“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.
— 5 —
the following is an abandoned draft from my archives titled ‘luckmaxxing’ from feb 2023
we’ve come too far
To give up who we are
So let’s raise the bar
And our cups to the stars
Longevity of songs
One of my favorite little things is pudding.cool’s depiction of the longevity of songs. Some songs last much longer than others in public consciousness. It’s difficult to know for sure what exactly makes a timeless song, otherwise they’d be made much more regularly. I think a lot about how Mariah Carey is arguably the only person to have successfully introduced a new Christmas song. Some of this seems to boil down to a certain timeless quality in the writing of the song itself.
An important thing to note is that we can meme things into existence. It’s not easy but if we repeat ourselves often enough and we’re dynamic enough we can make things happen. One of the ways songs- and also authors, thinkers, ideas, anything really – get a new lease of life is, they’re honored or celebrated in some other piece of media.
Will I single-handedly be able to boost the profile of the Daft Punk song just by mentioning it in a title of an essay? In the short run, unlikely.
This is a belief I have rather than something I know for sure. I know that things are possible. I don’t know that things are certain. I feel that some things are as good as certain. I’ve gotten lucky in some ways…
There’s a quote where Steve jobs is complaining about Microsoft, I have it filed in my mind as the “no taste” quote. He points out that Microsoft was aided by a Saturn 5 rocket called IBM, and they’re opportunists
I’ve had a few major lucky events in my life. The biggest one is probably imperceptible. I’m lucky to be born in 1990, in Singapore, with access to libraries and television and computers. This is access that billions of people don’t have. In retrospect if and when people write mythic narratives about me, it might be noted that it’s especially lucky that I’m Singaporean, rather than say, American or Indian (citizen). It gives me a relatively rare perspective and positioning. Singapore is small and well-positioned in the global scheme of things. For a few years now, when smart people are visiting Singapore, and they tweet “I’m in Singapore next week what should I do”, a lot of people reply with “you should meet @visakanv”. This is such a sick advantage.
L
I was lucky to have a series of unpleasant things happen to me that made me reconsider reality but not get depressed and despondent to function. My father lost a daughter to a motor accident and my mother witnessed my older brother convulse in fits from a high fever, both events I think contributing a moderate amount to my parents having a somewhat distanced relationship with me. I was raised by domestic helpers, and it took me a long time to realize that
I was lucky to get into Singapore’s Gifted Education Program, which something like 0.1% of people get into. I was luckier still to flunk out of it. My teachers said I was irresponsible and disruptive (true, I’m sorry. I was too busy being lucky to be blessed with excellent media like MTV and video games. I’d do it again. I’m sorry I made anything difficult for anybody else, but.) I remember one of of the education officers saying that me flunking was a disappointment to the local Indian community, which was an anxiety I was lucky to be anointed with.
Every bad thing that has ever happened to me made me stronger. So far. There’s always a chance that the next bad thing might kill me, but so far I’ve been pretty good at avoiding death. A lot of Singaporean guys will grumble and complain about how having to do National Service – 2 years of mandatory conscription – was a waste of time for them. A part of me relates, of course, but I also did the best I could to make the most of that experience. I got some of my best reading done during that time. And a bunch of writing too. I spent a lot of my time reflecting and meditating about life and I think I grew wiser from it. If you have the right attitude, it seems like you can grow wiser from almost any experience.
I got lucky with my bands in local music. I got kicked out of my first band, the second one fell apart, and I’m not sure if there were other attempts in between, but third time was the charm and my band Armchair Critic got to play the Esplanade Powerhouse Stage, which was a dream of mine. When I decided to start organizing gigs, I got lucky on my second gig, where we… fire fight. I got lucky on the last gig, where we lost all our money and it made me determined to never X again
The thing that wows most people is that I met my wife when we were 9 years old. We started dating when we were 14. We married at 22, and celebrated our 10th wedding anniversary last year. I’m lucky for all the ways
Address survivor bias / don’t die frustration
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tbc