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Hacking & Painting: Big Ideas from Paul Graham (II)

John Nicholas
John Nicholas
11 min read
Hacking & Painting: Big Ideas from Paul Graham (II)
Photo by Djim Loic / Unsplash

Welcome to part two of the series covering Paul’s ideas on:

I. Work,

II. Life, and

III. Writing.

In this part we go through life's journey with some tools from PG. From school and being a nerd to work and chasing prestige before coming full circle with how having kids helped him realize what matters in life.

On Nerds

In high school, I always wanted to be cool. I played sports (some well, others less so), attended house parties, tried bodyboarding... the works. Despite my best efforts, I never really fit in with the cool kids. Maybe because I was trying too hard, but probably because I had other passions.

My idea of fun was attending Maths Circle. On Wednesday afternoons, a group of high school kids would get together at the University of Cape Town for two hours to train for provincial and national math olympiads. The problems we got to work on were super interesting. We had to solve things like:

Prove that from any set of 17 whole numbers it is always possible to select five whose sum is divisible by 5. (Answer in the notes at the end1.)

University of Cape Town. The Maths Department, where Maths Circle was hosted, used to be (and probably still is) in the building to the right of Jameson Hall (centre of the picture).

I also got into debating. Monday nights were debating nights, where we would take on teams from other schools and try to outwit and out-argue them. I loved it. We debated a variety of topics, from the death penalty, to doping in sports, to the nationalisation of resources et cetera.

Needless to say, I was a nerd. Instead of owning this tag, I tried to fight it off. As a kid, you just want to fit in so you make the quirky, eccentric parts of yourself smaller so you can belong to the popular group.

I remember telling my dad I wished I was as popular as him. He always bumped into friends everywhere he went. He always lit up the room. Clearly he was doing things right. He would laugh and tell me about his scraps with bullies as a kid. Things would improve he said, I just had to wait for university.

He was right. The social game clicked for me when I was a bit older. At university I started making friends for life. People with similar interests, people I could relate to. I finally felt “cool”. I was surrounded by a bunch of other nerds in my actuarial science class. And in my residence (fraternity or campus boarding house for my non-South African readers) I found other armchair philosophers and debaters.

It all happened rather seamlessly and I never gave this transition much thought until I read Paul’s essay explaining Why Nerds are Unpopular. The answer was quite obvious (as most things are in retrospect). Nerds don’t fit in, because being cool is an all-encompassing game, and nerds aren’t prepared to give up being smart in order to be cool. While I was learning about the Pigeon Hole Principle2 (tip: this helps to solve the question above) and debating China’s one child policy, the cool kids were dedicating themselves to the zero-sum game of being popular. As Paul explains:

Of course I wanted to be popular. But in fact I didn't, not enough. There was something else I wanted more: to be smart. Not simply to do well in school, though that counted for something, but to design beautiful rockets, or to write well, or to understand how to program computers. In general, to make great things.
And that, I think, is the root of the problem. Nerds serve two masters. They want to be popular, certainly, but they want even more to be smart. And popularity is not something you can do in your spare time, not in the fiercely competitive environment of an American secondary school.

After school, the popularity contests are no longer relevant. You do not have to serve two masters. You can focus on your passions without trying to be someone else.

Why does this shift happen? Firstly, the real world is large. You can find your tribe and you can choose your niche out of a much larger pool of people (the internet is making this even easier now). Secondly, and most importantly, the real world also rewards doing good work, not only playing status games. Outside the simulated reality of school, the work you do has real effects and it is important to get the right answers.

I think the important thing about the real world is not that it's populated by adults, but that it's very large, and the things you do have real effects. That's what school, prison, and ladies-who-lunch all lack. The inhabitants of all those worlds are trapped in little bubbles where nothing they do can have more than a local effect.
When the things you do have real effects, it's no longer enough just to be pleasing. It starts to be important to get the right answers, and that's where nerds show to advantage. Bill Gates will of course come to mind. Though notoriously lacking in social skills, he gets the right answers, at least as measured in revenue.

It pays to be a nerd in the long run. Unfortunately, more often than not, nerds go through a tough time during high school. Paul compares school to a type of prison. It is a good way to manage a bunch of children and keep them busy while their parents are at work. Sadly the kids aren’t told they are in prison.

It’s important for kids to know that school doesn't represent life, as my dad pointed out to me.  It’s an artificial bubble set up to control kids. In real life, unlike ladies-who-lunch, what you do has real effects so it pays to be smart.

On Prestige

After school, we don’t have to try to be cool anymore, but there is another trap to look out for, especially when it comes to making the right study and career choices. Chasing prestige is the adult version of school’s popularity contest.

Paul’s motto is to do things that aren’t prestigious. This forces you to do things for the right reasons and oftentimes allows you to do more valuable, fulfilling work. His thoughts on this subject are echoed by David Perell in Don’t Chase Prestige.

We are social creatures and we want to impress others. We are attracted to the shiny things that get us recognition, but overlook the opportunities presented by less prestigious work. From Justin Murphy (via Perell’s essay):

“You don’t really outperform your peers with quality per se, you outperform your peers by finding underpriced quality that others don’t judge to be valuable.”

Chasing prestige creates funny behaviour. It can cloud your motives. Your desire to impress people can lead you astray and you end up doing things for the wrong reasons. This is especially dangerous for young people who haven’t figured out what they like yet.

People study certain things and apply to certain jobs because it looks good. I fell for this to an extent when I chose to study actuarial science. Sure, the degree suited my skill set, but a part of me wanted to do Act Sci because it was the hardest degree to study at the time. A part of me wanted to impress people. Like many other students I became disillusioned during the degree and didn't know if it was the right fit for me. Luckily I dug deep and finished the degree and subsequently found a career I enjoy in the wider field of actuarial science. But for many of my fellow students the prestige of the degree wasn't enough to carry them through and they dropped out or switched courses.

Another example is choosing a job that is prestigious, like investment banking or management consulting, where you end up working crazy hours on projects you aren’t necessarily mad about. Young, ambitious people fall prey to doing things we think we are supposed to be good at. As Paul describes in How to Do What You Love:

Prestige is the opinion of the rest of the world. When you can ask the opinions of people whose judgement you respect, what does it add to consider the opinions of people you don’t even know? This is easy advice to give. It’s hard to follow, especially when you’re young. Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.

You can’t satisfy everyone. A more sustainable strategy (to avoid being disillusioned) is to do work that you are drawn to even if it is not steeped in renown. Like working through the night to build a pricing model. Maybe no one will understand the work that went into building it, but down the line you will have a skill and you will have proven something to yourself. Or writing online. I have 25 subscribers, which is not prestigious by any stretch of the imagination, but I am very attracted to writing because I enjoy clarifying my thinking and maybe someone out there enjoys reading what I write about.

It's not that unprestigious types of work are good per se. But when you find yourself drawn to some kind of work despite its current lack of prestige, it's a sign both that there's something real to be discovered there, and that you have the right kind of motives. Impure motives are a big danger for the ambitious.

It’s also a case of doing things in the right order. "Prestige is just fossilized inspiration". It comes after doing great work. First do the work and let the recognition take care of itself. There is no point in doing something purely for the accolades it will bring. This also helps to find value in places others have not yet looked.

Paul concludes that he had his best results not chasing prestige. Viaweb (his web store startup) and Y Combinator (the VC firm he launched) looked lame at first. Painting still life (one of his passions) has never been popular. He still gets the "glassy eye" when he explains his online writing to random people, despite his massive following. From What I Worked On:

One of the most conspicuous patterns I’ve noticed in my life is how well it has worked, for me at least, to work on things that weren’t prestigious. [...] If anything is going to lead you astray, it will be the desire to impress people. So while working on things that aren’t prestigious doesn’t guarantee you’re on the right track, it at least guarantees you’re not on the most common type of wrong one.

Always check your motives. Are you doing this to impress others? Or are you doing it because you are genuinely interested? Chasing prestige is not sustainable. In the end authenticity is key.

On Kids

I've talked about school and careers, now it’s time for family. The first two parts focused on keeping perspective and avoiding pitfalls and I'll close with focusing on what matters.

Paul loves tweeting about what he talks about with his kids. It’s a mix of life lessons and jokes. There’s some great material. He seems to be having a blast with them. As he realised: “Not only are they really interesting, they also become your best friends.”

Here are some of my favourite tweets from him on his kids (there are too many to choose from).

Fun:

History jokes:

Life lessons:

By his own admission, before having kids he saw children as an obstacle getting in the way of doing valuable work. When he was younger he would spend all of his time and effort on his startup (Viaweb) and VC firm (Y combinator). Attention is a zero-sum game and you can only focus on one thing at a time.

Having kids meant he had to adjust his life. He couldn’t do all-nighters coding or working long hours evaluating which startups to invest in. He became less ambitious and productive, but this shows his development from the grim zero-sum view to finding balance. It's wonderful to observe this change in him.

The fact is, once you have kids, you're probably going to care more about them than you do about yourself. And attention is a zero-sum game. Only one idea at a time can be the top idea in your mind. […] On the other hand, what kind of wimpy ambition do you have if it won't survive having kids? Do you have so little to spare?

In two of my favourite essays, Paul describes how having kids helped him see how short life really is and focus on what matters.

Life is short. As a child he used to wonder whether life actually is short or if people just liked to complain about its finiteness. He had no way of telling and forgot about it. Only until he had kids did he realize how finite life actually is. He uses a wonderful example to convert an abstract concept like time into something tangible, the number of times you'll have Christmas-as-magic with your kids.

Having kids showed me how to convert a continuous quantity, time, into discrete quantities. You only get 52 weekends with your 2 year old. If Christmas-as-magic lasts from say ages 3 to 10, you only get to watch your child experience it 8 times. And while it's impossible to say what is a lot or a little of a continuous quantity like time, 8 is not a lot of something.

So now that we know life is short, what is it too short for? Life is too short for bullshit, things that are expedient. Some of these things are forced on you, but most are chosen by you. Be careful what you choose. Traffic jams, useless meetings, addictive, but unrewarding pastimes, dull work, bureaucracy. It is important to prune away bullshit and focus on what matters.

Kids are good at showing you what matters. They pull your arm and say “Look at me”, which is usually more important than whatever task you are currently busy with. Kids can provide moments of magic and endless happiness. He says his moments of happiness have increased after having kids. "Now I practically have it (happiness) on tap, almost any bedtime."

Jess and I don’t have kids yet, but we have a dog. Pacco fills our days with joy and laughter. He has his own little personality and craves our attention. When I’ve been working too long he comes to my study and jumps on my lap or begs for a snack. He forces me to get up and throw the ball at him and chase him around. Because of him I rediscovered an element of play, something I’ve lost as I’ve grown older. I’m certain having kids is even more rewarding.

When you focus on what matters, you don’t take things for granted. When you know life is short, you make the most of the time you have left. Paul opens up, coming full circle on how having kids made him appreciate his parents more:

You take things for granted, and then they're gone. You think you can always write that book, or climb that mountain, or whatever, and then you realize the window has closed. The saddest windows close when other people die. Their lives are short too. After my mother died, I wished I'd spent more time with her. I lived as if she'd always be there. And in her typical quiet way she encouraged that illusion. But an illusion it was. I think a lot of people make the same mistake I did.

Thanks to Jess Schanz for reading drafts of this essay.

Notes:

1. Answer:

Think of five boxes labelled 0, 1, 2, 3 and 4. Assign the 17 numbers to these boxes according to the rule: If a number leaves a remainder of r on division by 5, assign that number to box r. Suppose that there is at least one number in each box. Then selecting five numbers, one from each box, will give a set of five numbers with remainders on division by 5 of 0, 1, 2, 3 and 4, and their sum will be divisible by 5. On the other hand, if one of the boxes is empty, then another box must contain at least five numbers. These five numbers all leave the same remainder on division by 5, and their sum will be divisible by 5.

2. The Pigeon Hole Principle via Magnus Prep on Youtube: https://www.youtube.com/watch?v=wcVB3RLncyY

Writing

John Nicholas Twitter

Actuary and creator.

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