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

Hacking & Painting: Big Ideas from Paul Graham (I)
Photo by Florian Olivo / Unsplash

Paul Graham is my hero when it comes to writing on the internet.

I first came across his work via Twitter a few years ago and it's been a joy going down the PG rabbit hole ever since. His writing has given me better tools to describe the world around me. It has also inspired me to publish some of my own essays. We are lucky to live in an age where people can share ideas online and even luckier to be around to enjoy Paul’s writing.


Paul is a computer scientist (or hacker, as he explains here) and entrepreneur. He co-founded Viaweb, the first web app that allowed users to build an online store through their browser back in 1996. Following this experience, Paul and his team founded Y Combinator (YC), a company that helps people start startups. YC has invested in companies like AirBnB, Stripe, Dropbox and Reddit among others. Paul is also the foremost expert on the Lisp programming language. He wrote two books on the subject, On Lisp and ANSI Common Lisp, and continues to create new dialects in the language. See his work on Bel here.

Above all, Paul writes great essays. His body of work is astounding. He has published over 200 (208 by my count as of writing this piece) essays on his website, excluding subject matter specific pieces on Lisp. The essays are diverse, covering topics as wide-ranging as the benefits of reading, the perspective that comes with having kids, why nerds don’t conform and how to build a better spam email filter. His book, the wildly popular Hackers & Painters, Big Ideas from the Computer Age (2004) includes 15 of his best essays covering startups, hacking and programming languages.

Hackers & Painters


This is part one of a series covering Paul's ideas on:

I. Work,

II. Life, and

III. Writing.

Today we dive into his thoughts on finding flow (makers and managers have different schedules), working hard (startups and corporates allow for different outcomes) and the importance of thinking for yourself (some careers demand more independent-minded thinking than others).

Part one: PG on Work

1. On Finding Flow

We’ve all been there. The work days that are filled with meetings upon meetings and meetings about meetings. The days you look back on and wonder if you actually created something of value. You know how much these days hurt because you have experienced the opposite, the days of high output and productivity, when you are in flow. On these days there are zero distractions, it’s only you and the work and amazing things can happen.

For a long time the constant distraction of meetings and the lack of control over my work hours bothered me, but I always accepted it as part of the job. Until I read Paul’s Maker’s Schedule, Manager’s Schedule. This was the first time someone so eloquently described the problem and offered a solution, which reframed how I would approach work.

The premise is simple. There are two types of schedules. The Maker’s schedule and the Manager’s schedule. Makers are the creators, the builders, the developers, the coders, the writers, the people doing the work. Managers are the bosses, the coordinators, the leaders, the people checking if the work is being done. Makers operate in units of half a day. Managers operate in units of half an hour. Makers need deep focused uninterrupted time to work on a single task to write good code or a good essay. Managers employ the traditional appointment calendar with different time slots, switching between tasks every hour.

Via: https://tylerdevries.com/maker-manager/

There are Makers and Managers in every company and there is a Maker and a Manager in everyone. Maker mode is very important for creative, deep work. Manager mode is important for making sure you reach your targets. Just as you need both Makers and Managers to manage an organisation, you need both schedules to manage yourself. The interplay between them is vital.

“To direct and capture the value that focus creates, we need coordination“, as Cam Hashemi (@camhashemi), a fellow Write of Passage cohort member, describes in his article on Focus vs. Coordination. Effective companies and employees realize the importance of both schedules and the balance that needs to be struck between focus (making) and coordination (managing). Some jobs require more focus, while others require more coordination.

It gets tricky when the two schedules clash and usually it’s the Makers that suffer. It takes time to get into flow and constant context switching is a costly distraction. Paul explains how this kills morale:

For someone on the maker's schedule, having a meeting is like throwing an exception. It doesn't merely cause you to switch from one task to another; it changes the mode in which you work [...] ambitious projects are by definition close to the limits of your capacity. A small decrease in morale is enough to kill them off.

This is why it’s important for Makers to protect their schedules. Since there is an opportunity cost to being distracted, I try to move meetings around so that I can get them all out in one chunk (in the morning if possible). This clears my afternoons for ‘actual work’ (as I see it) on new product ideas, strategy and building tools and models.

Paul reflects on how he used both schedules during his time at Viaweb:

When we were working on our own startup, back in the 90s, I evolved another trick for partitioning the day. I used to program from dinner till about 3 am every day, because at night no one could interrupt me. Then I'd sleep till about 11 am, and come in and work until dinner on what I called "business stuff." I never thought of it in these terms, but in effect I had two workdays each day, one on the manager's schedule and one on the maker's.

Paul’s case is extreme, but the principle is important. Knowing when you are in which mode can help you stay focused and switch contexts less. You can partition your day to protect your focus time, while not neglecting the necessary coordination that comes with being a team player.

2. On Working Hard

I work for a small team in a big European corporate. The mother company does well due to its large market share. Steadily turning over profits and keeping shareholders happy. Having over 10,000 employees has its challenges though. The only way to manage so many people is through rules and bureaucracy. This comes at a cost. Despite our team being small, the red tape from the top means things move slowly. I don’t have anything against corporates. Great things can be achieved at scale, but there is a case for smaller, independent teams getting more done faster.

Enter Paul Graham. He uses a simple back-of-the envelope calculation to show how you can be 36 times more productive at a startup than in a corporate job.

You could probably work twice as many hours as a corporate employee, and if you focus you can probably get three times as much done in an hour. You should get another multiple of two, at least, by eliminating the drag of the pointy-haired middle manager who would be your boss in a big company. Then there is one more multiple: how much smarter are you than your job description expects you to be? Suppose another multiple of three. Combine all these multipliers, and I'm claiming you could be 36 times more productive than you're expected to be in a random corporate job.

Witty and spot on. Obviously it won’t be exactly 36, but he reckons you could be at least 10 times and up to 100 times more productive at a startup. Startups win because there is no HR chasing you to complete the latest cyber security awareness campaign this month. There are no pointy haired middle managers holding you back. You can move fast and maximise your capabilities.

Startups also win for another reason. Since they are smaller it is easier to measure individual performance. At a corporate, you can’t go to your manager and demand a higher salary for working harder or getting more done. The “official fiction” of your job is that you are already working as hard as you can. And even if they wanted to pay you more, it would be difficult to pinpoint your value. Apart from the CEO or salespeople, it is difficult to isolate individual performance in a company. In a large group, your work is entangled with the rest of your team. Each cog depends on the other cogs in the machine. Paul compares a galley of a thousand rowers to a ten-man boat with the best rowers:

A big company is like a giant galley driven by a thousand rowers. Two things keep the speed of the galley down. One is that individual rowers don't see any result from working harder. The other is that, in a group of a thousand people, the average rower is likely to be pretty average. [...] But the real advantage of the ten-man boat shows when you take the ten best rowers out of the big galley and put them in a boat together. They will have all the extra motivation that comes from being in a small group. But more importantly, by selecting that small a group you can get the best rowers. Each one will be in the top 1%. It's a much better deal for them to average their work together with a small group of their peers than to average it with everyone.
A galley

Regardless of where you work, the principles are useful. At any company Paul’s “36x” mindset can help you stand out from the rest. You can control how many hours you put in and your output per hour. Hopefully you are also a bit smarter than your role requires you to be. In addition, if you are in the galley like me, try to surround yourself with the best rowers and remember to point out where you are adding value.

3. On Thinking for Yourself

There are some kinds of work that you can't do well without thinking differently from your peers.

Paul explains that in some roles you need to think independently. You are required to be right, while everyone else is wrong.

A successful scientist can’t publish a paper that reiterates what her peers have discovered before. She needs to publish a paper that is not only factual, but also proves something other scientists haven’t realized yet. An investor needs to correctly predict the direction a stock’s price will move, but she can't agree with the market on everything, otherwise her portfolio will be no different to an index-tracker. A startup founder can't only work on projects that other people agree are good ideas, otherwise many other companies will be working on them. She needs to have conviction over projects other people might view as bad ideas.

Roles that require you to think for yourself don't always make for smooth sailing:

“Do you want to do the kind of work where you can only win by thinking differently than everyone else?”

If you choose this type of work you need a brain that can go anywhere. Some people are naturally independent-minded, while others can work on this skill. Paul describes the two main strategies to nurture originality:

  1. Surround yourself with other independent thinkers, and
  2. Retain a degree of skepticism.

First, surround yourself with other independent-minded people, especially those who don’t share all your views. Create a peer group that challenges you.

Online creator George Mack (@george__mack) also describes this concept in his mini-essay on centralised vs. decentralised friend groups:

“If you want to follow the crowd, opt in for centralized friend groups. If you want to think for yourself, opt in for decentralized friend groups.”

Second, adopt an attitude of skepticism. Be careful of what you accept as true. If you agree with everyone on everything that should be a warning sign. We are susceptible to accepting beliefs now that will turn out to be wrong later. If you were living in Salem, Massachusetts in the late 1600s you might have imagined witches to be lurking around every corner. Treat it like a puzzle, see if you can guess which beliefs society holds now that will be proved wrong in future.

There is one caveat though. It's not enough to only resist being told what to think. Truly independent-minded people do not only believe in things that are not false, they are also careful about their degree of belief. Your degree of belief can help you to think independently and also protect you from falling for conspiracies.

By nurturing your thinking in this way, you can do novel, creative work. As Paul explains in his piece on taboos:

“To do good work you need a brain that can go anywhere. And you especially need a brain that's in the habit of going where it's not supposed to. Great work tends to grow out of ideas that others have overlooked, and no idea is so overlooked as one that's unthinkable.”

I can always do more to add new perspectives to my writing and my work, but I can count myself lucky that I'm surrounded by a large, decentralised group of friends in my life. People who challenge my views, bend the rules and question the status quo. My parents have also always encouraged me to form my own ideas and not to accept things blindly.

That's a wrap for part one. Remember PG's principles on finding flow, working hard and thinking for yourself. The next piece will delve into his views on life and finding meaning. Stay tuned.

Thanks to Jess Schanz, Nic Rosslee, Ricus Goussard, Chris Wong, Rachel Koppelman, Siobhan Bamber and Mujidat Oladeinde for reading drafts of this essay.