How to Know When to Quit
Feeling stuck on something? Ask yourself these questions — they'll help guide what's next.
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: Grinding it out.
That one thing, better: Maybe it’s time to let go.
Want to be successful? You need grit and perseverance.
That’s what we’re told. Sometimes, people say it explicitly. Other times, it’s just built into the stories we hear — the founder who was told “no” 100 times before proving everyone wrong, or the celebrity who never gave up and just won an Oscar.
But here’s the thing: Grit and perseverance do not always work, because not every idea is workable. Some ideas will never work, which means they’re just holding you back… and if you quit them, you’ll regain the time and energy to put towards better, stronger ideas.
So how do you know the difference?
Today, I’ll tell you about something I just quit. It was hard. But it was also right.
Then I’ll tell you how I decided to do it — and a framework you can use to evaluate your own projects.
First, here’s what I quit
Since 2016, I’ve been making a podcast called Build For Tomorrow (yes, same title as my book). I loved this show. Listeners told me it changed how they think.
Each episode was deeply reported, highly produced, and took me a month to make. This required sacrifice. I pushed myself to the brink. I said no to other projects, so I could have the time for this one. A few years ago, I literally got shingles because I was so stressed about my workload. (Hot tip: Do not get shingles. Awful!)
But I kept going. Why? Because I loved the show. And how could I give up on it!??
In the past few months, however, my life got too busy. Too many demands for my time. Something had to give. And so I stepped back and realized…
This podcast I loved had to go.
How to decide whether to quit
Quitting is a decision-making tool. That’s what Annie Duke says — she teaches decision strategies at Wharton and wrote a great book called Quit. And she described the logic to me this way, in an interview with Entrepreneur:
Imagine if the first date you went on was the last date you went on, in the sense that you had no option to change your mind. You had to marry them. How hard would it be for you to decide to go on a date? How much research would you have to do? How long would it take you to pull that trigger? Oh my gosh, that would be so impossible.
So why is it that you can just go on dates? Because you're going to find out information about the person. Sometimes you stick to it. Sometimes — mostly — you walk away.
Well, every decision that you ever make is like dating. 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.
So, OK. How do you know when to walk away?
Annie suggests creating “a set of kill criteria” — basically, metrics that you set in advance and then see if you can meet. Your company should have X revenue by December. Your podcast should grow X percent in six months. If you can’t meet the metric, maybe it’s because something needs to change.
I thought a lot about that when deciding what to do with my podcast. A year ago, for example, each episode consistently got 25,000 listeners within the first 30 days of launching. But try as I did, I just could not get the audience to grow much beyond that.
Why wouldn't it budge? Maybe, I wondered, it's not for lack of trying. Maybe it's because I reached the limit of this project's success.
Now here’s the strategy that really made me quit
I ask a simple question of everything I do: What is it for?
That’s because everything I (and we!) do should serve an identifiable purpose. Some projects are to make money. Others are to learn a skill. Others are personally fulfilling, in a way that fills me with energy.
So, what was that podcast for? My answer had long been this: The podcast is an IP factory, because it allows me to talk with fascinating people and learn things I’ll use elsewhere, and it’s an opportunity magnet, in that it has drawn interesting people to me and sparked other projects (including my book!).
Then something happened. My friend Nicole Lapin, a best-selling money expert, asked if I wanted to collaborate on a new podcast called Help Wanted — and also help her build an entire podcast network about financial literacy.
These were bigger growth opportunities. Help Wanted (which, just like this newsletter, is all about helping you improve your work) could scale faster, and come out far more regularly, than my other podcast.
So once again, I thought of my old, beloved Build For Tomorrow podcast, and I asked: What is it for?
This time, the answer was different.
Sure, it’s still an IP factory — but is that reason alone to keep doing it? No, because I have many other ways to interview people and develop new material.
And sure, it's still an opportunity magnet — but what if this work with Nicole actually is the next opportunity it attracted? Build For Tomorrow taught me about podcasting, and now here's a chance to do it at a larger scale, and isn't that the point?
Once I realized that, the choice was clear. It was time to move on.
I made the announcement this week. It's sad walking away from something you love. It's sad not doing everything forever. But I don’t regret it. Instead, I’m excited.
Annie Duke used a dating metaphor to talk about quitting. I’ll use one to talk about what happens after you quit. You know that incredible line from When Harry Met Sally?
“When you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.”
That’s how we should feel about new ideas and projects too. The ones we move on to.
OK, fine, we aren't committing to these things for the rest of our lives. But they’re the thing that could inform or define the rest of our lives. And when you realize that one project is done, and the next growth opportunity is waiting for you, you should want that to start as soon as possible.
More things better:
Miss last week’s newsletter? Here's how to turn someone’s “goodbye” into “hello again!”
Newsletter growth tips! I interviewed Lenny Rachitsky, who has the #1 business newsletter on Substack, about how he did it.
Check me out in Variety! I mentioned above that Nicole and I are building a podcast network — and it’s making news!
You're Never Too Important...
I was crushed to learn that Lance Reddick died on Friday. He was an incredibly talented actor, known for his warmth and generosity, and he was also the co-star of one of my fondest memories in New York.
I just told the story on Instagram — I hope you'll watch. Here's a teaser: It involves Lance, one of the greatest basketball players in the world, and the revelation that nobody is as confident as they might outwardly appear.
I've told this story to friends for years, but never shared it publicly. In honor of Lance, it's time.
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