1. Don’t strive for originality; don’t fret over what’s fashionable.
2. Envy will be your most lasting, most reliable, and most fulfilling relationship.
2b. It helps to know the difference between envy (coveting something you lack) and jealousy (clinging to something you possess).
3. No intellectual is happy. I would go so far as to advocate against ever being so. But an intellectual will be less prone to misery if they know their convictions and take them seriously.
4. Convictions are discovered in two ways. (1) Writing an issue, a policy, or a creed down on a piece of paper and debating its merits before a mirror. (2) How you feel about a person expressing their own convictions more clearly.
5. You lose when contrarianism goes from useful tool to guiding ethic.
6. To forge a career, your first audience is the old. To forge lasting influence, your first audience is the young. To guarantee failure, your first audience is your parents, or your crush.
7. Two types of philistines: one who browbeats you for your refinement, another who shames you for your vulgarity. Abide them in dignified silence, pray for their quiet deaths.
8. Intellectuals advocate for intelligence but cannot fight stupidity. Stupidity is too clever. It takes many forms, appears in the last place you’d expect it, and leaves you demoralized at how far it spreads.
9. Editors, peers, and mentors take stock of your vibes and use what they need. What vibes they leave behind are not useless or bad; build a well-concealed side-door through which they can be free.
10. It’s not enough to read people with whom you disagree in theory. Embrace also those you hate on paper: the pompous dialectician, the shrill pundit, the revolutionary grifter, the plain atrocious stylist. Educate yourself on their wickedness.
11. Aloofness is a best practice, even — perhaps especially — among those with whom you are on friendly terms so far as you know. It is unclear to me why this is so.
12. Your medium and your temperament are yours alone to cultivate. If essays fail you, try memes. If podcasting is too involved, try Substack. If being a gadfly is too exhausting, try sagacity. Anyone who claims their way is the true way is either pulling a scam, clinging to a job, or racked with self-loathing.
12b. That said, adventurism and playfulness are not to be discouraged. Commodification engenders inertia and living death, unless living death is something you’re into.
13. No one resigns; they pivot.
14. Having a sense of humor is a more valuable asset to survival and long-term contentedness than being funny, or being cool.
15. Most intellectuals go their whole working lives without a direct impact on external events. When they do it is at a time they do not expect, brought about by people they do not trust, for causes that sicken them.
16. Befriending those with whom you violently disagree is a sign of security — mostly of the material kind.
16b. Moreover, the severity of the disagreement is not as stark in reality as it is in your fantasy.
17. Placing a premium on rational discourse or intuitional polemic is a matter of personal taste. The preference of either in the wider culture is a matter of fortune that you must roll with.
18. Hatchet jobs are formulaic in style and pyrrhic in substance.
18b. So, for that matter, are confessional essays.
18c. Never confuse confessional essays with personal essays. “Personal essay” is a redundancy.
19. Subtweeting is fine. Screen-capping or quote-tweeting is a judgment call.
20. You do drugs because you have a problem, not because they “clarify” your thoughts or “enhance” your charisma. Simple as.
21. Anyone who uses words like “dilettante” or “genius” almost certainly misuses them.
22. Unless the time is 1931 and the place is Madrid, your opinions against religion are neither interesting nor useful.
23. Accustom yourself to an understanding of power as an intangible concept of which you accuse others of having too much.
24. Where you went to college doesn’t matter because intellectuals are perpetually in high school.
25. Two realities of starting a magazine: (1) your first issue is more about the gesture than the content, overflowing as it is with over-leveraged ambitions and possible typos. (2) It will consume your waking — and sleeping — life for as long as it exists.
25b. (2.5) The saving grace is that it might not last for very long.
26. You have the pick of no more than the following: your battles, your poisons, very occasionally the style of your byline.
27. Whether because parties are so rare or so abundant, they always feel like dreams.
28. Heroics is a hobby; deference is a craft. Victory in an intellectual dispute may not depend on you, you may even put that victory at risk. Sometimes your role is one of support in the ascendency of someone else.
29. Taste is relative and largely for display. You put a friend group at ease by, at the very least, not questioning the agreed-upon books or TV shows. The material you cultivate privately forms your character, and should never be revealed to others unless causing anxiety was your goal all along.
30. Pessimists can be impressive survivors or deluded posers. This, again, is a judgment call.
31. Hatred is optimized courage; enthusiasm is eloquent honesty.
32. I have nothing to say about irony, just as no one has anything ironic to say.
33. You can affect the airs of an intellectual all you want, but the role of intellectual is dictated from without, often from above. This is clarified when the right to be an intellectual is rescinded.
33b. Rescinding the right, however, does not rescind the role. If anything, the role becomes more visible.
33c. Discovering and defining a crisis clutters the headspace needed for the mental doomsday prepping for when a real crisis arrives.
33d. If panic is your temperament and alarmism is your tone, a prose style of elegance and reasonableness strikes a good balance. No one will heed your warnings either way.
34. Know the difference between culture war and cultural obliteration. The former has no end; the latter has no middle.
35. Know the difference also between a striver and an achiever. A striver is an embittered achiever; an achiever is an oblivious striver. Yet both are entitled, venomously clever, never to be emulated, and to be avoided when you can afford it.
36. The pedant is an insatiable predator. If you leave the door open even just a little, they will blow it off its hinges. If the door is closed and locked, they will break through it with an ax. Once you have been sufficiently corrected, they will move to the next door. And the next and the next, etc.
36b. But everyone has their grammatical breaking point. Do your best not to bring about an embolism in someone by writing “nevermind.”
37. As a reader, demand respect from your author. As an author, demand intelligence from your reader. A reader who seeks validation is not to be trusted. A reader who is frightened chooses to be frightened.
38. After a time, close contact with other intellectuals reveals its redundancy. As their peer, they charm, disappoint, and gossip about you no differently than how you charm, disappoint, and gossip about your own reflection.
39. Style is voice and thought multiplied by fantasy. The more escapist a style is, the more distinctive it becomes. Though what is “distinctive” is not always what is “good.” And what is “good” is not always what is “worth reading.”
40. Be ever the alchemist who turns lead to gold. But instead turn a slight into a gift and a rejection into a pardon.
41. Obscure prose is what the reader makes of it. Two readers read one passage. For one reader it may be dull and impenetrable, for the other reader it may be intriguing and seductive.
41b. Lyricism is strategic obscurity. Not all strategies are successful.
42. In my 20s, Paglia told me, in so many words, never to read Rousseau. In my 30s, I read and reread Rousseau — then reread Rousseau some more. What bearing that has on you is, yet again, a judgment call.