Related to: Rationalization, Meditation on curiosity, Original Seeing.
Why aren’t you learning faster?
For me, one answer is: because I’m not asking questions. I blunder through conversations trying to “do my job”, or to look good, or elaborating my own theories, or allowing cached replies to come out of my mouth on autopilot. I blunder through readings, scanning my eyes over the words and letting thoughts strike me as they may. Rarely am I pulled by a specific desire to know.
And most of my learning happens at those rare times.
How about you? When you read, how often do you chase something? When you chat with your friends -- are you curious about how they’re doing, why their mouth twitched as they said that, or why exactly they disagree with you about X? When you sit down to write, or to do research -- are you asking yourself specific questions, and then answering them?
Are there certain situations in which you get most of your useful ideas -- situations you could put yourself in more often?
Lately, when I notice that I’m not curious about anything, I’ve been trying to interrupt whatever I’m doing. If I’m in a conversation, and neither I nor my interlocutor is trying to figure something out, I call a mini “halt, melt, and catch fire” (inside my head, at least), and ask myself what I want. Surely not stale conversations. If I’m writing, and I don’t like the sentence I just wrote -- instead of reshuffling the words in the hopes that the new version will just happen to be better, I ask myself what I don’t like about it.
Thus, for the past six months, several times a day, I've interrupted my thoughts and put them back on an “ask questions” track. (“Grrr, he said my argument was dishonest... Wait, is he right? What should it look like if he is?”; “I notice I feel hopeless about this paper writing. Maybe there’s something I should do differently?”) It's helping. I'm building the habit of interrupting myself when I'm "thinking" without trying to find something out, or taking actions that I expect won't accomplish anything. As a human, I’m probably stuck running on habits -- but I can at least change *which* habits I run on.
You've already identified the weakness of asking questions. It should come as no surprise to you that Pick Up ("that" subject) teaches one to never ask questions. It is advice for dating, but holds for generally any conversation. Compare and contrast a standard interaction.
Question: "What school did you go to?" This allows-> Answer: "" which segues into.... "...Ah, um, okay." It's a bad conversation track. You're asking for effort from them while forcing them to respond in a narrow field, which they probably aren't interested in.
Statement: "I bet you had your pick of colleges." This allows-> Answer1: "I never thought I'd get in!" Answer2:"" Answer3: "I went to , I loved the campus." They can respond in the way that's most interesting for them. It also weaves in an implicit compliment (eg, the subject was smart and had many opportunities).
Behind every question is a statement. The tricky part is finding out what your question says and how to phrase it best. A statement better expresses your feelings "How are you doing?" -> "I hope everything is going well with you." Statements are more confident and harder to say no to "Would you like to dance with me?" -> "I would like to dance with you" And the act of turning a question into a statement lets you know what you're really saying "Do you come here often?" -> "I'm interested in you."
As a rationalist, that last part is incredibly useful. It's easy for us to watch what we're saying when we're making statements, because the brain can skim the surface and catch the meaning. It's much more difficult to understand what we're saying when we're asking a question. A master conversationalist will understand "Where did you go to college?" as a statement of "I think you're cute/smart. I want to know where you went so I can relate stories," even if you aren't aware of it. If you had said the words explicitly as a statement, you would have obviously caught it. This is the reason you should always check your questions for statements.
Sometimes you really do want to know a particular piece of information. In this case you can actually ask a question, but you need to be aware that you are making a request for information. You should only ask a question if you would feel comfortable saying the statement "I want to know ". After practicing for a while you will realize that most of your prior questions were actually statements with question marks at the end. Try it out for yourself.
NB, questions can still be used to great effect. Especially for misdirection or anchoring bias. Naturally these are dark side techniques and I shan't discuss them here. Everything prior is simply good advice for having conversations with strangers.