Be Lucky

A few thoughts

I’ve always viewed luck at a macro life scale: born healthy, born in a safe part of the world with food & water, born into a family that deeply cares about me…the list goes on. These are all things beyond my control. If you get rid of any one of these my life would look very different. I was simply lucky enough to be dealt these cards.

After listening to an interview with Bo Burnham and Conan O’Brien, I started thinking about luck at a more micro scale. Conan asks Bo if he has any advice for people trying to succeed in the entertainment world. Bo says,

You’ve got to take a deep breath and give up. The system is rigged against you. Your hard work and talent will not pay off…I would say don’t take advice from people like me who’ve gotten very lucky. You know, we’re very biased. Taylor Swift telling you to follow your dreams is like a lottery winner saying “liquidize your assets, buy Powerball tickets, it works.”

Conan responds,

What I do agree with is that I give up a lot to luck. I say I work really hard. I have some ability, but I also got really lucky and when some people act like that’s not part of it it makes me a little crazy.

I was surprised by Bo’s candor. You don’t usually hear people acknowledging the luck they’ve had. Success gets chalked up to working really hard and execution. Achieve success and your path there gets airbrushed. Every decision and setback was guiding you to better waters. You were a visionary. You knew what to do and when to do it. Your rare clarity of vision carried you. In reality, a million external factors all had to fall into place too. I’m not saying people with wild success didn’t work for it. No author writes a best-selling book without spending countless hours crafting the story. No entrepreneur starts a flourishing company working a single hour a day.

Assuming baseline competence, I think luck is the most influential factor in someone’s life. For every Bo and Conan, how many people just as talented as them didn’t make it?¹ Tens? Hundreds? Thousands?

It’s a hard question to answer and there’s nuance. Even if there are thousands of people just as talented as them, did they work as hard as Bo and Conan? Were they resourceful? Did they capitalize opportunities? Did they have charisma? I wish there was data we could use to find a concrete answer but there isn’t. If Conan, Bo, [insert whoever’s name] are the objective best people in their fields then this whole discussion is a moot point: the best person won the whole pie—meritocracy works! The same applies to anyone else we know. Why Stephen King and not another author? Why Jeff Bezos and not another entrepreneur?

We can look at some examples to contextualize this:

• Tom Brady (NFL player). He got his chance to shine because the #1 QB for the Patriots, Drew Bledsoe, got badly injured. If that didn’t happen would Tom be who he is today? What if he stayed a backup for a few more years and never got signed with another team and got booted from the league? Tom Brady is, in my opinion, a psychotic obsessive about football. He got one real opportunity to shine and he took it. He capitalized and never looked back. It is the stuff of legends. Still, he needed the opportunity to shine. No matter how hard Tom worked, nothing he would’ve done would have gotten him the opportunity to showcase his talents at that stage of his career if his teammate didn’t get hurt. It’s a morbid kind of luck, but it gave him the chance to shine.

• John Krasinski (actor). He was waiting tables for years in New York trying to get a break. He told his mom he was going to leave New York and come back home after feeling he’d failed. His mom told him to stick it out for a few more months because she had a good feeling. He stuck it out and then landed an audition and the subsequent role of Jim Halpert in The Office. What if he had quit when he wanted to? How many people will give up on their dream today when next week could’ve been their audition for their big break?

• Van Gogh. He died a failed artist. The only reason his work wasn’t destroyed and forgotten is because his sister-in-law, Johanna, dedicated her life to sharing Vincent’s work after his death. How many artists didn’t, and won’t, have a Johanna in their life?

Timing and family are important factors in these examples. You can’t control your family and timing is a finicky beast. Again, luck doesn’t downplay someone’s hard work. You need competence in your craft.

Cate Hall wrote an article How to be More Agentic. It’s a great read on its own, but there’s one particular passage that captures how I think most people view the marriage of hard work and luck.

Increase your surface area for luck

The last couple times I was looking for a project, I made a point of meeting as many people doing related work as I could, even if there was no obvious benefit to doing so. At first, I did this just to advertise my existence to people as I entered a new field, because someone is always hiring or looking for a cofounder.

What I discovered by casting a wide net was that I have very little ability to predict how useful a call will be in advance. Relevance is easier to predict, but it’s not a very good proxy for usefulness, which is a product of lots of other things including the other person’s enthusiasm and the breadth of their interests. To some extent, the more confident I am that a conversation is relevant, the less likely I am to discover something exciting during it. Nearly all of my most fruitful collaborations over the last 3 years have come out of meetings I booked almost at random. My best conversation last week was with someone where the introducer told me “this person asked for an introduction but I’m not sure it’s a good use of your time.”

I’ve personally been told by a business executive that success is working hard and then letting luck happen.

It’s a phenomenal t-shirt slogan. It’s a great way to get employees to work hard; after all, if they don’t work hard they have no shot at the boss’s job. But what about the once-in-a-generation authors that won’t get published: their manuscripts in the inboxes of publishers who don’t appreciate the work for what it is. What about the gifted singers posting on YouTube who will never get picked up by the mystical algorithm. What about the brilliant students who won’t get the break for their dream job because they didn’t know the right people.

When I was younger I bought into the work-hard-for-luck-to-occur mindset, but the older I get the more worried I become. What if luck doesn’t happen? How many people worked their asses off and failed miserably? Not because they didn’t network. Not because they didn’t have social skills. Not because they weren’t competent. Just because they never got the right break. We don’t think about these people. I’ve thought “obviously that could never happen to me” and I’m sure those people thought the same thing. There’s survivorship bias.

You can increase the surface area for luck all day long, but luck still has to happen. Serendipity and good fortune has to strike.

Maybe there’s some natural relationship between hard work and luck. If you put enough work into the luck engine you might get favorable results? I can buy that. It seems logical that sitting on your butt at home all day playing video games isn’t helping you become an Olympic runner. If you want to be a high-level athlete you probably need to practice. That seems sensible. It still doesn’t answer whether luck will occur though. That’s still a sore spot for me.

Maybe we’re trying to answer the wrong question? Instead of asking if luck will occur if we work hard, the better framing is whether there’s another viable alternative we can live with. If your passion is to become a world class chemist, can you realistically accomplish that by watching TV (not Breaking Bad) all day? Probably not unless you’re a genius. You should be studying hard, spending time in labs, and doing chemist things. Sure, it’s possible that one day you’ll jump into a pool and hit your head on the bottom in a non-fatal way and wake up three minutes later with savant-level chemistry chops. Yeah, it’s technically possible but for pragmatic reasons it’s utterly impossible. Chancing your chemist dream on becoming a savant is moronic. Most people would feel uncomfortable sitting around waiting for their dream to fall into their lap.

The hard-work-to-luck pipeline feels the most palatable. Yes, there are people who’ve made millions because of stupid Tik Toks, but that isn’t the standard you can count on for yourself. You’ll have to work hard to succeed in whatever area you care about. So maybe taking that as baseline reality is best.

Luck is like death, it’s an amorphous concept we can see but don’t genuinely understand that deeply. If you just work hard and do the “right” things you’re putting your name into the hat of good fortune and that’s all you can realistically do.

I am in the work-hard-for-luck-to-occur camp not by choice but necessity.

1. Maybe people who’ve done great things are different. That’s possible and I’m somewhat open to that. How many times did successful authors trudge through the never-ending valley of publisher rejection? How many years did the Olympic athlete train before winning gold? It’s a grind fest I imagine few can tolerate. So maybe people who do well are literally better. I’ve gathered from people who I would consider to be very successful that there’s a whiff of a superiority complex; successful people aren’t lucky, they’re more talented & skilled. In a vacuum I could see that happening. The reason I don’t take this position is because I believe there are large numbers of exceptionally talented people and there’s a factor outside of raw skill that sorts success.