update: how to discreetly job search when you have a nosy boss

by Alison Green on December 23, 2021

It’s “where are you now?” month at Ask a Manager, and all December I’m running updates from people who had their letters here answered in the past.

Back in 2016, a letter-writer asked how to discreetly job search when you have a nosy boss. Here’s the update.

I finally have (a not very exciting, yet oddly long) update.

I finally, five years after writing my initial letter, got a new and very improved job. Weirdly, my takeaway from my letter (sorta forgetting I wrote it until you published it) and your reply was how terribly depressed I was. I’m smart enough that I knew every step you outlined; I was just looking for a magic bullet, which was not how I used to be. I didn’t recognize the “me” in that letter. But I trust that the questions I asked helped someone else out there.

So, it took me five years to find a new job. My update is mostly to expound that this site was immeasurably helpful in that time. I wasn’t a dedicated apply-every-day job seeker (bc, as noted in the first letter, the boss was good at getting employees just comfortable enough). I sometimes went months between application sprees. But I read AAM everyday and it helped me keep my head on straight.

Clearly there was low-level toxicity at the old job, and building up a wealth of AAM knowledge worked wonders both in helping me mentally remove myself from it and knowing how to avoid it in my next job.

I bought your book and, with the regular website input, kept my resume updated. During those intervening years I got interviews, each one felt better than the last, and some offers. Unfortunately the places that extended offers were dropping red flags as bad as, or worse, than my previous employer so I stuck with the devil I knew. (Again, things I would not have picked up on without AAM reading).

Finally this year all the pieces came together. And hilariously most of my concerns of the initial letter were moot by the time it happened. My old boss was training the new boss. It was clear that, while I did everything they asked, wanted, and a little more (if “more” happened to interest me any given day), I was beyond checked out. It was also clear that it was time for my position in the company to grow/change. While no conversations had occurred directly with me, I was getting a strong “how do we make this work” vibe given my abject apathy for the industry I was in. Because, for all the other faults of the company, they at least kept you on if you did the work. I actually was in a series of dental appointments when the interviews came through, and since it’s COVID times, the interviews were by video and easily scheduled to just come in late/leave early for “dentist appointments.” When I gave notice my boss(es) were happy for me (I think new boss had a tempering effect on old boss in that regard. Plus, I was solving a structural problem for them in the easiest way possible. My successor flew into my seat with lots of enthusiasm and ideas and is doing very well for them).

I wouldn’t be surprised if the new boss was an Ask a Manager reader, because some of the more toxic issues had been getting resolved in very AAM ways over the last couple of years.

The new job is in a very healthy company that is clearly clued into best business practices. I’m paid more for work that isn’t more challenging than my previous job, but is more fulfilling. They had a clear path of advancement they could explain in the interview process. They care about employee wellness, frequently and repeatedly encourage the use of alllll provided vacation, and have a much more generous health plan that includes mental health (which I am fully using).

(My one and only complaint being that this job can be fully remote, but upper management is mandating a couple days per week in office. On the flip side, this highlights how awesome my middle management grandboss is, who quite vocally advocates for us to get back to remote, and coaches us underlings on being advocates as well.)

To give a specific angle on how AAM helped me: I come from a blue-collar factory-employed family, among the first in my familial generation to go to college (and one of two to go beyond bachelors degrees). My upbringing also had shades of the toxicity I encountered in the working world (from my college jobs of fast food and retail, and later in nonprofits, to the job I was in when I wrote) so I didn’t know what was normal/healthy. It took a lot of reading here to name the problems I experienced from those jobs, and a few that I perpetuated having learned while growing up. AAM helped prepare me for the white collar world in a way that no one in my family could and has provided me with a vocabulary and labor-rights tool set I didn’t know existed.

Thanks so much Alison and happy holidays to you and the AAM commentariat!

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{ 18 comments }

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  1. Falling Diphthong*

    I wouldn’t be surprised if the new boss was an Ask a Manager reader, because some of the more toxic issues had been getting resolved in very AAM ways over the last couple of years.

    This is such a lovely update detail.

    1. Anonym*

      It is! I also loved “AAM helped prepare me for the white collar world in a way that no one in my family could and has provided me with a vocabulary and labor-rights tool set I didn’t know existed.”

      Alison should post that on her wall somewhere in case of a bad day. It really captures the impact of this site so beautifully.

      1. Candi*

        That counts at least a dozen posts and comments, that I can think of just off the top of my head, where someone has said “I came from X and AAM helped me adapt to the white collar world.”

        Public service, Alison, awesome public service.

      2. Barefoot Librarian*

        This comment was very meaningful to me as well. My dad always worked in manufacturing and my mom, when she did work, worked in restaurants. AAM has helped me over the years develop a realistic idea of how to handle white collar work. I’m just now transitioning from a tenured academic position to the business world (software developer specifically) and I’m turning back to the archives to get a feel for the differences in norms and etiquettes between the two. There’s such a treasure of things here.

    2. Prof Space Cadet*

      There’s no sure-fire way of knowing, but I’d be curious how many situations get resolved because managers read AAM and go “oh sh*t! This sounds exactly like my workplace.”

      1. Imaginary Friend*

        No, but we do believe that most good managers aren’t writing books or blogs, they’re just managing.

        1. Candi*

          Writing and giving advice in a palatable but straightforward way are both skills that can start with talent, but need training to really do right. Alison’s hit that sweet spot of talent, practice, and skill -not everyone does.

  2. The Smiling Pug*

    This is an amazing update, OP!! I’m so glad that you have a new set of tools to use in your career.

  3. Egmont Apostrophe*

    Back in the 80s and 90s in advertising, one tended to wear a suit for interviews, but not for everyday work, even client meetings. So turning up at work in a suit tended to produce people saying “Ah-ha-ha, Egmont, got an interview?”

    I would always say “No, a funeral.” That shut them up.

    1. Candi*

      I don’t remember where, but I once read a story of a woman who would wear suits randomly to work, even though her work’s usual code was more business casual, button ups and polos but no sports coat level. She originally did it because crunch time + laundry, but the reactions were so funny she started doing it for amusement, and then realized it worked great for when she wanted to interview.

      1. Egmont Apostrophe*

        That’s smart. Keep ’em guessing.

        What really solved it was that business casual took over, certainly for creatives like me. If you saw somebody in a suit he was probably a printer’s rep. The last known copywriter to wear a tie was in 1998.

    2. MAC*

      The dress code at my workplace is middle ground – jeans not allowed, but nobody wears suits/jackets either. I tend to dress up more than most anyway, so I’ve heard the interview question occasionally, but mostly in a teasing way. Additionally, I often serve as the media spokesperson on short notice, so they all know why I keep a blazer on a hook in my office. Came in handy last month when a job interview (for the job I’ll be starting after the holidays!) was suddenly scheduled for the following day. I already had a TV news interview scheduled that day so nobody suspected a thing!

  4. Zweisatz*

    Thanks for the lovely update, letter writer! Things don’t need to be flashy to be nice to read. Glad you were able to move on.

  6. Candi*

    Congrats, OP!

    And yeah, depression just chews you up and spits you out some days. You might be in a position where you have perfect access to help, but you just can’t get the motivation going to get out of the house and go get it. On the flip side, you can get so involved with something it takes all the resources you have, and then the depression hits harder since you “failed” at what you were working at. It bites hard.

    You didn’t fail, OP. You just delayed your success a bit. I hope you have an awesome life.

  7. awesome3*

    “provided me with a vocabulary and labor-rights tool set I didn’t know existed”

    What an amazing way to phrase this. I’ve found that part of reading this website so valuable as well

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