That time I unexpectedly told my boss that I’m quitting

69 thoughts on “That time I unexpectedly told my boss that I’m quitting”

  1. That conversation couldn’t have gone much better! Was there any hint of jealousy in his eyes? It’s cool that the boss man admitted he would probably do the same thing if standing in your shoes.

    Maintaining numerous certifications is a rather onerous part of my job, too. It’s not enough to do continuing medical education and be board certified any more. So many hoops to jump through. Sorry to hear its affecting your field, too. At least it won’t be affecting you, Steve. 🙂


    1. Hey PoF! Thanks for your comment. I can’t say that I sensed any jealousy, just the one comment about doing the same thing that I’m doing if given the chance. But yeah, certifications have long plagued the IT industry, mainly because there are just SO many people in this business and I guess certifications are one way to try and differentiate people from others in the field.

      Useless in my view, through and through! 🙂

  2. Congrats! I had a similar situation–not that I was retiring early but I was leaving a job and being asked to take a training and essentially a promotion. So I let the cat out of the bag sooner than expected. It’s always nice to know you’re leaving on good terms, even turning down opportunities, rather than feeling like you are out of options.

    1. Leaving on good terms is awesome. It really is. And you never know what’ll happen down the line – I might run into my boss again sometime in the future, so I never want to run away with bridges on fire. I want my bridges well supported and in good shape, because I may use them again in the future. 🙂

  3. Wow, your conversation with your boss couldn’t have gone any better! What a position you were in to have to have that conversation, but hey, now it is over. Congrats on letting the cat out of the bag! Just over 7 more months…

  4. Hey, Steve. Very encouraging. I face a similar dilemma. I don’t need to acquire a certification, but my leaving will make things a little awkward for my boss, and I want to give her plenty of time to hire my replacement. I’m retiring in October. So I’m thinking of letting my boss know in July. I dread the conversation. My boss and my company have treated me very well. But like you said, you got to strike when the iron is hot. And I have a funny feeling that my boss will be as supportive of my retirement as your boss was of yours. Congratulations, Steve, on surviving “the talk.”

    1. Thanks Mr. Groovy. I completely understand your position. I think that if you approach this not necessarily from the standpoint of “I hate working” and instead a “I have an opportunity (outside of ANY job) that I need to pursue now”, it comes across as a little easier to take. Good luck with your notice! I’m sure it’ll go very, very well. 🙂

  5. Funny how a work moment tips the balance to accelerate the conversation. I am sure that gut instinct played into this also. Now go enjoy the planning with one less thing to worry about. Well done.

    1. Hehe, it’s true. That morning, I got up, “went to work” and everything was normal. A couple hours later, I told my boss that I’m quitting in December. Weird turn of events, but luckily it went well.


  6. That’s awesome! Glad it all worked out and your boss understood

    You are running through your checklist rapidly, has to be a good feeling

    A boss that actually cares about employees over the org is a rarity these days, I am lucky enough to work for one right now – it makes coming to work a lot easier

    1. Thanks Apathy. Yup, things are coming along nicely. And it’s very true that it’s rare when bosses care more about their staff than the organization. Couldn’t agree more, unfortunately. Appreciate the comment and the read!

  7. Very cool the conversation went so well. Hopefully your remaining months on the job will be pleasant. My wife told her bosses she was planning to quit almost two years before she eventually quit and there were zero adverse consequences as far as we can tell. In fact, since they knew her motivations (reduce workload, spend more time with family, travel, etc) she was able to negotiate two (2!) paid sabbaticals during her last two years and then switch to part time, remote work for her last six months of employment (and still get paid full time). Maybe something similar will happen in your case?

    1. Thanks Justin. Yup, I’m hopeful that things will end at work pretty smoothly – so far, so good. Definitely sounds like your wife managed to work that situation to her advantage. I don’t see that happening in my case. I just want to finish my time and be done with it, personally. But you never know…anything can happen! 🙂

  8. Congrats on having a good conversation and having one less thing to do. Bonus that you don’t have to spend extra time getting certified too!

    It’s probably nice that your hand got forced because now it’s just counting down another 7 months and you’re set.

    1. Amen to that, Mr. SSC! And yeah, in the end, I’m happy with how everything turned out. I’d rather the cat be out of the bag than in it. Just makes things easier, and he knows that I probably won’t be interested in some of the things that the more career-oriented folks would probably be more willing to accept. 😉

  9. I think the lesson to be learned here is that transparency and honesty are often rewarded. Steve, it sounds like you are always upfront with your boss and that is why you have such a good relationship with him. You must be very relieved to have all of this in the rear-view mirror now.

    I agree 100% that certifications and pedigree often mean very little. When I review resumes and applications, I glance at this items, but it is easy to get a sense for a candidate who tries to rest on his/her resume rather than skills and abilities. In my line of work (education), interpersonal skills are far more important to me, as I can teach a few skills that may be lacking.

    1. I like that point of view, FinanceSuperhero – and I agree, transparency and honesty almost ALWAYS work out better in the end…for everyone. And yup, the interpersonal skills are so very important to getting along well with your co-workers and communicating effectively. A lot of that stuff you just can’t teach!

    1. Thanks Ms. MoneyPennies – yeah, couldn’t have asked for a better conversation. In general, I’ve worked for people who aren’t complete a-holes. 🙂

  10. Sounds like the certification was a perfect way to bring the “I’m quitting” topic up early. I think that’s the general reaction when someone hears of someone else leaving the workforce early, like damn I wish I could do that. It will be interesting with the news out there now what type of questions/reactions you get around the office. So how does it feel?

    1. Honestly, it feels good – it’s nice to have that done with. Now, my boss won’t be surprised if I don’t exactly volunteer for extra work or go the extra mile, as I once did, to make myself look like a career-type who wants to keep working for another couple of decades. Yup, I’m a short-timer. Regardless of the places that I’ve worked at in the past, the short-timer feeling was always kinda special, and the closer it gets to the quitting date, the more special it seems to feel. 🙂

  11. It’s great the conversation went so well, Steve. I wish mine had gone that well. Instead my immature boss hurled expletives at me, before becoming super passive aggressive (once he realized I wasn’t going to stay for more money). Haha.

    Now that it’s out, it should be some pressure off of you two and allow you to more openly plan. Wishing you guys the best.

    1. Wow! Well hey, if that’s the way your boss reacted, then you know that he/she isn’t the right person to work for anyway. 🙂

      Two birds, one stone!

  12. Congratz on the chat! The subject is now in the open and this will allow your boss to plan ahead on your replacement. I guess you now have less stress on your secret that you carry with you.

  13. That’s totally awesome that your boss is so supportive, the conversation couldn’t have gone better. Now that the cat is out of the bag, does that mean you can start slacking off at work? 😉

  14. It certainly sounded like a perfect reason to announce your intentions early. It sounds like your boss must be pretty great for handling the news so smoothly. It may also give you more time to work an transitioning yourself out of your position, since it is no longer a secret.

    1. Thanks for the comment, Cathy. Yup, he’s a good guy and handled it very well. Makes me want to continue doing a good job for him until I’m officially a retiree. 🙂

  15. Sounds like your hand got forced to some extent. I’ve wondered about that… Like if we had a round of layoffs, then obviously I would let it be known sooner and try to angle to get my own buyout package! There probably a few other circumstances that would make me give notice sooner than we otherwise plant to. But in your case, it sounds like it went as well as it possibly could have, and hooray that your boss was so supportive. Do you think that your giving notice is going to count against you at bonus time?

    1. Yup, to some extent I suppose that it was. Definitely understand your predicament with all of this. Those end-of-year checks certainly add up to something very, very meaningful! 🙂

  16. Oh wow! That’s awesome he took it so well.

    This is giving me inspiration for my eventual conversation with my boss…still several years away, though! 😉

    1. I bet your conversation will go better than you might think. Ultimately, they might hate to lose you, but there is also an element of “Man, why didn’t I do that?” too. Some do a much better job of hiding that than others! 🙂

    1. Haha, that’s funny. Yeah, I’m kinda an open book myself, actually. Though I can keep a secret if there is a real need to, I don’t tend to enjoy doing it!

  17. I am so with you on the certification perspective. Those things are for marketing purposes, they surely don’t prove you know your stuff or how to work with people to get things done.

    I’m sure it’s a relief to get that conversation out of the way. Just think how much more relaxing the next months will be?


    1. I largely agree – marketing and money. I have never placed a lot of faith in certifications in general, especially within the IT industry. Unfortunately, some of our customers are beginning to require them for whatever reason. Looks like now is a good time to get out! 🙂

    1. Hey Fervent – I don’t anticipate any changes, no – but then again, you never know. We’ll see how it turns out, but I suspect that things will be pretty normal until the day that I finally call it quits. 🙂

  18. Congrats on finding such an excellent boss.

    Had you considered the Financial Samurai approach of negotiating your own layoff rather than just quitting? Leaving a company to retire early with a nice severance check sounds like icing on the cake.

    1. Hey Jack – yup, I have definitely considered that. I’m going to see how the future plays out. I might try to make this happen. 🙂

    1. I don’t see him FIRE’ing, but I guess I don’t know him well enough to make that judgment. I do know that he’s good at what he does, but he isn’t a “gotta work until I’m 70” kind of guy either. That and he has a couple of kids, I believe, which adds some complexity into the equation.

  19. Congrats Steve! I’m curious, do you foresee yourself becoming a role model at the office, with lots of people seeking advice from you on FIRE? Maybe your early reveal will give you the opportunity to inspire others to follow in your footsteps.

    1. Thanks Brandon. I work from home 100% of the time, so I am in a bit of a different situation. I don’t actively work with my co-workers nearly as much as an office environment would, so I don’t necessarily anticipate the “role model” thing going forward. I haven’t officially announced it to anyone other than my boss as well. When I get closer, I might make that knowledge a little bit more public. 🙂

  20. I had a similar conversation with my boss last month during my performance review. He already knew I was leaving in August, and I decided to divulge a bit more about my plans. It turned into a really nice discussion about personal finance.

    Glad it worked out well for you, too!

    1. Very nice, that sounds like an awesome conversation. And you never know how your boss will adjust his own personal finance situation based on that conversation. 🙂

  21. Woohoo! This is awesome! Finally you get to do what you really enjoy in life. It’s really great you were able to do it this way in that you haven’t burned the bridge and can return if need be. Or if you guys end up meeting on a beach somewhere it won’t make for any awkward moments.

    1. Thanks for the comment, Amanda! Agreed, no sense in burning bridges. It’s a small world out there and you never know when you’ll run into your co-workers again in the future. I like to keep things as positive as I can, 100% of the time.

  22. Congrats Steve, another step closer to living the dream. It’s great to hear it did work out that smoothly becuase that opens everything else up in transitioning out and having time to genuinely say goodbye to the coworkers

    1. Completely agree, Dr. J, and thanks for your comment. It does make things a bit easier now going forward. If I happen to mention something to a co-worker, it won’t be a big deal because the boss already knows. 🙂

  23. wow, what a cool and supportive boss. You cannot ask it better than this. Instead of talking you out of it, he understands you have your plans and give you space.

  24. Wow, as I read the conversation I thought it was something you had made up and picturing the ideal scenario. As others said, it couldn’t have gone better

  25. That’s awesome! I was quite surprised with all the positive reactions when I put in my notice, but I still wouldn’t have wanted it known for months and months that I was planning on leaving. I think an 80-hour study requirement might have changed my mind, though. Glad you did it and glad it worked out well!

    1. Thanks Matt! Yup, it couldn’t have gone better. Yeah, I didn’t necessarily need this much notice either, but man, I sure as heck don’t want to be studying for some certification that I’ll literally never use, so yeah, why not spill the beans? 🙂

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