“Luck is what happens when preparation meets opportunity.”
– apocryphal quote typically attributed to Seneca
I’ve been thinking long and hard about luck for many years. I’ve done lots of experiments, big and small. I think I’m pretty decent at getting lucky.
Some examples of me getting lucky:
- Girlfriend. I wanted a girlfriend when I was a teenager, so I literally (yes, I know it’s cringey, I was 14) slid into multiple DMs of girls who would tolerate me enough to talk with me on MSN regularly. The girl who said yes? We’ve been married 7 years now. (Yes, she knows the backstory and teases me about it from time to time.)
- Business. Around 2011 I posted t-shirt ideas on Facebook, which led to me selling t-shirts online. This went on to become a moderately successful side-business locally, which has led to some interesting opportunities for me.
- PM Lee. In 2012, I posted about wanting to interview my Prime Minister. A few months later I was invited (along with other bloggers) to talk with him.
- Dream job. The blogpost that I wrote about the above encounter went viral, which led to me meeting the man who would hire me to do marketing for his software company. I worked there for 5.5 happy years, making good money and learning a tremendous amount about all sorts of things.
- Viral essay. In 2014 I wrote an essay about the movie Mean Girls on Medium that went moderately viral and got me a bunch of attention from interesting and cool people, some of whom are now my friends.
- Invited to travel. I did a Twitter thread about books and nerds that led to me being invited to hang out with other Twitter friends halfway across the planet in San Francisco. I met some really cool people as a result.
- I did a Twitter thread about David Deutsch’s book The Beginning of Infinity. Turns out that we have a mutual friend, and she set up a call between the two of us – so I got to interview him on camera!
I’m sure I’m missing out lots of other little examples, because at this point I’m so used to “getting lucky” that I almost take it for granted. It would also be tacky to get a little too specific about some of the details.
The Four Kinds Of Luck
In 2007, Marc Andreessen wrote a blogpost titled Luck and the Entrepreneur. It’s worth reading in its entirety, but to summarize the key bits here, he quotes James Austin, a neurologist and researcher who’s written extensively about luck.
Here’s my interpretation of Andreessen’s interpretation of Austin’s 4 kinds of luck:
- Blind luck – this is when something literally falls out of the sky into your lap, like finding a $100 bill stuck to your shoe. You didn’t do anything to deserve it, and anybody else could’ve taken advantage of that luck. Being born wealthy and privileged is a matter of blind luck. (If you buy a lottery ticket and win, you got lucky, but you did have to buy a ticket. Blind luck is if the winning lottery ticket just appears in your life out of the blue.)
- “Persistent tinkering” luck – Austin says that “a certain level of action “stirs up the pot”, brings in random ideas that will collide and stick together in fresh combinations, lets chance operate”. This is the luck you get from doing things. If you write lots of tweets, eventually some of them will do better than others. Maybe you accidentally said something insightful-sounding.
People who don’t tinker persistently may not appreciate just how the process of tinkering itself fundamentally introduces variability. Someone with “B” level ability on average will occasionally produce A+ work by sheer chance. If you’re lucky, it will be recognized and you will be rewarded accordingly. (Notice the passive voice here – it’s significant, because…) - “Prepared mind” luck – This is when you introduce discernment into the equation. Austin’s words: “Chance III special receptivity, discernment, and intuitive grasp of significance unique to one particular recipient“. Louis Pasteur characterized it for all time when he said “Chance favors the prepared mind”.
The classic example is Alexander Fleming discovering penicillin from a “spoiled” experiment that most other people would probably have dismissed as some sort of error or fluke. There’s an interestingly similar story about how stainless steel was discovered by accident. Brearley was trying to make better gun barrels for WW1, shiny steel technically had no direct application to what he was doing. But he had the tinkerer’s insight to realize that he had stumbled upon something useful.
The difference between random Chance II and Chance III is discernment. You recognize when you’ve stumbled onto something great, when nobody else might have yet. - “Perfect storm” luck – “Chance IV comes to you, unsought, because of who you are and how you behave. […] By the time Chance IV finally occurs, the easy, more accessible problems will already have been solved earlier by conventional actions, conventional logics, or by the operations of the other forms of chance. What remains is a tough core of complex, resistant problems. Such problems yield to none but an unusual approach […] Whereas the lucky connections in Chance II might come to anyone with disposable energy as the happy by-product of any aimless, circular stirring of the pot, the links of Chance IV can be drawn together and fused only by one quixotic rider cantering in on his own homemade hobby horse to intercept the problem at an odd angle.”
Basically, for Chance IV to work its magic, you have to be a high-functioning weirdo. You have to be famous enough for people to know to come to you, and also weirdo-tolerant enough for people to come to you with weird observations, thoughts and ideas. And also productive enough to do something interesting with all of that, when it comes to you.
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Past threads I’ve written:
— 1 —
2020-April-19: You can design your life to take advantage of rare outcomes, this is non-obvious to a lot of people who have simplistic notions of luck. For eg, suppose you’re a musician. It’s rare and unlikely that you’re going to randomly bump into a gig promoter or record label person or whatever. But it can and will happen eventually if you meet lots of people. And you can prepare for this opportunity in advance.
I recently had a freak opportunity to talk with a famous author of a book. Luck!
I also happened to already have a YouTube channel, a microphone, and comfort/experience talking with people. Not luck.
Any one of my tweets going viral: luck!
Me having literally hundreds of threads I could follow up with: not luck.
while follower count is not a great measure, it suffices as a proxy to make this point:
If you look at the average # of tweets that the average account with 20,000 followers have, I would actually say that I’m less lucky (ie have a lower batting average) than the others.
— 2 —
2020-Jan-29 Sometimes I sit back and think about the vast amount of work I’ve put into the public domain, and how little of it is recognized, and how much more work still I have to put in to get it recognized, and how, when that’s done, and it blows up, people will say I got lucky.
Such is the nature of the game, and you have to have a sense of humor about it if you’re going to stay lively and good-natured rather than wither into some decrepit, bitter uncle.
Luck is of course always a variable, but you also have to show up every day for years and years to get lucky. You can’t win the lottery if you don’t buy a ticket. You have to build a web to catch luck, you have to go on long, meandering walks to stumble onto luck. It takes work.
I’m not entitled to get lucky. I think I’m being honest when I say that I’m psychologically ready to spend 80 years writing publicly for no reward. In some ways I’ve already been rewarded much more than I dared to dream even a few years ago.
If I’m being honest this is really about my frustration with constantly being mischaracterized my whole life. People aren’t used to dealing with someone like me. I get it. I navigate by mischief, warmth & delight and this is so utterly alien to some people that they think I’m bad.
I’m not even sad for me, I’m in a great place personally. I’m sad for the world, because this is a world where a person trying to do good things is automatically viewed as more suspicious than a person who doesn’t try.
I know, I know – base rates, statistics, lemon laws…
— 3 —
2019-Nov-21 I think luck is a lot more complex and nuanced than people tend to make it out to be. There are layers of luck. Some things, like being born in the developed world, having access to books & internet, etc are foundational. Past a certain point though you can build “luck catchers”.
Lots of people vaguely fantasize about getting a lucky break. The trick is to be precisely specific about it. What exactly does the lucky break look like? How prepared are you to capitalise on it if it actually hits? Doing the prep makes it dramatically likelier that it’ll happen.
Y’know how “Batman has a plan for taking down everybody”? I have a version of that: Visa has a plan for making friends with every person he’d like to be friends with. People much busier than me make time for me because they can see from my proof-of-work that I won’t waste their time.
Am I lucky? Yeah. Am I constantly being blessed with blind/random luck? Eh. I prepare for luck, and I move fast when I see a window of opportunity.
I think everybody underestimates how much luck they are bombarded with every day bc they don’t do the prep + they move slow.
I also think that most people are too fixated on whatever it is that they have in front of them in order to even recognise when they have a lucky window. You can’t be too hyper-focused, you have to be relaxed, flexible, playful, open, curious. Allow life to surprise you.
— 4 —
The big lesson of survivor bias is that you should optimize for being a survivor.
This sounds like a smartass tweet but I’m totally serious. You can’t win if you lose, so learn to not lose.
Most major failure conditions are avoidable with a little bit of foresight, planning, study, etc etc. just analyze failures and don’t do/be that. Most businesses fail because most (more than half of) businesses are started by people who don’t do any due diligence, ie using your life savings to start a restaurant without ever having worked in one, or even read about the specifics of the struggles involved.