#46: Luck Emerges in Positions of Uncertainty 🍀

making your own luck by seeking it out and letting it find you

I recently changed my mind on luck after experiencing enough positive unexpected moments that I knew it couldn’t be due to pure chance. I savored a private 9-course tasting menu at one of NYC’s finest Italian restaurants, free of charge. Partners at venture capital firms reached out to chat. I had breakfast with Fred Again’s uncle.

Some things are outside of our control. We don’t get to decide what country we’re born in or who our parents are, but that’s just one type of luck. The luck that I’ll be referring to from here on is the kind that’s malleable and entirely within our control. Just because it’s in our control doesn’t mean we can just think, wish, or pray and it’ll happen. We must seek out this type of luck. The other way is letting it find us.

What does it mean if you describe someone as “lucky”? How does it feel to experience a lucky event? It’s actually quite simple. What we perceive as good luck is just the experience of good things that we didn’t expect. When you spot a $20 bill on the sidewalk, you feel lucky because you just got some unpredictable money. On the other hand, if you tripped and injured yourself, you’d call that bad luck because it was unfortunate and out of nowhere.

Luck emerges in uncertain environments. Uncertainty is not inherently good or bad, it’s simply the presence of unknownness. If you knew your fate, you wouldn’t feel lucky whenever anything great happened because it would always be expected. If you got promoted after grinding for two years at a job, would you call yourself lucky or was that inevitable? The opposite of good luck isn’t bad luck - it’s regiment. If you lived in the same place, ate the same food, and talked to the same people everyday for the rest of your life, where would be the openness in your mind and your schedule for serendipity, spontaneity, and synchronicities to come alive? Just like plants require sunlight to grow, luck needs uncertainty to emerge.

Wading in uncertainty is uncomfortable though. It’s human nature to want things to go as planned. Unfortunately, luck suffocates in a vacuum of pure plans. Our human brains aren’t wired to thrive in uncertain environments because worrying about the future was a pretty useful skill back in the caveman era. Stressing about food and shelter made a lot of sense back when agriculture and buildings didn’t exist. Too bad our brains haven’t changed since.

Simply being in a position of uncertainty is not enough to be lucky. You have to be able to spot it. Luck is often disguised as a potential opportunity you have to act on. It’s like someone extending their hand out or leaving the door open for you. You still have to reach for the handshake or turn the doorknob.

Finding Luck

I think the four steps to “finding luck” are 1) Slack, 2) Awareness, 3) Taste, 4) Acting on it.

Slack in the system is the foundation or, in chemistry terms, the substrate for luck to emerge. Having an open mind and an open schedule allows for self-direct boundless curiosity. It’s hard to go down on any rabbit-hole if you already feel like you know it all or have your days filled with back-to-back Zoom calls. Sometimes people confuse slack for freedom, but they’re not the same thing. I could be completely free, but also be so busy that I don’t have any time for anything else. Having slack certainly requires a degree of freedom, but it comes with an intentional carving of time with an unassigned purpose or output required. What might at first feel unproductive or even boring is actually where all deviation, adaptation, and evolution is conceived.

If slack is having the ability to meander freely, then awareness is how you decide where to look. The fall leaves are at their peak in NYC, but if you were constantly looking down at your phone, then you wouldn’t see any even if you were in the middle of Prospect Park. Awareness isn’t just about the physical world. Many of us spend a majority of our waking hours online and are under a constant barrage of transient information. The people, communities, and platforms that we interact with directly influence what we’re aware of. This is why I subscribe to (probably too) many newsletters, but also muted half of the people I follow on Instagram.

Having the slack to explore and then the awareness to notice is just the start. Nowadays, we’re connected to so many people, places, and ideas that it can be hard to discern what’s right for us. Who should I hang out with? Should I live here or move somewhere else? What do I believe in? Cultivating a sense of taste is how we can sift through some of these questions and avoid getting swallowed by the masses. Knowing what brings us joy and peaks our curiosity is how we can spot potential luck which often starts out disguised as an extended arm, invitation, or open door.

The final step to finding luck is to actually take action. At this point, you have the openness, awareness, and taste to spot the opportunity. You just have to reach out and grab it. This is the simplest, yet hardest part. Hesitation comes from fear of rejection or lack of self-confidence. If you knew with certainty that your cold email for a phone call would be worth it for both parties, then you’d have no trouble sending that message. I didn’t learn this lesson until recently. For the first four months of my sabbatical, I didn’t reach out to anyone. It wasn’t until talking to several people who reached out to me that I realized I was missing out by being too passive. Sometimes the person asking to chat was someone that I actually looked up to and was too scared to reach out to. Since then, I’ve started taking more initiative and rarely doubt myself because I know it’ll be worth both of our time.

Being in Position for Luck to Find You

In surfing, the most important factor that determines whether you catch the wave or not is your positioning. It’s less about your board, paddle strength, or pop-up technique than where you are in relation to the wave. I’ve been in lineups where I paddle super hard for a wave and completely miss it while a small girl paddles once on each side and effortlessly pops up. To catch the wave, you have to be “in” enough that the wave doesn’t just roll over you, but also not so far in that it’s already breaking by the time it gets to you. In some sense, since you’re there first, the wave comes to you and you just have to be in the right spot to catch it.

This is relevant for how to be lucky because luck is just being at the right place at the right time. I’m trying to be in position for luck to find me just as much as I want to find it. I’m physically located in NYC because it’s the city that’s most conducive for serendipity. The combination of high population density and public transit makes it easy to get around, but also to fit more activities in one day than in any other city. One night out in NYC could easily take three weekends in SF to experience. It helps that many of my existing friends live here. But also, the kind of people I want to be friends with also live in NYC. That’s not to say I won’t be friends with you if you don’t live in NYC, but there is something about choosing to live in a loud, expensive, dirty city that self-selects. In fact, I spent three hours today having brunch at my new friend’s apartment near Prospect Park. Before today, we had only exchanged a few DMs on Twitter and had never even talked before. I’m sure there are other great places to live, but NYC is where I feel opportunities flow most abundantly.

In the physical world, the luck you can experience is constrained by how many people can fit in the room. In the digital world, it’s unlimited. The problem is that most people only consume and mistake sharing ideas online with pursuing the influencer path. At first, I also thought it was cringe to write about my life and narcissistic to think people would actually care, but now I realize the internet is just one giant matchmaking engine. In a special context and with predominantly pictures, it matches people into romantic relationships. With essays, blogs, and podcasts, it matches based on mutual interest in ideas.

Writing about who you are and what you’re interested in is just a bat signal for finding your people. It allows you to become familiar with someone before you ever meet them. I would go as far to say that some of you may understand me better than a friend who I hang out with, but doesn’t read these blogs.

Being in position by having an online presence is also relevant for work. The typical way to find work is to apply for jobs one-at-a-time via resumé. I’ve started to wonder why rely on a PDF that lists my achievements when I can just point people to the actual work that’s online? Rather than seek work, I can welcome it. Although I have yet to start any paid work (which I’ll aim for early next year) my positioning in the digital world has already led to podcast appearances, speaking opportunities, and plenty of 1:1 calls with interesting people.

Going Forward

Like I said at the start, I’ve been feeling lucky lately. By keeping an open mind and my days relatively unplanned and being aware of what I’m curious about, I’ve created the conditions for opportunities to arise. Hopefully I’ll leap on the right ones. In choosing to be based in NYC, I’m in position for anything this city has to offer (and also to offer to the city). By sharing online, I’m putting tiny little bat signals for people that I vibe with to come and find me. It seems like it’s starting to work. It’s also much easier than finding a four-leaf clover.