On Luck
January 19, 2026 • ☕️ 5 min read
This started as an email to my daughter. I’ve cleaned it up a little but kept the tone because, honestly, I think it’s better this way.
There’s a category of ideas I want you to get very good at recognizing. I’ll call them universal human blind spots, things our brains are naturally bad at. Not because we’re dumb, but because we didn’t evolve for the modern world.
Two big ones matter a lot.
1. Exponential thinking
We’re good at linear intuition. One step, then another step. But we’re terrible at grasping how small differences compound over time.
- 3% versus 7% interest looks tiny on paper, but it’s the difference between slowly losing wealth and quietly becoming wealthy.
- A million and a billion feel like neighbors, but they live in entirely different galaxies.
- A big mortgage looks terrifying next to rent. That is until you understand inflation and ownership, and suddenly you sleep well knowing future income is coming to you, your children, and if they hold it, your grandchildren.
But we’ll come back to this one. I’m sure.
2. Fear of opportunity
The second blind spot is even more important: fear, specifically fear of opportunity.
Fear made sense once.
On the great plains, every decision carried real risk. Pick the wrong path, the wrong fight, the wrong meal, and you could die. Make the wrong social move and you could lose your tribe. Lose the tribe, and survival got very hard very fast.
Life back then, like life today, was akin to rolling a pair of dice where you could roll as many times as you wanted. But with one key difference. Roll a 6, you’re dead. Game over. Finished.
So our brains evolved to be vigilant. Conservative. Very good at avoiding rolls.
That same instinct is what you feel today when you want to:
- Learn something new: a dive, a front flip, go to a foreign place
- Give a speech
- Apply for something you’re not “ready” for
- Talk to someone you’re attracted to
That tight feeling? That’s ancient fear protecting you from a danger that mostly no longer exists.
And here’s the important part: this fear is no longer grounded in reality. In almost all of these situations, there’s no real risk if you fail. Humiliation, maybe. But the game is still going. And you can roll again, and again, and again.
At this point you’re probably thinking, “Ok… where is this going?”
Fair. Let’s make this concrete.
The game
Imagine a simple game with two dice.
- Each player is assigned a number.
- If you roll your number, you win.
- If you roll a 6, you’re dead, and you do not get to roll again.
- Any other number is “try again.”
Before the game starts, we line everyone up from most capable to least capable, strongest to weakest.
The strongest gets first pick and naturally chooses the most likely number: 7. The next strongest chooses 8. Then 5 or 9, then 4 or 10, then 3 or 11. The weakest ends up with 2 or 12.
More generally:
- Low Skilled → very low probability numbers (2 or 12)
- High Skilled → mid-to-high probability numbers (8 or 6)
- Elite → the highest probability number (7)
Now imagine different strategies over a lifetime:
- Highly fearful: only roll if it’s perfect (1 roll)
- Fearful: roll occasionally (10 rolls)
- Motivated: say yes when opportunities appear (100 rolls)
- Highly motivated: actively seek rolls (1,000 rolls)
Scenario 1: The Serengeti
Back then, rolling itself was dangerous.
You could roll many times, but if you ever hit that 6, the game was over. No retries. No learning. No comeback.
| Player (number) | 1 roll | 10 rolls | 100 rolls | 1,000 rolls |
|---|---|---|---|---|
| Strongest (7) | 0 wins | ☠️ | ☠️ | ☠️ |
| 2nd (8) | 0 wins | ☠️ | ☠️ | ☠️ |
| 3rd (5 or 9) | 0 wins | ☠️ | ☠️ | ☠️ |
| 4th (4 or 10) | 0 wins | ☠️ | ☠️ | ☠️ |
| 5th (3 or 11) | 0 wins | ☠️ | ☠️ | ☠️ |
| Weakest (2 or 12) | 0 wins | ☠️ | ☠️ | ☠️ |
With those odds, by about 10 rolls, no matter your talents, you were already more likely than not to be dead. By 100 rolls, death was almost guaranteed. And winning was not.
So the rational strategy wasn’t to roll often.
It was to conserve rolls.
Spend your time improving your skills, your strength, your social standing. Anything that would improve your odds before you rolled.
In that world, fear of opportunity wasn’t a flaw.
It was correct.
Scenario 2: The new game
But here’s the thing.
The game has changed. Our brains haven’t.
Today, most rolls don’t carry the risk of death, exile, or permanent failure. Most bad rolls just mean embarrassment. And then you get to roll again.
Which completely flips the strategy.
| Player (number) | 1 roll | 10 rolls | 100 rolls | 1,000 rolls |
|---|---|---|---|---|
| Strongest (7) | 0 | 1 | 16 | 166 |
| 2nd (8) | 0 | 1 | 13 | 138 |
| 3rd (5 or 9) | 0 | 1 | 11 | 111 |
| 4th (4 or 10) | 0 | 0 | 8 | 83 |
| 5th (3 or 11) | 0 | 0 | 5 | 55 |
| Weakest (2 or 12) | 0 | 0 | 2 | 27 |
In the old world, where a bad roll ended everything, you’d want to roll as little as possible and spend all your energy on perfection.
But today? Rolling a 6 just stings, and then life continues.
So instead of avoiding rolls, the winning strategy is to increase the number of rolls.
This applies to everything: love, promotions, adventures, investors, careers, creative work.
What I want you to take from this
When you look at these numbers, here’s what I want you to notice and remember.
First: talent doesn’t matter if you never take a swing.
Second: the gap between low skill and medium skill is bigger than the gap between medium skill and the elite. Engagement matters, but you don’t have to be the best.
Third: it’s far easier to work to find 1,000 rolls than it is to become LeBron, Serena, Magnus, or Taylor Swift.
Fourth: some opportunities are incredibly rare, 1 in 10,000 or more. The only strategy to ever hit them is to roll often. Skill is a footnote. But when they hit, they change everything.
Fifth: being engaged, working on your craft, puts you in situations naturally where you are closer to opportunity. It puts you near luck. Rolls get you more rolls.
And that leads to the sixth thing:
Opportunities compound
The more you do, the more people you know. The more people who know you. The more doors will open.
Put yourself, your dreams out into the world and the world will respond.
So go out there, ignore the fear (it’s not real), and roll those dice. Roll them again and again and don’t stop.