In praise of quitting
You’ve got to know when to fold ’em
If you seek advice from people at the very top of competitive domains, you’ll probably hear a lot about the power of tenacity, grit, and determination. There is obviously wisdom in this: You won’t get very far in life if you’re constantly changing course at the first sign of challenge or boredom. And it’s probably true that you will never be one of the very best in the world at something without developing a singleminded and lifelong obsession with it.
But most of us don’t have a shot at being on one of those podiums, or even aspire to it. For us, there’s little danger in prematurely abandoning our latent potential to be the best gamer, or the best free diver, or the best developer. The far, far greater danger is in devoting our days to something that fundamentally doesn’t matter to us, because we’re too afraid to cut our losses.
For creatures such as ourselves, more should be said in praise of quitting.
As Kenny Rogers said, “you’ve got to know when to hold ’em, know when to fold ’em, know when to walk away,” and wouldn’t you know it, I have a poker analogy for this.
Poker comes in two basic formats: cash games, where you can buy as many chips as you want whenever you want, and tournaments, where you get one stack of chips to start with and you play until you run out of them. With cash games, you can take your money and leave at any point. In tournaments, all of the prize money is allocated according to a payout structure, with the people who last the longest earning the most.
Tournament poker is basically about finding the highest-value uses of a scarce resource, your chips. The fact that losing those chips means getting completely locked out of a shot to win major money means that their opportunity cost is high. This means it can be a big mistake to commit yourself to hands that are somewhat positive-value in expectation, if you have good reason to believe there will be better, higher-value opportunities.
Life is, of course, just like this: You get only one shot, and it’s up to you to make the most of it by rejecting okay or even pretty good ways to allocate your time or other resources — to hunt down the opportunities to make really great bets on yourself. Do not make barely positive-value bets with your life!
I think quitting is one of my primary superpowers. Success in multiple fields is only possible if you’re willing to quit multiple fields.
In 2023, my cofounders and I at Alvea decided to wind down the company when it became clear that our original direction wasn’t going to pan out, and that our alternative line of business was not going to have the impact on the world that our employees or investors had shown up for. Some years before that, I quit corporate law shortly before I would have made partner, because I knew that once I did the money would be too hard to walk away from.
At both points, I realized I was a ways down the road toward a destination I no longer wanted to get to, and rather than keep driving, I took an exit. This was indispensable in getting me to a place where I actually wanted to be.
It can be hard to quit sometimes because it feels like an admission that you made a mistake, that you took the wrong path in getting there. But this isn’t necessarily true.
The interesting thing about steady jobs is that they’re actually not so steady. They are static in a conceptual sense — in the sense that if you say you’re a “lawyer” when you’re 30, and say you’re a “lawyer” when you’re 50, there is the same label for what you do. And that can feel like steadiness, like a reassuring kind of coherence to your life story.
But the truth is that everything is in constant flux. Beneath the labels, life continues evolving all the time. Your interests change, companies change, and industries change. Given that your “steady job” is constantly evolving, even if you picked the highest-leverage option initially, there is a low chance that it will remain your highest-leverage option over time.
The same goes for places to live, relationships, opinions, and hobbies. Over time, these things can degrade in value or resonance — and yet still retain the emotional pull of their initial promise. And when this happens, people often stay too long.
One of the factors that underlies this is loss aversion, the psychological phenomenon by which losing $100 feels about twice as bad as gaining $100 does good. This asymmetry has deep consequences. In real life, it manifests as a reluctance to abandon sunk costs — we keep investing in doomed projects, relationships, or careers because leaving feels like locking in a loss, rather than setting ourselves up for a future potential gain. Retail traders double down on losing stocks rather than closing out their positions. Founders keep going with failing companies even when there’s a good opportunity to bail out.
As a result, quitting often feels emotionally wrong even when it is logically right. So if you want to be smart about it, you’ll have to learn how to see through the illusory weight of loss.
How do you do that?
It’s not an easy task, because research suggests that merely being aware of loss aversion doesn’t significantly reduce its influence on behavior. So you can expect strategic quitting to be difficult. However, making yourself painfully aware of your choices is often the first step in changing them.
By default, we tend to think of “choices” as the kinds of things that take us off the path we’re already on. From this stance, it doesn’t feel like we are “choosing” to go to our job every day, or choosing to remain where we live. The scary thing is that this means we can actually be making the biggest mistake of our lives on a daily basis, despite it feeling like nothing is happening at all. If we want to evaluate whether our current set of choices is really best or whether it’s just inertia keeping us where we are, it can be powerful to upend that frame.
Try it. Go around your day, narrating all of your choices to yourself. With everything you do, consciously say, in your head: “I am choosing to do this, because it’s the best course of action according to all the information I have available.” See if it feels true. It might — perhaps this exercise will reinforce your conviction. But you might also find that entire regions of your life suddenly look strange. The declaration that you’re doing the best thing will sound like hollow propaganda, an attempt to convince yourself of something you know just isn’t so.
Another powerful exercise, of a similar kind: Imagine that you were instantly unsubscribed from everything in your life. All of your choices undone — where you live, who you’re with, what you do with your time. All of a sudden, you’re a completely empty canvas. And then, imagine that you have the power to bring back each element just by hitting a “resubscribe” button, like it’s an email newsletter. Being honest with yourself, which elements would you hit “resubscribe” on? What percentage of your current activities are an unambiguous “yes?” What percentage would you unceremoniously drop, if you were given the opportunity?
Once you realize you’re choosing something, you regain the ability to un-choose it. Note that un-choosing doesn’t always mean quitting in the complete, traditional sense. It might just mean an alteration — working hard to establish a new phase in your relationship, or changing roles at your job, or moving to a different neighborhood rather than a different country. This, too, is strategic quitting: declaring that a given battle is over so that you can win the war.
Leaving can still break your heart even though it’s the right thing to do.
We human beings are adaptive creatures. We have the ability to develop fondness for our current situation, even when we don’t like it overall. When I was a young lawyer, it took me a couple of years to notice that I really didn’t like living in New York — it was too big and loud and indifferent for me to ever feel at home there. But I still found lots of pieces of it to love, and believed that it would feel like something important had been sacrificed once I moved away. In the lead-up to the move, I found myself romanticizing aspects of the city that I’d never really paid attention to before, because I suddenly saw them as pleasures I was about to lose access to.
But something to remember is that there is always some unknown part of the future that you will be equally fond of. Before moving to Washington DC, I couldn’t have imagined all of the attachments I’d have to it. And after every other transition in my life, there were likewise things to love that I couldn’t have previously pictured.
When people think about quitting, it’s hard because they’re comparing the rich web of attachments they have now to some mostly blank slate, or, worse, the possibility of disaster. However, what’s more realistic to imagine, if you’re leaving something you’re no longer aligned with, is a future with more to love than you have now. Those things you will be attached to in the future are currently obscured by the impassable barrier of time, but they’re still out there.
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Thank you for this - I particularly appreciate your analogy about subscribing/unsubscribing.
A counterbalance is noting that some experiences are very much not sunk costs. I like how Oliver Burkeman puts this: "To experience the profound mutual understanding of the long-married couple, you have to stay married to one person; to know what it’s like to be deeply rooted in a particular community and place, you have to stop moving around. Those are the kinds of meaningful and singular accomplishments that just take the time they take." (Four Thousand Weeks)
For me, my most important act of quitting has been the decision to depart from the collective hunt for career and status. I have found myself a very simple 30h-per-week job with zero pressure and plenty of downtime where I can read and write about whatever I want during my work hours. I feel this is the best work-life balance I have ever achieved in my life.