I love quitting

My friend Cary recently wrote about quitting and the complicated feelings that come with it.

If anyone has earned the right to talk about "never quitting," it's him.

He spent roughly 15 years as a special operations guy getting the shit kicked out of him. Now he's on something of a vision quest, figuring out what his next chapter should be.

Imagine spending that long inside a culture built around endurance, commitment, and refusing to quit. Then imagine realizing that the harder question isn't whether you can keep going. It's whether this (however you define that) particular goal still deserves you.

We use "quitting" to describe two very different decisions.

Sometimes quitting means running away because the work got hard or boring or whatever.

Sometimes quitting means finally admitting that the work is taking you somewhere you don't want to go.

Those are not the same.

Personally, I love quitting. Some of my proudest moments were when I quit things.

One of the things that helps me most is remembering to always ignore sunk costs. What I've already spent is gone. Time, money, effort, reputation. None of it becomes more valuable because I throw another five years after it.

Opportunity cost is the other side of that decision. It's what staying will keep costing me.

Example.

I had a great career in government. I worked with impressive people inside a high-performance organization. There was prestige, momentum, and a strong center of gravity pulling me toward the obvious next step.

Then I looked at the people ahead of me.

They had won the game I was playing….buttttt I didn't want their lives.

So I quit.

It was hard. I gave up status, certainty, and an identity I had spent years building. I didn't have a mapped-out alternative waiting for me. I just knew that continuing because I had already come so far was a terrible reason to stay.

That decision set me on the path I'm still on today.

Our culture loves persistence because it makes a clean story.

Someone keeps pushing, overcomes adversity, and wins. Strategic quitting is messier. You may stop something that still looks successful from the outside. Other people question you. There is no immediate proof that you made the right call.

But persistence is a tool.

Quit wasting your time.

Quit taking good people for granted.

Quit saying yes to work you secretly resent.

Quit getting involved in problems that aren't yours to solve.

Quit defending an old decision just because a younger version of you made it.

Of course, don't quit every time something gets boring, painful, or uncertain.

Most worthwhile things become all three at some point. The skill is learning the difference between a hard day and the wrong destination.

"Never quit" is useful advice when the goal is right.

But knowing the right goal is the hard part!

Yallah Habibi,

Jon