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

Published May 16, 2016   Posted in How to Retire

The day, as most of them tend to do, started like any other day. I made my way through my well-oiled routine without a squeak – wake up, grab a shower, make some coffee and sit down to check out what is in store for me at work. So far, everything’s cool – until our division-wide telecon.

Pinterest: I just told my boss that I am quittingActually, let’s back up a second. Up until this morning, I was “in the closet”, as it were, regarding my intention to quit full-time work in December and spend my remaining years traveling the country for a living…or at least doing something that I actually enjoy.

My wife, on the other hand, has already told her boss that she’s quitting in February. She needed to give her boss that much notice due to the nature of the business that she’s in. Me, on the other hand, could quit with two weeks notice and be done with it – though I was planning to give him at least 3 months notice.

But, it’s only May. December isn’t in two weeks, unfortunately. What the heck gives?

The conference call that sealed the deal

Like I said, everything was normal until the division-wide conference call that had been scheduled for weeks. This was my boss’s opportunity to address the entire division about our performance over the previous quarter and talk generally about how awesome we all are.

XOXO heart and love

You know me…all hearts, love, hugs and kisses, baby!

A little background is in order: As part of our compensation, we are given the opportunity to do additional work that directly benefits the company, which is generally capped at 20 hours per person for the quarter. A portion of our quarterly bonuses are made up of this work; the other portion of our bonus amount is directly tied to our performance and billing utilization – yada yada.

Towards the end of the conference call, my boss dropped somewhat of a bombshell on us…okay, perhaps more of a grenade than a bombshell. He wants us all to get certified in a specific area of information technology because more and more of our customers are demanding this certification. I’ve gone through the process of studying for certifications before, and it is typically a long process. Many nights of reading inane technical concepts buried underneath mind-numbingly dull technicalities, technologies, acronyms and fluff is necessary.

Typically, 80 or more hours of studying is required for most people to let this dryness sift into their brains enough to pass the test. After spending days writing code and sitting through hour-long conference calls, spending my evenings reading about dry technological concepts and taking practice tests doesn’t appeal to me in the least. In fact, it sounds downright horrible.

That, and I have a vehement distaste for technical certifications to begin with. Back when I “directored“, I generally ignored certifications on resumes because they tend to be extremely poor representations of a person’s fitness for almost any technical role.

The catch in all this? My boss wants us all to get certified this quarter as a part of this additional 20-hour workload. And like I said, the hours required to prepare for, and pass, this certification is three to four times the number of hours that we are allowed to work on this.

So anyway, here I am – still in the closet about my quitting date and my boss just hoisted upon me a fresh invitation to say, “No, I shall not get certified, and here’s why”.

But, I’m still conflicted. Taking this route would require me to divulge our plans quite a bit early, and I certainly don’t need to give my boss eight months notice that I’m leaving. I also don’t want this to affect the remainder of my employment with this organization. But on the other hand, I have to tell him some time anyway, and I certainly don’t want to spend hours of my time studying for a certification that I will literally never use.

What’s a future early retiree to do?

Please note: This is not a negative indictment in any way on my boss. He is doing what is in the best interest of the organization. It’s business and I know that. This guy has easily been the best boss that I’ve ever worked for and actively wants what is best for his staff. Thus, I have absolutely no anger or hard feelings in any way toward him or, quite frankly, the business.

I leaned back in my chair (actually, it was the nook in our Airstream) and quickly returned to my natural, confident, everything-will-work-out self and said “Screw it, I’m doing this”.

So I called, and my boss picked up his phone.

The “I’m quitting” conversation

More or less, the conversation went something like this (and no, it had no resemblance to my fictitious “I quit” letter!):

Me: “Hi Boss. I wanted to chat with you for a minute about that certification that you want us to get, as well as something else.”

Boss: “Okay, sure.”

Me: “Well, my wife and I have a dream of traveling the country full-time, and it looks like we will be in the position to make that happen at the end of this year. So, I’m going to be leaving the organization in December.”

Boss: “Are you going to travel around for a couple years, or…”

Me: “Really, we plan to travel for the foreseeable future. I don’t anticipate coming out of retirement anytime soon. I’m not looking for a sabbatical.”

Boss: “Wow, I’m shocked, but I’m happy for you and your family. Truth be told that if I were in your position, I would probably do the same thing”.

Me: “Thanks, I appreciate that. And about that certification, I would rather not go through the hassle of preparing for that test. How about I look elsewhere for ideas of what to do for those 20 hours?”

Boss: “Yeah, that makes sense. I will try to think of ideas as well, but if you come up with something, let me know ASAP.”

Aaaaaaaand, scene.

First, notice how supportive my boss was during this conversation – and for that I am very grateful. This, in large part, is why I harbor no anger or resentment in his direction whatsoever. He’s been a great guy to work for and will continue to be throughout the remainder of the year.

Second, he admitted that he would probably do the same thing if he were in my shoes, which is his way of saying “I hate to lose you, but I can’t say that I blame you“. Strike while the iron is hot, if you will. In fact, I may have used that phrase on the call with him.

Third, phew! The cat is officially out of the bag! I get out of the certification process and can put the whole giving notice thing behind me…a little earlier than I had originally planned, but it needed to be done at some point, and now my boss has plenty of time to plan around me beyond December.

Once again, I had a good attitude during this entire conversation, and once again, everything turned out wonderfully. My boss knows, so my job is done. All I have to do is finish out the remaining days, weeks and months and then slip gracefully into early retirement, camera in hand.

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69 responses to “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. 🙂


    • Steve says:

      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.

    • Steve says:

      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. Mr. Groovy says:

    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.”

    • Steve says:

      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. Mr. PIE says:

    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.

    • Steve says:

      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. Oh wow…. this went quite smooth 🙂 Much better than I imagined !!

    Woo…hoooo you are now all set to take the plunge in early retirement 🙂 Congratulations!

  7. Apathy Ends says:

    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

    • Steve says:

      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!

  8. Justin says:

    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?

    • Steve says:

      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! 🙂

  9. Mr. SSC says:

    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.

    • Steve says:

      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. 😉

  10. 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.

    • Steve says:

      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!

  11. That is awesome that your boss was so supportive! I work in IT and I have encountered people in management who would not have reacted so well. Congrats!

    • Steve says:

      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. 🙂

  12. 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?

    • Steve says:

      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. 🙂

  13. 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.

    • Steve says:

      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!

  14. amber tree says:

    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.

  15. Tawcan says:

    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? 😉

  16. 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.

    • Steve says:

      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. 🙂

  17. And after all that, you didn’t get to give him your dramatic resignation letter! 🙂 I’m glad it went so smoothly for you!

  18. 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?

    • Steve says:

      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! 🙂

  19. Matt Spillar says:

    Congrats Steve! Glad it went so smoothly, that’s a nice hurdle to be able to put behind you. Enjoyed reading the story of how it all went down.

  20. Jason says:

    And here I was waiting for the hammer to drop. That is great. Congratulations and now only 7 months away!

  21. Felicity says:

    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! 😉

    • Steve says:

      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! 🙂

  22. That is all you can hope for when dropping news like that! Congrats on finally announcing! Exciting news!

  23. That’s gotta be somewhat of a relief. I tend to get pretty pent up keeping secrets. I am a terrible secret keeper. Don’t ever tell me one. I’ll tell the world.

    • Steve says:

      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!

  24. 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?


    • Steve says:

      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! 🙂

  25. Congrats – I’m glad it went so well! Any way things could change once he spreads the news to the higher ups?

    • Steve says:

      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. 🙂

  26. Jack says:

    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.

    • Steve says:

      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. 🙂

  27. Wow that is a great story. You have a great boss. Maybe a potential FIRE himself? What a relief your must feel. Congrats on the milestone.

    • Steve says:

      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.

  28. 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.

    • Steve says:

      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. 🙂

  29. 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!

    • Steve says:

      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. 🙂

  30. 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.

    • Steve says:

      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.

  31. 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

    • Steve says:

      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. 🙂

  32. Working Bee says:

    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.

  33. Stockbeard says:

    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

  34. 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!

    • Steve says:

      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? 🙂

  35. […] remember, my boss already knows. Most of my immediate family knows. We’re all settled into our kick-ass Airstream digs and […]

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