was I wrong to quit my job?

by Alison Green on February 22, 2022

A reader writes:

I’m wondering if what I’m feeling about my resignation is normal, and how I can best position myself to still start my new role with confidence despite my fears.

I gave notice at my job last week. My company is extremely small for our industry compared to the one I am going to (think: tech startup vs Apple). I did really well in the role and my boss’s feedback became increasingly geared towards my taking her job in the future. But I was miserable for so much of my time there. Our workload was immense and there was constant pressure to be perfect, particularly because I worked with our company owners every day. I always doubted myself , even when I was told I was doing great, because it was so easy to make mistakes (especially as my boss isn’t the most effective manager, which is another letter entirely). Every other member of my team was either on a performance improvement plan, just off of one, or fired for poor performance. It felt like being a living wife of Henry VIII; I never knew if it was skill or luck that saved my head.

At the new job I accepted, I’ll be working on more complex projects and will have more flexibility, better internal standards, and a much higher salary. Of course, I knew there would be potential downsides, too. I will be one of many on a huge team (which I wanted after my most recent experience), and working for a large public company comes with higher risks than my small but stable employer. I’ll be starting from scratch building relationships with colleagues who live both locally and abroad. It is a big step, but I thought that I had weighed every pro and con before reaching my decision.

But now that I’m in my notice period, I feel like I’m always ten seconds away from calling my boss and saying, “Never mind! I want to stay!” I know at least some of this comes from nerves over making a big change, and I still suffer from a lot of the self-doubt that characterized my time in my current role. But some of it has to do with what has happened since I gave my notice:

* My boss has begun making offhand comments that make me doubt my decision like, “I would never work for a company that big,” “You should know we’ll be going into a second Great Depression so layoffs are coming,” and “You were my choice to replace me so I guess I’ll be sticking around for a while.”

* I received a heartfelt email from our company owner explaining that they don’t want to lose me. We also had a call where she shared the downsides of working for companies like the one I am going to and the perks of working for a small organization that “takes care of their people.” She said that losing me was an “unfathomable” loss for the company and that I should call her directly if I want to come back at any point.

* My old employer made me a counteroffer for about half the salary increase I’m getting in my new role, along with some other perks. While this was tempting given the conversations above, I opted not to accept because I couldn’t say for sure I wouldn’t want to leave again in a couple of months, and I’d rather keep this bridge intact than burn it by quitting a second time later.

There are other reasons for my nerves, too. I’m seeing articles about regrets over the Great Resignation, boomerang employees, etc. On top of the many great reviews of my new company, there are bad ones too. And I’ll miss the colleagues, work, and opportunities at my old job.

At this stage, my decision is final and there isn’t really any point to agonizing over it any more. So why am I? And how can I move past it so I’m not carrying this worry into my new job with me?

It’s so, so normal to second-guess your decision to leave a job. Of all the things people write me, “Should I quit my job?” is the single most common. “I feel too guilty to quit my job” is the second most common. (And just as an interesting point of trivia, the next most common is “I want to tell someone to stop doing X, but I’m afraid of making things awkward.”)

Even without the comments your boss and the company owner have been making, it wouldn’t be surprising for you to second-guess your decision. When you’ve been working somewhere for a while, it becomes comfortable. Even when you have good reasons to quit, it’s nerve-wracking to leave a situation where you know everyone, they know you, and you’ve learned how to get things done in a specific environment. Most people have anxiety about starting a new position: You can’t be sure exactly what kind of culture or team you’re walking into, you’ll have to establish your reputation all over again, and the details of the work may be unfamiliar. It’s legitimately unnerving.

Then throw in the commentary you’re hearing from your boss and the company owner, and it’s no wonder you’re questioning yourself. Those remarks, by the way, might not be purposely designed to undermine your confidence in your decision — but they sure sound like it. What exactly is your boss’s goal in saying things like “I would never work for a company that big” and “I guess I’ll have to stick around now,” if not to make you worry and feel guilty? Please see those for what they are: Your boss flailing at losing you and possibly lashing out as a result. Don’t give credence to input that clearly isn’t coming from a constructive place. (You mentioned that your boss isn’t a good manager, and it’s really showing here.)

As for the company owner’s regrets at not keeping you … well, if it’s such an “unfathomable loss” for the organization, the time for it to offer you a higher salary and other perks was before it had already lost you. If she was able to offer you that raise once you were leaving, she was able to offer it to you earlier, too; she just chose not to because she didn’t think she needed to. She’s trying to dress that up as flattery and appreciation now, but the timing speaks for itself.

The thing to remember is this: You started looking at other jobs for a reason. That reason is what’s driving that voice in your head now, telling you not to accept your company’s counteroffer. Because, as you say, you might want to leave again in a few months. You were miserable for much of your time in this job! Your workload was overwhelming, the pressure to be perfect was unrealistic, your manager was incompetent, and literally every other member of your team was fired or threatened with being fired (leading, no doubt, to your own job always feeling precarious as well).

You’ve traded all that for better work, more flexibility, and higher pay. And yes, there inevitably will be downsides you haven’t foreseen, because that happens with all jobs. But you carefully weighed the pros and cons and made what sounds like a smart decision based on all the information available. Don’t let a combination of very normal nerves and management undermining you make you doubt yourself now.

Originally published at New York Magazine.

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{ 196 comments }

{ 196 comments… read them below }

  1. Bookworm*

    Thanks for asking this question, OP. I’ve been there. I left my last job for the one that I’m at now for somewhat similar reasons (I liked my immediate team but the work was dull and there were office politics that leadership simply refused to address) and it’s relatable. It’s okay and perfectly normal to doubt. You’re going into a new thing and it’s ‘new kid in school’ sort of deal and so the nerves are understandable. I think Alison’s answer is pretty much on the money. You looked for and applied for other jobs for reasons. Maybe this new one won’t be perfect but it sounds like on paper that it’s a better fit for you. That’s important.

    Good luck!!

    1. Cookies for Breakfast*

      Bookworm’s comment is spot-on, as is Alison’s advice. The one thing I’d add (as someone who was in a similar place quite recently) is to remind yourself of what you said about your counteroffer:

      “I opted not to accept because I couldn’t say for sure I wouldn’t want to leave again in a couple of months”

      Turning it down for this reason made complete sense. In a similar way, imagine you did call your boss to say you’ve changed your mind: would you confidently see yourself staying for longer than a few months, and could you put thoughts of leaving completely out of your head? Judging from the rest of your letter, the answer is probably no, and so it keeps making sense to go through with your decision to change.

      I hope there’s lots to be excited about in your new role, and that you’ll look back to this, in a few months’ time, feeling even more confident that you’ve made the right move. Wishing you all the best!

      1. fantomina*

        I was also recently in that place– I left a little over a year ago with a lot of trepidation. They’re only now rehiring for my role, and out of curiosity I’ve been looking up past coworkers to see how they’re doing. Several major key players who made my job livable have left over the last year.

        If half of your coworkers are on PIPs, it’s safe to assume that some of them will be fired, and that others will leave because that precarity is too stressful.

        1. movingonup*

          OP, this was me almost exactly! I left a small, stable company (like, 30 people max) where I had huge capital and major influence to join a company of 60k+ employees. During my notice period, the owner took me to lunch and offered me a huge raise, title, and management opportunity to stay. He also told me I would get “stuck in the middle” of the huge company, whereas if I stayed with him, I’d be at the top. I agonized over it for several days before I was reminded that a good person would want to support my growth, not make me fearful of it. Moving to the new company took a lot of adjusting, but I’m now in exactly the role I was seeking for myself, I’m making even more than that previous offer would have been, and I work far few hours with much less stress than I would be otherwise. Essentially, I knew my own goals and values and stuck to them, and now I’m reaping the rewards. It is totally normal to second-guess yourself, so give yourself the grace to feel those awkward feelings–they won’t last! And good luck at the new job!

          1. Fran Fine*

            I was reminded that a good person would want to support my growth, not make me fearful of it.

            This. The fact that OP’s manager keeps Doomsday Prophesying all over this opportunity lets me know exactly the kind of person, and manager, she is.

            OP, you’re doing the right thing by leaving. Even if this new place doesn’t end up being your forever job, it’s still taking you out of the orbit of someone extremely petty, and for that, you should be grateful.

    2. New Mom*

      Yes thanks for asking this. I think a lot of people struggle with this and stay in jobs they don’t like/don’t pay them enough/hold them back for these very reasons. I really hate being new at work, and so does my husband. We’ve both been at our companies for years and have built up relationships and sort of know what to expect. I get really frustrated sometimes at my job and dream of leaving but then I get all the doubt that the OP mentioned. I worry about starting over from scratch, or not having the specific perks that I get at my current job. I’d also really miss the people. It’s hard to know. I think we both fall for the “better the devil you know” fallacy.

      For me in particular, a close family member left a secure job with benefits when they were 50 for a “dream job” that ended up laying them off a year later. My family member was never able to get another full-time job in their competitive and sought after field and brings it up regularly as a huge regret of theirs especially now that they are in their 70s and would have had a great pension had they stayed at the stable job. And I guess I’m sort of worried about history repeating itself?

      1. SofiaDeo*

        Unless the “dream job” is in a similar size company, with similar income stream and income source(s), with similar management strategies, similar products, essentially the same everything….I don’t think anyone really could say history could or would repeat itself. Do you know for a fact the old job didn’t lay off anyone? Unless your family member left a union/government job with strict rules regarding the ability to lay people off into a different employment situation, how can they be sure they would have been kept on at the “stable” job? Especially if non-union, non-government management could change and fire people for whatever reason? I don’t think American companies, at least, have demonstrated any “employee loyalty” for decades and decades. Unless the person was willing to be overworked and underpaid.

        Change is always difficult, and there are pros & cons to every decision. But for LW in particular, it sounds like getting out of the toxic situation is worth the anxiety and stress inherent to major life changes! Not sure what to recommend for this totally normal anxiety in these incredibly stressful times.

        1. Candi*

          In OP’s specific case, I’d recommend they repeat to themselves that the manager and owner of this company do not have the OP’s best interests in mind.

          They need OP to stay as a brace in their company, or they wouldn’t be pulling this crap. (Plus the manager sounds petty.)

          They need OP. OP does not need them.

    3. tenfour*

      On the chance that OP comes here: I am one month out from quitting a job with a small firm where I was “indispensable” and starting a new job for double the pay, at a huge company, in a far more complex role. It is SO HARD! And I’m NOT SORRY!

      A few things that have helped me to think about:
      + Worst case scenario? I don’t do well. And then I look for a new job, but now I’ve got a big name on my resume and a lot more knowledge and skill
      + Best case scenario? I wind up really liking what I’m doing and succeed.
      + No matter what scenario? I’m getting paid a lot of money to learn new hard and soft skills, and to learn more about what kind of jobs I prefer to work

      You might check out a book called The First 90 Days, by Watkins. I got a copy at the library, and it really helped me through the first panic spiral of me feeling like a dummy at work!

      I’m definitely still having up and down days, but I’m pretty sure that I will wind up really liking this job and doing really well with it. I bet you will too! And no matter what happens, good on you for extracting yourself from a company that doesn’t sound well run.

  2. HelloHello*

    Just to point out, your current employer has half your coworkers on PIPs or fired, and somehow believes their company is “more stable” than your new larger company? Don’t believe them, and look forward to a job where you’re not terrified you’re going to be fired every day.

    1. Ashloo*

      I did a double take at that sentence too. Literally the opposite of stability! And a large company will likely weather a prophesied depression better due to their size. Don’t let your previous workplace gaslight you, OP. They can’t match the new salary and they’re trying to poison the well? Pass.

        1. Tired social worker*

          I’d say Catherine of Aragon is next best in this particular situation. She ended up dodging a bullet (axe?) even if she didn’t see it that way, but Catherine Parr would be stuck with the company until it went under.

          1. Salymander*

            Yeah, plus Catherine Parr’s next “company” was a dud too.

            Anne of Cleves won the Ex Wives of Henry VIII Lottery of Doom for sure. Be Anne of Cleves.

    3. Artemesia*

      And it wouldn’t be the first time if the boss kept you on at the higher salary for a few months while she searched for your replacement at her leisure, then canned you. You are leaving because the job itself was wearing you down; why would you want to go back to that? The new job is an unknown of course — but I’m betting whatever downsides emerge, they will not be as ugly as a boss who is running off her employees, doesn’t reward her high producer until she gives notice and a workplace where you feel constantly overwhelmed and stressed.

      Sounds like you made a smart move no matter how it plays out over time.

    4. Chauncy Gardener*

      THIS!! This is not a stable company. This is not a stable management team. You have been miserable. They have beaten you down so much that you aren’t sure what’s good anymore. Please leave this godforsaken place and read all of AAM’s advice on recovering from toxic workplaces because sweetie, you’re in one.
      Good luck!

    5. Magenta Sky*

      Indeed. If everybody else is the problem except the boss, it’s not everyone else that’s the problem. Either the standards are impossibly, unrealistically high, or the company has no clue how to hire. Or both.

      The comments about what a bad idea leaving is are intended to manipulate the letter writer into staying in what sounds like a fairly toxic workplace, and those comments *are* *among* *the* *things* *that* *make* *it* *toxic*.

      And there’s always the conventional wisdom – never accept the counteroffer. (Especially when it’s not better than the outside offer.) Counteroffers are mainly a chance for them to dump you at *their* convenience, rather than lose you at yours.

      3. SarahKay*

        Seconding hard about the comments being one of the toxic issues.
        OP, I’m in the process of leaving my current role to go to a new site in a different city. I’m leaving a site I’ve been at for 10+ years with a team I love, but this is a good opportunity both personally and professionally. I too am having second thoughts, or perhaps more accurately regrets; it’s tough leaving somewhere I’ve been for years, where I’m comfortable, appreciated and respected.
        Here’s the difference: my boss congratulated me. He said how sorry he’d be to lose me, but that it’s a great opportunity and I would be a huge asset to my new team. Not once has he tried to guilt-trip me, or to bad-mouth my choice of new workplace. He announced it to the rest of the team as a well-deserved new opportunity for me. (Also, when he told the rest of the team he did it as part of a normal meeting and not at a short-notice 8am call…. just saying!)
        Your boss is trying to manipulate you into making their life easier, while not giving a damn about what is right for you.

        1. Glorial*

          Yes, this! They didn’t adequately value you whilst you were employed and are now making ridiculous statements and scaremongering. This isn’t about valuing you now, it’s about trying to make their own lives easier!

      4. Blue Horizon*

        Well put. Constant little passive-aggressive comments designed to dent your confidence and make you doubt your decision are NOT normal in this situation. Normal is some variant of “We’ll be really sorry to lose you but it sounds like a great opportunity and we wish you the best.” Even if they don’t really mean it, it’s basic professional good manners to say it – just like you might say “it was time for a change of direction” when you really meant “the place was a toxic dumpster fire and I couldn’t get out fast enough.”

        This is not a workplace that is operating according to generally accepted norms of professionalism – as if your “living wife of Henry VIII” comparison wasn’t a clue (great analogy, by the way!)

      5. londonedit*

        Yep – you just know that the minute OP accepted the counteroffer and stayed, the dysfunctional management would start with the ‘Well I don’t think we should give you that project seeing as you’re a *flight risk*’ and ‘How dare you ask for a day off, after everything we’ve done to keep you at this company’ and ‘You can’t have that promotion/more responsibility until you’ve proved we can trust you not to threaten to leave again’ etc etc.

    6. Sedna*

      Yes! That was astounding. You know the saying about how if you run into a jerk once, you ran into a jerk, but if you run into jerks all day, you’re the jerk? That really applies with your current employer. A few people on PIPs or fired is normal; if /half your employees/ are in that situation, the problem’s with the company.

      1. MissBaudelaire*

        This was what I thought. If everyone is on PIPs/coming off PIPs/being fired… golly, seems like it probably isn’t the employees.

        OP, of that company valued you as much as they’re claiming, they would have been checking in to make sure you were happy all along. If it was so unfathomable to lose you, they would have taken steps to prevent that. Closing the barn door after the horse has already run to a different farm isn’t going to help.

    7. Raboot*

      Right? Like in general, the claim that “working for a large public company comes with higher risks than my small but stable employer” is already sus – large employers are definitely more stable as a rule. But especially when it comes to this specific small company, “stable” is definitely not accurate.

      1. MissBaudelaire*

        I was wondering what that was even supposed to mean in this context. Looks after their people? When? Looks after the back of them after they’re fired?

    9. DJ Abbott*

      Yes, I was coming to say this. A company that has most of it employees on a PIP or fired is not good or stable and I’d be trying to get out ASAP. I’ve never had the kind of luck where I was the favorite and everyone else were the bad guys, I would be on your manager’s bad list. It’s only a matter of time before they come for you. Just because you haven’t been put on a PIP yet doesn’t mean you won’t in the future. Get out while you can!

      1. Fran Fine*

        I’ve never had the kind of luck where I was the favorite and everyone else were the bad guys, I would be on your manager’s bad list. It’s only a matter of time before they come for you.

        I can confirm because this happened many years ago to me. I was my manager’s heir apparent and was virtually untouchable – until, that is, I decided to try for a position in communications (and I even asked for her permission first – she told me to go for it). From that point forward, she nitpicked everything I did and tried a time or two to embarrass me in front of my teammates. It was so obvious what she was doing, one of my coworkers asked me what happened. He said, “She’s now treating you like Sally.” Sally was a coworker my manager ALWAYS talked down to and undermined.

        I ended up being promoted into another division, but I had to deal with a few months of that nonsense. It was one of the longest and most infuriating periods of my life.

    10. Gary Patterson's Cat*

      Yeah, no kidding. I’d take a chance on the possibility of Big Company layoffs over living in fear of a punitive owner anytime.

    11. nnn*

      That’s what jumped out at me too. Your current employer does not seem stable to me at all.

      Added to that, I don’t see how working for a large employer can come with higher risks than working for a small employer. My own experience has been that, in times of instability, large employers have the leeway to shift people and work around rather than having to downsize.

      Also, large employers have more leeway to provide things like paid sick leave, because it’s trivial to redistribute 1% of your work to the 100 other people doing your function, whereas a small employer where you’re the only one doing that function would have no choice but to hire someone to replace you.

      (Of course, large employers don’t always actually do this, but they have the resources and leeway to do so if they choose.)

      1. Candi*

        I’ve noticed that some of large companies that have failed since 2000 were ones where upper management repeatedly and actively undermined the company in their search for more profits, refusing to comprehend the reality of what consumers want, subscribing to theoretical models instead of practical logistics, and refusing to change processes that weren’t working. (Among many, many other things all adding on and cascading.) Even where someone realized things were going downhill and managed to get to where they could do something, it was too little, too late.

        They didn’t fail because they were big; they failed because they became too damaged to stand.

      2. Bryce with a Y*

        Spot on.

        It has been said here before, but bears repeating: There are certain problems that seem to be endemic among smaller organizations, particularly “family owned” organizations.

        First, they aren’t as well equipped with the resources, tools, talent, and know-how as larger organizations when it comes to all things HR and people management. This may be a function of several things, including the fact that the people who handle such functions aren’t all that versed in management best practices. Larger organizations have the resources to invest in things like management training, skilled HR talent, etc.

        Next, many smaller organizations, particularly those that are “family owned,” are such that when push comes to shove, no one can really overrule the owners, even when the owners are making obviously wrong moves. I have worked in organizations where, for example, the boss said, “we just can’t afford to hire extra help right now” and then the boss’ second cousin gets hired as a “director of special projects” who doesn’t seem to really do much of anything. This may be because the owners often don’t have an objective perspective on their organization; in other words, it’s not just a job.

        And in the case of all those PIPs, it seems that they’re being used improperly as a way not to help employees improve, but as a way to justify getting rid of people and possibly to deny them any severance or unemployment benefits, as well as cover their assets by saying, “Joe wasn’t performing well.” That’s but one example of failing to follow HR and people management best practices.

        That’s my 2 ¢.

    14. Beth*

      This is my thought too. OP, it sounds to me like your management is either delusional about your current company (no one would describe an environment like this as a ‘stable’ workplace that ‘takes care of their people’!) or simply trying to scare and/or guilt-trip you into staying. Either way, their comments aren’t worth your attention.

    15. Koalafied*

      I went from a small organization to a large one and have no regrets whatsoever. I’ve been here a decade, long enough to fully appreciate the downsides in terms of how strong the headwinds against change are and how slow decision-making can be, but those are small prices I’m more than willing to pay for having an HR department, clearly defined rules and processes for 98% of the situations I encounter, and a big enough budget that nobody bats an eye before approving a request for something that costs $1,000/year and will help me do my job better or even just with less tedium.

    16. Sleeve McQueen*

      Same. Even that point aside, I was trying to work on which planet working for the tech start-up is somehow more stable than working for the Apple. Because I know it’s not on my planet, Earth.

    17. Nanani*

      YSee it’s stable for the boss and owners. So it’s stable. Pay no attention to your actual colleagues. Total stability nothing to see here.

  3. Presea*

    That comment about the “second great depression” is so transparently manipulative that, as an outsider to the situation, I almost have to laugh to keep from crying. (Is your soon to be former manager promising job security in the event of such a severe economic collapse? I would think not!) It’s a good thing you’re getting away from folks who think saying things like that is okay, OP.

    1. Emotional Support Care’n*

      This right here.

      A smaller company isn’t going to ride out an economic crisis any better than a larger company, especially when half of the staff is constantly on a PIP, coming off of a PIP, or being let go because of managerial failings (you know, the very people promising you the stability they can’t guarantee).

    2. Annie E. Mouse*

      –(Is your soon to be former manager promising job security in the event of such a severe economic collapse? I would think not!)

      This is an important point. A smaller company is almost certainly less stable than the large Apple-like corporation. I started my career in small companies and now work for a behemoth, and have seen lay-offs and downturns all around. If a recession is coming, I’d rather be at the massive corporation. Your job is at risk either way, but Apple is not going to go out of business overnight, bounce your paycheck and leave you holding the bag with unreimbursed travel expenses.

      1. Snow Globe*

        Yes, with a large company, even when there are layoffs, they tend to provide decent severance packages and are less likely to challenge unemployment claims.

      2. DG*

        This was the most ridiculous part to me.

        Heck, even if American civilization as we know it underwent a complete Handmaid’s Tale-esque collapse, most of the Fortune 500 companies would remain in operation. Coca-Cola and Apple could literally outlast the US government.

          1. Koalafied*

            Or to quote a fast food kiosk in Indiocracy, “You are an unfit mother. Your children are now in the custody of Carl’s Jr.”

        2. Candi*

          That’s been the subject of some science fiction stories.

          The good endings are when the C-suite realizes they have to not be jerks anymore. They have humanity’s welfare on their hands.

          Not many have good endings.

    3. MK*

      That comment alone should be enough to convince the OP to leave this manager as soon as possible, it’s such a blatant attempt to scare them into staying. I would be very interested to know what qualifications this person has to pontificate about the future of the economy with such certainty.

      1. Candi*

        Especially since the Recession could have been as bad as the Depression -but thanks to the systems built since then, it wasn’t. We didn’t learn all we could from the Depression, but we learned enough to cushion the shock the next time around.

        It’ll be interesting to look back in twenty years to see what else we’ve learned.

    4. MCMonkeyBean*

      Seriously! OP, your boss is basically trying to brainwash you into staying–it is absolutely not true that moving to a larger public company is a “risky” move. Obviously there are large public companies that are risky and there are small companies that are stable, but I think *in general* it is basically the opposite of what your boss is telling you and the fact that 1) she is 100% trying to manipulate you and 2) it seems like it is working, means you need to get away from her.

  4. glitter writer*

    I’ve discovered that leaving a job you like has a lot in common, emotionally, with graduating high school or college. It can still be the right choice and the right time to move on, but it’s okay to miss what you’re leaving behind, too. And for that matter in a lot of sectors, industries, and locations, your career might involve boomeranging back or at least working with some of the same people again, so leaving on good terms and liking the folks is not a bad thing.

    1. Rainy*

      Yup. It’s breakup goggles in employment form, that’s all. Now that you’re leaving, OP, you’re seeing all the good things that you’ll miss. It’s normal, but not a good reason to abandon your plan, especially because it sounds like the new job is going to be a LOT better for your mental health and sense of stability, not to mention your bottom line.

      I am just aghast at the audacity of offering to raise you by only half what the new job will do, like that’s enough, not to mention doing it so casually, making it obvious, as Alison says, that they could have paid you more at any time, they just didn’t.

    2. Four lights*

      Yup. I get very nostalgic when I leave a job. Also, it suddenly feels nicer working there because most of the stress is gone, because there are a lot of things that are no longer going to be your problem or things you have to deal with.

      1. Selina Luna*

        I have one job that I’ve never gotten nostalgic about, but I’m frequently nostalgic about many of my other jobs.

    3. PT*

      There was an episode of How I Met Your Mother about the phenomenon of “graduation goggles,” where everyone suddenly gets attached to things they generally don’t care about, at the time they realize they won’t see anyone again. Like high school graduation, when people are like “OMG we’ll all be friends and visit each other all the time!” to people they didn’t even talk to regularly in high school.

      It is a pretty solid metaphor.

      1. MissBaudelaire*

        Like Lizzie McGuire. “Don’t ever change!” These people should, and hopefully do, change.

      2. Hollywood Handshake*

        I was looking to see if anyone else made the HIMYM “Graduation Goggles” connection. This is exactly what’s going on here. Watch that episode, OP, and go have a great experience with your new job. Don’t look back!

    4. GammaGirl1908*

      Agree.

      As I’ve noted in other forums, every time you make a choice of any kind, you’re giving something up. When you choose salmon for dinner, you’re giving up having chicken. When you choose to go to a party, you’re giving up staying in. When you choose to move to Denver, you’re giving up moving to Albuquerque. When you marry Jonathan, you give up marrying James.

      Even if you made a great choice, there likely will be good things about the other choice that you won’t experience. But you generally DO have to choose one, and it doesn’t mean anything is wrong with your choice just because you wonder about the road not taken.

      When you’re happy with your choice, you don’t generally dwell that much on the other options. You happily eat your salmon and you don’t think that much about the chicken that could have been. But now, when LW hasn’t yet begun experiencing the benefits of the new choice, she’s still mired in worrying about what she’s giving up.

  5. The cat’s ass*

    Your boss is gaslighting you. Resignation nerves are a thing and change is hard. I wish you the best in your new job and hope you update us all in about 6 months!

    1. HigherEdAdminista*

      Yup! A friend of mine was applying for jobs years ago when she got a decent sized raise from the company she was working for along with a glowing review about how happy they were with her work. Shortly afterwards, she got an offer for a salary a little above the raise and some other benefits she was looking for that her current company was never going to offer her.

      When she gave her notice they expressed their “genuine concern” about the stability of her leaving from one side of the business to the other. They guilted her about the raise and offered to scrounge up a little more money. They talked about how they had been counting on her to move up and they didn’t know who would take over now. She felt terrible, but she took the new job anyway, her life improved, and she went on to other things she wanted even more. Her first company? Still in business but nowhere near what it used to be!

    2. Classic Rando (she/her)*

      Seriously, less than halfway through this email I had to pause to say “holy emotional blackmail batman!” because wow. They’re trying to manipulate you into going against your best interests, don’t listen to them!

  6. Calvin B*

    Man, I literally wrote Alison this exact email today (with the exception that my current job has been very nice about me leaving). What is funny is that I can very clearly see that OP is just dealing with nerves, that the new job will almost certainly be a better fit, that the added pay will be great. But somehow that doesn’t make me any less nervous about my new job even though the exact same things apply there.

    Hopefully a month from now both OP and I are in a more relaxed place.

    1. Hlao-roo*

      I’m in a similar boat. I’m sad to be leaving my current company because I like all of my coworkers (and they have all been very nice about me leaving). I’m nervous to start my new job, because I’ll have to learn a whole new office environment. But I know why I started looking for a new job in the first place, and I am holding fast to those reasons as I make this transition.

      Best of luck to you and the OP as you move on to your new jobs!

    2. Alexander Graham Yell*

      I transferred to a different office to do my same job after petitioning for months to be allowed to go and I had the same nerves! Even when it’s a known team, change is hard and can be scary. Once you’re past all the unknowns and are started at the new job it’ll be way more relaxing/exciting/interesting than seems possible right now.

  7. idwtpaun*

    If the LW’s old company meant it when they said losing them in unfathomable and that “small companies take care of their own”, then the LW would’ve felt like a valued star employee and not “the wife of Henry VIII”. Alison is always a bit more diplomatic, but I see no reason not to call out all this behaviour as blatant manipulation that only goes to support the LW’s view of their old company as a stressful, toxic place to work. I wish them luck in their new job.

      1. idwtpaun*

        It sure does seem that way in light of this being said with, I assume, a straight face despite the LW knowing full well that “everyone was an PIP, coming off a PIP, or fired”!

    2. Observer*

      then the LW would’ve felt like a valued star employee and not “the wife of Henry VIII”.

      That line is SO telling, isn’t it.

      BTW, OP, that’s a phenomenal way to put the situation.

    3. Jesshereforthecomments*

      Yeah I would be so tempted to ask the owner for an exit interview and lay out every single reason OP is leaving and why their nerves are completely shot.

      Owner couldn’t poke “taking care of their own” with a 10 foot pole.

    2. Sherm*

      Yeah, it’s kind of like that saying that goes something like “If you come across a-holes all day long, you are the a-hole.” If everyone you manage is in PIP territory or was fired, what does that say about *you*?

      1. Sedna*

        Ha, I just said something similar above! Yeah, this is something that reflects terribly on the manager/company, not on the employees. Huge red flag imo.

  9. No Name Today*

    I’d honestly bring in a bottle of wine for your boss and the owners when you leave.
    Tell them you’ve seen how much they’ve enjoyed sour grapes over the the last two weeks, so here is a bottle of them to remember you by.
    They’ve been messing with your center for years. Of course they are going to keep doing this. Stay strong and climb out of that crab bucket.
    Dang, that’s a lot of food imagery. I need to go to lunch. And OP, you need to shake the dysfunction off of you.

  10. Dust Bunny*

    Your boss is a manipulative jerkwad. You must know that if you stayed you 100% would not be the person he chose to replace him. He can just say that to you because you’re leaving and he’ll never have to prove otherwise.

    1. CleverGirl*

      Yep, this is the adult equivalent of me telling my little brother that I WOULD HAVE shared my candy bar with him if he had asked me, knowing that there is no way to disprove that since the candy bar is eaten now.

  11. Wisteria*

    Big changes are scary, and being nervous is normal. You are moving beyond your comfort zone, so discomfort is normal! We believe as a society that anytime we are uncomfortable, it’s a sign that the situation is wrong and something about it needs to change, which is where your feeling that you made the wrong choice is coming from.

    Reframing can be really helpful. Try to cultivate a growth mindset and sit with your discomfort rather than trying to alleviate it. If you can acknowledge your discomfort without acting on it while cultivating excitement toward new possibilities, you will find that the discomfort is slowly alleviated as you gain confidence in your new job.

  12. CatLady*

    LW – you are having very normal doubts and the narrative from your current employer is meant to manipulate you into doing what is best for them, not you. I’ve known a few people who have changed their minds, usually for the counteroffer, and to a one, they regretted it. This is because when the employer entices you to stay, they now know you aren’t happy and are willing to leave. They have the option of changing the environment to keep you but typically they’ll just take advantage of your continued presence and look for your replacement. Maybe making you uncomfortable enough for you to leave when they are are ready or laying you off entirely.

    Side story – I was once in a similar position. I was planning to give my notice but had some serious doubts. I was in a conference room in a meeting thinking about those doubts when I was called back to my office (I had an actual office with a door!!!). The pipe had burst and the office was flooding. The flooding kicked up ton of mold and I was practically choking on it. I took that as a sign from the universe, gave my notice and never looked back. Let Alison’s reply be your sign!

    Take your chance – try a new environment. No one can read into the future and anyone who says they can, is trying to manipulate you.

    Good luck!

  13. Anonymous Pygmy Possum*

    Oof, I’m planning on giving notice on Friday (assuming everything works out with my offer that I’m getting today, fingers crossed and knocking on so much wood!) And I have zero idea how my boss and coworkers are going to react, since literally nobody has left the company since I started except one person who retired. I’m anticipating feeling a lot like the OP here and imagine my skip-level or boss might make similar comments to the boss in the letter. Thanks for publishing this one, Alison – it was really well-timed for me.

  14. a tester, not a developer*

    I think an important point is that the company owner said “I should call her directly if I want to come back at any point”. You haven’t burned a bridge with her, and it sounds like if you discover that Great Big Company isn’t a good fit a month or a year from now you could return. I don’t think you’ll want or need to, but it may help calm some of those jitters.

    1. Blaise*

      That jumped out at me too! That’s the ideal scenario- you’re getting out of a toxic environment, but if somehow the new environment is even MORE toxic, then hey, at least you can go back to the less toxic one lol

      Always nice to have a safety net in place, and hopefully you won’t need to use it!

    2. Gary Patterson's Cat*

      This is true and you it sounds like the OP is being very professional.
      Wanting to go to a larger international company is a generally seen as good career move! You’ll gain more global experience, and often have more formalized training and processes, even if you might be somewhat more specialized in your role. It’s good to have that comparison either way. Plus the pay is better ;-)

    3. AnonMom*

      I have been in this position where the CEO told me whenI gave notice they would always leave the light on for me and I really did end up boomeranging back. The leaving was hard and there were issues that were never going to resolve if I had stayed, but my departure forced the company to address them. They did, and several years later the stars aligned so I could return to a position tailor made for me, with far better pay than I would have ever earned had I not left, all the best coworkers, everything. On top of that, I learned so much at my interim job that I would have not been exposed to otherwise that I returned to a much higher level role than internal promotions would have allowed for.

      So OP, even if change seems hard right now, it sounds like things are in your favor all around.

  15. AvonLady Barksdale*

    When I gave notice at my last job, my boss’s first reaction was, “I heard that company is a terrible place to work,” followed by, “But we just gave you this huge project!” Yup, you did. Then he asked for a number to keep me and I refused to give him one because he had recently cut my pay due to COVID. He spent the next 2.5 weeks making comments.

    I did not listen to him and I am now happy. I jumped from a teeny company to a big corporation– I like the resources and the pay is much better. Your boss is doing these things in her interest, not yours. Remember that.

    1. Alexis Rosay*

      I’m starting with a huge corporation next week. I’m definitely a little nervous about it, and I’ve definitely heard comments from some people who think working at a start-up is superior but…that’s fine for them. This is something I want to explore with me.

    2. Morticia*

      That’s very wise. I’m sure if he cut your salary once he would have no problem doing it again as soon as you had rejected the other company’s offer.

  16. I AM Sparkling }:(*

    Wow, your boss is a manipulative jack@$$! They just don’t want to lose a what sounds like their lone competent employee and have to take the time to train someone else.

  17. Three Flowers*

    “ It felt like being a living wife of Henry VIII; I never knew if it was skill or luck that saved my head.”

    One of the most evocative things I’ve ever seen about unbearable work environments. I hope your new job recognizes your awesome writing skills!

    Also, your feelings are totally legit, especially given the guilt trips from your STBX boss and grand boss. Those guilt trips, though, are a good reason to leave all by themselves. Savor the good parts of this experience and go forth, hopefully into a work environment that understands work-life balance.

      1. Three Flowers*

        “Not everyone can be Anne of Cleves”

        I’m dying! Why is there no crying with laughter emoji on this thing?

      2. Where’s the Orchestra?*

        And honestly, the only reason Henry couldn’t mess with Anne of Cleaves is because he was scared of pissing off her male relatives with their powerful and fully paid Armies.

  19. Beautiful, talented, brilliant, powerful musk-ox*

    Awesome answer, Alison. And OP: large companies can take care of their employees too (and generally have the resources to ACTUALLY take care of them, which, frankly, many smaller companies lack. It’s not that those resources are always allocated properly, but they at least exist). I personally prefer working for medium-to-large-sized companies after a couple of stints at small companies (both of which had limited benefits and pay…and both of which laid me off because my positions became obsolete. Which is fine; stuff happens. But being at a smaller company didn’t prevent me from being laid off.)

    Based on what you’ve presented, you’ve made a solid choice and are just experiencing new job nerves. Change is scary even when it’s exciting! But your boss and even the owner of the company are showing some manipulation that I imagine extends beyond just this situation. A fresh start at a company that it sounds like you like will be a good thing.

    Congrats on the new job and best of luck!

    1. Gary Patterson's Cat*

      I’ve work for both kinds. Upsides and downsides to each. Agree that mid-market (but nationwide) is often best, but I’ve found it hard to find ones of that size in recent years as they tend to get “acquired” by private equity or competitors. :-(

      Big
      >Usually better pay, bonus and benefits + more opportunities to advance faster (tadpole, fish, shark)
      >May be more specific work within a department (swim along with the current for a while tadpole)
      >Often more processes, bureaucracy and hierarchy (can be good or bad thing) but get used to it
      >Generally better funded for projects, but many things out of your hands, decision by committee

      Small
      >Lower pay but may have other flexibility
      >Can be fun to be a big fish in a small pond
      >Opportunity to wear many hats or have more control over ones functional area
      >Can be dependent on owner whims or mismanagement!
      >Smaller budgets to work with > thinner margins, but easier to get decisions from top level

      1. Alternative Person*

        I agree. I very much value my time at smaller companies because I got skills and experience that are usually behind a big luck/experience/timing/pay walls in bigger companies but I was very much cognizant of being a medium fish in those ponds. In the end, I moved to a bigger company because there was nowhere to go in the smaller ones.

        (Unfortunately, even the bigger companies are eroding their middle management structures now, but whatever, between my skills, experience and the big company name, I can leverage a better job in the long run than if I had stayed at one of the smaller places)

  20. The Tin Man*

    You see your boss and the owner trying to give you advice for your career. I (and the other commenters I see so far) see people trying to emotionally manipulate their one solid employee to stay for their own, selfish reasons.

    If they value you so much and think they will be stable if you get laid off at the bigger company wouldn’t they be willing to welcome you back with open arms anyway? Not that I think you should ever return – it sounds like you are a big fish ready to leave your small pond.

    1. Observer*

      You see your boss and the owner trying to give you advice for your career. I (and the other commenters I see so far) see people trying to emotionally manipulate their one solid employee to stay for their own, selfish reasons.

      Exactly! And doing so quite dishonestly on top of it.

  21. Beth*

    Crab bucket!!

    Keep your eyes on the exit, OP, and don’t look back. These people do NOT have your interests at heart, or anywhere else (except possibly under their feet).

    1. Not Tom, Just Petty*

      I feel the same way! I hope OP reads the letter posted after this where that OP only wanted their boss to use correct pronouns. OP starting looking because the boss couldn’t make the literal least effort. (“Please use they when speaking of me.” “No.”) OP ends up with an actual manager level ally. Brilliant .
      .

  22. Hmmmm*

    A large company is almost certainly more stable than a small one. Likely better benefits and more, varied, opportunities for growth as well.

  23. TimeTravlR*

    As Alison said, you started looking for a reason. Use that as your mantra to get through. Repeat as necessary.

  24. Software Engineer*

    These comments are not a truly great workplace trying to convince you to stay

    It’s all SO PASSIVE AGGRESSIVE I can’t even take it. It’s all a sign that you made the right choice and should get out. Small companies can be very dysfunctional and it seems yours is. I work at a big company and when my boss is off their gourd I can talk to their boss or their boss or their boss. Or I can live around within the company easily, maintaining the reputation I’ve built but moving to a more stable or better run team

    All these comments are such red flags and you will look back and wonder at the Stockholm syndrome that made it seem appealing to stay

  25. Susanna*

    You answered your own question here:
    “But I was miserable for so much of my time there.”
    It’s pretty normal to have premature nostalgia for a place even as you’re leaving. Ask yourself – they come through with a pay/benefits raise ONLY when you followed through on accepting another job?

    And headed into “a second Great Depression?” Oh please. We have historically low unemployment. And no, that won’t last forever – never does. But this uninformed scare-mongering is enough of a reason to leave. Also – why would small company be immune from the ravages of a “Great Depression?”
    Your instincts were spot-on. Don’t look back.

    1. Me (I think)*

      Yeah, when the Second Great Depression comes along, the bosses at your old company will be axing everyone to save their own salaries. (Pardon, they will be “right sizing the company to adjust to current market conditions.”)

  27. Chriama*

    The comments from your boss and the company owner are so blatantly manipulative that I’m pretty sure if OP read someone else write this letter they would instantly advise the other person to run away screaming. I’m sorry you’ve been in a dysfunctional environment for so long that you can’t detach from it cleanly. You saw clearly enough to leave, and I bet once you’ve been away for a few months you’ll recognize how disordered your thinking was and how much of a relief it is not to be there anymore.

    1. Important Moi*

      +100000. I can barely type. I am so angry on behalf of LW.

      I tell myself and anyone who bothers to ask me advice –

      “Talk to yourself as though you were talking to someone you cared about” It has made so many decisions easier.

  28. ThursdaysGeek*

    I moved from a smallish family owned company to one of the largest employers in town, and had always wanted to avoid the large employers. I liked doing a lot of different things and suspected I’d be a small cog doing one task. But I was wrong to avoid them because they were large. They also had a more competent HR group (instead of 1 person), comparable benefits. Best of all, they had processes that actually made my job easier and more consistent. I still did a lot of variety of work, and had teammates to support me. It was a change, but it turned out to be a good change which allowed me to grow.

    1. GreyjoyGardens*

      That’s a good point about some advantages to larger companies. (Of course, Not All Large Companies and Not All Small Companies, etc.) There will be an actual HR department instead of, at best, the office manager who has little or not HR training doubling as HR. There will be processes in place instead of the boss/owner’s whim. Small companies can quickly become, well, tiny kingdoms, and Bastet help you if you get stuck with Henry VIII as the ruler.

      The same cult of personality and/or bad HR can happen at large companies too. But there is usually a dedicated HR department staffed by professionals as well as company manuals with processes to follow.

  29. AB*

    I went through this last year. Left a place I was at for 8 years because I had been miserable and burned out for awhile. I’d been in the industry for 14 years and knew all the local vendors, customers, and competition. I found a job where I knew no one in a completely different (but complimentary) industry. It was hard! Even though I hated my job I had a hard time giving notice and leaving. I was not looking forward to reestablishing a reputation. But it was ok! After the first couple weeks I felt so much better and less stressed. I realized just how disfunctional the old place was. Like Alison said there’s a reason you started looking, hold onto that and you can make it. Good luck!

  30. Dona Florinda*

    I’ve been there, LW. I even wrote on the open thread about it! So I’ll give you the same advice other readers gave me:
    unless there were red flags, don’t worry much about the new job. Also, the flexibility and higher salary can do wonders for your mental health and work-life balance.
    I’ve been at my new job for about a month now, and I have no regrets. Your mind is playing tricks on you and so is your manager, but read your own letter and you’ll remember why you wanted to leave in the first place. Good luck on the new job!

  31. KWu*

    * “I would never work for a company that big” => ok, good for them.
    * “You should know we’ll be going into a second Great Depression so layoffs are coming” => this is more likely to affect you at a startup than a big public company, where even if you were laid off, would often have severance packages or get vendors that help with finding new roles
    * “You were my choice to replace me so I guess I’ll be sticking around for a while.” => ok, good for them.
    * “I received a heartfelt email from our company owner explaining that they don’t want to lose me…She said that losing me was an “unfathomable” loss for the company and that I should call her directly if I want to come back at any point.” => forward this email to your personal email to keep a copy of, and assume that if it’s actually sincere, that means if you go to the new job and hate it, you can probably go back to the status quo. So they just told you that the risk for trying out the new job is very low.
    * “We also had a call where she shared the downsides of working for companies like the one I am going to” => possibly useful insights to keep in mind, but you get to find out for yourself whether you think those points are valid and even if they, if the downsides are outweighed by the upsides
    ” “the perks of working for a small organization that “takes care of their people.”” => I mean this doesn’t seem to line up with your actual experience of working there at all, you don’t seem to have ever felt “taken care of.”
    * “My old employer made me a counteroffer for about half the salary increase I’m getting in my new role, along with some other perks. While this was tempting given the conversations above, I opted not to accept because I couldn’t say for sure I wouldn’t want to leave again in a couple of months, and I’d rather keep this bridge intact than burn it by quitting a second time later.” => correct and smart call.

    1. Magenta Sky*

      * “I would never work for a company that big” =>

      “Glad to hear it. That means I won’t be running into you there.”

    2. AnonForThis*

      * “You were my choice to replace me so I guess I’ll be sticking around for a while.” =>

      Soooooo many problems with this:
      – When? Now? 3 years? 10 years? Some amorphous time in the future when cats are driving Teslas because they are the secret to true autopilot?

      Statements/promises such as these are nice for the warm fuzzies, and should be taken as the great compliment to your value that they are. However, they are not binding. They can be a tool to keep people from leaving though.

      Also, while still very flattering to you, does that show the best planning or best office culture if there is not even a consideration of doing a search…at some amorphous time in the future? Are other decisions being made years in advance and not changed regardless of what changes around them?

      1. Observer*

        Soooooo many problems with this:
        – When? Now? 3 years? 10 years? Some amorphous time in the future when cats are driving Teslas because they are the secret to true autopilot?

        That is an incredibly funny image. Especially when you’re talking about Tesla, whose Boss (Technoking, anyone?) does say some pretty outre things.

        And the rest is completely true OP.

      2. Magenta Sky*

        Plus, of course, it’s extremely unusual for *your* boss to get to choose their replacement. Ultimately, it’s *their* boss who makes that choice. And when *your* boss exhibits poor judgement, having their endorsement is a mark *against* you, unless their boss is an idiot.

      3. Artemesia*

        And doesn’t everyone know someone ‘who worked for peanuts because they were going to inherit the business’ and then the parents sold the company to finance their retirement leaving their heir underpaid and without job prospects. Or promised promotion and then when the day came, some brand new young man with little experience — but perhaps a relative or friend of the family — is announced as the new Director or CEO? Or the CEO is planning to retire and you are hired to take over when they do and it stretches into years with him never leaving. Without an actual contract these promises are just blowing smoke.

  32. oranges*

    One of my work friends resigned last summer, and he had similar doubts and nerves in the final days. Completely understandable! Change is hard! The unknown is scary!

    But having been his friend and watched him be miserable and ultimately turn more than a little toxic to the rest of us- NO, RUN, TAKE THIS JOB! TAKE THIS JOB AND RUUUUUUN!!

    Check in with the people in your life who got to hear all your terrible stories and see your unhappiness leading up to your decision to seek other jobs. Your memories (and the current gaslighting) may have rose colored glasses, but they’ll remind you.

  33. Essess*

    This sounds exactly like my Oldboss. I left a small barely-past-startup-phase company that had 15 people. I hated it with a passion. The hours, the pressure, the stress of worrying that one mistake might take down the whole company. Plus low-balled pay and constant coworkers that just sat there complaining all the time about the few perks we were given that were actually better than other companies.
    I couldn’t take it anymore and left for a large corporation. The owner of the company harassed me about how I would hate it and what a mistake I was making and had also told me that OldBoss hired me in order to take over the company if anything happened to them. This was also horrifying because in my interview I was very upfront about never wanting to be in management!
    I went to the new company despite all the horror stories from OldBoss. Loved it there. Within 4 years, I was making *3 times* the salary I had been making at oldJob and stayed there for almost 10 years before moving on to even better job at an even bigger corporation.
    The oldJob still exists, but I’ve never regretted jumping out of there for my own wellbeing. Don’t listen to others who tell you what you do or don’t like. Decide for yourself.

  34. Sara without an H*

    It felt like being a living wife of Henry VIII; I never knew if it was skill or luck that saved my head.

    Thank you, OP, for this lovely and very useful phrase. I suggest you copy it to a notes app on your phone and reread it occasionally, because it contains useful information for you.

    Your soon-to-be-former-organization is an example of high-functioning toxicity. (Rather like the Court of Henry VIII, as a matter of fact. That was also full of brainy, talented people who were very, very nervous.) Given what you know about senior management at your firm, based on their actual past behavior, why would you want to stay???

    Go forth and rock your new job.

  35. Lacey*

    That place sounds like a nightmare.

    When I left my first professional job I’d been there for a looong time and I’d been looking for a new job for a few years.
    Even though I was desperate to leave, I felt immensely sad after I gave my notice. No one tried to guilt me into staying, but people were so warm and friendly and excited for my new opportunity that I thought, “Oh no! What have I done?”

    And, the next place I went was a dumpster fire. Looked like a great opportunity on the outside, but it was wretched in a million ways.

    But it still ended up being a good thing, because I made contacts there that got me my next job, which I mostly love.

    1. Caraway*

      I just made a really similar comment a little farther down! I think OP knows it’s time to move on, and even if the next step isn’t as great as she’s hoping, it is probably still the right next step.

  36. HR Exec Popping In*

    First of call, congratulations! A) For getting this new job, B) for doing well at your current company for them to regret your loss and C) for surviving what sounds like an unpleasant job/boss.

    It is totally normal to have second thoughts. I agree with AAM, you started looking for a reason and that reason is still valid and hasn’t changed.

    The truth is working for a big public company is very different. Some of it is good (generally better comp and benefits) some of it not (more bureaucracy and more narrow roles). It will be an adjustment and at times you may doubt yourself and if you made the right choice. Give it some time to acclimate. I’ve always believed it will take about 6 months before you can even have enough information to know if you MAY not like a new job/company and another 3 months before you know.

    Your new employer selected you. Not by accident by the way as they probably had many many applicants (hundreds or more). Bigger companies tend to have very good selection systems and they most likely specifically look for skills, experiences and cultural fit. Feel confident in that. They picked you! You impressed them. They are excited to have you joining them.

    Good luck!

  37. yala*

    ‘We also had a call where she shared the downsides of working for companies like the one I am going to and the perks of working for a small organization that “takes care of their people.” ‘

    I…find that REALLY unnerving

      1. MissDisplaced*

        Eh. That’s just another one of those small company “We’re all like family here” riffs.

  38. I Wrote This in the Bathroom*

    These comments are similar to the ones I received after giving notice at my bait-and-switch job years ago. (Hired me promising experience with cutting-edge tech of that time, immediately contracted me out to a friend of the owner’s to support an old app at another company that was a 60+ mile commute for me.) Everything* from them trashing my new job and promising I would regret taking it, to the owner telling me “I did not know you were unhappy. You didn’t like working for (friend)? Consider that gone.” I didn’t believe a word they said, and went on to my next job. It wasn’t perfect, but I spent six years there, built up valuable skills, developed a professional network, and found good friends that I’m in touch with to this day, 15-20 years later. Godspeed, OP.

    * though I admit that “the next Great Depression is coming and everybody everywhere is going to lose their jobs, except for us here at (company), we’re safe” is a new and audacious one. Got a chuckle out of me.

  39. Caraway*

    I also think that a move can be the right one even if the job itself is not, if that makes sense. A number of years ago, I took a new job that I pretty quickly realized wasn’t great. It wasn’t horrible or anything, but it wasn’t the right one for me, my new boss was ineffective and hard to work with, my coworkers were kind of a mess, etc. But I don’t regret that I made the move, because that job put me in the right place for my current one. After about 18 months in my “bad” job, I was able to move into the work I’m doing now, which I love and which is a perfect fit for me. I’ve been promoted three times in 7 years and I’m now the director of my department, and I absolutely could not have gone from the first job directly into this one. It was the right move, even though at first I wasn’t sure.

    I hope this new role is perfect for you, OP, and you love the new environment at your new company. But even if not… something good may still come out of making the move. Best of luck to you!

  40. Casey*

    Hi OP! It actually feels like I could have written this exact letter a year ago. So, consider this your notes for the future.

    1) oh my god I am SO GLAD to have made the leap. Everything feels better now. I have a ton more opportunities and a reasonable, level-headed, supportive boss. It is awesome. I have learned so much. I would never go back.

    2) It was weird leaving my old company and I felt similarly guilty during my notice period. I missed the “small pond” feeling for a few months, especially when I was getting used to all the systems and tools and internal software that came w/ a bigger company.

    3) Similarly, it did take me a bit longer to make friends at the new place. Remind yourself that warm, pleasant working relationships is goal number one, and any outside-of-work socializing is a bonus! I’ve definitely had to shift that thinking a bit since my small company was very “we’re a family, we do everything together”.

    4) I think all the “second Great Depression” or “boomerang employee” talk is fear-mongering on the part of employers who don’t want to accept that the balance of power has shifted. It feels transparently manipulative based on how your letter describes it.

  41. Just Me*

    Left a toxic small workplace for a much bigger and more stable workplace ~6 months ago. My old CEO didn’t say these things to my face but apparently has been saying them to my old colleagues (e.g. “You don’t have to be as *smart* or *business savvy* to work for a big company” or in a dismissive, self-righteous tone “Well, she’s better off!” [meaning me]). What she’s saying isn’t really true and is clearly a manipulation tactic to make others feel that they shouldn’t leave (turn over is extremely high). Feel confident in your decision and know that if your company *actually* cared about you personally they wouldn’t be acting this way.

  42. Kim*

    Go get some experience at the new company . If your old company is sincere about their claim that you were the heir apparent to your boss’s job, they can contact you when the boss retires. I agree with others that a small company is not more stable than a large one. The Second Great Depression ? Really???

  43. WomEngineer*

    A job doesn’t have to be toxic for it to be a bad fit. There are advantages and disadvantages for both large and small companies. It’s okay to miss the old job but I think OP is on a good path with the new one.

    1. Observer*

      Sure. But in this case the job *IS* toxic. What the OP describes is not normal, not reasonable and not acceptable to people who have other choices and the experience to see what the reality is.

  44. Batgirl*

    Oh my goodness OP, these people are AWFUL. Even if they truly were the more recession proof company (they’re not), or would remain this grateful and appreciative once you’re back in the lobster pot (they won’t), just…run. I’m not saying it’s all gaslighting, because it could be genuinely delusional, or a display of low emotional intelligence or simply the garden variety type of manipulation. What it definitely is though, is bad manners and thoughtlessness and no way to behave when someone gives notice! You should get away from them in case you catch bad standards from them, and I don’t mean professional standards I’m just talking about being a good person. Good people don’t bid farewell to a valued colleague who has done wonderful work by being all doom and gloom and forecasting miseries that are highly unlikely. They don’t try to work on your insecurities or centre themselves in the narrative as an injured party and throw a pity party all over your good news. If they are really, really going to miss you and see you as irreplaceable they should simply tell you so, and that you’re always welcome to come back if you change your mind. While saying something pleasant like “congratulations” and planning something cheerful for your last day. That’s it.

    1. Gary Patterson's Cat*

      I literally snorted over this bit: They said losing me was an “unfathomable” loss for the company but their counteroffer was only for about half the salary increase of the new role.

      That should tell you all you need to know about these manipulative people.

  45. Observer*

    OP, One of the reasons you are questioning yourself is that your boss is trying to get you to change your mind and being highly manipulative.

    You have good reasons for the move you are making. Your employer’s reaction, if you step back and look at it impartially, actually bolsters some of those reasons. At the same time, nothing they have done really provides a good incentive to change our mind. A small counter-offer and some vague promises of rainbows down that line are not a really good inducement to turn down what sounds like an excellent opportunity.

    What you are experiencing is quite normal. But it’s the kind of thing you power through till you get away from the manipulation.

  46. Gary Patterson's Cat*

    Your current company and manager are trying to mess with your head! And that is so ‘effed up of them.

    Leaving is not an easy decision. I’ve worked for both very small and very large companies. Neither is good or bad, and this often depends on where you are in life and your career. I think it excellent to have exposure to BOTH types of companies.

    If it helps, I suggest you review WHY you started looking to leave:
    >Dysfunction: half the company is on PiPs? Something definitely wrong there!
    >Money: They say they want to keep you, yet their counteroffer was 1/2 of your new job offer? Not market rate!
    >Benefits: Larger companies generally have broader and better benefits.
    >Global Experience: New company is big and international. Sounds like good opportunity to grow.

    Is a big company more risky? Sure and layoffs can happen perhaps more frequently. But it doesn’t sound any more risky than your small company where everyone is on performance plans and under threat of being fired if not perfect. And even if you manage to work at Big Company for 3 years before that happens, you’ve made 2.5x more salary, which puts you ahead of the game.

    I get you are nervous about a new start (it’s totally normal). But No Regrets!

  47. Anne of Cleves*

    OP here! Thank you to everyone for the well wishes and support!! I really appreciate it after the past few months of uncertainty.

    I wrote this letter at the tail end of my leave period at the last job and have been at my new employer for a month now. I’ll be honest and say that the transition has been tricky – lots of self doubt coupled with the fact that the new company has very different (and much better) processes for our type of work has made me feel like an imposter, (perhaps some of which is a carry over from the last position). But I’ve been working hard, taking good notes, making mistakes (hopefully not big ones, sigh), asking questions, and just generally focused on being the best student I can. After some very panicked and scared weeks, things are kinda starting to click and my manager feels comfortable giving me more work to try out. And I’m trying to go easier on myself for said mistakes, knowing this environment doesn’t necessarily demand “perfection” and I’m still learning. My teammates are also supportive too and have all given me some version of the speech that is “Oh yeah, none of this makes sense at first. But you’ll get it and love it soon enough!”

    So all in all, I’m feeling more optimistic now than I was when writing. And Alison’s advice plus all the wonderful messages from readers helps solidify that for me just a bit more. Onward!

      1. Gary Patterson's Cat*

        You are not an imposter or they wouldn’t have hired you! sounds like you’re getting some good training time and mentoring. It’s sad how we can carryover so much dysfunction–it’s normal but good you see that it will also pass. It can take some time to get over it, but good for you!

    3. LDN Layabout*

      OP, I know it’s hard when someone tells you this to believe it, but this is pretty much everyone’s experience at a new workplace.

      You are going to Not Know Things and Do Things Wrong and as long as you’re willing to learn and improve a functional workplace (and your manager and coworkers seem to be that from your post) people know it’s part and parcel of getting a new person in.

    4. Fran Fine*

      I’m glad you left and appear to be doing better. Give yourself grace right now with the new job – you’re still learning. You’ll get the hang of this soon enough and the old job’s dysfunction that you’re holding onto will eventually fade from your memory. Good luck to you.

    5. Nails*

      Glad to hear it, Anne! Your comment about being a “living wife of Henry 8th” was absolutely fantastic.

      If you hadn’t posted this, I would have typed up a whole comment stressing another angle of the advice: that if you stay in a place that exhibits this behavior, YOU are not learning how to be an effective manager or a champion of good processes. Instead, as you’re probably finding at your new workplace, you spent a lot of time in a role that fostered poor habits and bad mindsets, instead of learning brilliant habits and effective mindsets. You are working with self-doubt and imposter-feelings and are grappling with expectations of perfection, none of which are ideal, and certainly none of which are part of the actual makeup of an effective and engaged employee!

      So that’s another reason not to regret the old job, and something to remind yourself of: even IF you had eventually become the boss, you would NOT have been equipped, effective, set up to win, or experienced with good processes and good skills. How would you have managed new starters in an environment that teaches bad habits and demands perfection? would you have taken your place as their new bully, as your manager was happy to do for you, or would you have fretted endlessly about how you couldn’t support or protect the people who looked to you for leadership?

  48. Jam Today*

    Go to the new company. Change is scary, and you’re always going to have that pang of “buyers remorse” while you exist in that liminal space before you start your new job. You’re walking away from the devil you know, which is comforting to you in its own perverse way, for the devil you don’t. Which is probably not a devil! Or if it is, its a devil in its own ways which you will discover, but for substantially more pay! (I have surprised myself by the amount of BS I can absorb for a really comfortable paycheck.)

    Go to the new job. Meet new people, do new things, learn new skills or concepts or approaches to how you do your work. Get paid what you’re worth. Its going to be great.

  49. Goldenrod*

    “Every other member of my team was either on a performance improvement plan, just off of one, or fired for poor performance. It felt like being a living wife of Henry VIII; I never knew if it was skill or luck that saved my head.”

    First of all, I love this analogy; that is hilarious.

    Second, I totally agree with Alison – your awful boss is trying to throw you off. I have been there, in a terrible working environment that demanded perfection, and believe me – show me a boss who demands perfection, and I’ll show you an abusive boss. It’s extremely abusive to demand perfection, because perfection is impossible.

    My terrible former boss ALSO made mean comments when I was working my 2-weeks notice – stuff like, “I would never take that job!” and “That sounds hard!” (When she said the latter comment, I replied, “Well, that’s okay because I’m awesome” and she couldn’t think of anything to say to that.) :p

    You are just experiencing the side effects of having been in a toxic environment for a long time. CONGRATULATIONS on your new job!! Once you are out of that place, you will NEVER regret it! I guarantee it. I thought I’d miss my pals at the toxic workplace too – I really didn’t. There were some nice people there – but there will be nice people at the new place too. You are going to be so happy you left!

  50. anonymous73*

    Look at it with your head and not your heart. A company will not hesitate to get rid of you if it affects their bottom line. This isn’t to say all companies are malicious and don’t care about any of their employees, but sometimes difficult decisions have to be made when business is failing, and a company is going to make decisions based on numbers not feelings.

    Good managers want their employees to succeed. They should be encouraging you to learn more and when you’ve gone as far as you can go in your current position, help you (or at the very least not hinder you) to move on. If you’re unhappy, they should figure out the cause and remedy the situation. Your manager and the company owner are trying to guilt you into staying. They don’t care about you, they care about how your leaving is going to affect them. It sounds like you were burned out and you need to move on. New jobs are always a little scary but you need to make the decision for yourself without feeling bad for those you’re leaving behind.

  51. Seriously?*

    I did a search on people regretting the great resignation. Almost every hit was from one “expert”. And most of the posts were from sketchy websites that all shared a particular political viewpoint. The more established sources had a great variety of views about quitting.

    So especially if these articles came from your unreliable narrator manager, I wouldn’t give them much credence.

  52. heismanpat*

    Textbook gaslighting. You say they are “stable”, but the rest of your team has been fired or PIP’d. That isn’t normal. When all was said and done, they didn’t even offer a real counter….half the salary increase? lol ..get real.

    You have stockholm syndrome. This new place may or may not work out, but your current employer is toxic and you need to get out.

  53. YarnOwl*

    I had this exact experience when I quit the first job I had after college! Complete with my boss telling me it was a bad idea. I talked to my friend about it and she reminded me that I had spent at least a couple of weeks during the course of the interview period thinking about the offer and the company and decided to accept it. Rational-minded Me thought it was a good idea. The me that was freaked out by leaving my job and moving to a job that wasn’t a known entity was telling me it wasn’t a good idea, but I had to listen to rational-minded me instead!

  54. ecnaseener*

    My boss has begun making offhand comments that make me doubt my decision like, “I would never work for a company that big,”

    Your boss who you admit isn’t a very good manager and who has contributed to your misery quite a lot? Yeah, he probably disagrees with you on a lot of things about what a good work environment looks like! This is good!

  55. Truly*

    OMG it sounds exactly like me when I changed jobs 8 years ago. Same move, from start-up to public sector. My boss got angry that I was leaving, then offered me a pay rise and then continued to make comments about how dull my new job would be. Guess what – I never looked back. Remember why you decided to look for a new job. Good luck.

  56. learnedthehardway*

    I’m going to suggest that neither option would be a mistake – you have a “Good” problem here. You’re wanted at your current company, and you have a new exciting opportunity.

    It sounds to me that your reasons for moving are very sensible – the workload is overwhelming, you’re feeling quite stressed, and you don’t feel at all ready to take your manager’s job. Now, you may have self-confidence issues at the larger company too, but one thing bigger companies are good for is providing training and people to learn from. A LOT of people progress very fast in startup type companies, without really getting the overall grounding in their function or industry that they need for sustained long-term career growth.

    You are going to learn a lot about your industry and your functional area by being in a bigger company. You’ll find out if a bigger company is the right milieu for you as well (at this point in time, it sounds like a start-up is not the ideal setting for you). Now, a major company might not be perfect either, but it sounds like a very good opportunity and when you strongly suspect that you’re in the wrong company/role, then a change is probably more likely to work out.

    I would take the new opportunity and see where it takes you. You may be very pleasantly surprised to find out it’s a better fit. If not, there will be other opportunities out there, possibly even with your current company.

  57. RB*

    Last time I left a company for a new job, for the first couple days I was there I was SURE I had made the wrong decision. But I told myself to give it at least a week, and it turned out to be very much better than the old job in many regards.

  58. AnotherSarah*

    None of soon-to-be-old-boss’s comments sound like reasons to stay. A real reason to stay might be some intel that something was really going to change, that everyone was getting an enormous raise, that personnel were shifting around…but old boss has given no new information that might impact a decision, just passive-aggressive guilt-tripping.

  59. Ellie Rose*

    “She said that losing me was an “unfathomable” loss for the company and that I should call her directly if I want to come back at any point.”

    Look at the secobd half of the comment and take heart in the idea that they’re saying they’d welcome you back.

    It sounds to me like you’re making the right call based on stress, bad management, and poor pay.

    But if 8 months down the line, you are *miserable* AND miss your old job…sounds like you could go back. You’re not burning a bridge; you’re crossing one.

  60. LKW*

    A big company doesn’t necessarily mean you’ll be lost. I work for a company that has over 600,000 employees. I am not a number, I am not a drone. We’re a very matrixed organization and I don’t have a “boss” =. I am on calls all the time where we are looking to staff a project and every time the conversation is “Who’s available and do they want to do this kind of work? What are their career goals?” I’m not kidding. My group is pretty serious about making sure people get to do the work they want to do and have the help they need to be successful.

    And the fact that everyone seems to be on the verge of being fired IS NOT NORMAL. So not normal.

  61. PB Bunny Watson*

    I have literally been going through this for the last two months. I received an offer at the end of December, accepted it, gave a month’s notice at the start of the new year… then spent the entire month with butterflies. Sometimes good ones, sometimes bad ones… but also the pervasive thought that I had made a huge mistake. After a few weeks in the new job, I’m feeling less like that… but on my first day, I wanted to run out the building and go home when I read my horoscope for the day… “People often return to what’s familiar, not what’s good for them.” I’m not arguing the merits of horoscopes, but I think it’s a good thing to keep in mind when starting something new. Change, even good change, is scary. But if you don’t do it, you’ll always wonder what could have been.

  62. The OG Sleepless*

    A lot of bosses at small companies act out when people leave, and the more the person is valued the worse it gets. My first boss used to buzz around people during their notice period telling them, and anybody else who would listen, what a mistake they were making and how terrible their new job/situation was, and assuring everyone that the person would soon see the error of their ways and come back. It was absurd, because that company was absolutely stifling, and the more of a rock star you were, the faster you wised up and left.

  63. Louise B*

    If it is true that you are such a rock star that they want you to be the boss, will take you back if you want, they can’t pay you as much as the new company can, AND your new position is rocky due to potential lay offs, then surely the correct move is to take the new job and return if mass lay offs occur? Like, that’s what they’re saying accidentally by trying to keep you, right? I don’t think from the sound of your letter that you SHOULD go back if the new job is a flop… just that they’ve accidentally made a much better argument for doing that then for staying for a so-so raise.

  64. YogaSloth*

    OP, I was right where you are about 5 years ago. I really needed to get out of my former department, but I was so scared. I had been there 7 years, and it was what I knew, good and bad. But I took a leap and I’m so glad I did. I got not only a better salary, but way better bosses and overall culture. I am now the manager of the team that I joined 5 years ago. I never would have been able to accomplish what I had if I had stayed at my old job. And they tried to get me to stay with some of the same language – talked about how “valuable” I was, how the new department I was going to “wasn’t stable” (it was an internal transfer at a large university), and all sorts of other things. I remember being so terrified my first month that I had made the wrong choice. But I stuck it out and I’m so glad I did. Give it time and I think you’ll be glad you left, too. Good luck!

  65. OhBehave*

    Did anyone else start screaming while reading the comments from boss/owner? If they thought this much of you, you would not be leaving, right? It’s all a bunch of passive-aggressive bullying. If they got you to stay, NOTHING would change. Good luck with your new job. You’ll love it! p.s. second-guessing yourself is normal.

  66. Alternative Person*

    I felt sad when I left my last job and it was a toxic mess. I was at a tutoring centre. Cultural issues top to bottom, I couldn’t even raise a concern about a student without Management making out like I was personally attacking their main tutor (and my concerns were consistently borne out by results too). Couldn’t win at all, was twisting myself in knots to try and support and shore up struggling students, running between branches multiple times a day, four days a week (I was five days but I cut a day off because I got a part time contract at the job I eventually moved to).

    I was at the point of tears when I finally turned in my notice, Management barely said a word, I think they had realized it was only a matter of time before I left. Sucked saying goodbye to the students. On my last day, I told the manager of one branch I was going to the other branch and I wouldn’t be coming back unless there was a reason to. Management was like ‘whatever’. I walked out with two bags of accumulated materials and stationary, and not a single goodbye. Same story at the second branch I visited that day. I was still worried I had made the wrong decision, especially leaving so many students behind, but it was the right one in the end.

    On the bright side though, one adult student, upon hearing I was leaving immediately quit the tutoring centre and became my first private client (we had already exchanged e-mails to facilitate homework). I wrote thank-you letters to the school aged students I was main tutor for (and slipped in my private contact e-mail) and gave them stationary as a gift. One child, according to their mother insisted on e-mailing immediately to request private lessons. I still teach them both to this day.

  67. Mama Llama Drama*

    Definitely agree with the above – the statements from boss and grandboss are extremely lame and toxic.

    Here’s another spin though. This could be a boomerang job for (in a good way though!) – lets say your boss was leaving, heck, lets say your toxic boss and grandboss are selling the company and you put in a bid/ they like the idea of having you take over since they like you and now you have all this awesome fancy Apple expertise to bring to the table. You could boomerang back into being the owner of a company and cleaning up the toxic spill that it used to be. That would be a win!

    Basically, the idea that you have to stay to take over from your boss is silly – you could still become the boss even if you left and then were rehired with more experience. It be a “boomerang job” but being a “boomerang” doesn’t necessarily have to be a bad thing. In a normal work environment your boss should be encouraging of you (maybe sad to see you go) but still encouraging of you, and want to keep in touch, and want you to grow in the “outside” world. And maybe that would mean that at some point you would come back if that’s whats best for everybody. But that would be in a normal positive work environment which this doesn’t sound anywhere close to.

  68. Sarah*

    Big decisions are a big part of life. Sure….regret sometimes occurs. However, sounds like you have a good relationship with your current owners. So…if it doesn’t work out…you can always negotiate a return. That being said….take a big deep breath and enjoy your new adventure. I have a feeling that you will take to your new position like a duck to water. Know that the universe has moved you in this direction. You are either moved this way to grow…or to show you what you do not want. But, I think you are going to grow. If you are experiencing feeling like a living wife of Henry VIII, I would venture to guess your neck is better off somewhere else. Enjoy your new adventure and don’t look back. You’ve gotten all you can out of your current position…it is time to move on.

  69. Coffee Bean*

    Any good manager would realize that any of their employees have the potential to leave and have contingencies in place to deal with departures. Any good manager with your best interests in mind would be happy to see you taking an opportunity that will allow your career to flourish. That is not what is happening with your current employer.

  70. HA2*

    That comment about “unfathomable loss to the company”…

    Look, companies have an excellent way of keeping employees. If it really is an “unfathomable loss” to lose you, the #1 most obvious way to avoid losing you is to pay you an above-market rate for your work, and good benefits. That’s not a guarantee – people leave toxic workplaces all the time even for a pay cut – but it’s a straightforward thing that all companies can understand.

    And they didn’t. They had plenty of time to realize how important you were and pay you accordingly, BEFORE you put in your notice. They chose not to. And even now, they’re giving you less money than you can get elsewhere!

    This isn’t “we are trying to prevent an unfathomable loss”, this is “We’re hoping that guilt will cause OP to stay because we’ve got nothing else to offer.”

  71. The_artist_formerly_known_as_Anon-2*

    I went through this process several times in my long career (now retired). The process they pulled on you is called, in cult terms, “love bombing”. This is a stunt that management pulls when they realize that they’re going to lose an employee that they can’t live without.

    Yes, kiddies – I know the mantra “no employee is indispensable” , heard that, seen it, heard it again. But the REST of that equation is = “If we lose a certain employee, we many not be able to continue to function as we had, because replacing him/her would not be an overnight process. Revenues, profits will go down AND we may need two or more people to backfill his position.” So while we may be able to function without him, life will never be the same without him.

    Think rationally – when you get “love bombed” after a resignation, caused by underpay / abuse / lack of advancement/ passed over…. it’s a tactic. CONTINUE TO THINK LOGICALLY AND RATIONALLY.

    1. The_artist_formerly_known_as_Anon-2*

      And one more thing – counter-offers aren’t ALWAYS necessarily a bad thing, BUT you have to be careful. I was in a situation once, where the boss put three members of a six-person team on probation (1980s equivalent of a PIP) — and two of us left within two weeks.

      They unbelievably tried to offer me money to stay., but I was in LW’s situation and ran for the door.

  72. Erica*

    Your company is trying to manipulate you into staying, because they don’t want to be left with the dirty work. If you stay, ALL of the reasons you had for giving your initial notice will be apparent again. They showed you who they were once, so you should believe them.

  73. RebelwithMouseyHair*

    OP, you’re having all these thoughts while working through your notice period… is there any way you could shorten it? Like, wrap everything up, make sure everything you used to do is documented, all of that preferably at home, then just one breezy visit to return laptops or keys or whatever you might need to return to the company?

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