Will Quitting Be a Massive Mistake new

Will Quitting My Job Be a Massive Mistake?

Photo: Tinou Bao

So, what’s it like in the real world?
Well, the food is better, but beyond that, I don’t recommend it.
—Bill Watterson, Creator of Calvin & Hobbes comic strip

One of the most common questions I’m asked these days is a version of: “Was it was a mistake to quit your consulting job at IBM?”

My answer is swift. “No.” I’m met with semi-skeptical eyes.

So I acquiesce. “Well, a steady paycheck would be nice. But that’s it.”


It started as a quiet voice in my head.

“You should quit.”

At first I ignored it. But the voice proved to be a persistent little devil. It continued to surface on my weekly Thursday or Friday late night commutes from New York to my home in Chicago, each time louder and with an increasing sense of urgency. And each time, I’d hurry to quiet the voice.

“Shut up!” I’d yell. “Back to the dungeon where you belong!”

And thankfully each time, I succeeded. As the voice cowered back into the depths within, I’d pat myself on the back. After all, I was operating like everyone else I knew with real bills to pay and a real lifestyle to uphold. I didn’t have time for such inconsiderate voices. Sure, working in the “real world” didn’t feel quite like I thought it would, and quitting it sounded romantic enough. And if the voice had the decency to provide some viable alternatives, or even justified it’s impulsive murmurings, maybe I’d entertain it.

If you’ve found this Essay, maybe you’re playing host to similar voices. If it’s not “You should quit,” maybe it’s one of its siblings: “Start that business,” “Publish your blog,” “Hike the Inca Trail to Machu Picchu,” “Write that book,” or “Go after the girl.” Hell, maybe the whole family’s shouting at you.

The thing that seems to hold us back from letting that voice come out and play is we’re worried that a rash decision to quit or ‘do something different’ will end drastically.

Rationally, this makes perfect sense. It’s easy to imagine failing. The decision to quit, to take a bold leap, to embark on an uncertain adventure is wrought with the potential of falling flat. It’s scary to consider that listening to that voice could be a massive mistake in time.

What Am I Running Toward?

One of the simplest questions we can ask ourselves when thinking about quitting a job is: Why?

Do you want to quit because you’re lazy? Because you want to sit back, twiddle your thumbs, and watch other people take care of you for the rest of your life? I don’t think you’d be reading this Essay or following Escape the City if that were the case.

Chances are you’re a talented and motivated professional. You’re thinking about quitting your job because you’re striving to better yourself and grow as a human being. Maybe you don’t feel as if you’re living up to your full potential. Maybe you’re excited about a new opportunity or business idea. Maybe you believe your best music is still left unsung, even if you don’t know exactly what kind of song you’re meant to be singing.

The impulse to quit likely signifies a running away from something — soulless work, a spineless boss, or just a nagging, empty feeling inside. Which is fine. But it’s imperative to ask another question: What am I running toward?

Travel blogger and entrepreneur Nomadic Matt (no relation) embraced this same question when it came to the long-term travel-based lifestyle he was building for himself. In his post Everybody says I’m running away, he expounds:

“People who travel the world aren’t running away from life. Just the opposite. Those that break the mold, explore the world, and live on their own terms are running toward true living, in my opinion. We have a degree of freedom a lot of people will never experience. We get to be the captains of our ships. But it is a freedom we chose to have. We looked around and said, “I want something different.” It was that freedom and attitude I saw in travelers years ago that inspired me to do what I am doing now. I saw them break the mold and I thought to myself, “Why not me too?” I’m not running away. I am running towards the world and my idea of life.”
—Nomadic Matt

While on the surface your desire to escape or quit may look like running away, the more realistic notion is that you’re running toward something better. Maybe you’re running toward a life you think you’ll be more proud of. Or just running toward work that makes you feel a little less empty inside.

But couldn’t quitting bring about some massive mistakes? Maybe. And that’s a scary thought.

Mistakes of Ambition, Mistakes of Sloth

In 2012 as I battled my own internal voice about quitting, I came across a quote by Niccolò Machiavelli:

“All courses of action are risky, so prudence is not in avoiding danger, but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer.”
—Niccolò Machiavelli

What I love about Machiavelli’s quote is that he reduces the concept of a “mistake” to a non-negotiable phenomenon. So long as we’re living, breathing, and free-thinking human beings, we will make mistakes. We act (or don’t act) based on the information we have available to us at the time, which is often incomplete or full of falsities. By definition, all courses of action are risky.

So if this journey toward mistakes is inevitable, Machiavelli reminds us that there are two routes to take: There are mistakes of sloth — of laziness, of entitlement, and of blind acceptance. And then there are mistakes of ambition — of progress, of growth, and ultimately, of love for the adventure.

As I thought about quitting, I realized that if I did quit, it wouldn’t be because I couldn’t handle the challenge at work, or the demanding travel schedule, or the fact that I was rarely sleeping in my own bed (because I was traveling so much. Get your mind out of the gutter!)— maybe quitting for those reasons alone would be a mistake of sloth. But if I had stayed in my job because I was too timid to listen to that voice, wouldn’t that be a mistake of sloth as well?

These became scarier mistakes to me than the alternative “mistakes of ambition”: quitting because I was running toward a life and career that made me feel more alive. I always believed that work — the act of pouring our time into something, toward something, and for something — was one of the greatest gifts we have to give. I just wanted to do work that realized that ideal.

Once I accepted that mistakes were inevitable, the question then became: Which kind of mistakes will you dare to make?

To know that whatever course we take will be met by mistakes might be scary. But there’s an even scarier thought, and it comes in the form of Mistake’s ugliest step-sister: Regret.

Jeff Bezos and the Regret Minimization Framework

In 1994, Jeff Bezos was deliberating quitting his high-paying hedge fund job on Wall Street to start a crazy concept called Amazon.com. This seems like a ‘duh’ decision now, but please remember what the internet looked like in 1994:

Internet in 1994

As Bezos was weighing his big decision to quit, he ultimately wished to minimize the number of regrets” he’d have. He dubbed this thought process his Regret Minimization Framework:

“I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. And I knew that if I failed, I wouldn’t regret that. But I knew the one thing I might regret is not ever having tried. And I knew that that would haunt me everyday. So when I thought about it that way, it was an incredibly easy decision.”
—Jeff Bezos

Watch: Jeff Bezos, Regret Minimization Framework

You may not be running toward an aspiration to build the next Amazon, but you’re probably running toward a similarly personal ambition. Maybe you’re just running toward a more fulfilling existence, toward something that makes you feel more alive. Maybe you’re running toward a long-forgotten dream, a bucket-list item, or just a life you can be more proud of.

Thinking about long-term regrets helps us discount more short-term hiccups, like:

What happens in the next year or two if I quit?

What if I lose momentum in my career?

What if I take a temporary pay cut?

And while these are scary questions, I’m afraid asking them comes from too short-term of a mindset. It’s this mindset that Bezos’s framework was trying to pierce through. It forces us to ask the more important (and even scarier) question: What happens if I don’t quit?

There’s great power in Bezos’s Regret Minimization Framework. Near the end of your days, when you’re 80, will your life be measured in the regrets you didn’t have the courage to act upon, or of the mistakes you had the courage to make? Will your life be driven by the fear of potential regrets or the fear of potential mistakes?

When I thought about it this way, I became less concerned about what would happen in the next one, two, or three years if I quit now. I became more concerned about what would happen in the next ten, twenty, or thirty years if I didn’t quit — if I didn’t do the things that were burning in my heart.

While I didn’t come across Bezos’s (super nerdy) Regret Minimization Framework until I started writing this Essay, I suppose I indirectly applied that same framework in my own decision to leave my job and pursue my long-forgotten dream of long-term travel.

The Often Neglected Art of a Temporary Escape

I realized that one of the things I was running toward was a concept of freedom. Freedom to do work that filled me up rather than drained me, freedom to work with people I wanted to work with, and freedom to work wherever I felt like working. One thing that best represented that freedom was an idea of long-term travel.

Travel, culture, and exploration always excited me. So when I thought about quitting, I realized that I was running toward this notion of unrestricted and unstructured travel. It was something I always wanted to do. I weighed my potential mistakes and considered my potential regrets. The potential regret of not taking a long-term travel trip when I was young (enough) and (fairly) unattached far outweighed any potential mistake I could craft up in my head.

I resolved to quit. I even booked a oneway ticket to Iceland, departing in approximately five months in the future to coerce myself into following through. I revealed my plans to my closest friends. But as the travel date approached, and as I thought about my exit, I noticed a buoy gone neglected.

Maybe I didn’t have to quit after all. Maybe I could keep my job AND still take this trip. A much less riskier (if less sexy) alternative to quitting entered my head: What if I just asked for time off?

So that’s exactly what I did.

Long story short, I was graciously granted a seven-month sabbatical to live out my travel dream, while still keeping the door open with my employer.

Nevermind that I did eventually quit after coming back, but that’s a story for another day.

[I’ll be speaking Monday night at our Escape Evening event, where I’ll dive into the nuts and bolts of my “temporary escape” that evolved into a permanent one. Tickets are available here.]

Mo’ Money, Less Problems?

Was it a mistake for me to quit my consulting job at IBM with nothing else lined up? In terms of a paycheck, sure, one big ass mistake. I didn’t (and still don’t) have nearly as much cash coming in than I once did.

But do I regret it? Hell no.

I’m working on projects I love, with people I admire, all with an undercurrent of freedom and adventure. Because I’m supporting just myself, I have the flexibility to do this. Yet the money issue is so often a mental hurdle, especially with people who have much more at stake than I did when I decided to quit.

I wish I could say I’m flush with cash — I’m not. You’re catching me in the middle of my journey. I’m making a fraction of what I was making at IBM. But I’m still feeding myself and not sleeping in gutter-ish things, so I must be doing something alright. Also, I’m now abundant in a currency that I value over money right now — freedom.

But I’d be lying if I said I didn’t hope money would come. Not because I need to buy a yacht or own seven homes, but because I want what most of us want — financial stability and the freedom to do the things we want to do. Regarding the money issue, I’m holding onto a sometimes blind faith that so long as I do the things I’m pulled toward, the money will follow.

Luckily this isn’t just a concept swirling around my own head. Some of the greatest business minds of our time preach hope in this arena. Take entrepreneur and social media whisperer Gary Vaynerchuk, for example. In this clip, he dishes encouragement in typical fiery and free-wheeling jolts:

“It’s been very common wisdom…that people that leave high-paying jobs should go do what they love and they’ll live a more fulfilling life. But what people don’t talk about at all…I actually fundamentally believe that if you end up leaving a corporate job or working for the man, or doing something that you hate, and start doing something that you love, and at a much lower cost at the beginning…that you’ll end up making so much more money too.”
—Gary Vaynerchuk

Watch: Gary Vaynerchuk, Doing what you love can lead to more than just happiness.

In Conclusion: Our Big Brains and Our Tiny Hearts

“A child has no trouble believing the unbelievable, nor does the genius or the madman. It’s only you and I, with our big brains and our tiny hearts, who doubt and overthink and hesitate.”
—Steven Pressfield, Do The Work

It’s probable your Big Escape will bring about some massive mistakes. But I bet if you try on Bezos’s Regret Minimization Framework, you’ll find that your potential mistakes pale in comparison to the potential regrets you could have.

And as long as those mistakes are ones of ambition — decisions made because you were running toward something — than you can live with confidence knowing full well you won’t have the regret of not having tried. You made the best decision you could at the time. You proceeded valiantly in the direction of your dreams; you stepped into the arena, understanding the potential for mistakes.

To me, this marks a life well-lived. A life marred with mistakes rather than one of regrets, is one to be proud of.

“A life spent making mistakes is not only more honorable, but more useful than a life spent doing nothing.”
—George Bernard Shaw

This may sound like an ambitious statement, but I’ve not once met someone who felt pulled by a tiny, confident voice to quit something, listened to the voice, and then thought the macro event of quitting was a mistake. I know Escape The City founders Dom and Rob don’t think their decision to leave management consulting was a mistake. Adele’s quitting law school wasn’t a mistake either. Nomadic Matt likely doesn’t regret leaving his job to build a lifestyle of travel, and Bezos, by boldly quitting his Wall Street job to start Amazon.com, certainly can’t label that move a mistake. While I’m sure many mistakes may have been made along each of these journeys, the big decision to head down a path toward mistakes of ambition was not a mistake itself.

The truth is that once that voice makes itself known, chanting “you should quit,” the wheels are already fast in motion. The train is leaving the station. The problem is, our tiny hearts are on the train, while our big brain’s still in our head, and we’re often stuck on the platform.

It’s going to take some time to run and catch up to the train, so it’s best to start moving. Now. Because if we want to, we will eventually catch up.

Maybe not today. Maybe not tomorrow.

But maybe tomorrow.

Which kind of mistakes will you dare to make?

This Escape School Essay was inspired by:


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Matt Trinetti is a former IBM consultant turned traveler, writer, entrepreneur, and founder of GiveLiveExplore -- an independent publishing company. He's currently the COO of The Escape School and leader of The Startup Tribe.

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  • Rachael Brookman

    Thanks for sharing this Matt – the risk minimization framework is a really interesting tool for getting out of ‘analysis paralysis’ – although as you point out on the salary front having financial/personal obligations can make it more complicated.

    • http://www.giveliveexplore.com/ Matthew Trinetti

      Thanks for reading, Rachael :) Yeah, it certainly takes a LOT of faith to look past short term set backs in order for the (potential) for long-term gains.

  • http://energysessions.at/ Julia

    Hi Matt, thank you for this article! It kind of touched me because I ran away from my job and “towards life” twice, and it ended in a big disaster the first time. Now I’m in the middle of my second attempt and it’s going quite well.

    I really think assessing risk is important when thinking about whether to quit a job. I made a big mistake by quitting without a plan and going abroad, which resulted in my being broke and unemployed. I had no idea what I wanted to do moneywise but believed things would work themselves out – well, they never did. I was quite naive back then and believed too much in what I read about this whole business of “quitting your job and doing what you love”. I just think that too many articles and books on this topic emphasize the freedom you might achieve, while dismissing the thought of real existential risk being involved by quoting a kind of new-agey, blind optimism (isn’t this a “mistake of sloth”, too?). This approach might work for people who handle risk well, and I have learned the hard way that I am not one of them.

    I appreciate that you wrote about both the joy and the risk of quitting. (And I think it was a good decision that you took the sabbatical first instead of quitting right away.) I also have to say that I don’t regret leaving back then, as I really hated my job and my city and had a great time abroad for a while. Also, I am not at all saying that we should waste our lives in jobs we hate just because of the security they temporarily offer. I just hope that me and others will be able to liberate ourselves without making a train-wreck out of our lives this time. Here’s what I did: After recovering from financial (and frankly, overall) disaster, I started a business while still in a job, and I’m on a sabbatical now :) (at home, though), taking the time to develop my business.

    Good luck and thanks for the article,



    • http://www.giveliveexplore.com/ Matthew Trinetti

      Hey Julia, thanks so much for reading, and for your thoughts. Maybe things didn’t work out for you the first time, but I’d argue that they actually did (or are in the process of) working themselves out, in time. Maybe you wouldn’t be where you are now if you hadn’t gone through that shit storm earlier. And like you said, you don’t regret quitting, even after all of that. So I guess it was the right thing to do in the end?

      Actually something I wish I’d added to this essay in hindsight: examples of mistakes, from people who failed along their journey. I feel that most people who we look up to as a “success” had catastrophic failures and mishaps along the way. Which arguably primed them for their later success.

      I just came across another quote that I think touches on something I didn’t dive much into either — the importance of persistence through those mistakes and setbacks:

      “As you begin to take action toward the fulfillment of your goals and dreams, you must realize that not every action will be perfect. Not every action will produce the desired result. Not every action will work. Making mistakes, getting it almost right, and experimenting to see what happens are all part of the process of eventually getting it right.” — Jack Canfield

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  • zooooooooom

    Good stuff, Matt. Keep it up!

    • http://www.giveliveexplore.com/ Matthew Trinetti

      thanks buddy. you too!

  • scottjohn80

    Interesting and enjoyable article Matt, best wishes in your endeavours.

    • http://www.giveliveexplore.com/ Matthew Trinetti

      Thanks Scott, appreciate you reading

  • Regret Free Life

    Great article, Matt. Love the point you make about mistakes of ambition v. mistakes of sloth. Keep it coming.

    • http://www.giveliveexplore.com/ Matthew Trinetti

      Thanks for reading & sharing! I’ll do my best :)

  • Leonie

    hi matt
    tks for this very, very interesting article. i recognise “that voice” but also machiavelli’s idea of putting the importance of yourself (your health, your happiness, your LIFE) above a situation that continues to drain your energy. i quit my job few months back and despite my intense fear beforehand, i did not regret it for a single moment afterwards. i’d decided i rather make a mistake than do nothing at all. while in my surroundings i do not even get the rather polite and curious question “do you regret it?”, but instead i keep on getting comments like “have you lost your mind? why on earth would you quit without having another job?”. all i can do is smile. it is just sheer joy to be in control of my own life again. so big thanks to you for writing it down, and best of luck.

    • http://www.giveliveexplore.com/ Matthew Trinetti

      I guess people have a hard time imagining taking a little time away from working IN your life, to working ON it. Thanks for reading Leonie, and for your thoughts.

  • Joe

    IBM?? I just retired from IBM!! I’m going through this very same process and this article was very helpful. Thanks Matt!!

    • http://www.giveliveexplore.com/ Matthew Trinetti

      Thanks for reading Joe! It’s reassuring to know this isn’t just applicable to those early in their career — it’s appropriate across the whole career spectrum. Best of luck.

  • http://www.LifeBootstrappingSystem.com/ Francois Paul Lambert

    Hi Matt, thanks for the inspiring story! :-)

    Funny, I’m a former IBMer myself and just like Julia below it took me two attempts to escape the career-cage and be finally running towards my life (love this expression!)

    The first time I quit my job, it was after reading Tim Ferriss’ The 4 Hour Work Week, back in 2008. I really hated that job at the time and I was starting to have health issues, clearly related to the stress of “being in that job”. I was looking for anything, an escape plan, that would remove me from this mind and body prison.

    So I left, moved to another country, started an online business, then failed, then had no cash, then had to go back to the cubicle-prison to refill the bank accounts…

    It was a depressing experience at the time, and I pondered for a long time what had gone wrong.

    Now, 5 years later, I’m out of the cage once again and never been happier! Looking back, I understand a lot of my past mistakes. They were both mistakes of ambitions and mistakes of sloth.

    Obviously, I didn’t put much thoughts and planning in my initial escape, but the most important lesson I take from this “first trial” was that I tried to replicate my previous job as a freelancer. In other words, I moved a job I hated from the cubicle to the open.

    So, yes, I was free and independent but after a few weeks I realised I had no will nor motivation to get up on Monday mornings… I was back at the same old grind, free, but alone and with less income. And to me that’s a HUGE lesson.

    If you dream of escaping the rat-race and run towards your life, I think it’s crucially important that you do it for the right reasons. For me personally, these reasons are to be free and independent, to enjoy life and contribute to the world. To live the life I was born to live.

    By taking with me a job I hated and trying to do it as a solo entrepreneur, I did a big mistake and was doomed to failure because I really didn’t match my talents to my passions. And these are the two most important ingredients to mix together if you want to contribute to an important need in the world (your market).

    So, thanks again for reminding us that we must make mistakes. These mistakes are important lessons on the path to success and happiness. They make us smarter, stronger and wiser.

    And to all those who have failed before. Start again. Do the mistakes. Learn. Then start again. And run after this train. We’ll all meet there and celebrate in the end! :-)

    Hope to see you there!

    With Love,
    Francois Paul

    • http://www.giveliveexplore.com/ Matthew Trinetti

      whoa! hey there Francois. I think we should just make this a former IBMers Anonymous forum :)

      Great story, thanks for sharing. I think it’s an important thing to realize those hiccups are actually all part of the journey. Even a necessary part. Although they really REALLY suck while you’re in the shit. So thanks for reminding us of that.

      Appreciate you reading and taking the time to post. Take care man.

    • GMEK11

      Hi Francois
      Your story sounds familiar !
      I left, moved to Cape Town, started an online business which failed, and now am back, dusting myself off and starting again, lessons learned.
      If you could slow the train down so i can catch back up that would be much appreciated.

      • http://about.me/francois.paul.lambert/ Francois Paul Lambert

        Thanks for the reply Giles.
        Cape Town. Awesome! Are you stil there or are you back to [where?]
        What really made it for me was to really let go of my past fears and limitations (“what will they be thinking about me?”, “What if my services suck?” “What if I’m not good enough?” …), to plunge all-in, and to not repeat what I was doing in the corporate world that I hated.
        In the end, I made a lot of efforts to get clarity about my strengths, talents and passions so I could mix them all together to solve an important problem somewhere in the world (my market).
        I now help people doing just that :-)
        Don’t despair about catching up with the train. If you persist, you will eventually be there!
        Enjoy the Journey & take care mate.

  • Elliot

    Nice post Trin! I just read Seth Godin’s “The Dip” yesterday, which was right on line with this post. So many of us get to the Dip in our careers, and don’t make that final push to get through to a new world of abundance. Looking forward to starting my own company soon!

    • http://www.giveliveexplore.com/ Matthew Trinetti

      thanks buddy, appreciate you reading!

  • sheryl swanson

    Matt, I loved this article. It is not what one expects to see but I am sure it struck a chord for many folks that are struggling with this thought. I love the concept of reversing the question to ask, “what if I don’t quit?” Yikes. Keep writing these articles and pushing people to think outside the norm!

    • http://www.giveliveexplore.com/ Matthew Trinetti

      Sheryl — thanks so much. Appreciate the encouragement, helps keep me going!

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  • Sophie

    Thank you so much for writing this. I just quit my job because I was bullied by my boss and had the feeling that there’s a future ahead of me I don’t know yet. This will be my last working week and I started to panick and started thinking I made a huge mistake. Your article made me realize there are so many opportunities ahead. I’d rather make mistakes of ambition than regret not making any decisions at all.

    • http://www.giveliveexplore.com/ Matthew Trinetti

      Thanks for reading Sophie. And congrats on beginning the new phase of your journey. Good luck :)

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  • Rachelle

    Thank you for this article. It inspired me that what I’m about to do is really for the best. It’s not about quitting but running towards a more fulfilling life. Of course I fear not having the very generous paycheck and bonuses I’m currently receiving (and enjoying!) but what I fear more is having an empty life that is only powered by money. Life is indeed short and it’s not always about making a living but making your life worth living.

    • http://www.giveliveexplore.com/ Matthew Trinetti

      Thanks for reading, Rachelle, glad it resonated! I think that’s a smart mentality to have.

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