A few years ago I went through a really rough health patch.
One afternoon I was lying on my mom’s couch when she looked over at me and said, with the grief and empathy that only a mother can convey, “You’ve had it so hard.”
I just grinned, quietly.
Not because the last few years had been easy, but because on the grand scale of things I knew I’d won the life lottery.
I was born white, male, in the suburbs of Philly, to middle-class parents who loved me, loved each other, stayed married, and valued education. That’s not a moral achievement — it’s a structural head start. I had every advantage you can imagine – a safe neighborhood, great friends, a stable household and awesome public schools – exactly the kind of context most of the planet would kill for. That’s not “hard”; it’s the f*ckng jackpot.
My mom looked at me like I was completely bananas.
We had lived the same story, yet our narratives were very different.
That little exchange stuck with me: how we internally frame our circumstances shapes our understanding of luck, and agency, and even self-worth.
My point isn’t that hardship isn’t real.
It’s that two people can look at the same hand and see different cards.
Recognizing how much of my hand was dealt for me gives me gratitude – and urgency.
It pushes me to think harder about what luck really is, how much of it we control, and how we can shape it in our work and our lives.
How Our Culture Keeps Redefining “Luck”
It’s hard to even agree on what luck is:
“Luck is what happens when preparation meets opportunity.” — Seneca
“Shallow men believe in luck. Strong men believe in cause and effect.” — Ralph Waldo Emerson
“I’m a great believer in luck, I find the harder I work, the more I have of it.” — Thomas Edison
“Luck is a dividend of sweat. The more you sweat, the luckier you get.” — Ray Kroc
“You make your own luck if you stay at it long enough.” — Naval Ravikant
These aren’t chronological — you can’t trace the changes through time in a linear way.
They’re all over the map. Ancient Rome, peak individualism, 19th-century transcendentalism, early-industrial America, Silicon Valley Twitter threads.
But each one reveals a point-in-time, a different perspective.
From Sweat to Serendipity: How Luck Keeps Getting a Rebrand
In the industrial era, the story was pretty simple: success was earned. Luck was a footnote, a concept mentioned much less. America was the land of opportunity, boasting a middle-class and the certainty that you could pick yourself up by the old bootstraps and fulfill your dreams.
Corporate, pre-internet America in the ’80s and ’90s celebrated agency — strategy, discipline, hierarchy, and grit. Business books like In Search of Excellence and Good to Great built billion-dollar consulting industries around the idea that results could be engineered. And corporate barons ruled the land by showcasing strength, leverage, and resilience (see: Barbarians at the Gate).
The subtext was: You make your own luck, and if you didn’t, you didn’t work hard enough.
Then the Internet Blew It All Up
Along came the internet / startup / VC era. Everything got louder, faster, weirder. People were getting rich overnight and phrases like first-mover advantage, network effects, and timing were starting to sneak luck back into the conversation.
Founders were waking up to the truth that success wasn’t just about skill — timing played its part too.
Yet the mythology of hustle held on — the 16-hour workday, the stocked Red Bull fridge, the belief that you could out-grind randomness if you just stayed awake long enough.
We started celebrating people who were both lucky and relentless — Bezos, Jobs, Zuckerberg — without ever being sure which side of that equation mattered more.
Today, in the modern era, we’re probably the most comfortable we’ve ever been saying the quiet part out loud: privilege, timing, and randomness all play massive roles.
We call it “structural luck” now -- the family you were born into, the networks you inherited, the timing you didn’t control.
But we haven’t gotten rid of agency.
Hustle still rules, but it coexists with a certain level of self-awareness. Founders talk about things like “luck surface area,” serendipity, and exposure — putting yourself in motion so that chance has somewhere to land.
We’ve evolved a bit from pretending we make all our luck to realizing we can increase our odds.
Because luck didn’t disappear — we just learned to design for it.
What We Can and Can’t Repeat
My friend Morgan Housel once wrote that people confuse luck with what’s repeatable, and sometimes we use them interchangeably when we shouldn’t.
He said it best: “You can learn a lot from Warren Buffett’s patience. But you can’t replicate the market environment he had in the 1950s.”
The conditions -- the timing, the competition, the regulation -- those things are out of our control. They’re not repeatable.
Similarly, we can’t copy Bezos’s early e-commerce play any more than we can recreate the main circumstances that led to Rockefeller’s oil monopoly.
What you can copy are the repeatable parts: the patience, the focus, the long-term orientation.
Jason Zweig takes it in a slightly different direction. He leans on psychologist Richard Wiseman’s research, showing that lucky people aren’t just lucky. They make their own chances by saying yes more often, trying more things, meeting more people, staying open to surprise.
They don’t wait for luck to happen — they stack the odds by moving, meeting, trying, saying yes. His point was that luck has habits, and we can design to have more of those habits in our lives.
And that’s also what newer research is finding. A USC Marshall study found that people who stay in motion, experimenting, learning, seeking novelty, being curious - they literally increase their odds of encountering luck again.
In other words, you can’t copy someone else’s home run swing - but, you can keep getting in the box. More swings means more chances for the ball to find your bat.
The Lottery & The Leverage
I’m sure like many of you, I’ve had my share of shit.
My dad died tragically just two weeks after my wedding day -- I was only 25 years old.
I’ve battled chronic Lyme disease, thyroid cancer in my 30’s, radioactive therapy, two surgeries, a weeklong NICU stay with my daughter, and as soon as I started to get healthy, a shredded labrum and brutal shoulder surgery for good measure.
Life throws curveballs at ya. That’s just how it works.
But the context matters, and that’s what I always come back to.
Because even in the middle of those hard years, I never lost sight of how lucky I am.
Just because life gets messy and crowded with stress, it doesn’t mean your starting line completely vanishes.
And that’s the heart of my own philosophy.
Here’s how I think about it:
The Lottery | The Leverage |
|---|---|
Context you inherit | Choices you make |
Random luck | Repeatable habits |
Circumstance | Character |
Leverage is the bridge between randomness and repeatability.
And for me, leverage comes down to four things:
Positive affirmation.
The voice in your head matters. The people who tell themselves they’re lucky tend to act lucky. Gratitude isn’t just perspective, it’s an alertness, too.Hard work.
No secret here. It’s the at-bats — the swings that create more chances for the ball to find your bat. Effort multiplies exposure.Resilience.
When things go to shit (and they will), staying in the game is its own kind of luck. More time in motion = more collisions with opportunity.Filtering.
Knowing what not to chase is important. Luck compounds when your energy’s pointed at the right stuff.
The Simple Math of Gratitude
When you combine lottery and leverage, you realize something simple but powerful: you don’t choose the cards, but you do choose how to play them.
Gratitude is what keeps it all in perspective.
It keeps my ego in check when things go well and reminds me how much I’ve been given when they don’t.
It’s easy to slip into extremes — to believe you’ve earned everything or to believe life’s just a game of lottery outside of your control.
The truth is always somewhere in between.
When you look at your own life, just remember:
The randomness doesn’t erase the work, and the work doesn’t cancel out the randomness.
You need both.
And gratitude, that’s what keeps you honest about which is which.
If you liked this blog post, you might enjoy this other one on why I stepped away from the role as a high-growth startup CEO.
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