Harnessing Luck is Easier Than You’d Think
How to Build Your First Serendipity Machine
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Our lives, and the sum of all of our experiences, can be boiled down to two things. The decisions we make, and luck.
Decision making is easy to understand. We sit and ruminate, make checklists, study the past, and ask for advice all in an attempt to make better decisions.
Luck however, is a wild stallion. It’s uncontrollable, fickle, and illusive. But what we often fail to realize is, our decisions can act as a saddle. A way for us get on and try riding.
Deciding to engage with luck, means that we’re welcoming the unknown, we’re making friends with chaos.
Luck is the unexpected wind that blows our ship off course. It’s the nudge we need to discover uncharted worlds. Luck takes us from the mundane, to the pyramids.
But that’s not to say it’s random. It’s something we can tame. The only question is, how?
I’ll show you a few ways I’ve been able to harness luck in my own life, and provide you with a starting point to do the same in yours.
Slide n’ DM’s
You're 17. One rainy summer evening, a few friends from school invite you to the local park for another weird idea they dreamed up. This time it’s a giant adult slip n' slide.
You load up the car, and head over. But you’re not so much interested in reliving your childhood, as you are in a girl you were told would be there.
A half hour later, you’re greeted by the pouring rain, 12 friends, and a 100 ft plastic tarp. You have a few good runs, each time laughing and sliding your way across. And each time, trying to build the confidence to talk to this girl.
But before you can, your friend calls you over to his car.
When you get there, he introduces you to someone new. A girl—but not the girl you had planned—someone you’ve never met. Shirtless, you introduce yourself. She scoffs because you look, and act, like an idiot.
You can tell she’s not interested, so you head back to the party. You never saw her again.
You've been dating ever since, and 13 years later she's editing your Substack article for typos.
Engage with Luck
Things don’t just happen to you. Luck, and life for that matter, need to be engaged with. Out of the 1,460 days I was in high school—and I mean this sincerely—only one of them mattered.
Showing up for this one weird summer night, was the single most transformative decision I have ever made. I can point back it as the reason:
I live in San Francisco
Read books (yes, I had never read a book before her)
Travelled for 3 years
Saw the pyramids
Reluctantly have a very cute cat
Taught myself to code
Have any sense of style
The list goes on.
Now, what was the actual decision that I made? I chose to go to the park, to hang out with friends, but mostly I wanted to try to impress another girl entirely.
I had plans. Luck didn’t care, and I will forever be in awe.
Luck has the power to take a single innocuous decision, and transform it into something unexpected, re-charting the course of our lives.
But this never could have never happened if I simply stayed inside.
Luck is Not Complicated
Luck is complexity in disguise. There is no magic behind luck, rather it’s the byproduct of a system far beyond anything we can perceive.
Now I didn’t say luck is complicated, but rather, it is complex. The difference holds the answer as to why luck is so illusive.
Things that are complicated, are things that have many steps, may involve higher level subject knowledge, and may build on many existing fields.
Things that are complex are because of relationships. That’s to say, complexity is the product of a system. Humans are notoriously bad at understanding how systems work, and are consistently baffled when they produce unexpected results. We call these unexpected results, luck.
Building a computer is complicated, building a human body is complex.
Luck is Not Random
Another way to visualize this difference is by examining pure and impure functions.
When a function is pure, it means that every time you put one value in you will get the same value out. Here’s an example of a pure function.
x + 2 = y
If X = 2, Y = 4. Every single time.
Now, here is an example of an impure function.
x + the current traffic speed in Brooklyn = y
If X = 2, Y = ?
It’s different every single second of the day. Every time you calculate this function, you will get a different answer.
Impure functions are a lot like luck. In some ways they are unpredictable, in others they are not. In the example above, we can say, with some certainty, that the average traffic speed in Brooklyn is not the speed of light, and it is not -5 mph.
That’s why we can call luck unpredictable, but not random.
This is a non-trivial point. Knowing that luck exists within bounds, means that we can refine our search for it, and more easily create ways to harness it in our own lives.
But how? Where do we start?
Luck Comes in Different Flavors
You can’t train a truffle hunting pig without giving him a whiff of the good stuff. That’s why the first step in harnessing luck is learning how it presents itself.
Not all luck is created equal. In fact, Dr. James H. Austin, writes in “Chase, Chance, and Creativity” that there are actually four types of luck. Each with different properties, and each giving us a unique opportunity to harness it.
Type 1 - Blind Luck
You’re headed to the store to buy some milk and in the parking lot you find a $20 bill. Boom! You’re right in the crosshairs of serendipity. All you did was leave your house, and you’re $20 richer. Congratulations!
We're not terribly interested in this type of luck because, inherent to its nature, there is not much we can do about it.
We welcome it, but it’s futile to chase.
Type 2 - Stir the Pot
This is where most of us will find luck. Its definition can be reduced to one word—movement.
Exploiting this type of luck is actually just engaging more fully with the world. It's as if you're getting handed a new lottery ticket with every party you go to, every networking event, every new job, and every encounter.
You're doing as much as you can to stir up the luck that’s around you.
Type 3 - Expert Luck
In 1938, Dr. Albert Hoffman was isolating different compounds found in a particular type of fungus. By some happy accident, he ingested a tiny bit of Lysergic Acid Diethylamide.
He then proceeded to have an absolutely face-melting LSD trip.
When he finally came down—and after years of continued research—he was able to understand and reliably isolate LSD.
You or I couldn’t just fuck up an experiment and then come to the same conclusion. We simply don’t have the necessary field understanding to know what happened.
Forty-five years later, Dr. Kary Mullis took some of this newly available LSD compound—also having a face-melting trip— which led him to the creation of PCR. Ya know, like the PCR tests you’ve been taking for COVID.
The creation of PCR not only landed him a Nobel Prize, but would change how all cancer and disease research is conducted to this day.
The reality is, there’s expert luck around us at all time. We're just not the right expert to exploit it.
Type 4 - Unique Luck
Unique luck is the least intuitive. So much so that I'll borrow Naval Ravikant’s example entirely to describe it.
Let’s say, for example, you're not just a scuba-diver but the best deep sea treasure diver on the planet. When someone finds a billion dollar treasure without the skills necessary to retrieve it, who do they call? Well, you of course.
The reason this is the most interesting type of luck is because you aren't actually lucky at all. You're harnessing other peoples’ luck, and funneling it towards you.
When someone else gets lucky, you get the call to help.
How to Harness luck
Now that we understand how luck presents itself, we can start thinking about how to harness it. Ideally, what we want is a reliable way to funnel luck towards us.
While this is not an exhaustive list, these are some of the ways that I have been able to harness luck in my own life.
I must say, they have all worked like absolute magic.
Find a Novel Mix
When I was 26, I decided to sell or donate nearly all of my belongings, and book a one way ticket to Europe.
Because I was poor, I stayed almost exclusively in hostels or cheap accommodations. An interesting thing I learned over the next seven months was that hostels are weird, and the people who stayed in them are equally so.
For example, I once met a Portuguese tech founder, a professional surfer, and three Yemenis refugees all under one roof. Where else does that happen? Where else do you get exposed to so much novelty, in such close quarters.
Remember what luck is? It’s the byproduct of complexity. It’s the interactions between people and places. A hostel therefore, is a breeding ground for luck (among other things).
Luck that manifests from unique encounters is one of its easiest forms to visualize. The more people you bring into your life—with uncommon perspectives and backgrounds—the more unexpected your outcomes will be.
Although I no longer need to stay in hostels, I almost always choose to for this very reason. You will not find novelty at resorts. Period.
Moving to Hotspots
Your friend wants to make it big in the fashion industry, where should they live? Boise, Idaho? Probably not.
Luck is a derivative of complexity, and cities are the quintessential complex system.
The reason you move to New York, San Francisco, Paris, or Los Angeles is because they are hot spots for luck. The sheer motion of the place is kicking up opportunities everywhere.
This is classic Type 2 luck—stirring the pot. But instead of working your ass off to whip up everything around you, you’re making the choice to relocate to a pot that is already being stirred.
There’s no guarantee that, if you move to a big city, positive luck will find you (hell, you could get hit by a car your first day). However, what I can guarantee is that if you stay home—in one place—you will never experience the power these hot spots have to offer.
Attract What You’re Looking For
After some time traveling, I became obsessed with the idea of remote work. I had met maybe a dozen people who were making six figures—while barefoot, sipping coconuts—and I just couldn’t shake the idea.
I resolved to learn how to do this through real people, through conversations. But cold emailing strangers has a pretty bad response rate.
So I brainstormed. Everyone likes feeling important, right? What if instead of cold emails, I made a podcast?
If I could make my guests feel special, then maybe interesting—or hard to reach—people would talk to me. I could then emulate those people, and make my dream of laptops and coconuts a reality.
It worked like a fucking charm.
As it turns out, when you reach out to a person—who is toiling in obscurity on their laptop—and make them feel like a celebrity, they’ll gladly talk to you.
The podcast, became a machine that could harness luck.
Some of my guest—that I can count as friends today—include:
Founder of a global hostel chain
A Career Coach
A Digital Marketer and Business Owner
A Virtual Concierge
A Footwear Entrepreneur and Guru
A Remote Dietician
Founder of a worldwide overnight shipping company
Each one of these people in-turn introduced me to another, and another. They knew my mission was to understand remote work and entrepreneurship—so when something or someone useful came to mind—they sent it my way.
This created a powerful feedback loop. I made my goal known, and employed the help of other people, to help me achieve it.
Luck was finding me.
Host the Party
This is the most powerful way I know of to harness luck. My first crack at it was at 17 years old.
I decided to start my first business. It would be an event business of sorts. Okay, it was a beer-pong tournament—but I was thinking big.
Over 60 teams showed up at my house to play. Dozens of tables were running simultaneously. After three hours, the bracketing system I created had whittled the tournament down to just two teams.
But before the final game—as if by divine intervention—a siren whizzed right outside my house. The jig was up, and the party was over.
The next morning, while counting the first real fortune I had ever made, there were two important reflections I had. By hosting the party I:
Became interesting for no particular reason.
Got to personally meet everyone.
Hosting the party can seem daunting, but it doesn’t have to be.
I have repeated this method several times in my life, most recently by building a crypto community of 1,200+ people in San Francisco. When I created this community, I was not an expert in cryptography, nor did I work in the field. By any reasonable measure, I am the least interesting person at any of my events.
But the host of the party is always imbued with an unjustifiable level of intrigue. You brought everyone together, that alone gets your foot in the door with people you may have never met otherwise.
Anytime you bring 200 people together in a room, and thoughtfully engage with them, you are in the crosshairs of serendipity. If you can create a reliable way to do this, week after week, you’ve made a luck machine.
This is once again an example of bringing luck to you.
Luck is tricky because most of us are afraid to admit the outsized impact it has in our lives. We want there to be a clear correlation between how hard we work and how much we achieve, but this simply isn’t the case.
The single greatest decision I’ve made up until this point has been showing up to a park. How hard did I work for that one?
I encourage you to reflect on the truly defining moments of your life: your greatest friendships, meeting your partner, the first real job that changed everything for you.
Were you in control of these? Could they have gone another way?
By accepting the beauty and richness that luck ushers into our lives, we can begin to work with it, instead of fighting against it.
In order to do so, we must first recognize that luck is not random, it is born from interactions. These interactions are the basis of all the incredible moments that punctate our—let’s be honest—mundane routines. By creating, and then capturing, these little moments we start using luck to shape our lives rather than being at its mercy.
You made it to the end!
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