The Art of Letting Things Go

low section of man against sky

“Do you really want to go?” He asked. We had been in that room for four and a half hours. He had pulled every rabbit out of his hat to have me stay at the startup that we had founded together just the year before.

The summer was brutal. My team crumbled under the unnecessary pressure of my business partners. Fighting for them was not enough, and besides empty promises, I could not get myself out of the mud of a failing business.

Should I stay, or should I go? If I stay, there will be trouble, but if I go, there will be double, just like the song.

I left the company with no money, no plan, and nowhere else to go.

The same evening, I called my dad and broke the news.

<< Again? Did you leave again? >>

It was not the first time I was quitting something. I was 33, and by then, I had left several jobs, a bunch of relationships, and infinite hobbies, among many other things.

Have you noticed how society constantly reminds us how perseverance is key to success? How should we endure pain to get some gain? How is stubbornness often confused with discipline?

You enter the office of a successful CEO, and there is a poster on the wall yelling: “never give up!

Even on mugs, they write: “keep calm and carry on.

While sipping coffee from one of those mugs in a cozy coffee house a few blocks away from the office I had left so suddenly, I wondered if it was perseverance the way to real success. Quite the opposite! I concluded that quitting things is the real key to a prosperous life.

We would be better off in many situations if we just had the strength to quit before it’s too late. Friends pushing us to pour yet another shot when we are already wasted. That partner who is not respectful of our boundaries, of our culture, of our desires. That concert we bought the tickets for, but then it’s four hours away; nevertheless, we drive in the blizzard to get there. It’s not even our favorite band!

In behavioral economics, they call it the “sunk cost fallacy.” In my book, it’s just another name for “you need to know when it’s time to give up!”

When I was a teenager, probably not older than fourteen, my father said, “you start a lot of things, but you don’t finish many of them.”

For a long time, I felt that comment as a critique of my character.

I now believe it was a compliment.

Over the years, I realized how by allowing myself to quit, I could accomplish much more.

I let go of dozens of hobbies, which allowed me to find the ones I deeply love. I quit hundreds of books just because I couldn’t go past page 20. It gave me the time to read many others. I left movie theaters in the middle of the projection; I didn’t care if I already paid for the ticket. I could spend that half an hour eating popcorn somewhere else instead of boring myself to death in a chair with a sticky floor.

I also realized that quitting is an art. It does not have rules, but just a few principles I follow:

I force myself to be rational, defining boundaries before any engagement, especially with myself. Business agreements are usually in place between the different parties, but I also commit to a contract with my future self: I write down a few different scenarios that would break the deal. For every item on the list, I make an exit plan. I also keep those plans up-to-date along the way. When the alarm goes off, I press the eject button, executing the plan ruthlessly—no hesitation and never looking back. 

I preserve my integrity in the process, so I make it graciously when it’s time to leave. There is no room for ego. There is no need to be cruel. I just look at reality and go, ready to face the consequences of my decisions.

At parties, for instance, everyone loves to welcome you, but no one likes to say goodbye. For this reason, I strongly avoid those mannerisms about “please stay another 5 minutes, the real fun hasn’t started yet…” – No way, I’m out of here, and I’m out of here now!

I go out for a smoke, and I never get back in. By the way, I don’t smoke, so I cannot use that excuse around my close friends.

I don’t like to break other people’s hearts, and most importantly, mine; I try to be respectful of all the feelings involved.

I’m aware that not everybody may agree with my decisions. But, have you noticed how usually in breakups, the one left behind is getting hurt? They will be upset, and you can bet they’ll let you know. It won’t change your mind, but be respectful of their feelings. Acknowledge them, maybe say a few words — no need to apologize. Just don’t be unnecessarily cruel to them. Be firm but kind.

After I left that company almost a decade ago, with no money, no plan, and nowhere else to go, I struggled for a few months; then, I pushed myself to apply for an impossible position at a dream company, which I got.

I have had a taste at more hobbies than I can even recall, dropped an entire floor of books, and I have no idea how dozens of movies end. However, my current employment has been the longest I’ve ever had in my whole life: 7 years and counting.

I cannot say what would have happened to me if I had stayed where I was, but I’m so happy I left that room with no regrets, a light heart, and empty hands. 

The only way to grab an opportunity is to have both hands open and both hands empty.


This essay is the second assignment of Write of Passage, a cohort-based online writing course I’m attending.
I want to thank a few people who helped me edit my initial draft and provided valuable feedback during the creative process: Chris Wong, Clarke Read, Karena de Souza, Mitchell Cohen, Paolo Belcastro, Sam Millunchick, Siobhan Bamber, Vishal Srivastava.

Published by Luca Sartoni

I lead a team of engineers across three continents at Automattic. I love hiking, photography, and 3D printers.

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