Not Sure Whether to Quit Something? Read This!

It'll change the way you think about quitting.

If you’re wondering whether to stick with or quit something, consider this:

Imagine that you had to marry the first person you dated.

Now ask yourself: Would you ever go on a date?

Annie Duke made this point to me recently. She’s the author of a great new book called Quit, which argues that quitting is a virtue. The way Duke sees it, we have it all wrong about quitting. Winners do quit, she says. And quitters do win.

We talked about this for more than 30 minutes for Entrepreneur. You can listen to or read our conversation. But in this newsletter, I want to focus on that dating metaphor — because it was the simplest, most impactful thing she said to me, and it changed the way I think about quitting.

I think it might change yours too.

First, let’s talk about why we don’t quit.

When we tell the stories of successful people, we often tell the stories of perseverance.

They stuck with it.

They wouldn’t take no for an answer.

I mean, here’s just one example — a headline from

Not Sure Whether to Quit Something? Read This!

People love these kinds of stories. They are inspiring. Validating. You’re not doing it wrong, the stories seem to tell us. You just need to keep doing it.

But imagine a different headline: “She Was Told ‘No’ 100 Times. Then She Realized They Were Right, Did Something Else, And Now Runs A $1 Billion Business.”

Doesn’t exactly give you goosebumps.

I have an idea about why: It’s because, when we hear these stories, we are not actually looking for a pathway to success. We are looking for a justification of our comfort.

When someone perseveres and succeeds, they get to stick with what they have. They had an idea, or a vision, or a goal, and they never had to hit restart. But when someone quits, they must change. They need a new idea.

That makes us think: But what if I don’t have a new idea? I need to make my current idea work!

Yes, sure, perseverance can be uncomfortable. Hearing “no” 100 times is not easy at all. But here’s what’s more uncomfortable: Believing deeply in something you’re doing, and then admitting that it’s not going to work out the way you hoped, and imagining a world in which you have to start all over.

Let’s be clear: Sometimes you really should persevere! You could be on the right track. Success could just require hearing “no” 99 more times. You could be right all along. I hope you are. I hope I am too, because oh boy, I do plenty of things that haven’t really paid off yet, but I still try and try and try.

But sometimes, we must admit: You are I are wasting out time.

So, how do we find the courage to quit?

Now it’s time for Annie Duke’s dating metaphor.

Imagine that you had to marry the first person you dated, she told me. What would happen?

Well, she says, you’d be incredibly cautious. You’d do endless research on every possible candidate. You’d take forever to decide.

Now think about our real world: Why are we able to go on a lot of dates? It's because dating is how we gather information! Sometimes we date someone for a short time, sometimes for a long time. But we quit on almost everyone. That is how we find the right person.

“Well, every decision that you ever make is like dating,” Annie told me. “You're dating ideas. You're dating projects. The reason why we can do these things, despite being so uncertain about them, is because we can walk away later.”

Now you see why this insight captured me.

Here’s what Annie is saying: Perseverance can be an asset, but it can also be a trap. We can waste too much time on things that do not work, at the expense of what could be our greatest opportunity.

How can you know when to quit? Annie suggests creating “a set of kill criteria” — benchmarks that you create ahead of time. How fast should something grow? How much money should it make you? “Whether you hit them or not will tell you if you should stick it out or quit,” she says.

But that’s really Step 2. The first step is to recognize that quitting isn’t failure. Drain the emotion from it, she says. Treat it like a tool. A decision-making tactic. Quitting is what liberates us to spend our time most wisely.

After all, we have to date a lot of duds before happily settling down.

"Are You Very Famous?"

Not Sure Whether to Quit Something? Read This!

"Are you very famous?" this guy asked me.

I wonder what would have happened if I said yes!

Here's the backstory...

Whenever I see a bookstore, I look for my book, Build For Tomorrow. If it's there, I sign all the copies — because the store will often put "signed by the author" stickers on them and display them prominently.

Good sales strategy!

So the other day, I popped into the Hudson News at New York's Penn Station and found three copies of my book. I signed them at the register (and set my phone up to take a photo for social).

As I did, this guy came up to buy a soda.

"Are you very famous?" he asked me.

I've never been asked that, so here's what popped out of my mouth:

"Very famous?" I said. "No, but I have... some level of awareness?"

This did not impress him 😂😂😂

Maybe next time, I just need to say, "Yes, and you get a free selfie with every book purchase!"

Want a signed copy of my book? Just respond to this email, and we can work it out. Cost is just the book plus shipping.

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Cover credit: Getty Images / Christoph Wagner