Paul Graham, Ben Franklin And The Value of Political Incorrectness

With the  school year starting up, I got to thinking about offering some avuncular advice about how to make one’s way in the world.

Fortunately, I resisted the urge. Instead, I’ll merely advise: read Paul Graham.

For obvious reasons, I don’t offer young people much career advice. And even if I felt like it, I might not see much point in doing it myself because Graham has raised the quality bar so high over the last decade with his self-help essays.

Graham is a Silicon Valley sensei who now runs the Y Combinator boot camp for young entrepreneurs. He coined the motto: Make something people want. And he is probably the most lucid exponent of the View from Silicon Valley—at a time when the high tech business is one of the very few prospering.

This is not to say that I particularly agree with Graham’s career recommendations, which usually boil down to: You should found a high-tech startup. Well, I’ve worked for two technology start-ups, one successful and one not. And let me violate my rule against giving career advice: not everybody is cut out for the role. In fact, hardly anybody is. (I certainly wasn’t.)

Graham only cares about persuading the tiny percentage of young folks who have the intelligence and determination, the relentlessly resourceful”. He admits at one point:

“I realize (a) I have no idea what most people are like, and (b) I'm pathologically optimistic about people's ability to change.”


But the reason to read Graham’s short essays is that you get to watch a superbly reductionist mind at work. (And you get to be able to recognize the kind of person who has What It Takes. One of Graham’s themes is that you want to work with the best people in your field, not against them.)

So let me I first praise Graham for the benefit of anybody not familiar with him, before discussing his two best known political essays: What You Can’t Say and Keep Your Identity Small.

Graham is largely invulnerable to cant, but he is not an automatic contrarian. For example, he wrote What You’ll Wish You’d Known for high school students:

“And yet every May, speakers all over the country fire up the Standard Graduation Speech, the theme of which is: don't give up on your dreams. I know what they mean, but this is a bad way to put it, because it implies you're supposed to be bound by some plan you made early on. The computer world has a name for this: premature optimization. And it is synonymous with disaster. These speakers would do better to say simply, don't give up. What they really mean is, don't get demoralized.”

In writing essays offering advice for those starting out in the world, Graham is following in a characteristically American tradition. Indeed, the first American book to achieve global fame, The Autobiography of Benjamin Franklin, was widely read as a how-to-get-ahead book.

Franklin probably did more to define American culture than anybody else, This was not just because he was a marvelous writer, but he was a ridiculously successful man. Enoch Powell famously said: “All political lives, unless they are cut off in midstream at a happy juncture, end in failure, because that is the nature of politics and of human affairs”. But Franklin just went on triumphing into his eighties. (Okay, granted, for all his success as a businessman, inventor, writer, physicist, and diplomat, Franklin still couldn’t get himself a good haircut. Yet, even the long, limp hairdo was a conscious ploy to get the French to adore him as the sage of the noble savages.)

Graham, born in England and raised in Pittsburgh, isn’t Ben Franklin. (In particular, Graham isn’t anywhere nearly as funny a writer as Franklin must have seemed to his contemporaries.)

But like Franklin, Graham has been successful in several endeavors, possesses a keen understanding, an urge toward reflection unusual in the successful, and a lucid prose style.

After getting a Ph.D. from Harvard in computer science, Graham resolved to become a realist painter and went to Florence to learn from the old masters. He wasn’t great at that, but the discipline of learning an ancient art form served him well when he returned to computer programming at the beginning of the Internet bubble.

He and a partner sold their web store startup Viaweb to Yahoo in 1998 for $49 million, so he doesn’t need to write for money. He merely posts at essays of whatever length he feels useful.

A half decade ago, he founded Y Combinator, a much-admired boot camp for startups he coaches. One of his grads explained: "His brain is a giant warehouse of startup failures and successes." 

But Graham is also very good at writing about much else involved with what he calls “making”. For example, his 423-word essay Writing, Briefly begins:

“I think it's far more important to write well than most people realize. Writing doesn't just communicate ideas; it generates them. If you're bad at writing and don't like to do it, you'll miss out on most of the ideas writing would have generated. … Write a bad version 1 as fast as you can; rewrite it over and over; expect 80% of the ideas in an essay to happen after you start writing it, and 50% of those you start with to be wrong …”

And ends:

Learn to recognize the approach of an ending, and when one appears, grab it”.

I would only add a piece of advice that Charles (The Bell Curve) Murray gave me: get a second screen for your computer to display notes and web pages on while you write on your main screen. That made me much more productive. Al Gore, a member of Apple’s board of directors, uses three huge and expensive 30” Apple displays.

Less successfully, so far, Graham has created a new dialect (Arc) of the programming language Lisp, which was invented by my old friend John McCarthy in the late 1950s. Graham works in Lisp because it’s the language pitched at the highest level of abstraction. And Graham is an unapologetic elitist:

“It may be that the majority of programmers can't tell a good language from a bad one. But … Expert hackers can tell a good language when they see one, and they'll use it. Expert hackers are a tiny minority, admittedly, but that tiny minority write all the good software, and their influence is such that the rest of the programmers will tend to use whatever language they use.”

Pragmatic elitism is a recurrent thread throughout Graham’s advice. For example, if you are living in Boston and have a great idea for a software startup, move to Silicon Valley, he says. Sure, Boston has the second most venture capitalists, far more than some loserville like New York. But it’s still second rate. (You’ll recognize this is a theme of the film The Social Network: Facebook founder Mark Zuckerberg realizes that Cambridge, MA can’t compare to Palo Alto for software startups.) For sure, this kind of brutal advice is common from some venture capitalist with a $10,000 watch, but it’s rare from an intellectual like Graham.

Graham is adept at noticing the common denominators. For example, his articles and his software have fundamental similarities in approach:

“I like to find (a) simple solutions (b) to overlooked problems (c) that actually need to be solved, and (d) deliver them as informally as possible, (e) starting with a very crude version 1, then (f) iterating rapidly.”

One of Graham’s recurrent themes:

“One difference I've noticed between great hackers and smart people in general is that hackers are more politically incorrect. To the extent there is a secret handshake among good hackers, it's when they know one another well enough to express opinions that would get them stoned to death by the general public.”

His 2004 essay What You Can’t Say is an important exposition of why so much hatred is directed at cognitive dissidents:

“No one gets in trouble for saying that 2 + 2 is 5, or that people in Pittsburgh are ten feet tall. Such obviously false statements might be treated as jokes, or at worst as evidence of insanity, but they are not likely to make anyone mad. The statements that make people mad are the ones they worry might be believed. I suspect the statements that make people maddest are those they worry might be true.”

He goes on:

“When a politician says his opponent is mistaken, that's a straightforward criticism, but when he attacks a statement as ‘divisive’ or ‘racially insensitive’ instead of arguing that it's false, we should start paying attention. … Labels like that are probably the biggest external clue. If a statement is false, that's the worst thing you can say about it. You don't need to say that it's heretical.”

Why discuss “divisive” topics? Graham offers threes reasons:

  • “Curiosity”;
  • “I don’t like the idea of being mistaken”;
  • “It’s good for the brain … Great work tends to grow out of ideas that others have overlooked, and no idea is so overlooked as one that’s unthinkable …”

But Graham doesn’t want his readers to sacrifice their fabulous careers over this. So, he advises, don’t say anything in the open. But then, again:

“The trouble with keeping your thoughts secret, though, is that you lose the advantages of discussion. Talking about an idea leads to more ideas. So the optimal plan, if you can manage it, is to have a few trusted friends you can speak openly to. This is not just a way to develop ideas; it's also a good rule of thumb for choosing friends. The people you can say heretical things to without getting jumped on are also the most interesting to know.”

True. But oral discussions among a few refugees in the catacombs, while better than complete inanity, are hardly as good for the country as a whole as written discussions and public conferences.

In Graham’s influential 2009 essay Keep Your Identity Small, Graham argues:

“… people can never have a fruitful argument about something that's part of their identity. By definition they're partisan…For example, the question of the relative merits of programming languages often degenerates into a religious war, because so many programmers identify as X programmers or Y programmers.”

He concludes:

“If people can't think clearly about anything that has become part of their identity, then all other things being equal, the best plan is to let as few things into your identity as possible”.

I would have agreed with this 25 years ago. Who needs sharing any part of one’s identity with other people? In particular, who needs identity politics?

But I’ve found that identity has a way of creeping up on you.

I suspect it’s creeping up on Graham, too, despite his public best and brightestness. For example, if Graham tries to keep his identity small, does that exclude, say, “husband”?His conversation with his wife over this might be interesting.

You turn out, for instance, to be not as flexible and relentlessly resourceful as you thought you were in your 20s. Consider, for instance, arguments over programming languages and why they are so fervent. When you are 25, if a new language gets hyped so much that soon you can’t get a job if you don’t learn it, well, cool. You’ll learn it. But if you are 55, the reputation of the languages you’ve mastered is important to your livelihood. Identity politics matters, even in computer programming.

Moreover, as you go through life, you start noticing patterns in humanity. You start to realize that you aren’t quite the very special snowflake you thought you were.

Perhaps the paradox of identity is that the older you get, the less passion you feel about imposing your personality on others. Yet, the more you also realize, as the late novelist David Foster Wallace observed, “Although Of Course You End Up Becoming Yourself.”