update: my boss makes me wear her clothes, eat her food, and say I’m grateful for my job

by Alison Green on December 22, 2022

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.

Remember the letter-writer whose boss made her wear the boss’s clothes, eat the boss’s food, and say she was grateful for her job? The first update was here, and here’s the latest.

Last I sent, I had just quit my job with the horrible boss in order to pursue freelance gigs. I’d been having enough freelance success while employed that I thought I could resign, achieve my Adobe certification within 3 months, and hit the ground running for a new job. That was early 2020 so… as my plan did not anticipate a pandemic, it didn’t quite shake out the way I’d hoped.

I limped on through 2020/2021, surviving on freelance work and a very lucrative translating opportunity that fell into my lap. (Think Latin or Ancient Greek, which I studied in college.) However, as much as I loved being a freelancer, with the ability to set my own schedule and allow myself to travel, I started to get nervous about the impending end of my translation gig. I definitely needed to up my freelance work intake or find gainful employment elsewhere. Also, I went back to assist Horrible Boss a few times, and kept in touch over email, but as the pandemic progressed my mental health took a downward turn, so I cut her off. Probably the best decision I’ve ever made.

So, I had settled on applying to full time jobs. I brushed up my resume (with help from your site) and started looking. I was actually about to email you separately about how to list a job in which you don’t want the recruiter to contact your former employer. I have plenty of wonderful freelance clients, who I have asked to give me references and they’ve all enthusiastically agreed. However, I was worried about the stealth reference check and I want to ensure my former boss is not contacted. I did not want to leave the job with Horrible Boss completely off my resume, because it showed some discernible progress in my skills, proves I can work in an office environment, etc. However, months before I quit that job, Boss told me (almost gleefully) about how she torpedoed a former employee’s next job reference. (For what it’s worth, the former employee was a college intern who was expected to work the day after Christmas. When the employee said no and quit, Boss trashed her on every reference call she received. Which, as I said, was a tale she almost told me giddily. I understand sometimes employees need to work holidays but… her reaction seems Dickesian Villanesque.)

Well, I was in the midst of contemplating this quandary when my partner was able to purchase a house! (Yay!). I’d done some real estate photography editing previously, but never shot it myself, so I asked my partner if I could go use his house as practice. Partner called his agent, the agent asked for my number and called me 10 minutes later. Apparently the agent had been doing all the photography for the firm but was a.) sick of it and b.). about to leave on his honeymoon for a month, so they needed someone fast.

So yeah, I did a test run with them, they loved my work, and now I’m a contract employee for their real estate firm. Honestly, the best of both worlds for me! I’m getting enough shoots a week to alleviate financial anxiety, but still maintaining enough flexibility to manage my time how I like. I didn’t realize work like this was possible. Even if it wasn’t, I had multiple relatives/friends comment on how after I quit that job my general attitude seemed significantly improved, and I FEEL it too. Thank you so much Alison to you and your readers for making it clear how NOT normal that job was, how I could and should deserve better, and should not put up with being treated like that. (Also, I ran the numbers from my tax returns, and for all Boss’s pontifications about how great a job that was, I still made way less money than I did bartending.)

I still wish old Boss the best, just glad I’m not involved in her life orbit anymore.

Once again thank you and your readers. Would never have the courage to leave that situation without your support.

You may also like:
{ 38 comments }

{ 38 comments… read them below }

    1. A Simple Narwhal*

      Yea, I’m hoping that whenever oldboss washes her hands she always gets her shirt wet no matter how careful she is, but super happy for OP!

    3. Slow Gin Lizz*

      Yeah, OldBoss doesn’t deserve the well-wishes at all. She deserves a penalty just for the tax issues and it’s too bad she can’t be jailed for being a terribly abusive human being because she deserves that too. OP, you are a saint for not feeling that way, and I’m SUPER pleased for you with how you got your photography gig, that’s awesome!

      1. Marna Nightingale*

        As my wife likes to say in situations like this, I wish her healing.
        Which sound quite kindly until you think about what the path from where she is now to there would look like…

  3. goddessoftransitory*

    Yay you! And frankly you are more generous than I would be towards your old boss; but she’s got to live with herself and all the debris she generates, so…yay you!

    4. WoodswomanWrites*

      I’m wondering about that, too. OP, if you haven’t contacted the IRS about the illegal 1099 set-up, I hope you will do so because you will likely get a hefty amount of money returned to you. You were an employee.

    5. Slow Gin Lizz*

      I also want to know this! Still not too late, OP, to go after her with the IRS if you haven’t already!

  5. Paris Geller*

    If you’re reading the comments OP-did anything happen with the tax situation? In the first update you were planning on reporting her to the IRS for the incorrect classification & I’d love to know if there’s an update there!

  6. A. Tiskit & A. Taskit LLC*

    I’m VERY glad you got out of there before your “manager” (who doesn’t sound as if she could actually lead a kindergarten class into a candy store!) really warped your idea of what’s normal in the working world. Alison has often warned against the dangers of a toxic workplace environment doing just that; people can become so inured to abuse that they normalize and internalize it.

    Seriously…making you beg for you job after you’d landed in the hospital? Telling you what food to eat? Insisting that you wear her hand-me-down clothes? And acting as if a paid position was charity for which you should be groveling in gratitude? Any one of those is a red flag! All of them together is a red flag factory!

    1. Slow Gin Lizz*

      Not just a red flag, downright abusive. Like, if the boss were a parent and OP were her kid, the poor kid would be taken away by social services. Very sad. I really hope that boss doesn’t have actual children of her own but if she does I’m sure they have gone NC with her a long time ago.

  9. Sloanicota*

    Solidarity from someone else who made the big, well-considered jump into freelancing … right before the pandemic brought the world crashing down around us. Like you, I hobbled along and then eventually found a new job. I don’t regret my decision because setting my own schedule (and ironically, working from home) was something I really wanted to try but whoof, not the easiest way to try and break into a business :(

  11. E*

    Yay! Great news all around. Yes, on top of all your boss’s unique shenanigans, you were getting the classic bad boss move — terrible pay! $35K in NYC even in 2019 was not a living wage

    1. Giant Kitty*

      I gasped at that. I live in a high cost of living area that is NOT as expensive as NY, and 35k is just over minimum wage here- NOT a living wage for darn sure. Terrible Boss is out of her gourd to think she’s paying generous wages.

    1. Giant Kitty*

      Right? I’m used to being around people with little money- who are nearly all generous to a fault.

  15. Empress Matilda*

    Oh, OP – thank you so much for writing in! Your old boss is truly one of the worst people in the world (and in fact came in 3rd for AAM’s worst boss of the year for 2019.) I’m very glad to hear that you’re out of that office, and you’ve got a great job that you love. You deserve every bit of this good fortune right now.

    All the best in 2023!

    1. ferrina*

      Yes! This boss was horrific! So glad OP is out of there and doing something she enjoys! (especially after having to fight through the last couple of years)

  17. Beth*

    Given how awful most real estate photos are, I bet that firm is incredibly lucky to have someone with a genuine eye for composition and visual design!

    Your ex-boss is a monster and I’m so glad you’re out of there!

    1. Hen in a Windstorm*

      Yeah, I don’t want to imply OP isn’t talented, but it’s a low bar to clear for a lot of them. I’m always thrilled when they actually show the interior, instead of say, a close up of a fancy candle stand on a side table. Or just a single photo of the front from the street.

  18. Keats*

    Hey OP! I stayed in a toxic job to achieve some publishing goals as well, so I completely get why you stayed. Having those physical products to reference is a huge CV booster. I’m so happy you got it and found your bliss! Your old boss sounds like an entitled, deeply unpleasant loon. It speaks to your character that you’re able to be so generous.

    Best of luck! Please report her to the IRS, I doubt this is the only dodgy tax situation she’s involved with.

  19. Calyx*

    In addition to the IRS, I’d recommend talking to an employment lawyer to get advice about your options re references. If possible, you don’t want it hanging over your head that she might lie and gleefully “torpedo” your future jobs. IANAL in any way whatsoever, but I do know employment lawyers can provide useful advice. There might be some option for getting her to agree what to say; or advice for what to do if she says something false.

Comments are closed.