update: should I stay at a job I don’t like if it could lead to a big pay-off in a few years?

by Alison Green on December 20, 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 wondered whether to stay at a job she didn’t like if it could lead to a big pay-off in a few years? Here’s the update.

I left my old company and started my new job in early September 2021. I absolutely LOVE the new job and have from day one. My work is interesting, I’m constantly learning new things, my boss and the rest of the team are amazing. The company really appreciates their employees and shows it with regular bonuses, raises and opportunities for career growth. In the year I’ve been here I’ve received two raises and two bonuses with the expectation of probably one more of each before year end based on normal company timelines.

As for my old company, that’s a whole different story. I stayed part time with dramatically reduced hours and about half my old pay until December 2021 when my replacement, Elsa, started. I answered a few one off questions for either her or my old boss, Hans, until mid March 2022. Hans then reached out and told me Elsa wasn’t working out and asked if I would come back part time again. While thinking it over (because I’m greedy lol) Elsa quit. I did end up agreeing to come back part time with the agreement that it would be short term and I’d come back about for about $20k/yr more than what I was making previously.

Then the founder and CEO of the company was fired by the board in April and the CTO resigned in May. That left Hans covering as both CEO and CFO while searching for replacements, meaning finding a new accountant was the last thing on his list. The new CEO, Olaf, started in June/July and Hans found my next replacement, Anna, who started in September. She lasted less than two weeks before she quit. I wasn’t even fully off the payroll yet! So I stayed again to help Hans even though it was even more dysfunctional than ever. At one point, in October I think, he tested out a part time accountant on a contract basis but that only lasted 2-3 weeks before Hans let him go.

It’s now December. Olaf was fired by the board for gross misconduct. Hans finally got sick of working 18 hour days, took my advice and found a new job (not another startup) starting mid January. As far as I’m aware he hasn’t told anyone other than me yet. The company is almost out of money so they’ve laid off 6 people, cut the salaries of everyone else by anywhere from 30-70% and if they don’t raise money before the end of the year they’ll go bankrupt in January. Definitely glad my horse isn’t hitched to that wagon anymore! Just waiting it out to see what happens and when I can hand over the job for good but Hans is well aware that I’m done immediately if I’m not being paid.

Overall I’m very happy that I left. I’m appreciated at my new job and I’m happy to wake up and go to work every day. That’s life changing! I like the company so much I got my 21 year old daughter a job there over the summer and she’s now full time. Thank you to everyone who commented on my original letter. I realized that I wasn’t being smart about how much money I “could” make, that the amount wasn’t even as large as my brain was trying to tell me it was and I was potentially ignoring the very real increase I would get by leaving. Honestly, due to coming back part time for most of the last year, we’ve been able to save a lot of it towards a house so I’m better off now than I would have been otherwise. In some ways I am still waiting for someone to yank the rug out from under me but I’m happier than I’ve ever been both professionally and personally. That’s not something I’m used to and I don’t know that I would have made the same decision without writing in and hearing everyone’s advice. Thank you so much!

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{ 24 comments }

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  1. Anonymous Llama*

    Allison was right – staying was a big gamble, and it would NOT have paid off! OP, I’m glad you got out of there and into a more stable position that has you so fulfilled.

  3. Critical Rolls*

    The best of both worlds — a great new job, and a profitable, low-commitment side project with a generous schadenfreude benefit. Well played.

    1. Twenty Points for the Copier*

      Yes, I also imagine if they’re paying her a high consulting rate for a few hours a week, it’s actually for the core accounting work instead of the side tasks that were taking over the FT position.

    2. ferrina*

      It must be so nice to know that you can walk away from that circus at any time, but still be close enough to watch the karma unfold. So, so glad LW decided to move on!

  4. Michelle Smith*

    No amount of money is worth your mental health and the instability that comes with a dysfunctional workplace. Even without the update that the company is going bankrupt, I would have said you made the right choice. I’m super happy for you!!

  5. fhrhh*

    20k + half their old salary for 4-5 hours a week for mostly HR work sounds like the most incredible deal in the world to me. Like to the point where I feel like I must be grossly misunderstanding something. I wouldn’t even bother with the other full time job at that point lol.

    1. fhrhh*

      I realized that this comment may seem jerk-ish and like I’m undervaluing OP so I want to add that I work in a very different field and have no idea what is normal for that kind of job.

      1. Eyes Kiwami*

        No, that does seem like a lot of money for very part time HR work for a small number of employees! Maybe OP was very underpaid before, or maybe OP is very capable that they can get it done in only 4-5 hours but it’s actually a lot more.

        1. Mid*

          If I’m doing the math right, $20k on top of the previous salary would be an extra $80/hour on top of the previous rate, assuming 5 hours a week and 50 weeks in a year.

          But considering they kept hemorrhaging people, and none of the replacements lasted a month, it was probably necessary to keep the company even slightly functioning.

          Good for OP!

          1. Diane Lockhart*

            I got the sense that it was a pro-rated 20k, not a hard 20k. So if the old salary was 80k, this would be a salary of 40k (50% of 80) plus 20k (retention amount) for 60k a year. But since it was explicitly short term, it would be that 60k over like 6 weeks or so, so that’s maybe $7,500. Certainly not enough to quit another job over in a HCOL city.

            Now, OP came back a few times, so maybe they earned in the 5 figures, but it’s not going to pay their rent for more than a few months.

      2. Cthulhu's Librarian*

        I didn’t think it was jerk-ish, but rather represented a view point that a lot of people could benefit from hearing. Particularly the part at the end about not bothering with the other full time job – mainly so that they could be aware of the thing that logic glosses over, and the potential fallout.

        From what the OP says in their update, it seems like there was a LOT of issues at the company – paying exorbitant rates for contractors while having major crises elsewhere in the business would be another symptom of mismanagement. When you encounter a situation like that, it is vital to question how much you believe the company is a long term proposition – will that cash flow still be there in a month? what about two? how about a year? If they’re willing to pay you a ridiculous rate because they can’t keep anyone else in a business critical role, are they healthy enough that they’ll survive this period? Or are they on the cusp of failing, and pouring the last little bit of capital they have into magical thinking about one or more areas of their business?

        A lot of people running startups and personal businesses have massive emotional investments in the dream of it working out, and they keep pumping capital in while thinking if they can just make it one more quarter, there will be a turn around… when in reality, they should have stopped operations. Then there’s the sunk cost fallacy that starts to take in – they’ve spent so much and tried so hard, how could they give up now? Success is right around the corner!

        If you ever encounter a business playing ludicrous rates for common business operations, because they can’t retain a permanent employee in those roles? It should be a red flag not to tie yourself to them too tightly. Something is wrong.

  6. Certaintroublemaker*

    It’s surprisingly hard to change what you’ve planned to be your set course and leave the devil you know. So happy you made this break, OP!

  7. Uhhhh*

    Op did right. In my experience promises of large increases or bonuses are always manipulation tactic. I’m sure it has happened but I’ve never seen it. Whenever I have gotten promotions or raises, it was never held as a carrot, it just happened with no build up. They just called me in and said “we’ve noticed your work and I’m pleased to let you know you’re getting a raise of x amount to show our appreciation and it goes into effect y day”

    1. Like your job or leave*

      A manipulation tactic isn’t inherently bad. Once, my partner was offered a $20,000 bonus (I’ve adjusted for inflation) if he’d stay another 6 months. It was quid pro quo arrangement and it worked out fine for both parties. He completed the product that they wanted before finding another job.

  8. MechE31*

    I was in a spot similar to you around 10 years ago. I stayed at a startup for ~2 years and had a 5 year full vest on my equity. I couldn’t take it after 2 years and was contemplating quitting and losing out on 60% of my equity. I had a very hard time actually stepping away when the decision was made for me. I should’ve done it sooner.

    My startup is highly successful and I still have some of the equity and it has ballooned to a semi-life changing amount (it moves my retirement up by ~5 years). It’s hard not to think about how different my life would’ve been if I could’ve made it the full 5 years. If I had made it the full 5 years, the only certainty is that I would’ve been divorced and my only identity would’ve been work.

    I see my old friends who still work there beat up and lonely. Many of them blew the money on cars or constant crazy trips or the like along the way (when it was real money but not life changing). Money can’t buy happiness and I know I made the right choice (even if I didn’t make it).

  9. Like your job or leave*

    I would never recommend staying at a start-up in hopes of getting a big payout, when the job is miserable.

    Over long careers in tech, my partner and I have worked for about 10 startups. One went belly-up, others were acquired, some stayed private and small indefinitely, and one went public. We didn’t get any money from stock options in some of them, and nominal amounts from others. We never got “can quit working!” money.

    One payout was “pay off student loans with enough left over for a house downpayment” size. This arrived after working at that company for 10 years. We only had that much stock by being a very, very early employee.

    The thing is, a similar amount of money came through 2 years worth of stock options at a huge company. Startups are not the only path to a useful amount of money, just the riskiest. ;-)

  10. Here for the Insurance*

    Good update, but I want to comment on one thing that made me go hmmm.

    OP, near the end you say “Just waiting it out to see what happens and when I can hand over the job for good”. I’m sure you know this but I figure it’s worth saying it anyway: you can hand over the job for good whenever *you* want to. You don’t need their agreement or permission, or for it to be okay for them. Even if they weren’t going down in flames.

    1. Mad Harry Crewe*

      +5 to this.

      OP, I’m very glad you made the call you did. You can get out whenever you’re ready to, even if they aren’t ready for you to go.

  11. Agua Caliente*

    “the founder and CEO of the company was fired by the board in April ”

    I’m completely at a loss about how a tiny startup based on the “genius founder”‘s tech idea thought they were going to continue after firing him. (I mean, it might be the right move, but I think it means 90% chance the company goes under)

    1. AbruptPenguin*

      And now they’ve fired a second CEO! I’m very doubtful they’ll raise enough funding to keep the doors open. Good for OP for getting out when the getting was good.

  13. Another person at a startup*

    OP, another thing you could have and maybe even still leverage is getting equity (or having vesting accelerated) if the tech is promising. Even if the company is going under as it is, there is a possibility that there’s an exit that might still prove lucrative for you if they get acquired.

  14. lilyp*

    I think this is my favorite update of the year! I’m so glad you reached out for advice and did not stay. Too often startups dangle the possibility/fantasy of a life-changing payout as a way to tempt people into staying underpaid, overworked, and underappreciated for years, and I think people without a lot of industry experience and/or financial education sometimes don’t know how to evaluate the cost/benefit analysis and end up getting screwed over.

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