss who is probably just a grouch with expectations that he’s come to see met so they don’t seem impossible to him.

        Every one of my former bosses have been grouchy and have been tamed quickly because I’m a grouchy old man whisperer. Personalities clash. Some are more difficult than others but they surely aren’t people who can’t be worked for.

        My bosses paid me a lot of money for my work too. And they never yelled at me or made me cry.

        2. OP - I need a vacation!*

          Well hello fellow grouchy old man whisperer!

          You made me laugh a bit about Joyce. She tends to temp all through our corporation so I’ve had to work with her now and then and it’s tough!

          Very recently she and I were sitting in a room waiting for a meeting to start and she reminded me of her experience so long ago. Apparently my boss actually stood next to her and said in a loud voice: “Wow, you really ARE blonde, aren’t you?” I nearly fell over! Respectful Workplace much?

          Big boss and I both have exceedingly high standards and his work is excruciatingly painstaking with no room for error. I know his expectations and have taken a lot off his plate as I enjoyed the challenge (and still do).

          For the record, he has never made me cry – but I will admit to random bouts of acute frustration! ;)

    3. OP - I need a vacation!*

      I do not have this experience with him at all. I love this guy. He’s salty and down to earth and super rough around the edges. He didn’t want to be a manager in the first place, but when the executive level says you’re a manager…..well, you’re a manager! This corporation has people who have worked here for 50 years. Many are around the 40 year mark. I’m a baby with only 13 years in. :)

      He has to be extremely focused on his work. One tiny little error might end up costing hundreds of thousands of dollars and horrific delays. It took him a long while to be able to trust that I am capable a similar attention to detail. If I create a legal document and need it signed, he barely looks at it….we’ve got to that point. I think I mentioned somewhere else that the workloads are crazy, and that’s during regular times. Toss in an emergency and you wouldn’t believe the goings on that are put in place.
      For me to be able to do even a small portion of his work relieves some of the pressure.

      I honestly wouldn’t consider leaving. In fact, the people in my division are mostly why I stay! Scary intelligent and funny as heck. Not a typical combination :)

    1. Ask a Manager* Post author

      The letter doesn’t say that the boss thinks that! She takes time off, but taking off three weeks at a time requires temp coverage, which isn’t unusual. (And really, it sounds like a lot of the pressure is coming from the OP, internally!)

      2. AdAgencyChick*

        It also doesn’t sound like the boss called her on vacation, since OP first heard about the temps leaving in tears only when she returned from that long-ago vacation.

        OP, has your reluctance to take another vacation of that length been because your boss pushes back when you talk about it, or because you feel responsible for how your boss is going to treat the temps while you’re out? If the former, then all in on what Alison said to do. If the latter, still what Alison says, but you also need to reframe your own expectations of yourself. You are not responsible for temps running away in tears; your boss is! You do not have to let your boss’s poor treatment of others turn into poor treatment of yourself.

        1. OP - I need a vacation!*

          Boss couldn’t call me. I was on a once-in-a-lifetime 22 day cruise all over the place. :)

          As for my reluctance, I haven’t spoken with him about this yet so I don’t know if he’ll push back. I highly doubt it, but I know he’ll get wound up inside. Although I don’t want temps to be so overwhelmed, I guess it’s really that I worry about him being able to get things done by deadline without assistance.

          Our corporation has a board of directors that reports to our provincial government (I’m in Canada) so there isn’t much wiggle room, if any.

    2. Eye of Sauron*

      Obviously the boss let her take 3 consecutive weeks off. That’s impressive. I didn’t see where the boss said that she couldn’t take 3 weeks off this time, either. Only that the boss wasn’t going to be very forgiving on the temps.

      It’s wonderful that the LW is concerned about the temps, but really that’s between the boss and the temps not the LW. If the boss is going to be demanding, well then they’ll have to deal with the natural consequences of having to lather, rinse, and repeat when they bail.

      Although, It’s been a long time maybe the LW can try to find Joyce again. Seems like she was able to stick in the position the longest :)

      1. Blue*

        It doesn’t stay a matter between the boss and temp, though. Even if the boss doesn’t bother her during the vacation, it creates a mess OP has to fix when she returns. And frankly, if any good feelings from your vacation are immediately drowned in work when you return, it makes it hard to see the point.

        1. Eye of Sauron*

          That can be controlled though. I always come back to mayhem from vacation (in fact prepping for one right now). It was not uncommon for my old boss to schedule a meeting with me upon my return to download everything that had gone wrong and was kept at a smolder while I was gone to have me pick up when I returned. Most of it had absolutely nothing to do with my team, it was usually all the ‘other stuff’ that I would do as a normal course of my work. In one of these calls where she did this while my counterpart (who was pretty worthless and whose work I usually picked up the slack for) was on the call I waited until she was finished and asked “So I didn’t hear anything concerning MY team or work… any issues there?” Her response was “No your team always runs smooth while you are gone, didn’t hear a peep out of them”. Ughhh…

          You know what… I didn’t let myself care about the dumping. It got attended to when I could and I didn’t stress about it. If I got hit by a bus, they’d figure it out and nobody ever died because of something that I didn’t get to.

          In other words, most of this seems to be the LW internalizing all of this stress and worry. My advice is to schedule vacation, schedule temps, and then let it go. Quite honestly if their boss depends on them so much it’s not like the OP doesn’t have them over a barrel, especially right after being gone for so long. Boss will be over the moon to have them back.

      2. Elizabeth*

        The boss doesn’t have to *say* she can’t take three weeks off in order to strongly suggest it, either on purpose or inadvertently, though. We read all the time on this site about bosses who put all kinds of pressure on people to not take vacation or sick days because of reasons. If my demanding boss complained a lot about what happens when I take three weeks off in a row (to the point where in the ten years since that vacation I only take partial weeks off (?!)), then I would definitely feel like I was being told not to take three weeks off.

        1. Amy S*

          But the LW said nothing about that in her letter. Sounds like all of the pressure was internal. And if the boss is a grouch and put up a minor fuss but still approved the vacation? Well that’s on them and I’m taking my vacation.

          1. Elizabeth*

            I didn’t think the pressure sounded internal at all (she wouldn’t have the same misgivings about taking more than three days off at a time and have concern for the poor temps if her boss didn’t behave the way he does), but it’s very possible we have different definitions of “internal” in this case. :)

            1. OP - I need a vacation!*

              I don’t know if I would necessarily refer to it as internal. Yes I don’t want things to go awry when I’m gone as it’s seldom easy to recover from. Nature of the work.
              Most of the corporation’s 8,000 employees are extremely engaged with the employer. We are all very, very, proud of what we do and work hard.
              If my boss needs something done and it’s urgent and a temp can’t even begin to understand what it entails…he’s going to blow up. He’s getting pressure from the top down, as in any job, and if I’m not there to help then I can certainly understand his behavior, I just don’t condone it. Hence my worry for any temps!

              2. Working Hypothesis*

                Reasonable adults do not “blow up” when something doesn’t go the way they need it go to, OP. Not even if it’s urgent and they’re “extremely engaged” with their job. Frankly, a level of engagement which makes it impossible to retain emotional control and civility when under job-related stress sounds counterproductive, and it might help if everybody involved stepped back a little.

                Which it sounds as if you’re trying to do, with taking the vacation you want! That’s great. Now you need to let your boss handle your boss’ job — which includes making things work *well enough* while you’re away, no matter how he ends up doing it, that he does not need to verbally abuse the temps!! — and stop trying to do it for him. It is NOT your job to ensure that there is absolutely no difference between the way things work when you’re there and the way they work when you’re not there… that’s unrealistic, and you shouldn’t buy into the theory that it’s the appropriate standard! It’s your job to leave things in a reasonable condition, give plenty of notice for when you want your vacation, and get your boss’ OK on the specific dates you intend to take.

                Then you *go away*, and leave it to your boss to handle himself, the temps, and the job while you’re gone.

  6. Mary*

    Also, while you’re there, ask for a raise. If you’re that irreplaceable, make sure that’s on your paycheck!

      1. TootsNYC*

        I feel that asking for a raise you deserve is not quite the same thing as accepting a generosity others want to give you.

        But yes, ask for that raise.

    5. OP - I need a vacation!*

      I hate to say this, but I’ve been fighting since 2011 to get a raise. Not a chance in hell. I went to the Manager of the entire division I’m attached to and a letter to HR was prepared and signed by 11 team managers. Turned down flat. My corporation reports to the government – ’nuff said.
      I can’t even get my job description amended to reflect what I do. The current description is from 1995!! Some of the major requirements are to know how to use applications that no longer exist. Honestly.
      There have been some workarounds in place over the years but once they’re caught, they’re shut down. I would receive a half dozen or so recognition awards in a year that totaled what my salary should be.

      1. Jerry Vandesic*

        It’s time to prioritize yourself over your employer. Take your vacation, let things drop, let your company deal with it. They have made a decision not to pay you appropriately, or to properly back you up when you take the vacation they agreed to. This is on them. If things go badly, they might realize their screwed up approach to management has its limitations.

      2. Mary*

        Ooof!

        In that case, if you haven’t already, is it worth doing some job hunting, just to see what’s out there and what your skills could command elsewhere? I know you said you love your job, and maybe you’ll decide there isn’t anything else in your area that you want to do, and that this job really is worth the lack of holidays and pay rises and whatnot. But at least you’ll know you’re making a fully-informed decision to stay!

      3. Oilpress*

        When will that fight lead to you applying for jobs elsewhere? Going years without a raise is pretty tough to swallow, especially with that much peer support. Are you better at your job than you were in 2011? Then get some more money.

        1. OP - I need a vacation!*

          Yes, no raises but more expectations are pretty normal when you’re overseen by the government.

          And, yes, I’m leaps and bounds better at my job than seven years back. I am proactive and look for opportunities to learn and make my input more valuable.

          Moving jobs isn’t really an option. I turn 59 this summer. Seven years to retirement and I have a good pension here.

          2. Working Hypothesis*

            My brother changed jobs at 65 and is now looking again at 70, OP. You can change jobs at 59 if you want to. If you’re that good at what you do, and you certainly seem to be! then you can be pretty sure of finding somebody willing to pay you what you’re worth, and treat you appropriately (including letting you take your designated vacation days every single year without anybody throwing a hissy fit).

            1. Ali*

              I’m in my 30’s and struggling through feeling “too old” to make the career change I want to make, so hearing about your brother has really made me feel positive! Thank you.

  7. Fabulous*

    I had a boss like this once. He drove away so many assistants. In fact, his wife was the one to train me and she kept talking about his “long term” assistant on my first day, I finally asked her how long she had been there and she told me 2 years. Even as a new-to-the-workplace person at the time I knew 2 years wasn’t long-term! It took about 2 years for him to drive me away too, come to think about it. BUT! It did help me prepare a bit more working for demanding people and I appreciate the time I did spend working for him.

    I do agree with Alison’s advice when talking to the temp agency, you need someone with thick skin who is fully prepared for the demands that will be expected. And definitely set expectations for your boss as well before you leave.

    1. many bells down*

      The real estate agent I worked for was kind of like this. Apparently, before I came along, no one had lasted more than a year. I worked for him for nearly 5, and I wouldn’t even have left except that my commute had become untenable for various reasons. And I didn’t find him particularly difficult to get along with! Occasionally he’d say something way off-base, and I’d basically just say “No, that’s not gonna work” and everything was fine.

      I think the woman he hired to replace me was even better at the job than I was; so maybe he better figured out what he was looking for in an assistant after that.

  8. Snark*

    I’d advocate for trying to be a little less personally invested in the temp’s experience. If your boss burns through temps, that’s a problem between the temp and the agency and him, and if temp agencies stop working with him because he’s a jerk and mistreats people, that’s natural consequences. Of course it’s unfortunate and not pleasant for the temp, but it’s also not your responsibility to spend your vacation fretting about a situation that involves you only tangentially. And don’t return their calls when they want to meet you to see how you did it, or whatever.

    2. Hills to Die on*

      To say nothing of having to fit 10 days of work into 3 or 4. Vacations shouldn’t come with consequences.

      1. Snark*

        I mean, everybody’s gotta do some scrambling right before they leave for an extended time, but “you still need to do all the things, just quicker” is kind of bonkers. But I do wonder if OP could create some templates, written guidelines or checklists, or otherwise front-load things for the temp.

        1. Victoria Nonprofit (USA)*

          I agree that it’s bonkers… but it’s also been how it works everywhere I’ve worked. I’d love to hear about anyone’s different experience (in the open thread — I’ll try to remember to start a thread).

          1. Haha*

            I’ve def worked in places where I had to cram two week’s worth of work into a week just to take 4 days off, and then get calls anyway because they just can’t deal. But the places I’ve worked where bosses genuinely seem to value their employees taking time off tend to have a saner, bigger picture approach. When I plan my vacations, I check my calendars to make sure the timing is okay for my workload and our dept, I have to ensure all of my non-negotiable deadlines are met before I go, and I make sure our team has everything they’ll need while I’m gone. After that, I have the freedom to move things around until after vacation, and on a few occasions, when something important popped right before I left or while I was gone, my boss took it on herself. I have only been contacted once in 6 years because they couldn’t find a spreadsheet they needed ASAP (and I didn’t realize they’d need), but otherwise, they actively discourage anything like that.

            It’s definitely a factor in me staying here. My boss’ attitude is “you’re an adult, I trust you.” I don’t feel guilty about taking time off because it’s not just encouraged–she backs that up and makes a real effort to make sure it happens, which in turn makes me feel like she means it when she says she wants us to take time off and recharge. And it tells me she’s thinking about this stuff over the long-term, not just day-to-day, because she not only wants employees who are rested and focused on their work, she wants a department that won’t live or die on any one person.

        2. Tricksy Hobbit*

          Good idea Snark, also the temp could come in a few days before the vacation and have OP give him/her a crash course on what needs to be done.

        3. Lynca*

          This is what I do for leave longer than 2 weeks. I’m currently prepping for maternity leave and I am creating templates, guides, checklists, and an active log of what projects are due when, plus what stage are they at.

          I have a quick 30-40 minute meeting with the management staff to go over what I’m leaving, where to find it, etc. Then let them have at it. So far the building’s still standing when I return.

      2. MassMatt*

        I’m surprised Alison didn’t push back more on this part. Yes everyone has stuff to catch up on (lots of email etc) coming back from vacation but this is far more severe. Having to do a week’s worth of work in 2 days before your vacation and another week’s worth in 3 days afterwards means you are not getting vacation. I remember a letter from someone taking leave and the boss talking about scheduling her for extra hours to “make up the lost time”. Alison rightly pointed out that this would not be leave, time off is time off. This is no different IMO.

        It’s great that the OP loves her job but the boss sounds unreasonable and abusive. I agree with those saying that, as an indispensable employee, she should make sure she is well paid!

        1. Ask a Manager* Post author

          I think it depends on what the job is and how senior the OP is. If she’s in a senior-ish role, in many cases you’re ultimately responsible for ensuring your work is covered and your goals are met, and in reality that means that sometimes you’re going to be doing extra work before you leave. (That said, the trade-of is that in a senior role, you get to make decisions like “I’m going to table X altogether because there’s no feasible way to get it done and also work sane hours.”)

          My hunch is that the OP is putting pressure on herself to do way more of that than she really has to, though.

          1. OP - I need a vacation!*

            Allison, I am the most senior person in a support role for our division, yes. And, yes, I’m 100% responsible for ensuring my work is covered in some fashion….hence the being in the office at least a portion of each week when taking time away.

            I’ve mentioned in a few other places that I work for a large corporation that reports to our provincial government. We’re constantly in the public eye and one misstep can create a huge amount of dissension and cost scads of money.

            I will agree that it looks like I put a lot of pressure on myself, but it’s nothing compared with the pressure the higher-ups have. Theirs comes from the ruling party in office and that can change on the voters’ decisions.

            I know I need to find a way to help myself take this time away, really I do. With boss being so hard on the temps though, I feel pretty sorry for them, especially hearing what happened that first time. The pressure has only become worse over the years.

            My thoughts are all over the place after reading most of the responses. I really appreciate all the different viewpoints and it’s allowed me to provide further details.

        2. LBK*

          My longest days in my current job have without fail been the days right before I go on a long vacation. It’s just how it works, there’s so much stuff I need to make sure is in order before I leave that it’s not realistic to cut and run without leaving a complete mess for my coworkers to struggle through while I’m out.

          Could I get away with it? Sure. The company’s not going to go under. Would it be a shitty thing to do to colleagues I like and respect? Also yes. And there usually are still issues I have to clean up when I get back, but the benefit of me setting my coworkers for success as best I can is that people know and respect that when I’m out of the office, I am out of the office – don’t call me, don’t email me, don’t text me.

          Having those lines drawn in the sand really does help me relax and recharge on vacation even though it often means more prep work before and cleanup work after.

    3. K.*

      I agree. I temped to stay afloat during the recession and the only time I spoke with the person I was replacing was the time she weirdly spent the first day of her vacation “training” me, which neither the agency or her boss was expecting – her boss was like “Why are you here?” (It was a receptionist gig. It took half an hour to teach me the phones and give me a tour of the office so I could direct people when they arrived. She stayed the ENTIRE day.) Otherwise I spoke with the agency and the person to whom I reported on-site. I never reached out to the person who was away because they were … away, which was the point.

      It’s kind of you to worry about temps, OP, but they’re really not your problem.

    4. 5 Leaf Clover*

      I agree – and 3 weeks isn’t very long. While working long-term for an abusive boss can be scarring, I doubt 3 weeks is doing any permanent damage.

      1. Jadelyn*

        Ordinarily I’d agree, but if the boss was able to drive away *multiple* temps *in tears* within the first couple days of working for him…we may be talking about someone who’s far more toxic than your average bad boss.

        1. Chinook*

          I would also wonder about the quality of the temps the agency was sending. I saw it happen when they went through 5 to replace me as a receptionist. None left in tears and I was able to train each one (I just transferred to another position) but I really had to wonder what the agency was thinking when they kept sending us people who lacked the skills we required.

      2. MassMatt*

        I think you are underestimating the amount of abuse someone is capable of hurling, or perhaps overestimating the amount of abuse someone should be willing to accept in the workplace. Harvey Weinstein comes to mind, even without the sexual harassment he was a nasty nasty piece of work. Screaming, insulting, belittling, objects thrown, etc. Some people are monstrous. Somehow the OP has learned to play the violin just right to soothe this savage beast but most people are not going to want to take the chance the damage is only short-term.

    5. Princess Consuela Banana Hammock*

      So much this. OP is going to have to put some emotional distance in, either in how she feels about her boss’s experience with the temps, or about the temps’ experience with her boss.

      And agreed that cramming work into fewer days is a bonkers approach that isn’t really fair to OP.

    7. Bea*

      Also you don’t know the temps. Wait until the one who stays the 3 weeks just screws up the whole thing so when you return you get to clean that mess. Been there. Made a career out of it.

      I would have rolled my eyes at Joyce wanting to meet with me honestly. I’m aware when my boss is a difficult person, I don’t know you, don’t act like I’m a sight to be seen because you had a bad few days.

    8. TootsNYC*

      if temp agencies stop working with him because he’s a jerk and mistreats people, that’s natural consequences.

      Then again, such a development might mean that the boss says, “no vacations longer than a week , because I can’t hire temps.”

      It’s to the OP’s advantage to do what she can so this works out more smoothly.
      However, I agree that she should frame it this way, and not as though it’s her primary responsibility.

      1. OP - I need a vacation!*

        The temp agency cannot refuse to work with him as they are under contract to our corporation. They are well aware of the stress most people work under but my boss seems to have a lower ‘impatience point’ than most. I’ve provided other details throughout the comments as to why.
        And we can definitely take our time off but if requirements are that no one can take time because of some urgent work or an emergency (which happens more than we’d like), we have to abide by that.

  9. Zip Silver*

    It doesn’t sound to me like the boss isn’t letting you go on vacation, only that you’re concerned about the temp’s fortitude. I wouldn’t worry about the temp’s feelings. Take your 3 week vacation and forget about work.

  10. Hills to Die on*

    I also think there needs to be some cross-training or support in place at the company. While nobody is irreplaceable a lot of this could be addressed by having a support person on site who knows what you do, has been trained on how to do it, and how to troubleshoot it. They don’t have to be as good as you, but they should be approachable and be on hand to help the temps instead of making their options 1. flounder alone or 2. go to your boss and a negative and unhelpful reaction.

    2. cheeky*

      Yes! It’s not wise for a company to have specialized knowledge sitting in the head of one person. Someone permanent should be cross-trained in your work.

      1. paul*

        As someone trying to train a replacement…so much this! I’m not a super star but I’m the only person that does what i do here and it’s going to be rocky for a bit after I leave. If we’d been able to actually do cross training on a meaningful scope (like I’d suggested *two years ago*) they’d be in a better place but oh well…

    3. PieInTheBlueSky*

      Perhaps this person could even fill your role in lieu of having a temp. An existing employee would be also be someone known to your boss and, presumably, someone he already has some trust in. Plus, once this person has been trained, there would be no need to start from scratch with a second temp the next time you want to take time off.

      1. KL*

        This! I cover for another assistant when she is out and she covers for me when I’m out. We go over what projects were working on before we leave and let each other know what needs to happen while we’re out.

    4. Squeeble*

      I was going to suggest this. When I was hired, it was literally part of the job that when one of the EAs is away, I fill in to support that exec. Maybe a few weeks a year I kind of have two jobs so that the regular EA can get a real vacation. It works well–not sure if it could work in OP’s case, but might be worth considering.

    5. Detective Amy Santiago*

      Agreed! OP needs to create a “If I Get Hit By a Bus” file that includes pertinent information. That would be useful for the temp or anyone else that ends up covering for her at any point.

      1. Totally Minnie*

        I have one of these, but I call it the “In case I Win the Lottery and Move to Tahiti” file. Better vibes. :)

    6. Jadelyn*

      This is a great idea. Ideally, anytime someone is out, if you ask around *someone* should at least have a basic understanding of the important stuff. Maybe not all held by the same backup person, there might be different backup people for different stuff, but it should be rare that literally nobody else can step in on a task when the point person is out of the office.

    7. Elizabeth West*

      Yes yes yes yes. Cross-training is a beautiful thing. If they have to have a temp, this might also go a long way toward making the boss feel more secure about having the temp do the work.

    8. Chicken*

      This. What if you get sick or injured and are out for a month with zero notice and zero ability for you to help while you’re out? I mean, I’m sure they’d muddle through somehow, but it would be better to have some kind of backup to ensure that the essential functions of your job are adequately covered.

    9. Pay no attention to the man behind the curtain*

      This was my immediate thought as well. It sounds like they need a longer term solution than getting a temp. If she doesn’t already, the OP should have detailed documentation for her job that anybody can use to fill-in and maybe have the same temp or a part-time employee come in 2 days a week on as ongoing basis who can then cover during vacations of any duration. Some temps would welcome a semi-permanent placement like that.

      1. OP - I need a vacation!*

        I do have a complete user manual for my desk. I update as needed. It’s rather large and mostly confidential :)
        There are a few issues that arise though. For instance, some of the applications I use are very specialized and require some pretty intense training to be able to use. Not even my boss knows how.
        As we are a large corporation reporting to the provincial government, there are huge amounts of confidentiality requirements. No one can use my profile to log into anything. Much of my work sits in restricted folders.
        One of the applications I use takes a lot of time to gain approval for, and uses a license that is assigned only to me (and available licenses are limited). I can’t very well have this in place for a temp as they are not employees.
        Our head count is such that we have to fight for new positions. If Joe Blow’s team has a Sr. Engineer retire or change jobs, that head count can be re-purposed for something totally different in an entirely different city – – maybe even an admin asst :) It’s an ongoing battle.

        2. ElaineS*

          Lack of redundancies and fail safes are the corporation’s problem, not yours. Especially if you haven’t gotten a well-deserved raise in over 7 years and you aren’t even getting credit for the work you do.

          Even when a Prime Minster or President is assassinated, the country keeps turning. Sounds like the option you find most promising to date is to cross train your more senior assistant to step in for you. It’s not normal or natural to be so very irreplaceable. It’s a danger to the company, too, should something happen to you given the state of things. Serious health issues do happen.

          1. Ecce Wombat*

            I have been one of those “hit by a bus”cases. Went to work on a normal Saturday as a 24 weeks pregnant housing case manager and never came back after that day. I loved that job too, but my son was born 15 weeks early at a small but mighty 1 lb 9 oz and ended up in NICU for 6 months, and part of working with homeless young adults was just knowing you were going to be exposed to a lot of germs and get sick more than was typical because homeless youth usually don’t have access to private beds when sick so eeeeeeverything spreads. My progress notes and reports were universally acknowledged to be the best in the agency, to the point that new hires were specifically told not to imitate them because “[Wombat’s] notes are insane”. Nobody envisioned my entire caseload being dumped in everybody else’s lap but at least everybody had a complete AF guide as to what was being worked on.

  11. Snarkus Aurelius*

    Even though I’m in my 40s, I’m still surprised at how many people sincerely believe that only one person can do this job and no one else, and what’s worse is that those same people think it’s a compliment.

    It is not a compliment.

    If only one person can do a job right, that’s a problem. Multiple people can do the job right in different ways, it’s just that stubborn people want it done by that person in that one way so they don’t budge on their expectations and create this misconception as a weak defense.

    I’ve also heard this excuse from people who are desperate for job security, but not as often. I even heard it from one guy who wrote an annual report. He was genuinely shocked when I pointed out that it’s only a report and it wouldn’t be difficult to find someone else to write it.

    1. Snark*

      Right? It’s definite mismanagement. If you have a particular way thing ABSOLUTELY MUST be done, have that person create some guidance docs or best practices or templates, and then crosstrain others in how to do it the same way – and recognize that “exactly the way Jane does it” is not a reasonable expectation.

      1. NW Mossy*

        I operate under what I call the “rule of three” – for any given process that’s critical to the business, at least three people need to know it well enough to do it on short notice. It’s amazing how many otherwise well-run organizations fall into the trap of not having enough coverage for really critical stuff, and it’s part of my managerial mission to stamp out that stuff when I find it. Sometimes you have to metaphorically drag people by their hair to make it happen, but it’s worth it in the end when that essential person can actually take stress-free time off.

    2. Countess Boochie Flagrante*

      This.

      You don’t really get into it, OP, but at least on a discussion basis it’d be worth asking your boss what his “won the lottery and moved to Fiji” plan is for you. If no one at your company can even temporarily fill in for you, and your boss runs through temps like tissue paper, that’s a massive, massive problem in institutional planning.

      1. Polaris*

        I’ve heard this described before as the “bus crash” scenario – where if a specific person was suddenly hit by a bus, the entire place would collapse without them. As the chief EA, this is my mother’s position at her office, and she had to give her retirement warning three years in advance and start training everyone to survive without her right away. It’s not a great set-up.

        1. BurnOutCandidate*

          I’ve had the “bus crash” conversation with my boss and my boss’ boss about my own position — it’s quite specialized, and it’s essentially at the core of my company’s operations (and, quite frankly, at the overall industry’s operations). There’s no plan at all. There’s no budget to hire someone to back me up (which is what I’ve lobbied for), and there’s no one else on the team that they want to cross train on even a few of the things I have to do. It’s very frustrating for me, as I’m mentally exhausted (it’s been eight years since I’ve taken more than two vacation days in a row — so I’m jealous of the OP), I feel trapped, and I know I’m near my end.

          1. Specialk9*

            Burnout – I encourage you to reframe this, hard, as your bosses’ problem. They need something specific and rare, i.e. their problem. You have that skillset, i.e. you are the solution. So are they treating you like a vital solution to their problem, or have they gaslit you into thinking you own the very problem you solve? Because that’s ridiculous. Further, if you’re really that important, you have leverage and they should be courting you to want to stay. Sounds like they’re doing the opposite. So Burnie, you’re smart and hard working enough to be indispensable, you’ll find a new place. Walk away and don’t look back.

        2. Cinderella's Mistaken Identity*

          WTF – three years notice? I wouldn’t have given them the satisfaction. I can at least relate to your mom’s situation and also to the OP of this thread, as my workplace relies on me waaay too much, expects me to wear too many hats and be the “expert,” refuses to cross-train anyone, and I rarely get to take more than a couple of days off at a time. (The amount of vacation time I’ve lost in the last 10 years is staggering.) But my get-even is coming. I’m planning to retire by the end of the year, and I’m keeping it quiet until the very end. How much notice are they getting? Two weeks. Not one second more. If they can’t get along without me, well, not my circus . . . not my monkeys.

    3. AMT*

      Agreed. The other consequence of this is that horrible people stay in their jobs for decades, driving away talented people and making their workplaces toxic, because they do one important thing well and their managers want to avoid training someone else to do that thing.

    4. AnotherAlison*

      Eh, I think there’s a difference between thinking no one else can do your job, and no one else can do it as a 3-week temp, or as a cross-trainee.

      I used to have a job that they only needed a handful of people in the company of 10,000 with that particular skillset. I absolutely think someone else could do it. I left the job; the position was filled. But, no one was going to step in for me when I was on vacation. The others in my department didn’t have the same analysis and spreadsheet skills. Others in the company did, but they didn’t have the department knowledge or availability to be a shared resource. It was also the type of thing you need to do regularly to be able to do it.

    5. Lil Fidget*

      Agree, it can by easy to feel good about this – “I do a hard thing so well, nobody can replace me!” but this is legitimately a management failure by the company (and in my experience, may actually hold you back from new opportunities – because you’re so necessary in your current role, if something exciting opens up for you in the future you may not be able to get it).

      1. OP - I need a vacation!*

        Nope….do not feel good at all. I have one person that my boss sort of/almost/kind of is okay with covering for me in certain basic jobs but she has her own huge workload.
        I have actually applied on three other positions over the years, just to see. They’re all within the corporation.
        As soon as I sit through the interview I know immediately we’re not a good fit. Each time. :)
        I am a walk in and take over person. I know what I do adds a lot of value. I’m proud of my work.

        I am in awe of the sheer talent around me. Two of the people I work with have 5 PhDs between them. Their word in their field is law. They travel the world to present to massive groups of Specialists and Engineers.
        There isn’t anything else that I find this exciting, believe me. Especially after working in accounting for so many years! :)

        I just want to take vacation now and then! LOL

    6. neverjaunty*

      Exactly. “But they can’t live without me!” is very ego-boosting, but 1) it’s untrue and 2) it’s damaging in so many other ways.

      OP, you’re trying to square a circle here. “It’s okay and necessary for me to have a real vacation” does not jibe with a belief that your workplace cannot do without you, or that it’s ok and actually a compliment for your boss to drive out temps because they aren’t you.

    7. The Original Flavored K*

      THIS. It’s not a compliment. It’s a sign of gross mismanagement and poor staffing.

      “You are not allowed to leave, where shall I go, what shall I do” crap is why I am currently taking a full course load while also working mornings and trying to maintain availability for as-needed reception coverage, specifically because there is nobody else in the hospital’s clinic network who has both the skills AND THE TIME to replace me while they hunt for another candidate. (They had someone on the hook, but that person turned out to be ineligible for rehire, to put it very delicately, and I am laughing at how poorly administrated this county hospital is. I laugh about it literally every day. If I don’t laugh, I’ll have to write letters to whatever governing body I can find.)

      I know with complete certainty that if I walked out the door at noon today and didn’t come back in tomorrow, patients would be unable to get authorizations for their surgeries. Anybody who thinks that’s a GOOD thing is welcome to explain to my network’s patients how this is not a problem.

      1. wendelenn*

        “You are not allowed to leave, where shall I go, what shall I do” crap

        –Gotta pull a Rhett Butler. “Frankly, my dear, I don’t give a damn!”

        2. The Original Flavored K*

          If I was just dicking over a company, or even just the hospital’s business office, I would absolutely pull a Rhett. It gets a little stickier, ethically (for me at least — I get that not everyone might feel this way!) when it comes to potentially interfering in patient care.

          And, now that I’m in the “Broke College Student: Take Two” phase of my life, I’m okay with working a little longer to keep cash coming in, so long as I’m doing so on my terms.

      2. TardyTardis*

        All this reminds me of how Albus Dumbledore ran the Order in the Harry Potter books–which pretty much collapsed the second he died. Very poor leadership, really.

        1. Ecce Wombat*

          Dumbledore in general is a crap personnel manager. “Attempted murder of Slytherin students is totes okay as long as it’s done by a Gryffindor” See also “attempting to kill someone then changing your mind halfway through is NOT the same as saving their life”.

    8. Bea*

      I’ve fought tooth and nail to teach business owners and executives to stop giving so much power to any individual.

      I’ve seen former bosses to struggle to replace me. It’s not a specialized field but they get so anxious they start throwing people at it trying to make it stick.

      I mean it’s great for me because I’m paid to write procedure documents on things that feel like writing directions on how to use shampoo.

    9. Lia*

      My ex works as a consultant, and one of his clients had an “irreplaceable person” who was the only one trained to deal with financial matters. Irreplaceable person was planning to retire, and ex’s firm was brought in to recruit a replacement.

      Guess what? Irreplaceable person DIED suddenly from the flu before the recruitment effort even kicked off. There was NO documentation on how various functions had been done, where files were…nothing. And the auditors were due to arrive. Ex worked massive overtime and got them half up and running, but what a cautionary tale.

    10. Lara*

      And it’s not just that believing that only one person can do the job is bad management — but when someone believes that they’re indispensable or irreplaceable, it can also affect their behavior and relationships in and outside of work. I don’t mean to suggest that the OP is sabotaging romantic attachments or friendships by allowing the feeling of “no one else can do what I can do, and therefore I am very important, and therefore I need to let these lesser things slide” to take over increasing parts of her psyche, because there’s really nothing in the letter to suggest that.

      But this is something that people DO, in some circumstances, and it’s baaaaaaaaad, and it’s another reason that real time away from the job is important — just for a hint of Total Perspective Vortex and reminding you of your (and your job’s) place in the universe, but you know in a non-psychologically-destructive way.

      1. OP - I need a vacation!*

        Oh good heavens! I know I’m not the only person who *could* do my job. It’s just that for much of my time there, I *am* the only one. So much depends on getting certain permissions for access to applications, taking specialized training, but having a very restricted budget. You can’t just have x-many trained people. There are a lot of approval levels to slog through.

        I’m only trying to do my best to find a way to take this time while causing the least amount of impact possible. I don’t want to stress out my boss. I care about his health too. We have a really, really, good working relationship. I just feel sorry for the temps who obviously don’t have that so are subject to the impatience that bubbles up and over (way over apparently!)

        2. Lara*

          Oh, totally not implying that you’re falling into this trap! The comment was more for someone reading this thread in the archives six months from now because they’ve lost their significant other/emotional support person to her/his demanding boss. :)

          OP, I just wish you a vacation. Or a new job with a bigger paycheck that will let you take vacation with no worries.

  12. Jubilance*

    OP this isn’t your problem to solve. This is your boss’s problem to solve. What would he do if you were injured and needed to be out for months at time, or if you won the lottery and immediately quit?

    1. OP - I need a vacation!*

      Depending on the injury, I know I’d have a courier at my door with a laptop and a VPN dongle. It happened in 2007 for three months :)
      If I won the lottery I wouldn’t walk out though. In fact there has been one large lottery winner and one very large winner and both employees still come in every single day. This is a rewarding career and they are talented.
      I’m part of a team and any problem to solve that involves me, should have me as part of the solution. That’s how I feel and have always felt.

      1. Ali*

        That’s not really the point Jubilance was making. What if you were literally incapacitated and unable to work for x amount of time or forever? Like, you suffered a brain injury or fell into a coma or what have you. The staffing of your job would not be your problem, it would be your bosses. This isn’t about you deciding how you would react to certain hypothetical situations, it’s about reframing this issue as being your bosses problem and not yours.

  13. Wannabe Disney Princess*

    I can relate to this. Strongly. I am my own department and when I do find replacement for my time off I always come back to a chorus of “OHMYGOD Please never ever ever ever ever ever leave again” and multiple emails from the poor person covering me stating “How in the world do you handle this?”. People think it’s funny to tell me I can’t go on vacation or that my time off has been denied because they didn’t approve it when I send my email (hahaha – no, I do get time off and you are not my supervisor).

    When I first started off I would stress out about getting coverage and making sure the office had support. Now? I’ve removed myself from that. If there’s a mess when I get back, well, there’s a mess. Nobody is going to die if the teapots aren’t glazed the same way I glaze them.

    Most importantly: the office will survive if I am not at my desk. I am not irreplaceable, no matter what I’ve been told. And adopting that mindset has released an insane amount of pressure that I have put on myself and internalized from my coworkers.

          1. Snark*

            that didn’t work. Crap. Go to the commenting rules page and it’s near the bottom – it’s HTML b, i, and u tags.

        2. Princess Consuela Banana Hammock*

          It’s basic HTML! <b>bolded text goes here</b>. You can do the same for italics (<i>), strikethrough, and blockquoting. Alison has the tags listed at the bottom of the commenting rules.

          1. The Original Flavored K*

            Holy crap I’m so used to other comment boards not using/allowing HTML that I didn’t even think to try it.

      3. OP - I need a vacation!*

        I hear you, and although I agree in principle we aren’t a typical office. I also support specialists who might be one of two dozen or less, world-wide.
        I have been tasked with doing background reporting for them, taking info from various databases and combining them into a report using special software. For one department in particular, it can definitely be life or death, for the public.
        As mentioned elsewhere, due to budgetary limitations, not very many of us have access to this stuff, or knowledge of how to use it.

        Wow…responding to all these comments really points out a lot to me about my job that I’ve always thought of as ‘well, that’s just how it is’.

        1. MM*

          Here’s the thing. This provincial government agency you work for exists, presumably, to provide certain services and protections, right? Do they not have a public responsibility to make sure that if one single solitary person (you) fell off a cliff tomorrow (god forbid), the public wouldn’t be left unprotected? I know civil services are always stretched, but it seems to me that for all you’re worried about the pressure on the higher-ups, they’ve really set themselves up for a political disaster in addition to whatever else by virtue of having things set up this way, and that’s neither your fault nor your responsibility. I mean I can see the hypothetical newscast now, and it comes along just the same whether a temp flames out while you’re on vacation or you collapse on site after twenty straight years of overwork, or whenever the clock runs out.

          And if your falling off a cliff tomorrow wouldn’t really leave people in danger, then there must be a bit more wiggle room than you’re making out here, no?

          1. OP - I need a vacation!*

            I’m not sure why so many people want me to fall off a cliff, or get hit by a bus…. lol

            There may be more wiggle room, granted. But if I’m not doing what I’m trained to do, and not there when one of the executive team needs a quick response, then things are not running smoothly and it feels awful to know you have a part in that.

            As an example, we had an emergency yesterday at noon (second in 3 weeks). All hands on deck – helicopters out, Engineers doing patrols up in the mountains – and my boss is tied to his desk taking calls from satellite phones while another group I work with is desperately trying to get LiDAR and orthos put together so maps can be pushed out. I was busy gathering photos and info about prior incidents in that area using three separate databases.

            Each person has a role to play. With our headcount decimated by a prior ruling party, each body is important.

            For the record, I really do not think I am any more indispensable than anyone else in the corporation. I’m simply trying to find a way to take some massive vacation without making it difficult for a bunch of colleagues (and temps!)

            1. Working Hypothesis*

              The thing you’re missing, OP, is that your taking vacation is not what “makes it difficult” for a bunch of colleagues and temps.

              The fact that your business is massively understaffed is what makes it difficult for your colleagues and the temps.

              The fact that your business has histrionically absurd policies on secrecy is what makes it difficult for your colleagues and the temps.

              The fact that your boss chooses (yes, CHOOSES; he doesn’t have to, no matter how much stress he’s under!!) to act like a jerk every time something doesn’t go as smoothly as it would if you were in the office 24/7 is what makes it difficult for your colleagues and temps.

              Not a single one of these things is your fault. Not a single one is within your control. You really have to stop taking on the burden of fixing corporate fault-lines which you had zero role in creating, and which you have zero power to repair.

              Go take your vacation and let your boss handle this. If the place falls to pieces without you, it may cue the government that they really do need to allow your business to hire some damned staff already.

            2. Ali*

              For an office engaged in such critical activities, they take a pretty lax approach to crisis planning. Everyone keeps making the “fall off a cliff” point because it doesn’t seem to have been answered. If your work refuses to implement a plan for how they will continue their activities in the temporary or permanent absence of key staff members, then either their activities are not that critical, or management is exceedingly incompetent. Either way, it’s not your problem, so just go enjoy your holiday.

  14. C in the Hood*

    What bothers me is the boss blaming OP for “setting the bar ridiculously high” and that’s why he/she is impatient? No, it’s not the OP’s fault that YOU are impatient.

    1. OP - I need a vacation!*

      THIS! I’ve spoken with him about this often over the years during performance reviews. It’s downright depressing to come out of those with a “fully performing” rating when some people on the admin team I lead are getting “high achiever” and “excellent” ratings. Grr.

      I can’t get him to change his attitude. He says it’s to give me incentive to work even harder next year. LOL He knows I give absolutely everything I have and then some. I decided to opt out of these. We submit a blank document with both our signatures at the end of each fiscal.

      1. Jerry Vandesic*

        He can say whatever he wants, but it doesn’t change the fact that he’s a bad manager and a bit of a jerk.

        1. OP - I need a vacation!*

          You know, I won’t debate the bad manager part. He’s not warm and fuzzy and doesn’t really like many people. BUT, I love working with him and have the utmost respect for him.
          His other direct reports enjoy having me as a buffer most times. I have a ridiculous sense of humor and don’t hold back when things are tense.
          I mentioned elsewhere that I’m not a youngster. I’m 59 this year. I can hold my own without any trouble.
          This particular vacation/temp issue has me confused as to the best direction to take, is all.

          I think I’ve provided a good sense of what my work entails and why I do have the concern.
          I’m appreciating the feedback as it forces me to sit back and really look at stuff.

      2. TardyTardis*

        Once upon a time there was a school district in Arkansas, where teachers were warned to work only one year and then leave as rapidly as possible. See, because if you stayed longer, you received such terrible performance ratings that only that school district would ever hire you, possibly for the rest of your life. It sounds like you’re in a similar trap.

      3. ElaineS*

        So, you’re indispensable but are paid what you’re worth, feel guilty going on vacation, he abuses temps when you’re out, makes inappropriate and derogatory comments about women (blonde joke) and you can’t even get your position description updated.

        Sorry, he’s a bad manager – a good one would fight for at least one win (of the aforementioned list) for someone so valuable, even if that means lobbying the provincial government for adequate resources. Perhaps the lack of Excellent ratings are effecting your chance of increased compensation.

  15. Snark*

    “I always come back to a chorus of “OHMYGOD Please never ever ever ever ever ever leave again””

    I would shut this DIRECTLY the f*ck down. Nah fam, you don’t get to lay that on me, I get to leave and you get to deal. Obviously I’d phrase that differently with actual coworkers, but I’ve had people say this to me, and it’s SO DAMN ANNOYING. They do not get to lay that on you.

    2. Lil Fidget*

      Yes, I’d push back on that one right away. “Everybody deserves to have their time off respected, we all cover for each other during vacations around here.” Say it mildly, but say it, to cement the idea both in their heads and your own.

    3. Wannabe Disney Princess*

      If someone stops by my desk, I calmly raise an eyebrow and ask if they want me to continue being the teapot glazer. When they agree, I smile and say, “Good. Then you want me to take vacation.” Then swivel back to what I was working on.

        1. Wannabe Disney Princess*

          Sadly, it was taking bereavement leave which forced the point home. I didn’t have time to find back up and, magically, the office was still standing when I came back.

          I did have someone whine to my face that I took a lot of time off in December. I managed to not rip their hair out of their skull and replied with a calm, “Well. Have a close family member dropped dead unexpectedly and you can get more time off too.”

          They never bothered me about taking time off again.

    4. Amber T*

      My coworker does this to me. She’s back up to me on a (very not complicated at all) system. While the system and interface is the least user friendly thing ever (not by our design and we’re forced to use it – trust me, I could go on and on about how monopolies do very well exist today and they suck), it’s fine once you get some practice in, plus the customer service is pretty decent. I’ve written clear, step by step guidelines (click this button, then click this button, then click this button), followed by shit-hit-the-fan protocols (this SHOULDN’T happen, BUT IF IT DOES, do this), I’ve sat her down and walked her through how to do everything, answered her questions a million times. And each time – “OMG YOU’RE NOT ALLOWED TO GO ON VACATION EVER.” My response to this is always “Oh, let me tell you where I think I’m traveling to next…”

      It’s actually funny, because when she first started she didn’t think I had enough work and would balk when I would tell her I was busy and would ask our boss what my priorities should be (it was never her work). I actually heard her loudly complain to our former boss “But what does she actually do here??” (I didn’t hear my boss’s response because his voice didn’t carry like hers, but I trust he backed me up.) Lo and behold, I go on vacation for a week and she’s my back up… she never bitched about what I *actually* do again. But she’s spun it that “you’re never allowed to go on vacation” is a compliment, which I’m still trying to shoot down every time, because I am using my vacation days as I see fit, thank you very much, and you can take your panic elsewhere. (She’s also tried the “I’ll just call you when this happens,” to which I’ve responded “and I’ll just let it go to voicemail.” She’s not pleased with me.) /rant

    5. Elizabeth West*

      Yep, I would too.

      I went on holiday for three weeks at Exjob, and my boss covered me. When I got back, my coworkers — who had assured me they would be fine — were saying “OMG you were gone foreeeeeeever!” They didn’t actually say I couldn’t go again, but the implication was maybe not so long.

      I ended up working remotely a little bit on my next holiday, but mostly to score brownie points with my boss and because I really didn’t have enough PTO to cover it (I couldn’t pass up the trip because of an event). But I don’t regret that three-week trip for a minute. For the first time ever, I actually had a chance to thoroughly relax on vacation. That has never happened to me before and now I don’t know how I’m going to manage without it next job. :{

  16. Amber Rose*

    I think I read this book. Is your boss secretly a vampire or some other paranormal creature?

    I kid, of course. You’re a kind person to care about the temps, but that’s not really something you can do anything about. Go on vacation. Understand that the temp(s) who went home in tears had a few drinks and ranted and cried at a friend/loved one for a bit then got over it. You can also let it go.

    But if you have a really good rapport with your boss, as it sounds like you do, Alison’s script is the way to go and maybe gently point out that abusing temps is a good way to be cut off by the temp agency, which isn’t really great for anyone.

    1. OP - I need a vacation!*

      Haha! Perhaps? ;)

      Someone responded with a suggestion to train a person who is already a part of the team and use a temp to cover that person’s work. It would be so much easier. I had approached someone years ago who didn’t feel confident so it didn’t go further, but I’m going to speak with her this coming week. Keeping fingers crossed!

  17. Bridgette*

    I used to worry about taking a chunk of vacation like this because I was afraid of making more work for others and also that my boss would be disappointed that I was taking so much time off. Then one day I realized that if I didn’t take my time as I needed/wanted , I would never be able to stay long-term. My boss never ran off a temp in tears, but I do usually have a few days of scrambling when I get back.

      1. OP - I need a vacation!*

        Elizabeth – I agree! It took me a week to relax but then I had time to enjoy the travelling, and a few days to be worried about what I was coming back to! But, I had that downtime.
        I took my much beloved mother on a Panama Canal cruise leaving from Vancouver Canada and finishing in Ft Lauderdale FL. 22 days….22! We used to live just outside Clearwater on the Gulf side and it was a weird sort of home coming for her.

    2. OP - I need a vacation!*

      Interesting. When I left my old job in accounting, they hired three people to take my place. Gratifying as heck. It was the private sector so I got paid *very* well, but not as well as three people!

      Our budget is government dictated and there is no business justification that would get through the approval system for two temps. I’ve had trouble getting one sometimes, for other areas in my division. Crazy.

      1. TardyTardis*

        Every time I left a job at OldPlace, it took two and a half people to replace me. One reason, I might add, that I am no longer at OldPlace.

  19. Roman Holiday*

    Would it be possible for you to cross-train another colleague to be able to pick up some of the slack and/or act as a go-between for the temp and your boss? If your company is prepared to devote the resources towards hiring a temp, maybe they would consider putting some of those resources in-house, if someone has the capacity?

    I was specifically hired at my former job so I would be able to cover for a colleague who hadn’t been able to take more than 1 – 2 days off at a time for 10+ years. The year before, he’d had some serious health issues that resulted in him being hospitalized for a couple weeks, and that finally gave the company the kick in the pants to hire someone whose duties included covering for him on vacation.

  20. I'm A Little TeaPot*

    So, what happens if you win the lottery and quit your job? More realistically, what happens if you are injured or seriously ill and are out for an extended period of time? Your boss is really shooting himself in the foot here, he just doesn’t know it yet.

    Go on vacation. Let him figure it out.

    2. only acting normal*

      If they’re injured or ill…
      Suddenly I’m picturing the boss who stalked a LW into chemo. :-/

  21. TBoT*

    I was a temp at a couple of points early in my career. Once I had to fill in for an administrative assistant when she took a week of vacation. She supported a trio of very demanding, particular and unkind upper managers, each of whom had very specific and completely distinct expectations about how she wanted things done. The admin had done all kinds of legwork providing detailed instructions for me, but at the same time … I was a temp there for a week. I could read through that sheaf of instructions over and over and still not have it all down by the end of my assignment.

    It was such a weird experience, because usually in my work as a temp people’s expectation seemed to be that I would be, at best, slightly below competent, so they’d be delighted to learn that I was actually pretty good at doing administrative work (which is how I wound up turning a one-week “help us catch up” assignment until one that only ended because I got permanent work elsewhere). But this trio had totally unrealistic expectations, that I could just drop into someone else’s role and do it flawlessly.

    So I agree with this advice so much. There needs to be some serious expectation-setting for *anyone* to be able to temporarily fill in for this role.

    1. Bea*

      Any time a temp walks into a sheet of instructions like that it’s like a big red flag of doom. This is a job…not babysitting “Junior won’t eat carrots don’t even try!! Bedtime at 8, a minute later and hell will be paid.”

  22. kms1025*

    I read that “setting the bar ridiculously high” as a back-handed compliment, but still silly. OP take your vacation. Dont worry about work. Life will go on : )

  23. Bea*

    Holy crap, I had a flashback reading this. Only I wasn’t able to even try to slide a temp into place and the idea of three consecutive weeks out would have murdered my former bosses brain. I had to be out over a week for medical purposes and that was doable but everything sat on my desk waiting for me. Granted I also took the job with six plus month’s of backlog waiting to be dealt with. And my work isn’t specialised it’s just my personality that is.

    He’s never going to change but you can at least ask him to chill out since at least he’s trying by allowing a temp to be used. He has to lower his expectations, I’ve never met a temp who can hang with this kind of demand, they’re a warm body to keep work from piling up, not a replacement who is going to kill themselves to please a guy they’re working for to cover a 3 week vacation.

  24. Peggy*

    OP, as a teacher, I feel you – I try not to have a sub unless it’s unavoidable (like, I can’t stop vomiting) because I know that my position isn’t one a temp can step into successfully – but a lot of that is pressure from myself. Sometimes you need to be out (professional development, mental health day, family stuff, etc.) even if that does mean chaos at work while you’re gone!

    I’m lucky that we have built-in breaks, but when I have a sub I have grudgingly accepted that “my students didn’t run riot and burn down the school” might be the best I can hope for (and yes, they have driven subs out in tears… haha). I’ve been spending this semester getting my current classes ready for my upcoming maternity leave, but luckily the person who will cover that absence is someone who also works in the school and knows the policies, procedures, and students!

    If your boss is like my students (easily disturbed by changes to the routine, used to a lot of moving parts being handled smoothly) I second the advice above to make a list of what reasonable expectations are, for boss AND temp, and then taking the time you need. And @Hills To Die On gives great advice about cross-training (which is what I’m doing with my maternity sub now!) so that in case of a crisis (my first kid was 10 days early…) somebody is able to step in.

    1. Bea*

      I’ll never forget the sub that didn’t leave in tears but got blacklisted because the guy gave explicit details to middle school kids how to kill themselves…

      I can’t imagine what it’s like being a teacher and having to depend on that system. All the more reason it should be a higher paid and respected position, bleeeeh.

      1. Peggy*

        Yiiiiiikes. Our worst of that sort so far has been the one who told a kid in band, “On you play sax? That must be a real panty-dropper.”

        The student immediately asked for a bathroom pass and went to tell the principal, so at least that sub didn’t finish out the day. Not sure the agency fired him, though. :/ (We no longer contact through that agency… Mostly because of incompetence and unreliability, but that guy didn’t help!)

    2. blackcat*

      I had one relevant documentary for each unit I taught. I rarely used them, but the two sudden sick days I had to take, it was movie time for the kids. But I also never took time off, precisely because a sub couldn’t be expected to do my job to any reasonable degree.

      1. Peggy*

        Yeah, I have “emergency sub plans” that are usually something innocuous and flexible (“independent reading, then write a summary of what you read and a reflection on your response to it!”) that’s as independent of what adult ends up in my room as possible. It helps that the students have Chromebooks now, so I can remove plausible deniability/sub sabotage by posting instructions right to our classroom page from home!

      2. TardyTardis*

        My husband taught chemistry, and a sub can’t run labs, unless they, too are certified in chemistry. He used to be one of those Die for the Emperor people, too–he once went in three days after back surgery to make sure grades got in on time.

        Then he got lymphoma (he’s doing fine, but is now retired). Life changes things.

  25. Remarkable*

    This letter really made me mad. OP has a terrible boss. I’m a boss and I encourage my people to take time off. This boss clearly doesnt care about the employee. All that matter to the boss is that she come to work everyday.

    1. Ask a Manager* Post author

      Maybe. But the boss could be a good boss to the OP in many ways and just be overly demanding with temps and not understand the impact it’s having on the OP, particularly if she hasn’t laid it out for him yet.

        1. Ali*

          Yep, this is one of those “A nice person who’s mean to the waiter, is not a nice person” things.

    2. Myrin*

      It doesn’t say anywhere in the letter that the boss discourages OP from taking time off (unless you count his harsh words about the temps as some sort of passive, roundabout discouragement) – it sounds much more like the problem is within OP herself, so to speak, in that she feels a certain responsibility for the temps who’re having a hard time getting along with the boss.

      1. CM*

        Yes, exactly. It doesn’t seem like there are actually any consequences to the OP here, except ones that are self-imposed. She feels guilty about the temps’ bad experience, and feels like she needs to front-load all her work because the temps can’t do it. I like Alison’s suggestions but I think the OP should keep in mind that she’s giving herself a lot of work to make herself feel better. Neither the temps nor the boss are asking her for this.

        If the real problem is that the OP is left with a mountain of work when she gets back, and not that everybody had a bad time while she was gone, that can be dealt with in different ways and I think that’s another discussion the OP can have with her boss.

  26. neverjaunty*

    LW, thing is, your boss doesn’t actually have to say “you’re not allowed to go on vacation”. He’s trained you to do it to yourself without him.

    Let go of the worry about how mean he is to temps. And let go of the emotional boost from being told you’re irreplaceable and nobody can fill your shoes. If things are so dire that the place will burn down in your absence (narrator: it won’t), make lists and cross-train others.

    1. Marthooh*

      Yeah this guy’s scary. “You’ve set the bar too high so it’s your fault I abuse the temps. And also I give you mediocre performance reviews so that you will work harder.”

      If I were you, OP, I’d take a permanent vacation.

  27. Alli525*

    Whooooo boy I have been there, OP. I went away for two days once, and my boss–lovely man, but very high-needs–emailed me “Please never leave me” (like, “please don’t quit,” not “please never take vacation”). It was cute… but then when I took two WEEKS off, and the CEO refused to hire a temp for reasons that made absolutely no sense, I asked Boss what he was planning on doing, and he replied “Pray.” Everything ended up being OKAY, but that vacation, and knowing the mountain of backlog I’d have upon returning, was a large part of why I decided to leave that job for the non-profit world.

  28. AlwhoisthatAl*

    How awful you have a boss with that line of BS.
    You need to turn the tables on this, if you are so vastly important you need to wreck your life then they can 1) give you a large raise and 2) train someone appropriately because you are going to have 3 weeks off a year every year because you are so so superb at your job and it makes up for the 13 years of not being able to have a decent vacation.

  29. Noah*

    The ability to be available for the occasional email or call during vacation might help. A three-week vacation with zero availability (which it seems like is what LW wants) isn’t a terribly reasonable expectation.

    1. Amber Rose*

      If you say it’s not reasonable, then nobody can ever travel to remote locations or overseas where communication is expensive (when I travel, I don’t even bring my phone, I could never afford the roaming). That’s more unreasonable. Unless you’re the head of a country, no job should prevent you from going on work-free vacations. It’s not really a vacation if you have to answer work emails.

      1. Noah*

        I’m saying nobody (in most jobs) can ever travel to places where communication is impossible for three weeks.

        If you’re gone for a long time, then you or your employer can pay to have access the internet to respond to emails when you’re in a foreign country.

        You can still take an unplugged vacation, just not for three weeks. Even OP doesn’t seem to have any issue getting away; the issue is getting away for three weeks at once. That’s a Long Time.

        1. Amber Rose*

          It’s really not though. It’s just three weeks, not three months or three years. Even the most important person in our office was able to spend 4 weeks hiking in middle-of-nowhere, Peru without it being a big deal.

          That you feel that three weeks is that long is a pretty unfortunate mindset, and doesn’t reflect reality for most workplaces.

    3. K.*

      I disagree. Three weeks isn’t that long, she’s not doing it that often, and if the company puts some templates and cross-training measures in place, it’s fine. I had a colleague who was out for three weeks for surgery, during which she was totally unavailable because: surgery. She was a department head. Everything was fine while she was out. They reported to her boss (a VP), and they were all trained enough to keep things moving while she was out. This department head also liked to travel with her family, often internationally, so her vacations were typically at least two weeks long (the company was generous with PTO). There was no expectation for her to be reachable.

    4. Detective Amy Santiago*

      Absent a catastrophic event, it is perfectly reasonable to expect to be able to take a work free vacation.

        3. Yellow Bird Blue*

          That is a management decision more than anything else, right? I work in a place where three week vacations are common (non-US) and there’s a system in place to keep projects moving. It might not work exactly the same way in other jobs, but I think there are very few jobs where people are really, really indispensable and you cannot work around an absence. I mean, even Heads of States have vacations.

    6. Bea*

      This drastically depends on the size and scope of the company. I live in an under 20ppl world, so I’m still spinning out thinking if 3 weeks out. But many other places allow that kind of absence without thinking to bother a person.

    8. Max from St. Mary's*

      Considering that in many countries three week (and longer) vacations are the norm, and the companies survive, it’s definitely possible. I’m in the US, but my job has substantial breaks built into the system, so I get multiple weeks off with no contact.

      It really is a reasonable expectation, but as long as it’s presented as being undoable companies will continue to believe it’s unreasonable.

    9. Ali*

      It’s completely reasonable to have 3 weeks off. In Australia it is mandatory for employers to provide 4 weeks annual leave (not including sick, maternity or bereavement leave) which many people take all in one go, and our economy hasn’t come grinding to a halt. The CEO of the multinational investment firm I work for takes his 4 weeks every year and we’re still doing 80 billion in investments annually. I have friends who are neurologists and HIV vaccine researchers and they still take their 4 weeks in a row to travel the world or volunteer with Medicins sans Frontiers.
      Just because it’s not the norm in the US, doesn’t mean it’s unreasonable. It’s just an indication that the corporate culture in the US has managed to convince employees that they aren’t deserving of adequate breaks.

  30. Samata*

    OP, if you don’t take anything else away from Alison’s advice, take this:

    In fact, the deal is often that there will be impact, but people survive.

    This applies to so much. I need to write it down and study it every day.

  31. I Coulda Been a Lawyer ;)*

    I was an “inside temp” for a large company in the 70’s and one hard nosed boss refused to work with the temps, so he wouldn’t let his assistant take vacations. HR said, you don’t have to take a temp but you have to let her use her time. 3 days into the vacay he realized that a temp who knew the business was better than no one, so there I went.

    But as a temp for an agency I got a gig I didn’t really want, but over 6 months of trying to find a temp to perm receptionist no one had stayed more than 2 days without ghosting or leaving in tears. They were all offended that everyone else was foreign and spoke their native language to each other while conducting business that wasn’t hers to worry about. They spoke to the temps in English but not each other. Many temps are temps because they want to be, often temps are temps because the job market is tight, but sometimes temps are temps bc they don’t play well with others.

    1. Bea*

      Having tried to slide temps into jobs and being a temp at the start of my career, this is so true. I burnt out so quickly trying to find a temp to fill openings. Even though myself and a friend of mine both used temping to get long term employment at some point.

      Also most temp agencies won’t blackball a client for running a few temps out. Unless you’re physically threatening or breaking contractual agreements agencies will keep sending in warm bodies.

    2. OP - I need a vacation!*

      I have to tread a bit cautiously. :) Our corporation has a board of directors that report to the ruling provincial government. (I’m in Canada)

      If we don’t do our work correctly, a person can die, and our workers can die (and both of these have happened and it’s devastating). They can also die if the work is done perfectly fine, but they suddenly find themselves in a dangerous situation involving what we do. More often there are *only* injuries but those can often be life threatening with huge physical tolls.

      We have people in my division who are so specialized there may only be a couple of dozen like them in the world.

      We design specific things in my division with input from 11 different departments, and we work corporation wide as needed.

  33. Cordoba*

    The presence of an employee who is perceived to be “irreplaceable” is a red flag for a poorly-run organization. A well-run place will invest in the personnel and systems that will allow work to continue relatively smoothly even if somebody goes on vacation, quits, or drops dead.

    When somebody tells me that there is nobody else who could possibly cover all of their responsibilities and workload they’re actually telling me that their boss probably isn’t very good. If she was, she would have arranged for cross-training and depth of critical skills in her department.

    There are exceptions to the “nobody is irreplaceable” rule, but not many, and these exceptions tend to be paid millions of dollars.

  34. She Who Must Be Obeyed (formerly Laura)*

    Many years ago, I was the lead in a unit of Data Transcribers at IRS. I took one night off because I had a big midterm the following day. When I got back, my supervisor told me I was *never* taking a night off again! I had three fully trained backup leads, plus her, to do the work I usually did (pretty much alone) in about less than 2 hours (30-45 minutes at the beginning of the shift and about an hour at the end). I don’t know why. I think they just panicked or put the end-of-night stuff off too long. She also *hated* the paperwork I did at the beginning of the shift, which involved a lot of math, so it took her several hours (with an adding machine–which I used, too). Anyway, it was hilarious!

  35. bo bessi*

    OP, I was in similar shoes a couple years ago. My boss was very dependent on me and got frustrated with whoever covered for me while I was on vacation. He and I had a great rapport, and he was a really good boss to work for, but the work was demanding and did take a certain personality. When I got promoted to another position in the company, he was happy for me, and then went through two replacements in six months. The person in that position now is doing an amazing job, and they seem to have a good relationship. I insisted on being a part of the interview process that last time, and I think it helped.

    Can you coordinate with the temp agency to make sure they send someone with a similar personality to yours? Ideally someone who has worked with difficult/demanding people before and doesn’t get their feelings hurt easily.

    1. OP - I need a vacation!*

      Our temp agency is kind of in-house and we get what we get most times. If temps who have an understanding of the very basic general skills are not available, they pull from outside agencies so we have ended up with people who don’t even know how to use excel, let alone have an aptitude for the type of work needed from them.
      This is not to criticize the temps….not at all. They’re dumped into a world that is pretty unique. I just don’t have time to train someone from the ground up. If we’re lucky, we can get an experienced temp a day or two in advance to run them through specific requirements, but that isn’t often.

      An aside: there isn’t anyone else with a personality like mine….for which people should be grateful! I’m
      pretty intense myself with a ridiculously odd sense of humor. ;)

  36. Hey Karma, Over here.*

    Graveyards are filled with indispensable people.
    As AAM writes, what your boss needs while he is away and what he wants can overlap a bit, but they cannot be exact. You are actually in a position of power here. Use it wisely. but USE IT. Set boss’ expectations. Take your vacation.

  37. A Nickname for AAM*

    If you are that indispensable, you are going to have to set firm boundaries. I have a job like this: I’m a program manager of an organization that provides services and programs. I am expected to be on call and promptly deal with any problems that arise during operating hours (about 100 hours a week) or immediately before operating hours (an early morning staff person calling in sick.)

    Of course, I do my best to train my staff to function on their own, but these issues always arise at a bad time. Hop in the shower? Something goes wrong. Go to sleep? Something goes wrong. Go to the dentist? Something goes wrong just as they start drilling. Shut off my ringtone for a movie? Something goes wrong 5 minutes in. Visit a friend in a nearby town on my day off? Something goes wrong. Finish a drink and can’t drive to work? Something goes wrong.

    Invariably, someone who’s frustrated at holding down the fort while they wait for me gets upset and says, “I needed to reach you and you weren’t available!” and tries to put me on the defensive. When I was younger, I’d interpret it as my job being threatened and apologize. Now, I don’t. If you’re not paying me 120 hours a week, I’m not changing my plans around. If it’s my personal time, I’m going to sleep, shower, go to the doctor, and otherwise make personal plans. If something happens to go wrong during that time, the person who is ON DUTY is at fault, not me for having a life outside of work.

  38. mf*

    By never taking more than a few days off, you’re essentially enabling your boss. You’re letting his (her?) bullying of the temps control your vacation schedule. And he has no motivation to change his behavior, because the end result is great for him–you’re taking less time off, thereby making his life easier.

    The best way to deal is to *start taking time off.* Once your boss realizes that he’ll just have to deal with the temps, then maybe he’ll chill out a bit about it.

  39. Agent Diane*

    I want to pick up the point that OP’s normal vacations are five days split across two weeks. This is not relaxing! Especially if you are still actually doing 10 days work.

    If you take a full week or two more regularly, your boss will start to adjust to the concept. It’ll be better for everyone’s mental health, including any temps.

    You deserve proper breaks. They help you relax and get your head out of the workplace for a while. Please break this pattern of behaviour that encourages your boss to see you as irreplaceable. It’ll be better for everyone in the long run.

  40. WG*

    Not sure if it would be helpful, but you might want to remind your boss that it took a year for the trust to build in your abilities. A temp with a few days, or even a week, of training can not be expected to be at the level it took you a year to achieve.

  41. Oxford Coma*

    There are some legit “no one else can do my job” situations. For example, my company can only afford one PE. Drawings are not getting stamped when he is out.

    But if your position allows for the use of a temp, that argument is off the table. The presence of the temp proves the need for cross-training, so your boss has shot his own reasoning in the foot.

  42. Liz T*

    Wow did I cover OP’s maternity leave a year or two ago?

    When I was temping for Insanely Demanding Bigwig’s assistant, the company threw whatever they could at me to keep me at that desk–a slight hourly raise, free lunch, another temp to work alongside me, near-promises that they would find me a perm job afterwards (despite, I later learned, a hiring freeze). It worked, but it SUCKED. The second temp got fired halfway through because IDB didn’t like him (I think). I had to be out one day; when I came back I heard that the temp covering ME told someone he’d considered lying about being unavailable, just to avoid working that desk. I’m genuinely surprised I don’t have any sort of PTSD symptoms. (The worst feeling at that desk was when I’d googled “what are symptoms of panic attack” and realize the first few links were purple.)

    I have no advice. Just really glad I’m out of there. And they did get me a perm job–in another building.

  43. Tacos are Tasty*

    As i live in Australia all this talk of 3 weeks off being a nono in most US workplaces makes me feel really sorry for you guys. 2 weeks isnormal here. 3 is aok generally. And 4 to 5 or6 is doable in most workplaces with a lot of notice given.

    I already hate how Aus is turning more and more into the US slave economy but if they were to take any chance of a decent holiday away from me I would be emigrating. That shot is craxy to me. You’re not allowed a life. What do they expect? That traveling overseas to somewhere like aEurope is 1 week affair. Crazy!

    My family all live in Switzerland, going by these employer entitlement rules would mean I never see them.

    A friend rejected a US job offer exactly because of this ridicoulous holiday bullshit. We have lives bosses, we’re not slaves despite the slave economy taking off in the Western World.

    Sorry for the rant but this really grinds my gears

    1. OP - I need a vacation!*

      I’m in Canada. :) I have TONS of time available to me. I usually manage to use plenty of it up, but a day or two or three here and there. There isn’t a problem taking your time off, it’s finding a good time to take it. I’m far from the only one with this dilemma, believe me!

      If you are strictly an administrative support person it’s much easier. One of the admins on the team I lead went to Japan for 3 1/2 weeks back in January and another one will be gone the entire month of June. I just don’t have the luxury of that type of work. I support at a much higher level with responsibilities of my own. When they are away, we share their duties (and yes, I will help where I can).

    2. ElaineS*

      Many in the USA don’t even earn 3 weeks of vacation over an entire year. In fact, my last job granted only 15 days PTO – meaning if I got ill I got even less time off. A multiple week vacation seems like a dream. At my last job, which had unions, I had 5 weeks of vacation plus tons of sick time if needed.

  44. Meißner Porcelain Teapot*

    I think there are a couple of factors at play here:

    1) Long vacations: While I do understand that long vacations are great (I effectively had three weeks at the end of last year and it was great) most employers do not like it when people take more than two weeks at any single time, because the longer you are away, the harder it is to hold things together with just a temp. Think of it this way: hiring a temp to cover for someone’s vacation/sick leave/whatever is only supposed to be a very short term fix, like wearing extra sweaters if the heater is broken, until the repairman can come over to fix it. The longer you are away, the more difficult it is to cover for you, especially if you do it repeatedly (say taking three weeks in a row every year). That doesn’t mean you should never ask for it, just… you know… think about it from the other side for a minute.

    2) Your boss’s expectations: as Alison pointed out, you really have to make it clear to him that no temp is going to be able to do what you’ve been doing for 13 years, unless they happen to have been employed in a similar job in the same field for 13 years and just ended up unemployed. He needs to lower his expectations for your vacation time, if he really insists on hiring temps to cover your work (the other alternative would be you preparing as much as you can and then letting your colleagues handle things, but that might not be possible in your job).

    3) The temps: I am assuming that you are leaving them as much information as possible to make those weeks you are gone as stressfree as possible, but even so, it sounds like your temp agency does not understand that they need to send someone with thick skin and good stress management. Please get in touch with them and update them on the situation.

  45. ZucchiniBikini*

    I’m a self-employed freelancer, so I take holidays when I choose to (of course, making sure to give clients and projects plenty of notice, and trying to get things to a neat pause point before leaving). I always take from Christmas Eve til 2 January, but as all my clients shut down for that week, no one cares or notices! I do take other time throughout the year as well, usually in week-long increments, but occasionally longer.

    I’m also in Australia, where most salaried employees get 4 weeks annual leave (vacation) and taking it in 2 x 2-week blocks so incredibly normal, and as Tacos says above, 3-week vacays are not unusual (although I have worked in workplaces where 3 weeks was a problem and had to be requested well in advance, and was sometimes knocked back).

    What I found when salaried, and even more now as a freelancer, is that two things are equally important to being able to take and enjoy holiday time (and not get endlessly bugged while away or come back to a steaming mess). The first was arranging adequate coverage of day to day things that HAVE to keep ticking over while you’re gone. The second was explicitly communicating that project work that COULD be paused, WOULD be paused – thereby managing expectations about what will occur in your absence. I realise that, in an assistant position like the LW’s, a lot of work probably falls into Category A, but if there are any things that are Category B, I’d look at identifying them and being very upfront about the fact that they will basically stop for 3 weeks.

    I’m taking the entire month of April off to travel to Japan with my family. I notified my ongoing clients of this last September when I made my travel bookings, and have been working closely with each of them to ensure that projects get to a point where they can progress elements in my absence. I’ve also arranged a reliable subcontractor to monitor my business email and deal with emerging issues that can’t wait, and she knows what level of stuff is sufficiently serious that she will have to refer it to me (we’re hoping there will be little to none of this!) The basic position will be that things will NOT be normal in April, business will NOT continue as usual, but that essential cover will be provided.

  46. Biff Welly*

    A couple thoughts on this:
    No one is that irreplacable, I mean really. It seems like maybe this has become a co-dependent relationship between letter writer and boss.

    LW likes to feel valued/the only one who can satisfy boss’s “demands” which gives them some power/cache. Boss gets to keep being a jerk and unprofessional.

    Hire the temp, take the vacation.

    1. OP - I need a vacation!*

      Hi there, I hope I didn’t give that impression.
      We all like to be valued, that’s a given. My boss is hardly unprofessional, he has major pressure from above – and when I say above, I don’t simply mean his own boss. He has extremely high standards, and expects the best from everyone, including himself and his direct reports.
      I’m sorry if my emphasis on making the temps cry makes him seem like a jerk, as he most certainly is not. He’s a grumpy hard working dude – I’ll give you that!

      In my other comments I’ve provided some information on what my job entails so as to better explain my concerns. :)

  47. Burhaan Dhaler*

    I am in the same boat as you
    I have my usual 23 days that i have to take in the upcoming few months,otherwise i risk my leave days expiring …therefore i lose out in the end

    I have some rough ideas on how to work Around this

    (1)Either you ask your boss to pay you out for that days
    (2) Take one week regularly off or certain days of during a time period
    like my boss only allows me to take a week of before coming to work
    (3)Im in a position where i manage people
    (So if i go on leave,i leave certain people in charge of certain places in my warehouse (i’ll make sure before i leave everything is sorted out,and if i return and the work is not right in certain places,i hold that team member responsible)remember before i go i fully train them in that situation

    Hope that helps

    1. OP - I need a vacation!*

      Thanks. I’m going to try taking Mondays off for this month and possibly next. I’ll still have to fit 5 days of work in, but at least I’ll have a long weekend every week. Boss is agreeable about this. :)
      I still need to do the full sit-down with him but I’m working up to it!

      We are discouraged from getting paid out for untaken vacation. They want us to take all our time away but in certain cases it’s just not that easy.
      Sorry we’re in that same boat!

  48. TG*

    I’ve been in the situation where I took on some duties in a field that I had no experience with, working for someone who expected me to immediately be able to work as well as someone who had been doing the work for 20 years. It’s impossible to please someone who has impossible expectations, and I sympathize. I left that job last year and am much happier.

    This is honestly your boss’s problem and not yours. You are entitled to your time off.

    1. OP - I need a vacation!*

      That sounds awful for you.

      I love my job like crazy and am very happy to be a part of the grand scheme.

      If only this one thing (getting time away) wasn’t such a pain in the neck, it would be all good!

  49. HyacinthB*

    I came in as a temp into a situation similar to this, in that the boss was pretty demanding. Apparently in the past he had also been borderline abusive to some of his assistants. Fortunately, he had sought out and received anger management for that and it seemed to stick. However, he was still very particular.
    He and I got on quite well right from the start mostly due to his by the book way of wanting things done and my by the book way of doing things! Because of this, he turned my temp position into a regular full time well before the temp period ended, with the hours I requested and at an increase I requested.

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