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Why “all-in” is often a losing bet
Going all-in sounds noble. But it’s usually a trap.
Michael Girdley
May 10, 2025
Hey everyone!
There’s a piece of online wisdom that’s always felt off to me:
“You must go all-in to succeed.”
I don’t think that’s entirely true. And I don’t think it’s how most successful people live.
Let me try to change your mind.
Before we jump in: I’ve got two free events coming up!
Thurs June 5 — How to hire offshore devs. I’ll be chatting with Near CEO Hayden Cohen about the ins and outs of hiring offshore developers. Beginner-friendly, with lots of time for Q&A about offshoring in general. RSVP!
Thurs Jun 12 — The best franchise models on the market. Franchise-curious? There are a ton of different options out there, and they’re all over the map. Connor Groce will walk me through the best opportunities you can find this year. RSVP!
I’ve always been someone who likes lots of varied action..
I’ve been in fireworks, software, coffee, staffing, YouTube — none of them were part of some master plan. I have multiple businesses because I followed my interests in many different directions.
And people far more successful than me do the same.
Natalie Portman has a Harvard degree in psychology and has published papers.
Ben Franklin invented bifocals, discovered electricity, and made the first public library.
Warren Buffett plays the ukulele (kind of) in addition to running Berkshire Hathaway.
But we’re obsessed with this idea that obsession and singular focus are the only paths to greatness.
But I think it’s more like this: winners don’t overly obsess.
The story of Steve Magness hits this perfectly.
He was a natural talent — the fastest high school miler in the country at 4:01.
Relentlessly focused. Skipped parties, trained obsessively, did everything “right.”
But once he reached a 4:01 mile, he hit a wall. Month after month, he coudn’t break his time no matter how hard he pushed.
Ready to give up, he sought help from a renowned sports psychologist, who suggested he broaden his interests and introduce some variety into his routine.
We want the story to be, “and then he broke his record!”
But he didn’t. Steve Magness never broke 4:01. But he succeeded as a performance coach… advocating for a “holistic approach” to sports.
—
Here’s the kicker: the data supports it.
A survey of 5,000 would-be entrepreneurs found that those who kept their day jobs were 33% less likely to fail.
And Nobel Prize winners are 2.8x more likely to have a hobby.
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So what’s going on here?
It feels counterintuitive. Shouldn’t devoting all your energy to one thing put you ahead?
The answer is yes… but only up to a point.
Then your ego gets in the way.
Because when your whole identity is one thing, fear takes over. You can’t take chances — or worse, you freeze up. If you have only one thing, your whole self is at stake every time you step up to the plate.
Another pattern I’ve seen amongst “maniacal focus” practitioners:
They’re often horrible at other things in life.
Kobe was all-in on his game, but also, y’know, the sexual assault stuff. Anna Wintour was such a nightmare they made a movie about it. Michael Jordan punched his teammates. Bobby Fischer was the greatest chess player in the world, but was a recluse for decades before he died.
Great player, terrible interview guest.
So what do you do?
A couple of things come to mind.
First: Don’t forget to live.
My friend Matt Willes told me that recently, and it stuck. Don’t let work crowd out family and friends.
Second: it’s OK to have varied interests.
I pick up lessons from one business that help in another. Exposure to different problems makes you a better problem-solver. There’s real compounding that comes from range.
Lastly, but maybe most important: big opportunities can come from going against common wisdom.
Everyone thought the Airbnb guys were considered nuts. Columbus definitely was.
If everyone thinks your idea is reasonable, it’s probably not a breakout. Real upside comes from going against the grain.
That’s where I’m at!
What about you? Have you felt pressure to go all-in on something? Or found success by doing the opposite?
Hit reply and let me know.
3 things from this week
Appetizer: The best businesses are "toll collectors" — my buddy Kevin Dahlstrom wrote a list of 10 “toll collector” businesses, and how he defines it. Some good discussion in the comments.
Main: My take on how to survive 2025 as a business. It’s going to get harder before it gets easier.
Dessert: Send me your best pope memes!
That’s all for this week.
Thanks for reading!
Michael
P.S. Don’t forget to RSVP to my events coming up! Sign up now and you’ll get the recording afterwards. 👇
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