Happy Monday
One idea, one quote, one question. 90 seconds.
The Idea
Most of the founders I’ve had on the podcast will tell you the same thing if you ask them honestly, which is that the hardest part of building a company isn’t the part where nothing is working. It’s the part where things are working and you still feel like you’re behind.
Dave Ramsey got into this on the podcast last week. The episode is called Why Most Entrepreneurs Are Miserable Running Their Own Companies, and I expected him to talk about the grind, the hours, the early years. He did, but the thing that stuck with me is bigger than that. Dave had $4 million in real estate by 26. By 28 he was bankrupt and the sheriff was at his door trying to take his daughter’s crib. He rebuilt from there into a company doing $300 million a year with 1,100 employees and 18 million people listening every week. And what he kept coming back to is that even while he was building all of that, the thing that made him miserable wasn’t the difficulty. It was that he was always looking at how far he still had to go instead of how far he’d already come. And the further along he got, the worse it felt, because the target kept moving.
There’s a study from Cornell that I think explains what Dave was describing better than anything I’ve read. In 1995, a group of psychologists went back through footage of the 1992 Barcelona Olympics and watched the faces of the medalists on the podium. Gold medalists looked happy, obviously. But between silver and bronze, the bronze medalists consistently looked happier than the silver medalists who’d finished ahead of them. They ran the same analysis across every Olympics from 2000 to 2016 and it held up every time. The reason is that silver medalists think about the gold they almost won, and bronze medalists think about how close they came to going home with nothing. The person who did better feels worse because they’re looking in a different direction.
I think that’s what happens to a lot of people who start companies or pursue anything ambitious. You go in as the bronze medalist, looking back at where you came from, grateful for the shot. And somewhere along the way you become the silver medalist, looking at everyone who’s further ahead, and the thing you’ve built stops feeling like an achievement and starts feeling like a gap. Dave told me the weight finally lifted when he stopped measuring himself against where he thought he was supposed to be. He didn’t say it like advice. He said it like something that took him years to figure out and he wished he’d learned it earlier.
Quote
“No man is happy who does not think himself so.” — Publilius Syrus
He was a freed slave in ancient Rome who ended up becoming one of the most quoted writers of his era. That line is two thousand years old and the Olympic research landed on the same idea with a camera and a podium.
Question
When you think about where you are right now, are you measuring from where you started or from where you think you should be?
Listen
Dave Ramsey: Why Most Entrepreneurs Are Miserable Running Their Own Companies. This is the conversation that got me thinking about all of this, and there’s a lot more in it than what I covered above. Dave talks about the early years when he was doing everything himself and it felt like a treadmill that never turned off, and he gets very specific about what actually changed for him, not just financially but in how he thought about what he was building. If you’ve ever been in the middle of something you chose and wondered why it doesn’t feel the way you expected it to, this one is worth your time.
Read
The Paradox of Choice by Barry Schwartz. Schwartz uses the bronze medalist research as one of his main examples and builds a much bigger argument around it about how more options and more ambition actually make people less satisfied with what they end up with. It changed how I think about why some people can build something genuinely impressive and still feel like they’re losing.
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— Scott