Have you ever been called out by your own kid?
I have. I was at dinner with my son a while back, trying to talk to him about how buried he was in his phone. He looked up and reminded me that I’d done the exact same thing two nights earlier.
It didn’t feel great. But it was nothing compared to what happened to Jason Cohen.
Seven Years of Waiting for the Right Moment
Jason spent 25 years in the corporate world of agricultural commodities, in C-level roles with teams across multiple continents. By any external measure, he had a successful career. But for the last seven years of it, he knew something was missing.
He had always wanted to build something of his own, and he felt drawn to the idea of a baseball and softball training facility. With three athletic boys, he understood the problem firsthand. There was a shortage of good indoor space in the New York suburbs, the kind you need to train through the winters and the sweltering summers. The hard part was finding a building with real height clearance and no poles in the way.
He went in front of town boards. He looked at real estate. And every time it got close, he had the crutch of his corporate job to fall back on.
So he waited. For the right space. For the right moment. For conditions to be better.
The Sentence Nobody Expected
Then one day he was with a group of friends, all of them doing what a lot of adults do when they get together. Talking about their jobs. Venting about what wasn’t working.
His 13-year-old son walked into the room, looked around, and said something nobody saw coming.
“You guys are full of it. All you do is tell us to go for our dreams and none of you do it.”
Jason told me that one hit him in his core. And it wasn’t the only thing hitting him at the time. He had recently read about a study of hospice patients, people at the very end of their lives, asked what they most regretted. Almost none of them named something they had done. The regrets were almost always about the things they had never tried.
His youngest son calling him out was the final straw. So he quit, and he started looking.
It wasn’t a straight line. He tried a plumbing business first. Then he started an NFT fund he ultimately couldn’t believe in enough to launch. Neither felt right, but he kept moving. Then one day he called a guy who owned a large building he thought might work. Within 24 hours, he was talking about buying it. Jason went on to double the revenue and quintuple the profit in the first two years.
But the part that stays with me isn’t the business outcome. It’s what finally got him to act after seven years of waiting.
The Framework Bezos Used
Jason didn’t commit until he started thinking through the lens of regret. And he’s not the only one.
In 1994, Jeff Bezos was at a similar crossroads. He had a comfortable job at a hedge fund called D.E. Shaw. Good salary, clear path, a lot to lose. But he had an idea he couldn’t stop thinking about, an everything store on the fledgling internet. His parents told him to stay put.
You know he didn’t. Years later, he explained that the decision was actually easy, once he used what he called his Regret Minimization Framework. He projected himself forward to age 80 and asked one question. Which choice would I regret more? Not which was safer. Not which made more financial sense. Which one would an 80-year-old version of him look back on and wish he’d made differently?
His answer was clear. Trying and failing, he could live with. Not trying would haunt him.
The Answer Isn’t Always to Chase the Dream
I’ve been thinking about regret a lot lately, after reading Daniel Pink’s book on it and hearing Bezos describe his framework on a podcast around the same time. Which is funny, because I’m someone who has said for years that I don’t believe in regret.
That’s not entirely true. A couple of months ago I shared a story about a business I almost launched in the fashion industry. I ran some tests, wrote a rough business plan, built a financial model. But when I sat back and considered what it would require, and what it would take away from the things I’d already started, I decided I would regret spending 5 to 10 years chasing it. So I killed the business before it ever launched. No branded name like Bezos, but the same thinking.
The framework doesn’t always point toward the leap. Sometimes projecting yourself to 80 tells you to let something go, the way it did for me with the fashion business. The point isn’t to chase every dream. It’s to make the choice you can live with when you look back.
Bezos had to construct a framework to get himself there. Jason’s son did it in about ten seconds. Most of us won’t have a 13-year-old walk into the room and name the thing we’ve been avoiding. But we all have access to the same question.
At 80, looking back, which version of this decision do you think you’d be more at peace with?
Don’t quit your daydream.
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