I actually had in mind less personal questions, that might take some research, insight, and work to get a real answer to.
You're not talking about 'rhetorical' questions, are you? Something like "How could someone do something that stupid?" Can be intended rhetorically even though it's a question that should probably be answered for real (unlike the more obviously rhetorical "does a bear shit in the woods?")
The only other non-trivially answered questions that I can think of getting an ignore response are still personal (e.g. what's your life plan?).
Do you have an example?
I'm guessing, but I think JGW probably was talking about "open questions" rather than rhetorical ones.
Rhetorical ones imply that they shouldn't be answered. Open questions are ones that, by their nature, require you to answer in more depth than just a single response.
Consider the following. If you start with: "where did you go to school?" or "what did you study?" as opening questions (which could have simple, one-word replies)
Compare the followup question: "what subject did you enjoy most?" where a one-word response ...
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.