How to Feel Better About Quitting Something

Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that's me) shares one way to level up — and build a career or company you love.

Today’s one thing: Leaving something.

That one thing, better: Building upon something.

You’ve worked at something for a long time. Now you wonder: Is it time to stop?

That’s a hard thing to consider, because it leads to two additional questions:

First, a scary question: What comes next?

Then, an even scarier question: Am I giving up everything I’d done before?

The second question is harder because it’s invalidating. It’s like saying, “There was no point to all that hard work, and now I have nothing.”

But there’s another way to think about it. Today, I’ll show you the difference between leaving something and building upon something. I’ll also tell you about a friend facing this problem right now, and how this idea helped him think through it.

First, let’s talk about quitting.

If something breaks in our home, we throw it away. But if something breaks in our life, we often keep it.

We keep the job that doesn’t fulfill us. We stay in the relationship that no longer sustains us. Why do we do this? Fear, insecurity, convenience — there are all sorts of reasons. Economists might say it’s the sunk cost fallacy, which is to say: It’s worth continuing to do something, because we’ve already invested in doing it.

And what are the costs of chasing sunk costs? I once interviewed decision-making expert Annie Duke, who put it like this:

But I know — that all intellectually makes sense, but it’s hard to personally apply it. Because, fine: You leave the thing not worth pursuing, so that you can find the thing worth pursuing…

And then what, smart guy? Doesn’t that mean throwing everything away? Starting from scratch? Saying phrases like: I am too old for this, because you are too old for this?

No. It doesn’t have to mean any of that.

Let’s play it out with a real-life example.

A few weeks ago, I had dinner with an old friend I’ll called Eric. And Eric has a problem: His work makes him miserable.

He used to love his work. But these days, he mostly loves the idea of his work. He worked hard to be in the role he’s in, at the company he’s in, and he takes a lot of pride in being there. But then he shows up every day and… deals with a crappy boss, inside a terrible company culture, where he does unfulfilling work.

Could he go to another company? Maybe, but not easily. He’s in media, where the job pool is shrinking. That’s especially true at his senior level.

“What if you left media?” I asked him.

“I don’t know how to do anything else,” he said. “I’d have to learn something new and work my way up.”

And there it is — the fear of starting over.

I wanted to show him that he’s wrong.

So here’s what we did. First, I asked him to describe what he does every day: He writes, he edits, he manages, etc.

Then I asked him to describe the underlying skills that enable him to do those things.

“I can write, I can edit…” he said.

No, no — that’s too literal, I told him. Those aren’t skills. Those are expressions of skills. What is his actual skillset? What is he really good at doing, that he currently does through writing and editing, that could be done in many other ways? (Btw, chapter 5 of my book walks you through this process in great detail.)

Eventually he had an answer: He’s great at taking complex things and making them simple.

Ah HA! Now we’re getting somewhere. I asked how else he could do that, and we started brainstorming. Communications consultant? Advertising? He was intrigued. Excited, even.

“This gives me a totally different way to think,” he said.

And that is the point.

Let’s go back to my two original questions:

First, the scary question: What comes next?

Then, the even scarier question: Am I giving up everything I’d done before?

The second question often inhibits the first. If you’re afraid of starting over, you’ll never consider what comes next. But Eric had now put that second question to rest — because he understood the answer.

The answer is no: You are not giving up everything you’d done before. You are building on top of it all.

You are good at something. I am good at something. Eric is good at something. Throughout the course of our careers and lives, we refined that talent. We tested it against the real world; we built a body of knowledge around it. And all that stays with us. It comes with us. No matter where we go.

If Eric took a job in advertising, he’d easily call upon his media background. He’d know how to take a complex idea and turn it into something engaging and digestible. He’d think: Oh, wow, the lesson I learned from editing that old story gives me a great idea for how to solve this new problem today!

This is the difference between leaving something and building upon something. To “leave something” is to start over — which is not actually what happens when you leave something! Instead, you take what you had before, and then build on top of it, or utilize the old thing in a way that makes you excellent at the new thing.

You face new challenges, and you find new purpose in your old skills.

You discover the instincts you didn’t know you had.

You are prepared in ways you do not know.

And to be clear: You do not need to make a massive change to make this useful. Maybe your career or relationship is mostly good, but one part of it is not. Maybe you’re afraid of throwing out the whole thing, which is stopping you from identifying the part that’s broken and solving for just that. And when you make this change — or any change! — you are not starting from scratch either.

You’re saying: Here’s what I have, and here’s what I need, and here’s what I’ve learned that can help me get it.

There are a lot of ways to succeed.

At the end of my conversation with Eric, he realized something: There was another, deeper reason he’d been holding onto his crappy job.

Leaving it felt like failure.

After all, he’d worked for years to get there. He’d sacrificed a lot. And for a long time, the work was good and satisfying. If he left now, were those years all a bust? Was he a failure at the thing he wanted to achieve?

But as we explored this, we remembered an amazing post-game interview that Giannis Antetokounmpo just gave. Maybe you’ve seen it. If not, you should watch.

For context: Giannis is the star of the Milwaukee Bucks, who were the top seed in the East and considered a contender for the NBA championship. Then they lost in the first round to the Miami Heat. It was a shocker. Very unexpected. (Except by me, because I’m a Heat fan and the dream always lives!)

After the final game, a reporter asked Giannis if he saw the season as a failure. Giannis replied:

Here’s a little of the transcript:

Then he kept going. Truly, watch the whole thing.

Giannis is right. His season was not a failure. Instead, it was an experience. It was a defined moment in time, with a start and a finish, in which he tried to do something. But its value is not defined by its outcome — because so many other things happened along the way, and so many other things will happen as a result.

This year, he became a better player. He learned things. Adapted. Adjusted. Had fun. Helped others. Created joy and memories. These are good things. Worthwhile things. They are the opposites of failure, even if he failed at one specific goal.

We all have seasons. They start, they end, they start anew. Each time, we’re better than before. Each time, we’re more prepared than before.

And when that new season starts, bring every single thing you’ve got.

Because you've got a lot.

That’s how to do one thing better.

Did you miss last week's newsletter?

It was about how to feel like your work matters. Multiple people emailed me to say it made them cry (in a good way). I hope it helps you too.

Here it is.

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