Lately I’ve been thinking about how my thinking works, and how it can be improved. The simplest way to do so is probably to nudge myself towards paying more attention to various useful habits of mind. Here are the ones I've found most valuable (roughly in order):
- Tying together the act of saying a statement, and the act of evaluating whether I actually believe it. After making a novel claim, saying out loud to myself: “is this actually true?” ” and "how could I test this?"
- Being comfortable with pausing to reflect and thinking out loud. Trying to notice when my responses are too quick and reflexive, as a sign that I'm not thinking hard enough about the point I'm addressing.
- Asking for specific examples, and using more of my own. Tabooing vague abstractions and moving away from discussing claims that are too general.
- Being charitable and collaborative, both towards new ideas and towards conversational partners. Trying to rephrase other people’s arguments and pass Ideological Turing Tests on them. Helping my conversational partners build up their ideas.
- Noticing the affect heuristic, and which claims stir up emotions. Noticing when I'm talking defensively or heatedly, and when it’d be uncomfortable to believe something.
- Thinking in terms of probabilities; cashing out beliefs in terms of predictions; then betting on them. I haven’t done enough bets to calibrate myself well, but I find that even just the feeling of having money on the line is often enough to make me rethink. Being asked whether something is a crux gives me a similar feeling.
- Thinking about how the conversations and debates I participate in actually create value, and when they should be redirected or halted.
Then there are social influences. I think one of the greatest virtues of the rationalist community is in creating an environment which encourages the use of the tools above. Another example: my girlfriend fairly regularly points out times when I’ve contradicted myself. I think this has helped me notice and limit the extent to which I behave like an opinion confabulation machine.
I’d classify most if not all of the tools listed above as tools for evaluating ideas, though, rather than tools for generating ideas. What helps with the latter? I’ve personally found that one very useful strategy is to make and then justify bold claims based on vague intuitions. In the process of defending my position, I’m forced to actually flesh it out and make it coherent (although I do need to be careful not to become overly attached to the untrue parts). And what's helped the most is that after having interesting conversations, I now write posts inspired by them much more frequently. I often feel like Feynman in this story: "When historian Charles Weiner found pages of Nobel Prize-winning physicist Richard Feynman's notes, he saw it as a "record" of Feynman's work. Feynman himself, however, insisted that the notes were not a record but the work itself." Arguing and writing are not just ways to transmit my thoughts, but also the key mechanisms by which I generate new thoughts.
(Edited to add: a friend pointed out that the last line is a good indicator that I'm being insufficiently empirical. I think I agree; it should also include the mechanism of looking at the world and noticing something confusing going on.)