How do these mesh with Proverbs (long + bad version)? ctrl+f other mentions of advice in here.

You should write for people who are kind, busy, and clueless, not people who are cruel, patient, and knowledgeable. Philosophy writing advice often merges the two together.

  • Another piece of advice is to start writing the essay that will take the least work to finish, not the one you think you will be most satisfied or excited to have finished.

When writing about advice or internet writing, mention Patrick collisions example of the dwarkesh podcast introducing the current scroll prize winner to the problem.

Section of old proverbs essay on advice in general:

Good advice should be informative. Proverbs are often good advice. But proverbs don’t seem to be very informative. This is partly because they’re old, so everybody knows them already, and partly because they’re very general, so they can’t carry much information about specific situations.

This suggests a dilemma for would-be advice-givers. Suppose someone wants advice on how to make a risky decision, and you offer the proverb “Nothing ventured, nothing gained”. On one horn of the dilemma, if you know enough about their situation to say something more specific, shouldn’t you do so? Aren’t you just violating Grice’s maxim of quantity by not doing so?

But on the other horn of the dilemma, if you don’t know enough about their situation to say something more specific, then why are you even giving them advice? Putting aside self-serving motives, if you can’t say something more specific than a proverb, why should they think that following your proverb is even a good idea?

At first, it’s tempting to take this second horn of the dilemma, and insist that proverbs are still informative enough to count as good advice. For one thing, even if the wisdom they contain is perennial, it can still be useful to be reminded of that wisdom. On this model, people have certain systemic biases, and proverbs act as a counterweight to these biases. Maybe people are generally too cautious, or prone to thinking the grass is greener, or whatever. Proverbs exist to prompt people to correct for these biases, either by reminding them of what they’ve forgotten, or by advising them to act as they already know is best. Since these biases are so widespread, it’s typically positive expected value to use proverbs as a counterweight, even if you don’t know much about the situation at hand.

This theory might explain some proverbs. People are forgetful, and akratic, so it can be useful to remind them of what they already know they should do, even if such advice isn’t especially informative. But this theory runs into a difficulty, namely, the fact that so many proverbs contradict one another.