I Quit

I did it. I quit.

I had never resigned from a job before. I’ve had a handful of employers over the past decade, but every job I’ve ever held seemed to come with a predetermined end date – a summer-long gig, a four-month internship, or a multi-year consulting contract. For the past five years, though, I’ve worked for one company. For the first time in my life, I needed to sit down with a boss and break the bad news.

I’m not good at breakups.

Walking away from this job was different, too. Five years ago, the company didn’t even exist. As the first full-time employee, I spent a year working on whiteboards in garages. For months, I slept on a friend’s floor when we traveled to meet our first prospective client. I went a year without a paycheck. That dynamic changed quickly, though. Investors took majority control of the company, brought in new leadership, and relocated our corporate headquarters 2,500 miles away. It’s not the little startup it once was. But in some ways, it still feels like my baby. All that history has certainly made it difficult for me to walk away.

I spent most of the day this past Wednesday writhing with anxiety. Over and over again, I rehearsed how I would break the news. I would have preferred to do it in person, but it had to be by phone. I envisioned all the disgruntled reactions I might get from our CEO – disappointment, anger, frustration. I pictured our General Counsel being called in to have me sign non-disclosure and non-disparagement agreements. I envisioned my e-mail being immediately cut off and a request for my laptop and phone to be sent back by end-of-day. I imagined awkward phone calls with colleagues and clients as I was forced out.

And then, everything went just fine.

In fact, it was literally the best conversation I’ve ever had with our CEO. Though he expressed his deep disappointment, he shared that he was excited for my travels (and a bit envious). He opened up about his life, sharing his own experiences traveling and living abroad. I learned more about his personal life in 20 minutes than I had in all the time I spent working with him. He complimented my working style and my work ethic. He heaped on more praise and positive feedback in 20 minutes than I had ever received from him. “Wow, maybe I should have threatened to leave a long time ago,” I thought.

Just before the conversation, I had been reading about the Mad Fientist’s experiences with quitting. Three times, he’s resigned from a job and been offered far superior working arrangements: higher pay, more flexible hours, or location-independent work.

He was right. Quitting didn’t restrict my career options, it expanded them:

  • “Is there anything we could do or change about your role to persuade you to stay?” (Not really, but I appreciate the offer)
  • “Would you be willing to do some contract work for an hourly rate while you travel?” (I’m certainly open to talking about it)
  • “If you ever decided you wanted to come back to the company, we’d be more than happy to find a place for you” (Thank you; it’s always nice to have a safety net)

There’s an old saying that goes, “I have known a great many troubles in my life, but most of them never happened.” Looking back, I don’t know why I was so stressed out about the encounter in the first place.

We talked about timing and transition planning for a while, and then I hung up the phone.

It was over. I did it.

Call Ended

I had fantasized about this exact moment for years, but I didn’t feel ecstatic or even particularly happy. Just relieved. I felt free in a way I haven’t felt for a long, long time. Like a massive weight had been lifted off me. Like I was floating.

Every ordinary experience over the past few days has felt extraordinary: the warmth of flannel bedsheets, the first sip of morning coffee, the sound of my favorite album playing on the living room speakers. I remember feeling this way once before: my senior year of college, after handing in my very last paper. It was short-lived then, and I suppose it will probably be short-lived now.

But there is one notable difference:

I never have to work a real job again.

Years of living frugally and banking 60-80% of my income have paid off with the ultimate freedom. I have no idea exactly what the future holds or if it might include full-time work. But if it does, it will be 100% my choice, on my terms – because I want to be doing it, not because I need the income.

Meanwhile, Daniel also put in his notice last week, in much less anxious fashion. We’re wrapping things up a month or two earlier than originally planned, which will give us time to sell some of our things and prepare for full-time travel. Or, maybe we’ll try to take advantage of ski season and do some road-tripping in February and March. We’ll figure it out.

No rush.


  1. AND THE ADVENTURE BEGINS! When is your last day of work? Congrats! That’s a HUGE deal! I’m excited to follow your travels!

    • Thanks, Maggie! It feels a bit surreal. We’ll be formally finished at the end of the month. Just two and a half weeks left now!

  2. CONGRATULATIONS!!! Huge news. I’m so glad it went so well. Isn’t it so often like that after we build something up in our minds? Maybe I’ve missed it here, but I’m so curious — did you guys save enough to be FI for good, without working, and including a home base? Or are you going full nomad? Planning to work part-time? We’d love to know what your financial plan looks like (broad strokes is good enough!) moving forward, and how long it took you to get to this point. But most of all, hooray for you guys!

    • Thank you so much! I suppose my financial backstory and our plan moving forward probably warrant their own posts. The short answer is that I’m declaring myself officially FI for good (woohoo!) including a home base, though we don’t plan to have a home base in the near-term. At the same time, I don’t have a great sense of what our spending (and therefore, my withdrawal rate) will look like for the next few years with a completely different day-to-day life.

      With regard to ongoing work, I’ve always enjoyed having a few side projects, so I expect that I’ll continue to have some modest income from “side hustling” and contract work here and there — partly to assuage my risk aversion, but also because I enjoy that kind of thing. I suppose that probably disqualifies me from using the “retirement” word, much as I enjoy being provocative. 🙂

  3. Awesome congrats! I have all the same questions as ONL! Maybe you could write a post about it 🙂

  4. Congratulations, Matt!! How incredible the CEO was that supportive – that must’ve been a huge relief. I could only imagine the feelings of euphoria you have right now. Can’t wait to hear further about your adventures!

  5. Totally awesome and congratulations Matt! It’s so cool that the CEO was so supportive and shares his experience with you. Would love to hear more about your financial plan while you traveling around.

  6. Congrats! That is awesome news! You can’t get a much better quitting experience than that. Even though you would wish you could get that praise during the entire time you are there instead of only getting it once you resign. Now the fun part begins!

  7. Congratulations! This is what it is all about! You have earned the feelings you are experiencing. Relish in it. I’m looking forward to reading all about your future adventures. Now, go fire up some Pink Floyd 😉

    Carpe diem!
    Mrs. Mad Money Monster

    • Thank you, MMM! Amusingly enough, I have a vivid memory of sitting in rush hour traffic the first week of one of my first jobs, and “Welcome to the Machine” coming on the radio. It was so apropos it hurt.

  8. Congratulations! I’m glad it went well for you, and I bet it’s nice to know that you don’t have to work again if you don’t want to 🙂

    • Thank you! I suspect I’ll still do plenty of work in the coming years (whether on my own “passion project” or something more traditional), but it’s a great feeling knowing that’s purely optional.

  9. Hot damn! Congrats on that wonderful milestone! I am looking forward to when I can do precisely the same thing. In due time! I’ll be following along as you guys embark on the new lifestyle. Maybe one day we’ll see ya out there. 🙂

    • Thank you! Even with a couple more weeks of work left (and the stock market tumbling), it already feels like the best decision I’ve made in a long time. I think an Arizona meet-up is order when we head south. First beer is on me!

  10. Wow that is so great! I’m so happy for you
    And given your tag line it looks like you reached your goal early!

  11. I read this on Twitter last week and am FINALLY getting around to commenting. Congratulations! I cannot wait to hear about all the new adventures that await. Cheers!

  12. Congrats! I am a couple weeks behind you and having so many of the same thoughts that you had before giving notice. I just scheduled the meeting yesterday – for 2/9. Fourteen more work days between then and now. I am nervous and excited at the same time.

  13. Congrats! Can’t wait to see how your plans unfold. Do you and your partner own your home base or are you renting?

    • Thank you! We’ve already had a few changes in plans based on some friends’ travels and wedding schedules, so I’m still not sure exactly where we will end up over the next 6-12 months. Embracing ambiguity is just part of the fun. With regard to housing, I own a condo that will become a full-time vacation rental when we start traveling, and we also rent a small place near Daniel’s work that we’re getting rid of after he wraps up his job shortly.

      • That’s super exciting! We’re about the same age as you (28/29 this year), but we don’t want to travel full-time and have I think a bit fancier lifestyle than you two, so we have a few more years of work in us.

  14. Full time travel! That’s fantastic. Congrats on quitting the job. I just left my job to focus full time on some online projects. It certainly is crazy to quit, but it’s exciting! Best of luck on future adventures and I hope to read more about them here.

    • Thanks, Rob! It definitely feels a little crazy; it’s the first time in my life I’ve not had something formally lined up (like work or school) for the future.

  15. Hey Matt,

    Congrats dude that’s amazing news! Im sure youre relieved everything went well and that you have that safety net but a smart guy like you should do fine if he wants!


    • Thank you for the kind words! I do have confidence that I’ll make this work no matter what, but we can all use a little external validation once in a while!

  16. Just today I discovered your blog! what story…! congrats with your independence and enjoy the travel. Keep us posted on your adventures.


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