Photo: “Life Passes By” by 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 comics

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. I acquiesce.

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

(c) Bill Watterson

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 don’t like to work? Because you want twiddle your thumbs and have other people take care of you for the rest of your life? I don’t think you’d be reading this post if that were the case. When work sucks, you might convince yourself, “well, maybe I just don’t like to work.”

But maybe deep down you believe what Kahlil Gibron does: work has the potential to be “love made visible.” Maybe work – this activity we spend so much of our time toiling away at – could be directed toward something we deem worthwhile? At least for ourselves. At best, for the world.

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 whose minutes on earth are numbered. 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’d like to realign yourself with a more beautiful potential for work. 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 — 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 This seems like a ‘duh’ decision now, but please remember what the internet looked like 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

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.

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

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, 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?


Inspiration & Further Reading:

This post originally appeared at Escape The City.


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