Self-Knowledge

• What would my 80-year-old self say?
• If I were to give advice to someone in my position, what would it be?
• Do I feel like a noun or a verb?
• Is there something in my life I think I'm “passionate” about but I'm actually just addicted to?
• What annoys me about other people that I sometimes do myself?
• What do I think is ambition (a good trait) but is actually envy (a terrible one)?
• Do I spend more time defending what I already know instead of trying to learn something new?
• What would I do if I knew I couldn't fail?
• What are the subtle, unobvious reasons I've achieved what I have?
• What traits are inversely correlated, basically they add up to 100, so a point for one is a point taken from the other?

Life & Philosophy

• Can you hate someone if you fully understand them? Are judgment and understanding opposite sides of the same spectrum?
• What false belief did you shed that liberated you?
• What do I believe is true only because believing it puts me in good standing with my tribe?
• Which of my current values would be different if I were raised by different parents?
• What do I believe the most with the least amount of evidence of it being true?
• What is partially true but I believe in it so absolutely that I've turned it into a dangerous belief?
• What legacy ideas would be banned if they were invented today?
• Are feelings just lower-frequency thoughts?
• What was true a generation ago that no longer is, and who is clinging to that old truth?
• What will someone from the 25th century respect in someone from the 21st century? What would they admire?

Business & Building

• What is one thing I believe to be true that almost everyone else is wrong on?
• What would need to happen in 10 years for me to think these 10 years have been a success?
• What are skills I'm in the top 25% in? What combination makes the smallest Venn diagram?
• What is something I spent a lot of time doing that others should skip entirely?
• What core skill do I wish I developed earlier?
• What mindset shift or realization did I make much too late?
• Tell me about a real-world system you've broken or gamed.
• What do you know more about than most people?
• Is it a good explanation? Is it worth paying attention to?
• What decisions would be beneficial to outsource to an algorithm? Which ones shouldn't be?

Relationships

• Are there people in my life who I consider kind and compassionate but they're actually just too shy to tell me hard truths?
• Who has the right answer but I ignore because they're a bad communicator?
• Who is full of it but I pay attention to because they're a good communicator?
• What's something you respect or admire about someone at the table?
• What is the one activity or person that makes you happiest in the world?
• What's the kindest thing anyone has ever done for you?
• What do you consider a forgiving person? Is most forgiveness just “no harm no foul”? Does true forgiveness require mercy?
• Name an example when you were trustworthy when it wasn't in your best interests to do so.

Inertia & Change

• Inertia is a bitch. What are you doing that you are only doing because you are already doing it?
• If you started with a blank sheet where you currently are and designed your life from scratch, what would you do? Why not just do that now?
• Are you being dragged or driven? Dragged by insecurity, listening to what everyone else wants out of you, or driven by your innate desires?
• Have you already achieved goals that you said would make you happy?
• Is this thing I'm worried about actually a problem, or am I looking for problems to worry about because they make me feel in control?
• Are there things going well in my life today that I will look back on and wish I had quit while I was ahead?
• How much of my nostalgia is a false or incomplete memory of the past?
• What in my field do I think is a law (works all the time) but is actually just a rule (works some of the time)?

Dinner Table

Questions I actually use at dinners. The best conversations come from questions that make people pause before answering.

• What are the most interesting and unique beliefs you have about the world and how things work?
• What is ignored by the media but will be studied by historians?
• What class would you teach to 18-year-olds?
• What's the modern-day version of the cigarette?
• What are you running from? What are you running towards?
• If you could give a TED Talk on anything but it can't be about your main thing, what would it be on?
• What trait or value do you respect the most?
• What are the last one or two things we give AI control over?
• Does society owe you anything?
• What's a story from your childhood that bugs you that you don't think should bug you?
• Are you building your life to be an infinite game? How so?
• What are the failures you cherish the most?