Writer Spotlight: Paul Graham

Meet inside The Shops at Waterloo Town Square—we will congregate in the indoor seating area next to the Your Independent Grocer with the trees sticking out in the middle of the benches (pic) at 7:00 pm for 15 minutes, and then head over to my nearby apartment’s amenity room. If you’ve been around a few times, feel free to meet up at the front door of the apartment at 7:30 instead.

Paul Graham—A Brief Biography

While the rationalist community has some very obvious central figures, there’s also this whole constellation of really interesting writers who’ve shaped rationalist thinking over the years. This week, we’ll be doing a deep-dive into one of these other voices—not just to understand their specific ideas, but to see how different writers approach rationality and reason from different angles. And trying to hammer out a consistent format for these that we can use going forwards, because there are so many good writers I want to highlight.

First up is Paul Graham, who’s kind of rationalist-adjacent without being explicitly part of the movement. He’s got this pretty big back catalog of really good essays that many of people have stumbled across at various point, and his essays tend to be short and sweet.

(He also, you know, cofounded Y Combinator (YC), which invented the modern startup accelerator model and helped launch companies like Airbnb, Dropbox, and Reddit. But let’s focus on what’s really important—his Good Poasts.)

Many of his essays touch on themes that would later become important to rationalist thinking—the importance of noticing confusion, challenging conventional wisdom, seeing both baseline reality and social reality clearly without mistaking one for the other, and writing. He also noodles a lot about the nature of work.

He’s still pretty active, writing a few posts a year, and his recent blog posts are still quite good.

Format/​Prep

Everyone read:

  • Graham’s latest essay, Writes and Write Nots, from October this year. I think it’s a pretty standard PG piece.

  • What You Can’t Say, one of his fun spicy pieces.

  • Then head to https://​​hn.lindylearn.io/​​from?site=paulgraham.com , and read just like, two or three essays from the first page with interesting titles that grab you. (The URL directs you to a list of PG essays sorted by net Hacker News karma across all submissions. For bonus points can someone email the lindylearn guy and tell them that lindy hn has been broken for over a year now and I am sad about it.)

I’m interested in seeing what themes emerge when we look at his work as a whole, and how his ideas connect to or contrast with other rationalist thinking.

At the meetup, we’ll discuss things related to his Big Themes, like:

  • What do you think are the moral fashions of our current intellectual communities?

  • What’s a commonly accepted idea in your field that you suspect might be wrong, but that would be socially awkward to question openly?

  • What’s something you understand much better through direct experience than you did through reading about it? What was different about the direct experience?

And then like, going up a meta level:

  • What are some surprising or counter-intuitive claims that you came across?

  • Did you come across any claims that you strongly disagree with?

  • How does his perspective differ from other rationalist writers?

  • What appears to be his biggest blindspots or biases?

And anything else that seems interesting to discuss from his work.

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