update: my former boss won’t leave me alone

Remember the letter-writer whose former boss wouldn’t leave them alone? Here’s the update.

When you published my email, I was so grateful for your advice, plus I read all of the comments. At first, I decided on the most boring but easiest option (for me, anyway), which was to never contact my former boss again.

But then, in April, something interesting happened: The woman who had become his second-in-command quit working for him with no other job lined up. What I didn’t know back then was that this would be the last time my former boss would ever manage anyone. After her departure, his role changed into a more advisory/senior role. (I learned this through the grapevine months later and I still don’t know if it’s permanent, but by this point, it seems to be.)

In early May, only a couple of weeks after that shakeup at my former boss’ company, I was planning to go to a work event that I was 99% sure my former boss would attend as well. In the lead-up to that event, I realized two things. First, in the wake of his senior employee’s departure, I had an opening to check in with him and even offer him some advice. Second (and perhaps more important), I realized I was extremely anxious about running into him. I just wasn’t sure how eloquent I would be able to be in person as compared to sending him an email, and I didn’t think it would be possible to avoid him at the event.

So I wrote a long email to him, which I sent the day before the work event. In the message I apologized for ghosting him, and I explained that in the time since I had been working at my current job (where I still am, and still loving it), I realized the ways that he had let me and his team down. I used specific examples of times when his conflict-avoidance and desire to be “liked” caused problems in the workplace, and I even recommended one of my favorite management books (The Five Dysfunctions of a Team) — a book I had read during my last few months working under him. It really opened my eyes to how dysfunctional our team actually was; we truly had all five dysfunctions down to a science. I concluded the message by telling him that I liked him as a person, that my disappointment in him was professional and not personal, and that I really just wanted to clear the air between us before we saw each other again.

He responded with a message saying that he wished me well, wouldn’t be at the event, it had been a joy to watch me excel, and he had his own complicated feelings about the company where we had worked together. He said he had done a lot of reflecting and apologized for letting me down. He also said, “I’m confused by your assessment that your options were to ghost or write me a long email. To me, there’s a third option: a conversation, with mutual trust, aiming for mutual understanding and healing.”

Unfortunately, I found this message to be very annoying. I appreciated that he apologized to me for letting me down as a boss, but the rest of the email was “I” statements and came across as a weirdly “poor me” type of email from a man who has been extremely successful and, although he no longer manages anyone, I doubt he has gotten a pay cut, and he still has a very cushy and influential position in a small and cliquey industry. I also was confused that he said he didn’t understand why I emailed him instead of having a “conversation.” An email thread can be a conversation, no? I would guess he would want this to be a phone call or a lunch, but … all that comes to mind for me when I imagine that is the number of times I told him I disagreed with his decisions when we worked together. Reading his message just made me feel freaking exhausted.

So I’m kinda back to square one, wondering if I shouldn’t have contacted him in the first place. I never responded to his email (so I guess it wasn’t a “conversation,” then… my bad?) and I haven’t seen him since. I’m sure I will run into him at some point, and I’ll just put on my best friendly face and try to act normal, which… is also maybe what I should have tried to do in the first place. Oh well.

Thanks for helping me through this entire saga!

{ 225 comments… read them below }

  1. Ask a Manager* Post author

    A note from below: This is becoming a pile-on, which I hate to see when someone has been kind enough to give us an update. I’m asking that comments from here on be constructive advice, not just criticism (and have turned on comment moderation on this post to ensure that happens). Thank you.

  2. Caramel & Cheddar*

    “So I’m kinda back to square one, wondering if I shouldn’t have contacted him in the first place. ”

    I went back to the original letter and the very first line of Alison’s response is “I don’t think sending Bob a message about his failures as a boss will result in much meaningful change to how he functions as a manager” and I think that advice is still pretty on the mark.

    I appreciate that maybe this email acted as a stress relief valve for you ahead of the possibility of seeing him at this event, but I’m not sure that the contents of this email accomplished whatever you might have been hoping. I’m not surprised Bob thinks it was a lot, even if he’s the one who was a bad boss.

    1. Sloanicota*

      Yes, I think it’s Captain Awkward who wrote about the FeelingsBomb letter or email, and why it’s almost never effective to send one (better to write one and then delete it, giving yourself closure). I just read another advice column saying the same thing, and although these are both referring to relationship rather than workplace emails, the same thing applies. Nobody wants to receive a list of their past sins either. It’s a very one-way form of communication by its nature, and few people will appreciate that.

      1. reg*

        ugh, i was on the receiving end of a feelingsbomb and it blew goats. i’ve also sent at least one, so i’m not judging! they’re simply not productive or helpful. i really like the idea of writing it all out and then deleting it.

        1. TechWorker*

          And then for the exception that proves the rule, my friends ex sent him a very feelingsbomb letter (5 pages), and they got back together & are now happily married.

          1. Not a Real Giragge*

            lol my partner did this too after I had broken up with him and while I do not recommend this tactic generally it was a real turning point for us to communicate better and we’ve been happily together for several years!

          2. Falling Diphthong*

            Was the 5-page feeling bomb on the theme “Why you are still wrong about everything” or “Why I have realized that you are a wonderful person, and that what we had together was rare and important and worth working to preserve”? Because while both can fail, I can see the latter occasionally hitting a ready-for-this-message recipient. The former not so much.

      2. Interrobang*

        Ughh, I feel like I wrote a very “FeelingsBomb” letter earlier this year when I had an issue with a coworker. My manager told me I had to deal with my coworker somehow by either 1) email or 2) conversation (but the issue was the co-worker was gaslighting me so that didn’t feel like it would be productive). First draft was total feelings bomb. Second draft felt way to accusatory. Third draft, and what I actually sent, spelt out what was actually done, how it made me feel, and what action I will be taking in the future if the same happens again (i.e. setting my boundaries). Not sure if it helped at all because coworker was just like yup I got it. Although the same issue hasn’t happened again, so…?

      3. Kelly*

        I got one from a disgruntled client once. It was two full, single spaced pages of criticizing my every move from our meeting that didn’t go well. I skimmed it and threw it in the trash because reading a long personal attack doesn’t help anyone.

      4. Always Tired*

        I am a chaotic monster, so I have been known to respond paragraph by paragraph, in line if it’s an email. But it also takes a ton of emotional labor to do that.

        I totally understand OPs feelings and her reasoning (though I don’t really feel it was the best idea). I think the closing plan to let sleeping dogs lie and be publicly polite and bland when required is the way to go. There won’t be any productive resolution here.

    2. Tinkerbell*

      “I took the option that would result in maximum drama and my boss responded in a way that left some drama lying around. I don’t know what to do!”

      1. Elle*

        This is a perfect encapsulation. When the LW said they didn’t like the boss’s response very much, I was thinking that it sort of sounded like a surprisingly calm response to their manifesto.

    3. Slow Gin Lizz*

      Yeah, writing an email like this can be extremely cathartic. I love to write these kinds of emails in a Word document and then delete it without sending. I’ve also sent a few when I was a lot younger and more inexperienced, and they mostly turned out pretty badly, which is why now if I want to send an email like this I take a deep breath, walk away from the computer, and write it later but don’t send it. Sorry it didn’t turn out the way you’d hoped, OP. Here’s hoping you never hear from him again.

      1. MigraineMonth*

        I recently found a (fortunately never sent) FEELINGSBOMB letter to my ex-manager from 5 years ago, and I can’t understand a single thing that I wrote. I was clearly very upset about something she had done and was feeling persecuted, but I can’t figure out why I was so upset.

        I even ended up getting fired by that manager, (the best thing that ever happened to my career), and when I ran into her last month I couldn’t remember where I knew her from.

        This too shall pass, if you let it go.

    4. Gemstones*

      Yeah, it feels like this is the kind of letter you write and put in a drawer for a day or two before you actually send…and then ideally realize that you just needed to write it out rather than to actually send it.

    5. Snow Globe*

      While I wouldn’t have recommended sending the email (for reasons already stated), now that it is done, I see one positive thing: Bob now knows why you haven’t responded, and will likely stop telling people that you are ignoring him. He won’t want people asking you about the situation in case you tell them why you think Bob let you down. So I think that’s one less thing to worry about.

      1. goducks*

        Honestly, Bob’s telling of this story is likely to make the LW look bad, not Bob. Sending a long unsolicited list of his failings years after she stopped working for him, along with books he should read to fix himself is likely to make Bob seem sympathetic to any neutral third party. Even if they circle back to her to ask her for her point of view, her credibility is severely damaged by her decision to send him a lengthy email about all the things he let her (and others, she’s speaking for the rest of the team, too!) down.

    6. Quantum Possum*

      Yes, this is exactly what I was thinking.

      It’s definitely not the worst thing in the world, OP, but I don’t think it was helpful to you or to Bob. However, I’m not you, and I don’t want to armchair-quarterback your decision too much. What’s done is done. At this point, you’ve said what you felt you needed to say, and it’s probably better to cut ties with Bob.

  3. BluRae*

    He… Kind of had a point. Ghosting him and then sending a long email out of the blue with a list of grievances was kind of odd.

    Just let this drop. If you ever see him in person again, be polite and then excuse yourself.

    There’s no real reason to keep thinking about this situation.

    1. Excel Jedi*

      That’s what I was thinking. Best to just let this drop.

      Your old boss from 3 years ago is just not worth expending this much mental energy on.

    2. ABC*

      I have to agree. It sounds like the LW (sort of?) realizes that was a mistake, so hopefully she is now ready to let this go.

    3. spiriferida*

      It’s kind of fascinating to go back and look at the original response Alison gave, because you can see the reality of her advice playing out in real time here – she advised against sending a message about his failures as a boss because it wouldn’t result in any change – “You can’t fix any of that with an email to Bob.” And it didn’t. It’s understandably disappointing when you feel like you can see the problem and want to believe articulating it will fix everything, but… yeah, usually it just pans out like it did here.

      1. Falling Diphthong*

        And so I’m grateful to OP for sending this update. Sometimes an OP takes the path Alison said was unlikely to give them what they wanted.

        Hopefully someone out there nursing a grudge (against a person who is genuinely very annoying! and who was in the wrong multiple times! and you have evidence!) will take the advice to heart, with this example of the post-job email not giving resolution, and the dude continuing to be exactly who he was before.

        1. YuliaC*

          Yes, oh oh yes. I am also very grateful to the OP for doing this and telling us exactly how it went. I had a situation so very similar to theirs that I had to quadruple-check all the available details to see it was not actually about my last job. I am so happy now I had deleted my similarly-reasoned bad-feelings-bomb email draft.

        2. suomynona*

          I agree! It was kind of the letter write to share the update, even though some might say “told you so”…sometimes you need to find things out on your own but hopefully this update will help folks in similar situations see the wisdom in Alison’s original feedback.

    4. Wallflower*


      It’s weird to invest that much energy into suggesting ways a former boss can improve without being asked to do so. Just move on with life.

      1. Betty*

        “Weird” is a little unkind– I think it’s more an example of how (as Alison has often pointed out) toxic workplace dynamics warp your sense of what’s normal. Healthy, functional workplaces don’t get under your skin and entangle themselves with your identity– but dysfunctional ones really can be like an emotional Superfund* site, where there are things that are really hard to get out of your system even after you’re gone. (Which I say as someone who’s still working through this, 4 years after leaving my toxic “we’re a family” job.) OP if your new role has an EAP, short-term counselling might be a good, more productive place to work through some very valid hard feelings.

        *Since this might not be familiar except to US readers of a certain age: “Superfund sites” are highly contaminated industrial sites in the US that required decades of intensive cleanup and rehabilitation.

      2. But what to call me?*

        It’s not weird so much as unlikely to produce any satisfying results (as, indeed, it didn’t).

        I’ve got a couple of former bosses who I’d love to tell exactly what they did wrong and how to do it better. It would be extremely satisfying and might even feel helpful… right up until they inevitably responded in a completely unsatisfying way that wouldn’t remotely resemble the script I’d made for them in my head. Because chances are that they’re still pretty much the same people they were and a feelings-bomb letter is not going to change that. The desire to send one is perfectly understandable, though. Some bosses impact you deeply enough that it’s hard to move on while knowing they get to go along living their lives continuing to think they were right.

    5. I edit everything*

      Yeah, I have to agree. There are many degrees between ghosting and a long email about everything he did wrong, and here probably the best middle ground was what Alison originally suggested or a note saying, “Thanks for your continued interest, but I’d like to focus on the future now. Wish you all the best, and I’ll see you around.”

      There’s nothing more to do here, and I suspect the email only made everything more awkward.

      There’s no such thing as closure.

    6. Sandro*

      Yeah, it’s a rather extreme and odd way to behave and I’m not surprised he was confused. I think OP may have some rather strange notions of their own and isn’t quite seeing how they come across to others, unfortunately. Their boss wasn’t really wrong.

        1. A. Nonymous*

          I think it’s necessary for someone who got very good advice, chose to ignore it, and the outcome was exactly as expected. Judgement isn’t in and of itself mean — it can be an incredibly useful tool to teach someone “if this is how you behave, this is how people are likely to interpret it.”

        2. Sandro*

          Well, there’s not too much to go on, but based on the OP’s original letter, their decision to send the email against all the advice they received, and then their reaction to the response they received as documented in this update, I’m OK with my level of judgment, but thanks for the feedback.

      1. Elle*

        I honestly feel like the boss’s response was surprisingly measured (from what the OP shared- obvi I don’t have all the info), considering they basically sent him a manifesto with recommended reading.

        1. MigraineMonth*

          Yeah, I’m shocked OP got an apology. Given the description of the ex-Boss, I’m surprised he reacted so maturely to this unsolicited criticism of his management practices 3+ years ago.

          One of the questions Captain Awkward asks is, “What is your goal here?” If it was to minimize drama and time wasted on this guy, this was a failure. If it was to release the pressure of all those unspoken feelings… success, I guess?

          If the goal was to get a man who has repeatedly ignored all OP’s attempts to point out a problem to suddenly have an epiphany and completely change the way they interact with the world (because “doesn’t act on racist remarks and discourages reporting to HR” goes far beyond professional behavior), that was never a real possibility in the first place.

    7. lunchtime caller*

      Agreed, and then they proceeded to still be annoyed at him anyway because well, frankly, he was being his normal self and they obviously don’t like that (for valid reasons) but I’m not sure what response they expected that would make things LESS weird.

      1. Sloanicota*

        Yes. It’s pretty unrealistic to assume anyone is going to get a letter like this and say, “wow, thank you so much for sharing this, you’ve really made me think and learn and grow as a person, I’m indebted to you.” That’s a fantasy. Most people are going to think you’re Being A Bit Much with an added side of ‘what does *she* know, anyway.’ We all see things mostly from our own perspective and are blind to what other people experience, and we have a blind spot for our own ego.

        1. Distracted Librarian*

          This. And TBH the people I’ve known who were inclined to school others on their shortcomings this way had plenty of shortcomings of their own (as do we all). Ex-Boss responded about as positively as one could expect to this kind of message.

          Sorry, OP, but I think you’d be much better off to let this go. It’s a cliché, but you’re letting a former boss live rent-free in your head. Do you really want to do that?

        2. Heidi*

          I was reading about the Suffering Martyr Daydream yesterday and this email reminded me of it. Even if Bob were the worst boss ever, he still “has been extremely successful and, although he no longer manages anyone, I doubt he has gotten a pay cut, and he still has a very cushy and influential position in a small and cliquey industry.” What incentive does he have to change? Or seek advice about something he doesn’t do anymore?

    8. Dust Bunny*

      Yeah, this struck me as the kind of email you write to get it out of your system, but then don’t send. I’m not sure how well I’d respond to somebody ghosting me and then sending me a long lecture on all the ways I failed them, either. It’s much better to let go of the fantasy of being able to fix this in the step before you actually act on it.

    9. Sloanicota*

      I agree. OP was lucky to get as gracious a response as she did. It could have been a lot worse as in my experience this *rarely* goes over well.

      1. ABC*

        I really hope it doesn’t get a lot worse for the OP. She said that the boss is still very influential in their very small industry and has already complained to others about how she ghosted him. This email could trigger another round of complaints from him about her to other people in the industry.

        I suspect that the OP is mentally framing it as, “But they shouldn’t listen to him because he’s wrong and I’m right,” but alas, life doesn’t always work that way. OP might want to have a line ready to go if anyone brings up the email to her, like “That’s all in the past, and I’m happy to say that Bob and I have both moved onward and upward” or something.

        1. goducks*

          If the LW was hoping to make a future interaction with Bob less awkward/stressful, they achieved the exact opposite, most likely.

          1. A. Nonymous*

            Achieved the exact opposite after ignoring the (very good, in retrospect) advice not to do exactly what she did.

        2. Festively Dressed Earl*

          And now it’s in writing. I hope ex-boss never shows it to anyone; it would suck to become a meme in your own industry.

    10. Fluffy Fish*


      Closure is largely a myth. What we want from closure is a satisfactory response to our concerns – and that almost never happens because we cannot control someone else’s behavior.

      Your energy is better spent at figuring out how to move forward then trying to make others fill your wants.

      1. Elle*

        I wish more people understood this. IMO the myth of closure is that it’s something you need to involve other people in. To me, it’s something you can only achieve within yourself. Im sounding like one of those pseudo profound statements you read on tea bag strings, but this has been my experience.

        1. Myrin*

          I’m right there with you. “Closure” absolutely does exist for me but it’s an inward thing – I achieve it inside of myself once I’ve made my peace with something and can leave it behind me (which is, despite sounding quite passive as I read back what I just wrote, just as often an active “I will let this go now!” I’m saying to myself).

        2. UKDancer*

          Yes, I’ve a friend many years ago who sent several lengthy feelings emails to her ex boyfriend to tell him why he sucked and she dumped him. He didn’t respond and she kept asking me what she should do to get him to engage and talk to her about why she ended it and all the things he’d done wrong (which admittedly were fairly numerous). I couldn’t get her to understand that she couldn’t make him respond the way she wanted. He didn’t want to talk to her, accepted the relationship was over and didn’t want a post mortem.

          You can’t make someone respond the way you want to give you closure because people don’t do what you want to make you feel better.

      2. Dust Bunny*

        THIS SO MUCH, in so many different contexts.

        It doesn’t work because it depends on the other person giving you the answer you want, and the odds are that even if you get an answer, it won’t live up to what you hoped.

      3. Ellis Bell*

        Closure is the excuse word people use before opening up Pandora’s box. Luckily, I don’t think the OP did open Pandora’s box (or get any closure either). It seems more like the life lesson which might be entitled with the hypothesis: “Do people want a reiteration of the logical advice they already know and yet ignore for emotional reasons? Experiment result: People in the thrall of internal emotional processes do not actually want logic, as it turns out. Also see: Unsolicited advice and the low demand for it.

        1. Fluffy Fish*

          Oh for sure – My comment is more to OP and others that the *desire* for closure is very normal – dare I say human – and it’s a hard lesson for most of us that what we *think* closure is – it’s not. And that’s why OP is still feeling unsatisfied/unsure.

          I think I’ll add all this as a stand-alone comment because I feel bad OP has been so piled on for something close to all of us have done in some aspect of our like or the other.

    11. Momma Bear*

      Agreed. I wouldn’t have said anything until/unless I saw him at the event and then just been civil and professional. An email out of nowhere like that is a little odd. Kind of feels like LW wanted the floor for an airing of grievances instead of a real discussion. Email can be more of a monolog and I think that Old Boss had a point. LW seemed to have specific expectations that were not met, and thus found the response irritating.

      But now that it’s said and done, I think LW really needs to just move on.

    12. No Longer Gig-less Data Analyst*

      I feel like that email is one of the ones you type to get it out of your system, but then delete it before sending.

      Also, if the only purpose was to clear the air before seeing him again at the conference, a little due diligence to make sure he was actually going to be there might have been advisable. Like an initial email or text to say “I know it’s been a long time, but I was wondering if I might see you again at ABC Conference next month?” And then go from there.

      A long email out of the blue 3 years later, about what an abject failure he was as a boss, along with advice on how to be a better manager when he’s had managing duties taken away from him seems a bit over the top to me. Moving on and living your best life is the best revenge you can have on a former crappy boss.

      1. Tattoo'd Librarian*

        Yes, the part about LW thinking it was the perfect time to send this email on how Old Boss messed up is what got to me the most about this update. While I can see LWs thinking that hey, someone he was managing just jumped ship without a life vest to get away from him, he’s probably confused about what he did wrong and I can tell him exactly! This was probably the worst time to tell him. Like kicking someone when they’re down. Very few people might be in the headspace to be receptive to hearing how they failed in the past at a time like this.

        And I do agree with Allison’s original advice that this email was a bad idea for the reasons she said, coupled with the fact this was the first response Old Boss has heard from the LW after she ignored his messages for so long. I think the only thing to do here is to try to forget about it and if LW runs into him, be polite and move on.

    13. Busy Middle Manager*

      The reason to keep thinking about it is because in the original letter, they say it’s a small industry and expect to cross paths either at a conference or new job at some point.

      They should have invited boss for coffee or something and let some of the truth out in a way more subtle way.

      These sorts of things are “funny” to me. I’m a manager and we have 10001 books on how to give feedback and motivate people. Everyone is hyper aware of everything we could do better. They can give us advice like giving us tips for books. But then they themselves don’t even follow 1% of advice their dishing out. Well, not being a manager doesn’t 100% absolve you from the need to be a tad human when giving feedback.

      In this case, Bob most likely needed some sort of heads up that feedback was even coming in order for his brain to actually accept it. I would’ve done it long winding conversation over coffee where I asking him how he thought things went, asked what he thought could’ve been done differently, etc. to sort of draw it out of him

      1. Bunny Lake Is Found*

        I feel like this is also why the “have a conversation” aspect is a useful thing to consider. Bob had been trying to have a dialogue (even a superficial one) with LW for a while and LW expressed no interest in interacting with him–it is hard to go from “well, this person obviously does not want any professional relationship with me” to “this person is now giving me pretty blunt feedback on my management style” and not think “why should I listen to this person?” It also accounts for what I believe to be the legitimate confusion at why the LW didn’t say any of this in response to the many attempts he made made to communicate with them.

  4. College Career Counselor*

    I’ve got to say, I’m impressed with the LW here. Writing a blunt and factual letter like this to a former boss is difficult, and I hope she found it somewhat cathartic, even if Bob said he was “confused.” Spoiler: He’s not confused, he’s fishing for sympathy. Also, he clearly demonstrates his desire to control the circumstances (“conversation about mutual healing/trust”) of receiving the information so he can feel better about himself and his lack of management/leadership when the LW was reporting to him. Why the hell would she want to have a conversation with him about his actions AFTER she left when he clearly never listened while she was there?

    TL;DR: Bob’s gonna Bob.

    1. Bog Witch*

      Why the hell would she want to have a conversation with him about his actions AFTER she left when he clearly never listened while she was there?

      Because she wrote him a long-ass screed about all the ways he let her down weeks to months after they stopped having a formal work relationship?

      I don’t agree at all that LW did anything remotely impressive by writing and sending that email. While ghosting isn’t great, sometimes it’s necessary (the subject of the original letter is literally “my former boss won’t leave me alone”) and even when it’s not, it is what it is at this point. Write the letter if that’s cathartic, sure, but then delete/burn/literally anything except send it. There was absolutely nothing to be gained by doing it.

      OP, it’s time to let this go and move on if you haven’t already.

      1. dot*

        Not weeks to months. Years. The original letter is from 2023 and specifies that they’ve been at a different company away from the boss in question for three years.

      2. Lilo*

        I agree with this. Writing this email years later is just really strange. How was Bob supposed to respond to this?

    2. wilma flintstone*

      Yeah, Bob’s not ‘confused’. He just wants to be able to control a conversation, which he can’t do with an email.

      But I agree that letting it and Bob go is the sensible approach. Live your life!

      1. Dust Bunny*

        I mean, the LW is trying to control the outcome of a situation of which they aren’t a part and of which they won’t be a part in the future, so . . .

      2. Fluffy Fish*

        it’s years later and Bob got essentially got a random grievance email from a former employee he hasn’t had contact with.

        Bob likely is confused. I certainly would be.

        1. Impending Heat Dome*

          On reflection, I don’t think I would really characterize LW’s letter as “a random grievance” primarily because LW’s industry is small, and Bob keeps telling other industry partners that “LW is ignoring him”.

          If LW had sent it after months/years of no contact or discussion with colleagues at all, then yes, it’d be a bit weird. But Bob himself clearly felt disturbed enough by “being ghosted” (as if quitting a job is ghosting) to bring it up multiple times and have that get back to LW. I don’t think sending an email acknowledging that fact is terribly out of left field.

          1. AvonLady Barksdale*

            The email did much more than that, though. “Hey, Bob, I heard through the grapevine that you’re upset I haven’t been in touch. Sorry about that, things have just been crazy. Looking forward to seeing you at the next conference, if you’re going. Happy New Year!” THAT would have been an acknowledgement of the rumors (and, honestly, completely unnecessary). An email with an airing of grievances plus self-help book recommendations is overkill.

          2. Fluffy Fish*

            my point was that going utterly no contact for years and then sending an email to that person of that type is random to the recipient.

            Its not a comment on OP’s thoughts or motivations.

    3. HR Friend*

      No, he’s probably confused. He hasn’t heard from LW for months, and then – out of nowhere – receives an email with a bunch of months-old grievances and book recommendations (cringggge). To your question, “why would LW want to have a conversation with him?” Well because clearly they still care deeply about how Bob is doing. Enough to let it take up space in their head for a long time and spend time writing a letter.

      I might have written the letter as an exercise and for catharsis, but never actually sent it!

      1. Anna*

        You are right: major cringe here. Neither of these people are handling this well. LW needs to get a grip: it’s been three years and this email was so out of the blue and unnecessary. Everyone needs to move on.

        1. Heart&Vine*

          I think they’re both in the wrong. You’re right that OP should probably have kept her thoughts to herself since 1. she was warned Bob wouldn’t take it seriously (and surprise (!) he didn’t) and 2. spouting off all your past grievances in a greatly belated email while not necessarily uncalled for might be seen as just a little inappropriate.

          Meanwhile, Bob *almost* apologizes but then ruins it all by asking why she wouldn’t do him the courtesy of telling this to his face. As if she hadn’t been attempting to do just that while she worked for him.

          But at least now the air is clear and OP can move on with her life without worrying about what she would do/say if she ever ran into him again.

          1. reg*

            that’s a very good point. at least now LW doesn’t have to worry about future encounters. she said her piece, flawed though the route was, and he can’t tell mutual acquaintances he doesn’t know why she didn’t keep in touch.

      2. Angela Zeigler*

        Ughh, I forgot about the book recommendations. That just makes it worse.

        It went from ‘My personal observations as your direct report’ to ‘Here’s my professional advice because you need help’ to someone who sounds like a veteran in their industry.

    4. In a Spin*

      I mean, I’M confused by OP’s choices, so I’m pretty sure it’s reasonable for Bob to be confused. OP is being weirdly over-invested and dramatic about this whole thing. It’s just not that deep!

      1. Falling Diphthong*

        I’d kind of divide people into “People whom I care enough about to have a conversation about a problem” and “People I expect to be no help, and so I avoid having a conversation with them.”

        I don’t expect any people in the latter group to take my opinion to heart if I send a long email explaining their faults. That’s why I don’t interact with them beyond whatever minimum is required by our relationship.

        1. Sloanicota*

          Even for the people who I care deeply enough about to engage in a long conversation, this ain’t the way. Bob was actually kind of right that a one-way letter listing his faults is unlikely to be a productive way to move forward. I get that OP felt awkward about potentially seeing the boss at the event, and apparently had un-earned guilt about “ghosting” (which is not really a thing with ex employers, IMO) but this wasn’t the move.

    5. AngryOctopus*

      This. You told him your issues, he responded with mostly deflection and “why didn’t you do this in MY preferred mode (where I’d be able to talk over you or otherwise bulldoze you)”. LW, I’m proud of you for sending the email, and you should feel free to just politely say hello and maybe make a tiny bit of innocuous small talk, should you see him again.

      1. Falling Diphthong*

        It’s a good example of how people who have hurt us in the past can continue to take up mental space for years. Like we take on the role of reciting their lines at ourselves and seething, even though they are not here to do it in person.

        1. UKDancer*

          Yes. I had a toxic boss about 10 years ago in a different company. She was horrible, bullying and unpleasant. For several years afterwards I felt angry towards her and my memories of that job were preoccupied with how much she was unpleasant. But I realised it wasn’t doing me any good and it wouldn’t make my life better.

          So I too a decision not to give her room in my mind and think of the good parts of that job which didn’t involve her (e.g. it was the job that let me travel to the USA and visit Baltimore for the first time). As a boss I try and be better than she was and treat my team better. Once she wasn’t taking up space in my mind I was a lot better able to move on and think of the past with more contentment. I do think that’s a better way to go on.

      2. lunchtime caller*

        If anything, we should make it even harder so that people are dissuaded from doing this more! (I joke, but…)

    6. DaniCalifornia*

      Agreed. I like that she took a chance and got to express her feelings. If Bob were mature he wouldn’t have even reached out to her current colleagues and current boss in the first place. She was happy to let it go and he kept trying to barge into her life.

      Bobs everywhere are going to barge.

  5. CubeFarmer*

    Can we get over the idea that when there is a power imbalance there any opportunity to have “a conversation, with mutual trust…”? There is no way someone over whom you have supervisory authority could or should feel comfortable offering unbiased, blunt feedback. First, that’s not their job. Second, that could blow back on the junior employee in a very bad way.

    1. Throwaway Account*

      I agree with the others who say just let this guy go and stop giving him rent-free space in your head.

      But also, I want to take CubeFarmer’s points and write him another email to say,
      “lol that you think that when there is a power imbalance (you are the supervisor), there is any opportunity to have a conversation with mutual trust! And by conversation, I think you mean in-person conversation? I assumed you would recognize that this online conversation was a conversation; I don’t trust you enough to have any interest in an in-person meeting.”

      Maybe write something like this but don’t send it; write it just to get him out of your head?

      1. AngryOctopus*

        For sure I think it would help LW to write a “LOL WHUT” response that never gets sent. It can really help to get those things written out! And then you feel good about throwing it away!
        *Just maybe don’t write it in the email thread so you don’t send it by accident. Write it down on paper and then burn or recycle it.

    2. Radioactive Cyborg Llama*

      He mentioned the conversation as a third option to ghosting and the email the LW sent, which were both after her employment ended, so he didn’t have supervisory authority over her at that point.

    3. RagingADHD*

      I mean, if you’d said “how can there be mutual trust when the entire problem was that Bob proved himself to be untrustworthy due to spinelessness / lack of principle,” I’d be right there with you.

      But Bob hasn’t had power over LW in years.

  6. Mad Harry Crewe*

    You are giving this guy WAY too much space in your head. Let the whole thing go. You don’t need the good opinion of someone who kinda sucks – even if he’s figuring stuff out, even if he’s making progress. He can go make progress with new people he hasn’t harmed. You get to (and probably should!) walk away.

    1. Falling Diphthong*

      Yes. You get to walk away. You DID walk away. Keep walking! Do not keep turning and cycling back, either in your head or via email.

      This is reminding me of the current Captain Awkward letter, from someone who successfully executed a slow fade but now wonders if they should reach out to check that it worked.

    2. Sloanicota*

      Agree. Play the Frozen song a couple times and maybe do a dance expressing your joy at no longer having to care what this guy thinks. Next time you see him, great him politely but resist any attempt to engage you in more than surface level greeting and move on to put more ice in your drink. The cold never bothered you anyway.

    3. BRR*

      Yes, this. I’m an anxious person and I completely get being worried about running into someone you’re not fond of (for me it was seeing a boss who fired me at a conference). My advice in this type of situation is for you to set the tone. A friendly and breezy “Oh yeah I was busy getting settled in my new job.” I would make an educated guess that if you identified what your ideal outcome is, it’s probably not likely to happen. Sometimes you just have to move on (easier said than done).

  7. Waiting to leave*

    I feel like I’m in a similar situation now, at a job I’m about to leave. I have tried to “have the conversation” multiple times in the past and it’s just met with defensiveness and gaslighting. I’ve found the best solution is to minimize communication as much as possible, keep necessary communications professional, and count the days until I’m gone. Denial (“What? No, I’m just really busy”) is honestly a wonderful tool.

    1. Sloanicota*

      Yessssss. There was no way to win here through further engagement. An in person conversation would have gone terribly. The letter was, I’m sorry to say, pretty cringe. This is like trying to get your ex to admit he was wrooong multiple years after a bad breakup. It’s not going to happen and the fact that you’re still fixated on this isn’t a good look for you. Your revenge is being happy and not sparing any more brainspace for this guy.

    2. Angela Zeigler*

      I think the key is that you actually tried to have that conversation in good faith. Even if the boss doesn’t deserve that kind of care, it’s good on you for at least making an attempt. *Then* you can shrug, tell yourself you tried, and move on, and leave the old boss firmly in the ‘Past’ category of your life.

      In the letter above, if OP never tried to raise any of these issues while they worked at that company- it’s especially strange to have them listed, in writing, out of nowhere 3 years later.

      1. Waiting to leave*

        Completely agree. I told my wife that once I’m gone I doubt that I’ll think about this person ever again. It’s odd that they’re still taking up so much space in the OP’s head. If you run into them, keep it “light and polite”, then excuse yourself.

    3. AvonLady Barksdale*

      This is a good plan.

      Years ago I left a job because my relationship with my boss had gone sour and I didn’t know why. I tried to talk to him, got nothing. So I left and just let it lie. I later learned that he had been experiencing a mental health crisis and that contributed to his about-face with me. Still, I said nothing. He got in touch with me one day, told me how much he missed working with me, how we were a dream team– he didn’t exactly apologize, but he obviously felt bad, and we’ve been in touch (and friendly) ever since.

      Often better to just… let it go.

  8. Pastor Petty Labelle*

    Imma gonna be blunt here — There’s a reason Alison advised against sending an email detailing his failures as a boss. His response shows exactly why. He is who he is. he’s not going to change just because you laid out a whole long list of reasons why he was a failure. If anything it would put someone on the defensive, which he did. Which rubbed you the wrong way. What you wanted to hear was – Yes I was terrible, I will change and be better because you showed me the light. That was never going to happen.

    You can’t change other people. You can only change how you deal with them. In Bob’s case, its no contact. If you see him at an event, its polite oh hey hi, how you doin, gotta run. Because if you try to persist in changing him, you are adding to the dysfunction of the situation. You can’t fix it. Leave it alone.

    1. Angela Zeigler*

      It’s a good example of ‘In the box’ thinking:

      Expect Boss to react badly and not listen to feedback > Send first message after 3 years with a list of things Boss did wrong, personally and professionally > Boss reacts badly, unhappy at the message > Reassure oneself that boss is unreasonable and that you were right about him all along

      1. Prismatic Garnet*

        I would agree, I think the thing to examine next time is the previous tension between “I don’t trust myself to think fast at the convention”, “I wish he knew what he did wrong”, and “He wanted me to keep in touch and I didn’t.”

        The triangle of tension resulted in a situation where you started taking as a given the idea that you had to tell Bob what he did wrong at some point, presumably because then you could move forward with some kind of collegial relationship without that hanging over your head. But that was what tripped you up – thinking that he had to be told at all, let alone by you. (He’s not in charge of anyone anymore so it’s moot.)

        If next time you get in this kind of quandry, “I don’t trust myself to think fast at the convention” can be resolved with “So I’ll just be bland, vague, and polite and move on.” It’s the imagined pressure to do something substantial that was the mental rock in your shoe.

        That said, don’t beat yourself up over this! I think it’s probably going to be fine and really appreciate you writing with the update.

  9. Quinalla*

    I understand wanting to clear the air before you potentially had to see him in person again, but I’d try not to give it another thought. Let him assume what he wants, Bob is going to Bob no matter what else you say. If you see him again be cordial and brief and don’t worry about what he thinks anymore. It doesn’t matter and he is very good at telling himself what he wants anyway (we all are, but he seems especially good at it) so I’d just reframe Bob gonna Bob and be polite but brief on your end so people you DO care about don’t think you are weirdly rude.

    I do think not responding to his response if 100% the right call, don’t second guess. Would it have been better to not send the long email? Maybe? But you’ve sent it, don’t send anything else and try to focus your energy on the people and work you DO care about.

    1. All het up about it*

      This is the best comment! Things are starting to feel a little like a pile on when, eh – it is what it is. And I TOTALLY get why OP might have started to feel anxiety about seeing Bob at this conference and being afraid of what they might say in person.

      The other thing I hope the OP is able to glean from all the comments is reflecting on their “why” and what they hoped to get out of the email. Was it because despite Alison’s advice and all the years, they still just had that NEED to tell Bob their experiences with him? Goal met. Was it to inform Bob why if OP saw him at said conference they wouldn’t be grabbing chummy drinks? Goal met. Was it to get Bob to admit he’d been a horrible manager? Honestly, kinda goal met. He acknowledged and apologized. Sure, there might have been some other annoying items he followed that up with – but a feelings dump email 3 years later is a lot. It sounds like maybe you didn’t get the closure you wanted, but what exactly would that have looked like and was it truly realistic?

      Take your wins and move forward with your awesome job and networking with others at future conference. And if you ever see Bob again – polite and cordial all the way without any anxiety about it being a “thing” is the way to go.

  10. Health Insurance Nerd*

    I have to be honest and say that if years later I got a message from a former employee with a list of my failures I don’t know how gracefully I would respond, either. You said your peace, and it sounds like Bob did as well. Now, LW, you really just need to let this go.

    1. Happy meal with extra happy*

      Yeah. I was a bit taken aback when OP described the letter she wrote, and, really, my opinion of Bob improved a bit from his response. I don’t know if I would have been as seemingly gracious as he was.

      1. Sloanicota*

        The line that made me pause was “I had an opening to check in with him and even offer him some advice” – this was sort of a bad instinct, OP. I don’t know if the advice was what you put in the letter about not wanting to be liked or reading that book, but if it was, that was not a good idea. There was no need to check in because you wanted to put this behind you and were succeeding at that. I think you might just have panicked at the idea of seeing him again. I’ve been there. It probably wouldn’t have been as bad as you pictured though.

        1. Elspeth McGillicuddy*

          Yeah, a whole email full of unsolicited advice is generally a bad idea. Especially to Ex anythings. Ex boyfriends. Ex mother-in-laws. Ex bosses. Bad idea.

          Too late now, of course.

        2. NotARealManager*

          Yeah this was odd to me too. I’m not sure how LW perceived this (a direct report leaving without another job lined up) as an opening to give him critical feedback. I know he was a bad boss, but kicking someone while they’re down doesn’t make you look better. It might be the time for that kind of feedback if you were close friends and Bob asked for it, but you weren’t even in touch.

    2. Falling Diphthong*

      And I understand his point about how if you want to have an emotionally charged conversation, then that is better in person. Where you can control your tone and body language, observe their tone and body language, and it allows for back and forth in the moment as issues are raised.

      Closure is a thing you give yourself. If you try to get another person to bestow it by reciting the right lines (how grateful they are for your absolutely correct analysis of their faults, etc) then it’s likely to end like this. Even if you are absolutely correct in your analysis of their faults and an outside observer would confirm that.

      1. Flailing Up*

        I wish there was a way to get your second paragraph highlighted. This is such an important lesson to learn, and I hope the letter writer understands this now.

    3. Filthy Vulgar Mercenary*

      You would probably not have repeatedly bugged your employee for contact for a long time and complained to mutual acquaintances about their lack of response to you, though, either.

      1. Happy meal with extra happy*

        Okay? That’s super weird he did it. The answer isn’t to be super weird back. Engaging only feeds the drama.

    4. Ricci*

      Yeah, I actually think his response was remarkably restrained and reasonable considering how odd the OP’s email was.

    5. Angela Zeigler*

      Yeah, That’s a good point. I’m sure everyone has a ‘dream message’ they’d like to send an old boss or coworker with all the things they’d wished they’d said, letting off steam or being upfront about issues they noticed. But it’s usually from a place of ‘having the final say’ or exerting control over the old situation, and not really a good-faith effort to help that former boss/coworker improve.

      I’d also be concerned if the criticisms/feedback was never actually offered during the time of employment. If none of the points were raised at the time, it’s not realistic to expect the boss (good or otherwise) to actually change.

  11. Joile*

    You gave him the advice you wanted to give him. If he learns nothing from it and keeps centering himself – as we say in Romania – “may he be healthy”. Not your problem anymore.

  12. Emily*

    Thank you for the update, LW. I am so glad you are continuing to like your current job. I do think, though, that the response you got from your former boss, and how it has frustrated you, perhaps shows why sending these types of emails is not a good idea (and something Alison advised against doing in her response to your original letter). I think not responding any further is a good idea. I don’t see what there is to be gained, and clearly your former boss is not going to do any meaningful soul searching.

    As another commenter said, you are giving this former boss way too much space in your head. I understand that it is a small industry, but please do what you can to emotionally disinvest from him.

    I hope your current job continues to go well!

  13. Bilateralrope*

    He wants a “conversation” so he can pressure you into admitting that you are wrong. Just like he pressured all those people into not going to HR. Anything that lets him avoid having to think about the substance of your email.

    Don’t feel any guilt about ghosting him.

    1. Naomi*

      Yeah, while having that conversation was an option that existed, it doesn’t sound like there was actually a foundation of “mutual trust” to lead to “mutual understanding and healing.” But I don’t think Bob is ever going to grok that, because that would require admitting that OP had reason to worry about his reaction to criticism. OP, I hope you feel some catharsis from having aired your grievances and can proceed to think about Bob as little as possible in the future.

  14. Addison DeWitt*

    I’m still friends with my first boss. By which I mean, we occasionally.chat on Facebook– he takes road trips, so I suggested some things to see somewhere he was going, that sort of thing.

    That seems a pretty normal ex-boss interaction. These people seem way too wound up in each other for the nature of their relationship.

  15. Filthy Vulgar Mercenary*

    I am in full support of having sent the email. Sometimes thing s just need to be said!

    I’d also follow up with an actual response to his response (because I can’t help myself) and explain exactly what you said here, LW. “I sent an email because I wanted to have my thoughts clear and didn’t know how eloquent I’d be in person or on the phone. I also didn’t want to take care of any response (or your emotions) you might have to my feedback, given how you had responded to my feedback when we were working together, the way you reacted when I ghosted you, and the way you have responded to my email now. I know this is pretty blunt of me to say now, especially via email, but it’s what works for me now given the context. I genuinely wish you well and happy new year.”

      1. Frankie Bergstein*

        This is an incredibly strange action to have take. on so many levels! I think the rest of the commenters have said why — but just one thought here: I wouldn’t automatically assume that seeking an in-person conversation is the former boss trying to steamroll the LW. I think it’s reasonable to have emotionally charged conversations in person. It’s okay to do so by text or remotely when needed, but that doesn’t seem to be the case here.

        Let it go – fill the space in your life with something fun!

      2. myfanwy*

        Yes, good lord, please please don’t send him any more emails. There are lots of things that would be satisfying to say to all kinds of people, but that doesn’t mean you just go ahead and do it. This will just be more drama – which I’m guessing LW would rather not develop a reputation for in their industry? I wouldn’t assume Bob will keep this all to himself. And no one will benefit one iota. It doesn’t matter how right LW is about Bob, she can’t make him see the light and she won’t come out of it looking good if she tries.

      3. c-*

        Yeah, what’s done is done, but let’s leave it here. Bob is no longer your boss, there’s no reason to spend another second on him.

        No good and much drama will come from continuing to interact with him.

      4. Lilo*

        Adding to the chorus. Don’t email Bob again. There is absolutely nothing good that can come of this, and some potential bad.

    1. Mighty K*

      I absolutely would not recommend this!
      What response would you want to get from the ex boss? What do you think you’d actually get?
      Spoiler: you’d get more of the same, and it’d be even more frustrating.

      Let it go.

      1. Falling Diphthong*

        He was like this in the past, he’s like this now, but what if one more email will cause him to see the rightness of her criticisms and become someone else altogether?

        (This is sarcasm. Do not send the email.)

    2. Dust Bunny*

      No, this is my mother, who Must Have The Last Word no matter how dead the horse being beaten. The LW ghosted him and then gave him chapter and verse on how s/he thinks he failed and could improve.

      But holding onto all that years later is also just weird. Like . . . you don’t work for him/together any more. You’re not his supervisor. Drop it and move on.

    3. Pastor Petty Labelle*

      Please no. It needs to be dropped. Bob is gonna Bob. She is not magically going to change him. Continuing to try is like wrestling a pig. Gets you dirty and annoys the pig. Bob is not suddenly going to say yeah after all these emails I realize you are absolutely right and I am absolutely wrong. I will change.

      The best thing OP can do is forget Bob’s existence. Completely.

      Someone up above said it best — closure is something you give yourself. She needs to close this matter and never open it again.

    4. Bunny Lake Is Found*

      Please LW, I beg you, DO NOT DO THIS.

      Bob was already saying you were “ignoring” him to mutals in a small industry–a statement most people would take with a grain of salt because, well, you have a life and a job, and he’s your old boss! Now you sent him this “all the reasons you were a bad boss” letter. Do not follow it up with a “But you are STILL a bad boss”.

      For Pete’s sake, LW, Bob has been promoted to a senior level position which means, terrible a manager as he may be, he has VALUE in the industry. Do not risk your ability to succeed by becoming “the former employee who keeps sending me emails about how bad I was as a boss years ago” that Bob mentions far and wide at conferences.

      No, you don’t NEED to say every thought that comes in your head. Ever.

    5. RagingADHD*

      Ever heard the saying, “First thing to do when you find yourself in a hole is to stop digging?”

      LW’s original stated goal was to get Bob to leave them alone. Your suggestion could not be more opposite to that.

      Though perhaps it is closer to the mark of whatever LW’s unspoken goal is. The email in question certainly runs counter to leaving-alone, so perhaps the real goal is something else — closure? vindication? punishment?

      Might do LW some good to unpack that, because the messy real world we live in rarely provides any of those things.

  16. Lorac*

    I kind of have to agree with Bob. Not hearing from your employee for months and then suddenly getting a long email with a list of grievances out of nowhere is…really odd. Even the best of managers would struggle to respond civilly to that.

    That’s not a conversation at all. It’s not even something that can spark a conversation. Intentionally or not, that puts the other party on the defensive from the start. He actually responded surprisingly gracefully to that. A lot of horrible bosses would not do the same.

    1. Angela Zeigler*

      That’s a good point. Just because the boss might be professionally successful and rich that doesn’t mean they don’t deserve basic courtesy like a message or two.

      In my experience, people who refuse to confront issues with someone usually have strong negative views/assumptions about that other person, and by not talking to the person they dislike, it’s easy to mentally demonize them and cling to assumptions. If confronted, and that person reacted with more understanding and sympathy than expected, for example, you’d feel guilty for assuming the worst about them.

      While OP’s boss certainly doesn’t sound innocent, they did react gracefully to being treated rudely, at least.

    2. Opalescent*

      Yeah, Bob comes off surprisingly well here in my opinion. He seems much less unpleasant than the OP’s original letter made me expect. And the OP seems much less reasonable after reading that email.

      1. Myrin*

        I agree. In the original letter, OP seemed level-headed and like she had a clear view of things, if a bit strongly focused on a boss from more than three years ago; but that could easily be explained by the letter’s main grievance of the boss still asking after/talking about her to all and sundry. Bob came across like a bad boss and like a boor in general.

        I’m assuming Bob is still a bad boss and a boor in general but you almost wouldn’t know that with this update because he reacted with an amount of grace I would’ve neither expected nor think I could’ve pulled off myself, honestly; I get what OP and others criticising his response are getting at but it actually seemed pretty restrained and understandable to me. OP seems so incredibly fixated on the conference issue in particular (which also came up in the original letter) that it almost sounds like she panicked herself into sending this email if it weren’t for the fact that she already mentioned this possibility in the original letter (which I have to admit I found odd back then, too).

        The worst thing to me is that Alison actually gave OP several really good scripts even in the unpleasant case she would meet him at their work event and yet the way OP chose was the one thing Alison explicitly warned against. And like, obviously nobody has to follow anybody’s advice on anything ever if they truly don’t feel like it but man, OP, you weren’t alone in this and yet you reacted in a way where you might’ve as well not written in to Alison at all.

        1. Bunny Lake Is Found*

          I agree that had the possibility of an air-clearing email not been floated in the first letter, my assumption would 100% be that the LW was so panicked/anxious about potentially running into Bob that she made a poor, but understandable, choice to send the letter. Anxiety really does create a mirrorverse where ideas we 100% know are bad seem suddenly like the only option.

  17. DC Cliche*

    There are some posts that I’m convinced are sent by people in my industry and this one is the best example.

    I’m sorry you didn’t get the response you were craving. I think asking yourself that question — and “why am I sending this email?” — is always a good self-check before hitting send.

  18. redflagday701*

    He wanted it to be an in-person conversation because then he could push back and try to talk OP out of their assessment of him. You can’t argue with a long email of grievances laid out in black-and-white, or persuade it to like you. Agreed with everyone who says to let this go, OP, but do so knowing that, truly and deeply, this man sucks.

  19. Csethiro Ceredin*

    Unfortunately there is a specific brand of defensiveness that immediately segues to “how you told me about the problem is also a problem and that is what we should be talking about.”

    I don’t think he’s going to get it – but maybe someday some of what you said to him will sink in.

    1. Quantum Possum*

      how you told me about the problem is also a problem

      But this is a perfectly valid response to poorly-given feedback. Part of communicating with other humans is considering their feelings and the overall context of the situation.

  20. John*

    I can relate to LW because, nearly three years after leaving a really toxic situation, I’ve entertained thoughts of messaging one of the executives who sold me out (because I disconnected from him on LinkedIn and he somehow realized it and recently sent me a connection request, which put him back on my radar screen).

    As constructive as it sounds in my head to enumerate for him just what a terrible, duplicitous leader and colleague he was, I realize it would accomplish nothing.

    LW: it’s fairly normal to periodically think about how messed up things were at old job. May his annoying reply be what you need to let it go.

    1. MsM*

      Yep. Every time I’m even tempted to check and see how Old Terrible Bosses are doing, I remind myself that the entire reason I left was finally coming to terms with the fact they were never going to change. If they’ve somehow managed it in the interim, I’m happy for their current employees, but I can’t save anyone still there if they haven’t.

      1. Falling Diphthong*

        This. This is very wise, and not only about our relationships with old bosses who never realized how wrong they were.

    2. Pastor Petty Labelle*

      Feel free to write out so you can get it out. But never send it. Burn it, put it through the shredder, tear it into teeny tiny pieces, whatever is most catharitic for you. Then be done.

      1. Emily*

        Yes, writing it out but not sending it is a great idea (just make sure you do it on Word, or if you do it on email, just make sure you don’t put in an email address, in case you accidentally hit send). I have done things like that before, and I have found it incredibly helpful.

        I do get where LW is coming from. It is maddening to know that you are right about something, and the other person could benefit from your advice, and should also recognize how they harmed you, but in reality getting the other person to acknowledge that is slim to none, and more likely than not leads to the experience LW had, where she is now more frustrated than she was before.

        LW, I know you are not really seeking revenge on your boss, and are rather trying to get him to realize and acknowledge that he was not a good boss, but I do think the phrase, “The best revenge is living well” applies here, or my new favorite phrase from the one and only T. Swift, “I’ve also learned there’s no point in actively trying to defeat your enemies. Trash takes itself out every single time.”

        Focus on the fact that you got out of that toxic environment and are now at a job you like!

    3. goddessoftransitory*

      I consider this a very, very common and human kind of magical thinking–when a situation ends messily, or just doesn’t resolve in any particular way, it’s soooo tempting to think that the right conversation or email or confrontation or whatever will make the other person “get it.” They will finally grasp what they did wrong and change their ways, and my version of reality will be justified.

      It hardly ever happens. Not saying NEVER, but the fact is: most people see themselves as justified in their actions most of the time. Even when they are behaving in objectively toxic or bananapants ways, when even a sea sponge could look at their actions and say “hey, buddy, you might wanna rethink,” they truly don’t understand why their reports/friends/loved ones/classmates just don’t understand why they are right.

      Which is why letting it go is really the only thing anybody can do. Not in cases where actual harm may result (like deciding trying to convince the public that lead paint is bad is waste of time or similar issues,) but when it comes to personality problems, there’s no magic spell or action that can open a person’s eyes.

      1. myfanwy*

        Yes, this. I’ve never done it at work, but in personal relationships in my 20s there were several essaysemails that would surely clear everything up and make the other person understand and then they’d see it my way and apologise and everything would be better. It didn’t work. It doesn’t work. You can’t explain someone better. If you could, therapy would be a much faster process.

  21. NotARealManager*

    I understand the impulse to write the letter, but it would’ve been better to write the letter and never send it. You said it’s a small industry so that’s why you were hesitant to ghost him. But then you did ghost him and nothing really came of that so I would’ve just kept doing it.

    As for potentially running into him at a conference, I’ve also run into former colleagues at events or new jobs where we didn’t previously end on great terms. It was awkward for five seconds as we acknowledged each other, but then we went our separate ways and/or did our jobs with strictly professional interaction.

    Now you’ve said your piece. The next step is to just let him go.

  22. AcidQueen*

    While I get everyone is confused as to why OP emailed Bob, he had a habit prior to this of poking around their industry and dropping their name and asking for OP. Plus, it looked like Bob was a physical presence in that industry, which OP cannot escape. So there was just an uneasy amount of OP to Bob that OP was unhappy with.

    I totally get it, OP, and it sucks that Bob kinda blew the wind out of your sails a bit. I, too, am in a small industry with some Bobs, but let me tell you–everyone knows the deal. Even if Bob is awarded with certificates, is cited, honored at dinners–everyone knows. And they feel for the folks under Bob and are probably more nosy about where you are in your journey NOW than what happened then. Them mentioning Bob is to get a read on the situation.

    We now diplomatically say at events, “It was interesting/a learning experience/a journey working for Bob.” “Working how I am now is different and exciting, and I just don’t have room to think about Bob anymore.” People can read into it what they want. There were a few Bob fans that thought it was a great compliment but the people who ~knew~ just nodded in solidarity and passed us drinks.

    1. Pastor Petty Labelle*

      So now Bob has an email to show everyone what OP is really like. Whereas if she just kept ghosting him while showing through her work how good she is, he now has tangible proof she is part of the dysfunction.

      1. Nemo*

        Presumably the people to whom Bob could show this “proof” are the same ones who have heard years of complaints from him about how the LW hasn’t kept in touch, despite his pestering, and will most likely come to their own conclusions about whether a much-delayed and overlong critique of Bob’s neediness and his shortcomings as a mentor is “what OP is really like,” at least.

    2. Glimmer*

      Yeah, all of which made Bob look bad. Now he has this odd email response to tell people about which makes OP look bad too. Not seeing how that’s a win really.

  23. K8T*

    I really can’t get over how strange it was to write him in the first place and don’t think his response was out of bounds TBH.

    Please let this be the end of your interactions and just let this go.

    1. Stuckinacrazyjob*

      I would have written it in my journal and thrown it into the creek ( metaphorically)

  24. Lorac*

    But isn’t that even more reason to not email Bob? Because Bob already has loose lips and now he can spread gossip about how his former employee who ghosted him suddenly sent an email out of nowhere about XYZ.

    If anything that puts LW in a worse spot!

    1. K8T*

      Was thinking this too – and recommending a management book about dysfunctional teams??

      A scenario that should’ve stayed in the shower where we always win our arguments

  25. see you anon*

    I feel for this letter writer. Years ago, I was quite abruptly fired by a manager who I trusted, and had a history of wanting to be everyone’s best friend. In hindsight I can see that I was going through a mental health crisis at the time, largely caused by the stress of my job, and didn’t know how to ask for or seek help, and I feel like they also didn’t know how to support me (fair). I still feel hurt and let down by this manager — it didn’t help that they were still in my peripheral orbit as I remain social with some colleagues from that job, so I’d always hear things about my former manager.
    I have had some Charlotte York a la the Sex and the City movie, “I curse the day you were born”-type daydreams, should I ever run into this former manager. But ultimately it’s not worth my time or energy to dwell on this (I understand the irony of my now writing about this here — healing is a process). I wish you peace, LW, and hope that you can move past this, and refocus that energy on something that will serve you.

  26. Morgan Proctor*

    This whole saga is a really important lesson in what NOT to do in this situation. Folks… Elsa is never wrong. Let it go. You WILL run into these people later in your career. It WILL benefit you to be the bigger person in these situations. You WON’T get the results you think you need by dumping out your purse at their feet.

    If LW is truly concerned about what their boss is telling their peers about this situation… Well, they just gave their boss a HUGE cup of tea to spill to anyone who will listen. And people will listen, because people love gossip.

    People… please don’t do any of this. Take the higher road, just hold your tongue. A boss or coworker is NEVER worth it. Just let it go.

    1. ToDoList*

      I agree with Morgan’s comment and others about writing the email, but LW, if you can, let this go, too. You made a choice and it didn’t work out and now you’re wiser for it — and if you run into a situation like this in the future, you can make different choices. I hope you can take the situation with your old boss and this comment section where people are being critical and move on without letting it bog you down too much. We all make mistakes! It will be okay.

  27. HonorBox*

    OP, I think if I were in your shoes, I’d take the response you got as a win and let it be the end of the thought you give this. I’m not going to pile on and suggest that your email wasn’t appropriate. However, I’m sure it caught him off-guard. But it is apparent that he gave your email some thought. He apologized. While he also went on with some “I” statements and expressed confusion, he did recognize some failures on his part. I think it is just as likely that he could have responded in a much less kind way and you’d be stewing over that. Take the apology and put on a kind face if/when you see him, but please don’t dwell on the contents of the email or whether or not you should have sent yours.

  28. Former Retail Lifer*

    OP, I would have done exactly the same thing if I thought I was going to run into him at a conference, even if Alison also advised me against it. I am incapable of letting stuff go, so I fully understand this even if a lot of the other commenters don’t.

    You responded to him, he responded back and showed you he won’t ever change, and now you can close the loop and move on.

    1. AvonLady Barksdale*

      Being incapable of letting stuff go… That’s not a great thing. How does that serve you? Being able to gauge whether it’s necessary to pursue something is an important life skill. In situations like this, there is more to lose by letting a single person live rent-free in your head for a very long time.

      1. Former Retail Lifer*

        Of course it’s better to be able to let stuff go, and but I (and I’m assuming the OP as well) can’t always do that. Easier said than done.

  29. Marz*

    I just want to say that I totally understand all your feelings, I think it was pretty brave to put it out there, and, yes, it was always going to be frustrating, and Bob was never gonna change, but that doesn’t mean it was a failure. I know I have to learn the lesson of “if they wanted to know, they’d know” over and over again, but just in general, I struggle with direct, hard conversations and I have to tell myself over and over again, it doesn’t have to “feel” like it went well, because it never will for me (or at least, not without a lot more practice) even if they react “perfectly” (which they won’t), just bringing up something fraught for me opens up a deep fear pit inside me.

    I know people here think you just shouldn’t have and should’ve let it go, and, yes great, probably, in a perfect world, but I definitely know that feeling of “Well, he just *is* and *will* take up space in my brain, if I can do something, I will.” I was going to be in an “intimate” leadership program with my still-takes-up-brain-space boss, and I asked if they could do anything about it – they could delay me to the next year, but I decided I would rather do it with him there then wait, and I don’t regret that, or asking, even though it didn’t change anything and meant I cried, a lot, to strangers, and it felt awful.

    I’m sure this isn’t the healthiest way to think about it either, but I DO resent how much brain-space he takes up, and so I would think, “okay, he didn’t change, but I KNOW he wants everyone to like him, and I bet that took up space in his brain, and I’ll take that”. Sometimes it feels like I’m taking all the brunt of that person’s failures, and they just sail along doing great, and look, it’s okay if they are mad at you. You’re mad at them! it makes sense, it is what it is.

  30. tinybutfierce*

    Respectful conversations with mutual trust require both parties to have established they’re capable of that; Bob certainly hasn’t.

  31. I should really pick a name*

    Think of it this way, you’re not at square one. You’re at square whatever the last square is.
    He’s your former boss and that’s all he has to be. There’s nothing you have to do.

    I think you’ve unrealistically built up what running into him in person would be like.
    Keep it simple, short and sweet. There’s no need to get into any resentments you’re holding onto from when you worked for him.

    “Hi Bob”
    “Hi LW”
    “How’s it going?”
    “I’m at X company now”
    “Congratulations! Nice running into you”
    Then go searching for some appetizers to munch on.

    If he asks if you’re upset with him, “Not at all”.

    1. Myrin*

      “I think you’ve unrealistically built up what running into him in person would be like.”

      I have a comment stuck in moderation where I mention that feeling, too. I’m imagining OP as some sort of prey animal mingling and ducking behind poles with Bob being the stalking predator – or rather, I’m imagining OP is imagining that.

      I totally know the uncomfortable, weirdly haunting feeling of really, REALLY trying to evade and avoid something or someone but most of the time, it turns out to be not nearly as bad as I’d previously made it out to be. (And Alison even gave some excellent scripts OP could’ve practiced in the event that she should indeed run into Bob!)

    2. Czhorat*

      This is the same thing I meant about “bland pleasantries”. Once you don’t work for someone it’s not impossible to put them at arms’ length, even if they overstep a little. Just return to something noncommittal and general.

      You’re doing well at your new job. You like the people, like the team. You’re glad he’s doing well. Etc, etc.

  32. iglwif*

    Hey LW, I so appreciate this update! It sounds like Alison advised against emailing Bob, you emailed him anyway, and it didn’t change much … but I have to say, if I were in your shoes and expected to see Bob imminently, I would probably have done pretty much what you did, rather than risk encountering him with this thing hovering over the encounter.

    I want to pick up one particular point: the thing where you thought your email was the beginning of a conversation while he think an email and a conversation are entirely different things. I bring this up because in my current volunteer role, I have recently been hit with the “why did you send a cold impersonal email to this person instead of calling them??” stick a few times. I would send someone an email explaining a complex thing and inviting them to get in touch (in whatever format they wished) to discuss further, and in 2/3 cases the person did not respond to me in any way but subsequently complained about me to all their friends in the community. And then I would be told, well, sometimes email just doesn’t work; you should have just called them.

    I then had the following indignant thoughts:
    (1) my emails were very warm and personal! They explicitly invited connection!

    (2) I have pretty bad phone anxiety, I struggle to have a difficult phone convo without rambling, and cold-calling someone is especially horrible for me. When I talk to someone via email or text, I can think through my replies, seek information or advice when I need to, google things, fine-tune my wording, etc. On the phone I just flail.

    (3) In my personal life I know ZERO people other than my 82yo mom who like getting (or would even pick up) a random unplanned phone call from someone they don’t know well. How am I supposed to know which people will welcome such a call?

    Nobody is wrong in this situation, exactly. Some people are comfortable in writing and anxious and flaily in speech; other people feel differently about each of these mediums. But — maybe because I work in a writing-heavy industry and gravitate naturally towards people who prefer email and text over phone calls — it genuinely had not occurred to me before this that an email full of warm wishes, exclamation points, and explicit requests for connection could come across as “cold” and “impersonal” … and yet it did. So that’s a lesson for me.

    1. Prismatic Garnet*

      While I think there’s some truth to that, I think it’s worth reflecting on the disconnect between OP feeling like the email could be a conversation in itself, but then thinking the boss was wrong to engage with OP’s points and explain himself / provide his perspective. OP, you note that he used “I” statements as though that’s defensive, but those are what you’re actually supposed to use in a tough conversation! And how else is he supposed to respond without using “I” did this / though that/ think that, etc – he himself is the subject of your letter.

      Basically, while you may not have known you were doing so, you seem to have both expected your letter to be a one-way trip (you tell him how he was wrong, he says “yes, now I get it!” and nothing else) and yet treat it as though you were being reasonable by starting a conversation (with a wall of critiques you expected no further discussion of).

      This is why something like this – a difficult conversation or one involving rumination on the past with someone with whom you’re not current, or a critique/request for understanding – should be done in person, or not at all. It’s not fair to Bob to spring a letter on him like this as unprompted, and he’s right that if you felt you couldn’t let things be, a coffee-and-closure date is what you owed him.

      (And if that sounds too uncomfortable, unnecessary, or not merited by his past behavior, or too out of left field… those are some of the hints that tell you to just do and say nothing! :) )

  33. The OG Sleepless*

    When I got to the part where the LW wrote a long email about every grievance they had against Boss, I kept expecting them to say, “and then I deleted it. I feel so much better and will now move on.”

    1. Czhorat*


      I get where the LW was coming from and I think we’ve ALL had that impulse. The former boss was kinda right though: “completely ghost” and “long email” are two opposite ends of a spectrum with far more reasonable points between.

      One undervalued career skill is being able to maintain professional and cordial relationships with people who you not only dislike but who you have REASON to dislike. I’d send bland pleasantries rather than a missive 12 times out of 10.

  34. I Am On Email*

    OP, I never would have guessed that you’d end up sending him unsolicited grievances/advice – you work in a small close knit industry! Alison kinda advised against it in your first letter! I’m not really sure what you were expecting but it was clearly something you needed to get off your chest.

    Bob does sound difficult and frustrating so I hope you’re able to focus on your excellent new job and continue thriving. When you do eventually run into him I hope it is a short low-key interaction.

  35. Raisin Walking to the Moon*

    LW, I’m so glad you wrote that email. I think Bob’s response about the “third option” was just his need to have the last word, to ignore your advice one last time.
    “Oh if only she hadn’t emailed me…” Then what? He’d just have had more opportunities to disagree with you.

  36. Annie*

    I am confused the LW chose to send this long email the day before she expected to see him. That is a short time to read it, react and respond! What if he hadn’t seen it? What if he reacted badly in person? Part of me wonders if the mail was the reason he didn’t show up. Ultimately I think this was the best possible outcome the LW could have gotten from sending that mail.

  37. Happy meal with extra happy*

    I am concerned regarding the handful of comments that seem to think this was a net win/positive for OP.

    1. BBL*

      Same here. Bob came off looking reasonable and unfortunately the LW didn’t – and now we know it’s a close knit industry which makes it even potentially more fraught for pitfalls for the LW.

      I write stuff like that in a notebook, then I rip it out and literally burn the pages in my fireplace. It’s very cathartic.

    2. Lilo*

      Yeah this is not good. Do not act out revenge scenarios at work. Do not air grievances that are years old in your industry. Complain to your spouse, your friends, etc. Do not do stuff like this.

    3. Tobias Funke*

      Same. And I think it’s an interesting contrast to the propensity commenters have to label folks described in letters as exhausting, needy, inappropriate, problematic, (insert your word here) when much of the time they’re just humans trying to do their best except their best is kinda weird.
      Support and kindness doesn’t mean uncritically cheerleading.

    4. lunchtime caller*

      I try to remind myself that there’s a reason we’re the ones reading the advice column and not the ones writing it… more of us have been the troublesome coworker in some way than not

      1. Softly Skilled*

        Yes! I look back at myself and I mentally write letters to Alison from the perspective of former colleagues based on my past behavior. It ain’t cute. But it wasn’t out of malevolence. It was just out of not knowing what I didn’t know. That obviously doesn’t change the impact and I am 100% aware of that. I just can’t go back and fix it (as much as I would like to/as much as I spend nights awake remembering how awful I was and the destruction I left in my wake). But it does not make me, or you, or anyone a supervillain. We can call it making excuses for my past self. Or we can recognize that cringing at past behavior means we’ve grown. Can’t go back (again, as much as I wish I could, I’ve humiliated myself beyond measure) but can go forward.

    5. Bunny Lake Is Found*

      I feel similarly. Sure, the LW made a bad choice, but she is well aware that this was not a “win”. Hence the “back at square one”. She views this as a net neutral–she didn’t get the response she wanted from Bob, so it didn’t give her the catharsis/closure/change she needed not be frustrated with Bob and the prior workplace. So where is the positive outcome for LW? I just cannot find it. Maybe it is a vicarious thrill for us on the outside to imagine taking Bob down a peg, but legitimately, the LW is TELLING US that it doesn’t feel like this benefitted HER! We should really trust her own assessment of how she feels about how this all went down.

  38. OrigCassandra*

    It seems possible that one reason Bob was namedropping OP all over the place was wanting to ride on OP’s coattails. “I managed OP — isn’t OP awesome? I taught OP everything OP knows” style garbage. If you’ve been rising in your career, OP, this is even more likely. Triply likely since Bob… apparently hasn’t been.

    Fortunately, it seems likely Bob will cut that out from here on.

    Unfortunately, it also seems likely that Bob will replace his former flattering verbiage by telling his new “OP — what a flake, amirite?! Let me tell you what OP did…” story.

    I don’t think this an improvement, OP. That’s your lesson for the future: you protect yourself by staying well clear of the Bobs of this world, once you get free of them.

    1. Happy meal with extra happy*

      Yes, excellent advice. One of my early bosses was absolutely awful, and my hope in life is that he never has reason to think of me again.

  39. Anonymousse*

    It is too bad you didn’t just send an “hey, so sorry, I’m so busy!” text just once or twice. This is exactly what the social lubricant of white lies are good for. You could have phished to see if he’d be going to that event or just had continued ignoring him, since you were no longer working with him. I am surprised you landed on “send lengthy email listing man’s deficiencies from nearly 4 years ago, unsolicited,” and think that he would take it gracefully. I know you and other commentators think he needed that and that you needed to be the one to send it, but I think this was poorly handled. I actually think he did take your email with a lot of grace and although you may have felt uncomfortable giving feedback to him face to face, I don’t think an email out of the blue was the way to handle this, either. It’s been years, time to let the man stop living rent free in your head. Let him go.

  40. Ask a Manager* Post author

    This is becoming a pile-on, which I hate to see when someone has been kind enough to give us an update. I’m asking that comments from here on be constructive advice, not just criticism (and have turned on comment moderation on this post to ensure that happens). Thank you.

    1. Jake*

      Can you pin this to the top? I didn’t see it before commenting, and while I don’t think I piled on, seeing this may have made me recheck for tone before clicking submit.

    2. Ittook3marriages*

      Came here to say that she may have made a mistake in delivering a “feelings-bomb”, but comes to the comments and gets pretty much the same delivered to her.

      1. Bunny Lake Is Found*

        I suspect because, while the LW admits that the letter didn’t get her the reaction she wanted, she only “wonder[s] if [she] shouldn’t have contacted him in the first place” when it is abundantly clear this was a bad decision. It would be disingenuous for people to not point out that she definitely shouldn’t have sent this, that Bob’s reaction was way more reasonable than anyone would have anticipated based on what we know of him, and, most importantly, that sending this email could have caused, and may still cause, more issues for LW. If only so when she encounters a similar situation in future she doesn’t think “maybe this time I will get a response that I am happy with and it can’t make things worse”.

  41. different seudonym*

    W/r/t the original Bob drama in the original letter…people who constantly ask your advice and never take it just like having your undivided attention. They don’t respect you, or even think of you as a full person with experiences and desires of your own. That’s probably why you told him off, to try to make him actually pay attention, and it’s also why his answer was awful: he just reasserted the dynamic of “I am the main and you are an NPC.”

    Forget his ass, and if you’re feeling vindictive tell other people that the way he’s obsessed with you is weird.

  42. Not A Manager*

    LW, you’ve gotten a lot of tough love on here. I really understand the impulse to want to force the other person to understand what they did to you.

    My advice, when you think about communicating in a similar way in the future, is to think, “what’s the best outcome I can possibly expect from this?” Not, “what is my preferred outcome in a different world with different personalities,” but an actual, real-world, best-case scenario. Usually realistically gaming out expected outcomes is enough to prevent me from attempting this kind of communication. Usually.

    1. ABC*

      I once saw someone on here asking the following question to an LW who wanted to double down on a questionable move in order to “win” (their exact word):

      “If you win, what is your prize?”

      Always a helpful question to ask yourself in situations like this. Many times, the answer will be “nothing.”

  43. Falling Diphthong*

    Constructive advice: Some time back I wrote brief letters to three relatives about my frustrations with the way they had treated me. By hand, which I recommend for both length and for not going back to tweak tweak tweak. Then I burned them. It was surprisingly freeing, and helped me stop going around the grievance treadmill. I recommend it: Print and burn his reply, or burn a brief reply you write by hand, or burn a candle and recite something about how you are dragging the tangled mess of this past out of yourself.

    Two of the relatives were dead and so nothing was changing, and the third certainly wasn’t changing their ways to make me happier, especially not when they were right about everything. What changed was how much mental space I gave these grievances, helpfully providing not only both sides of the conversation, but also input from objective onlookers about how right I was.

    I think this is a recurring theme in human relationships, where the person who is hurt gives it tremendous mental space and feels like, surely, the other person must give it just as much space. When the other person has in fact moved on and barely or never thinks about any of it.

    1. UKDancer*

      Yes, I did this when I broke up with my first boyfriend at university. I wrote a long list of all his horrible traits and why he was awful. Then I burnt the list while cursing his name forever (and unfortunately set off the fire alarm in the very bad student house I was living in and then fell through the chair switching it off). I fell about laughing at my own dramatic tendencies which cheered me up no end.

      I felt so much better for it and it’s really freeing to feel the negativity burning off and vanishing into smoke. I think it’s good to write these lists or letters and you’re right that the best thing to do is to destroy it.

  44. Bunny Lake Is Found*

    Ok, LW, let us focus on the super brave email you wrote–the one here, to Alison. You didn’t take her and the commentariat’s advice and it left you, emotionally and mentally, back at square one. And obviously didn’t lead to Bob having a “come to Jesus” moment. It ended up as predicted by everyone. You COULD have just never sent an update out of embarrassment or frustration or whatever, but instead you were secure enough to come back here and say “Yep, I did the thing everyone said not to do and it didn’t help.” You were willing to be the quasi-cautionary tale that hopefully helps the next person thinking “I am so overwhelmed, maybe I will throw this Hail Mary and it will help” to realize the Hail Mary is a hand grenade–best case scenario it’s a dud, worst, it blow up in everyone’s face.

    So while your email to Bob didn’t help you, Bob, or any of the people he manages, the email you sent here actually will probably help a lot of people.

    1. Quantum Possum*

      This, 100%.

      Thank you, OP, for sharing this. It’s so hard to be vulnerable, and so easy to be judgmental.

      For every 1 commenter piling on, know that there are probably 1,000 readers who got something very meaningful out of your letters.

  45. A Simple Narwhal*

    This feels similar to a parent who chastises you for not coming to them with a problem, when every time you did they yelled at you or you got in trouble.

  46. Lola*

    LW, I left a horrible job about 10 years ago and I *still* occasionally have dreams/nightmares about it. Usually it’s me back in my old role, still trying to prove myself to a group of people who never even gave me a chance. Sometimes I wish I make them see me now in my success elsewhere.
    And I recently read that managers can have a greater impact on one’s mental health than even a spouse of therapist!

    So I totally empathize where you were coming from, even if I’m not sure you took the right course of action. Take it as a lesson learned.

    I’m hoping you are now able to put this all behind you, mostly because it’s not worth it. Think of it this way: do you WANT Bob to continue to take up this much room in your headspace? Don’t give him and an old job that much power.

  47. Rich*

    +1 for Five Disfunctions of a Team — I’ve found it to be hugely beneficial to me and my work.

  48. Lurker*

    I completely understand why you did not want to speak to him in person, but I think the response you got is why Allison told you writing an email/message to him wouldn’t work. He was never the kind of person who would take it well. I think moving forward you should strive to keep all interactions with him polite and short. Try not to continue getting drawn in by him.

  49. Lurker*

    LW I don’t think any further communication on this matter is required. He has apologized, and it’s time to move on as best as you can and not let this go on further.

  50. Matilda Jefferies*

    OP, I’m on Team Let It Go as well – this is a lot of energy to be expending on someone who has been out of your life for four years! But since we’re here, I want to gently challenge your response to Bob’s email – I had a very different reading of it than you did.

    he wouldn’t be at the event: this is a factual statement, and also (I assume) exactly what you wanted to hear. Nothing to unpack here.

    it had been a joy to watch me excel: this is a very kind thing to say! And yes, it’s his subjective opinion, but it’s not an “I” statement – it’s a compliment to you.

    he had his own complicated feelings about the company where we had worked together. This is likely true. One of the things that comes up a lot on AAM is that toxic workplaces make people behave in toxic ways, that they often don’t recognize until afterwards. Unless he went into great detail about how terrible it was for him in particular, I don’t read this as an “I” statement – it sounds to me like an acknowledgement that you both were in a shitty situation at the time.

    He said he had done a lot of reflecting and apologized for letting me down. Further acknowledgement of his role in the toxic workplace.

    I’m confused by your assessment that your options were to ghost or write me a long email. It’s understandable that he’s confused – he probably didn’t expect to ever hear from you again, and would have been very surprised to get this email out of the blue. There’s nothing wrong with him saying that!

    To me, there’s a third option: a conversation, with mutual trust, aiming for mutual understanding and healing. I don’t read this as an attempt to draw you back in. He’s just suggesting it might have been a better strategy for resolving your feelings, if that’s what you wanted to do. Your email didn’t “clear the air” as you had hoped – he was probably surprised and confused to suddenly be confronted with something he thought had been resolved a long time ago. It’s a bit unfair to dump something like this on him out of the blue, without giving him a chance to respond.

    In any case, I don’t think you’re going to get any more closure from Bob than you already have! This is a perfect moment for the serenity prayer – the serenity to accept the things you cannot change, the courage to change the things you can, and the wisdom to know the difference. I hope you continue to enjoy your new, Bob-free workplace.

  51. SereneScientist*

    LW, thanks for the update. There’s enough piling on in the comments about your choice to send the email to Bob and I’m not going to add to that chorus.

    Instead, I want to share a story of my own in an analogous, though personal, situation to show why ultimately, though cathartic, the email you sent probably caused or will cause you more problems than it solved. About 10 years back, I had a friend, some years younger than myself, invite me to his college arts fest celebrating seniors graduating. In the lead up to this event, he kept asking friends both at school and around the country for letters and emails reflecting on him and our relationship with him. In my youthful naivete (because I too had built up a number of resentments towards him about how he conducted himself), I wrote and sent him a long email praising him and his tenacity after hardship earlier in life and all the ways I thought he was entirely too arrogant, full of himself, and in need of greater intellectual humility to get ahead in life. Yes, I really did put all of those thoughts to virtual paper. Can’t say it was my best moment.

    Did I truly believe I was doing him some kind of favor? Yes, absolutely. Did I do this because I wanted to get ahead of these crappy thoughts getting in the way of our having a good time at this arts festival? Oh yes. Was it also entirely about my feelings towards him? Absolutely. And it didn’t do anything intended, because however much I may have been right about him, the email offended him greatly, put him on the defensive, and that reaction subsequently came out in our interactions at the festival. We are now no longer friends because of that falling out.

    As other commenters have pointed out, it can feel deeply satisfying and even righteous (!!) to put such criticisms to paper and send them to the recipient. In your case, I’d say you even had a solid case for providing this feedback….in some form while you were still his employee. But sending this letter years after the fact, to get ahead of a *potential* and *likely brief* interaction with Bob tells me you probably have some residual feelings about the situation you haven’t worked through before seeing him again–perhaps feelings of shame/guilt for not doing more then, anger/frustration that Bob continued on as he was, warts and all etc. You’re not wrong to have these emotions, they’re entirely understandable! But by externalizing them instead of processing them yourself, you’ve actually made it difficult to move on. You deserve peace but only you can really give yourself that now. I wish you all the best.

    1. ferrina*

      I did this a couple times with toxic family members, with equally bad results. The toxic people never changed, barely apologized (“I’m sorry you feel that way; now let me tell you all the ways you are ignorant”). And it becomes huge drama.

      The thing is- the people that have the awareness to change will have already started making changes. If they wanted to hear your thoughts, they would have asked. The people that aren’t asking generally don’t want to know. They will absolutely blame the messenger.

      Honesty, an awkward email exchange seems like best case scenario. I also agree that Boss’s response of “you should have had a conversation” was weird (what, after 3 years set up a meeting so you can tell him what he’s doing wrong?). But hopefully this is all the end of this.

  52. Fluffy Fish*

    Hey OP – I commented this in a thread above, but I wanted to post it as a stand-alone because you’ve gotten piled on ant that’s not fair.

    The *desire* for closure is very normal – dare I say human nature- and it’s a hard lesson for most of us that what we *think* closure is – it’s not. We all want to be heard and understood – and that often take the form of trying to make people hear us.

    We’ve all done it in some fashion whether its a boss or colleague, friend, enemy, ex boyfriend or parent.

    The thing is though – we can’t make people. We can’t make them understand, hear, listen, or give us the satisfaction we’re seeking.

    I think that’s why you are still feeling unsatisfied/unsure.

    I’d encourage you to try to reframe the situation to be more about you and less about him. You did your utmost to be heard – that’s admirable in a world where 99.9% of these letters are about people not using their words. It didn’t go quite the way you hoped? Thats ok – that part is out of your control. People here pointing out you should just have let it go? Well ok – but we all do things that are ill-advised at times. Again – human.

    What he did or didn’t do with that info doesn’t matter anymore – you don’t work for him, you have your own successes, you’ve physically moved on and now it’s time to mentally do it. Embrace that you did what was in your control in the situation and let go of the parts that arent in your control.

    Thank you for the update!

  53. Coyote River*

    Just as good people are seldom perfect, those who are less than good are seldom universally bad as well. It’s easy to apply a filter to everything they do, coloured by our experience of them, and interpret things in a way that may not look the same to a third party.

    Case in point, this boss. I’m not doubting for a second he was a terror to work for, but his response in this email actually seems quite reasonable. LW, I would encourage you to take his apology as the best closure you’re going to get, and continue on with your life. If you happen to run into him again just remember the words of Jim Matthis.

  54. Kay*

    You found his response annoying, and he likely found your initial email annoying. You said in your original letter that you’re in a small industry – so small, in fact, that Bob interacted with people at your current job! Take it from someone also in a small industry/circle: sometimes, you just have to deal with incompetent people like Bob. It’s not okay, but it’s the reality. Spend your energy on things that can make the industry a better, more welcoming place – the email you sent won’t accomplish that. Just be glad Bob isn’t managing anyone anymore.

    You’ve built up goodwill through your time at this current job – focus on that. You don’t want to undo it by being known as the person who sent a weird email to her old manager from years ago and won’t let it go. Think about things you can do or promote to make some real change, even if it’s baby steps. It’s a more productive use of your time.

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