♟️ The Metagame #038: The 37% Rule

Talking about the 37% Rule would’ve been fitting for the 37th Metagame edition, but alas.

Here’s what’s in store for the 38th edition of The Metagame:

• What is the 37% rule?

• Regret minimization

Read time: 4 minutes

There’s a concept from the book Algorithms to Live By called the 37% Rule.

And once you understand it, you’ll never look at decision-making the same way again.

What is the 37% Rule?

Imagine you’re apartment hunting. You have 100 apartments to see. You want the best one, but once you pass on a place, it’s gone forever.

The question is: When do you stop looking and make a choice?

If you jump too early, you might miss something better.

If you wait too long, you might settle for something worse.

The 37% Rule gives you the mathematical sweet spot:

Spend the first 37% of your time (or opportunities) just observing, without committing. Then, after that, be ready to select the next option that's better than anything you've seen so far.

In the apartment example:

• See the first 37 apartments without making an offer.

• Starting with the 38th, pick the first one that beats all the previous ones.

It seems counterintuitive.

But statistically, it gives you the highest chance of landing the best option.

(I won’t bore you with the actual math. Instead, I strongly recommend that you read the book. It’s a game changer.)

Decision-Making is a Race Against Time

Here’s where it gets even more interesting:

The 37% Rule only works when you know how much time (or how many options) you have.

Life rarely hands you a schedule.

• You don’t know how many people you’ll date before meeting "the one."

• You don’t know how many job offers you'll receive.

• You don’t know how many business ideas you'll come up with before one sticks.

And that uncertainty changes everything.

In real life, decision-making becomes a balancing act between two forces:

1. Optimizing for the best choice

2. Minimizing the risk of future regret

Regret Minimization: The Hidden Player

Algorithms to Live By introduces another important idea alongside the 37% Rule: regret minimization.

When you make a decision, you’re not just trying to maximize success—you’re also trying to minimize the pain of what could have been.

Basically, you want to make choices that your future self won't obsess over at 2 a.m. while staring at the ceiling.

You have to walk the fine line between:

• Deciding too early, regretting what you missed.

• Waiting too long, regretting what you lost.

Regret minimization means accepting that you’ll never have perfect information, but making peace with the idea that you acted as wisely as possible, given the information you had at the time.

Good decision-making isn’t about avoiding regret altogether. It’s about choosing the kind of regret you can live with.

How to Use the 37% Rule (and Regret Minimization) in Real Life

You don’t need to run complex formulas every time you make a decision.

Instead, build these instincts:

• Set a deliberate "sampling phase." Before committing to anything, give yourself permission to just observe. See what’s out there.

• Figure out what “success” looks like. Define your "good enough" before emotions cloud your judgment.

• Remember: delaying forever isn’t risk-free. Waiting can cost you just as much as making a commitment.

• Think about your future self. Will you regret passing too quickly? Or dragging things out and missing your window?

At the end of the day, smart decision-making is less about maximizing outcomes and more about minimizing future regrets you can’t control.

Playing the Game

You’ll never have perfect information.

You’ll never know if there’s something “better” just around the corner.

You’ll never eliminate regret completely.

But you can live—and choose—in a way that leaves you proud of how you handled uncertainty.

The 37% Rule isn’t about perfection. It’s about peace.

And sometimes, the most powerful decision isn’t picking the best option.

It’s choosing to stop searching, and start living.

Quote of the week

Thanks for reading!

If you have any questions, hit me up on LinkedIn or on Twitter/𝕏 at @sam_starkman, or feel free to reply to this email!

— Sam