Imagine a party. At the beginning, the host tells the attendees there are only two rules:
- You can’t talk about work
- You can’t talk about cities
Standard conversational crutches will not work tonight. Yet, projected in a prominent place, is a list of questions. Conveniently, these are the sorts of questions you’d ask someone at a specific kind of gathering. They’re a little quirky, slightly strange. Each wants to land at the intersection of probing and whimsical.
Such a list might look like this:
- What’s the worst advice you’ve ever received?
- What simple thing still blows your mind?
- Which of your personality traits has been the most useful?
- Imagine you have a closet full of robots at the ready. Which of your various obligations would you assign to a robot? Which tasks and activities would you keep to yourself, because you enjoy them too much to delegate them to even a robot who is better than you?
- Would you plug yourself into Nozick’s experience machine?
- What’s the last thing that made you laugh hard?
- What keeps you up at night?
- ‘The first thing we do, let’s kill all the lawyers’ (William Shakespeare). Discuss.
- What’s something you’re doing now that you probably shouldn’t be?
- What’s a mainstream belief you’re totally in agreement with? (Tyler Cowen)
- Why is the idea of apocalypse appealing?
- What’s a mainstream belief you disagree with vehemently? (Peter Thiel)
- If you had to write a book, what would you write it on?
- What do you understand that 99% of people don’t?
- What do you not understand that 99% of people do?
- What is one thing everyone should experience?
- What’s a formative experience you’ve had over the last 2 years?
- What’s the most useful concept you have that doesn’t have a name?
- What is one unwritten rule you learned the hard way?
- If you had a clock that would countdown to any one event of your choosing, what event would you want it to count down?
- What browser tabs do you have open right now? (Tyler Cowen)
- What are three of the most significant numbers in your life? (Can’t do anything birthday related)
- Which question can you ask to find out the most about a person?
- Why is communication so difficult?
- What are you addicted to?
- What’s the most outrageous advice you can come up with? OR what advice are you scared of giving me because you think I’ll blame you if it fails?
- Should the beautiful be taxed? Should the ugly be compensated?
- How do you want to raise your kids?
- Invent a new idiom
- Is the future of the humanities teaching Great Books to engineers?
- ‘The caterpillar who knew himself would never become a butterfly’ (Andre Gide) Discuss.
- What history would you teach your children?
- Improve the rules of any one sport.
- When we make contact with an extra-terrestrial civilization, what should we tell them is humanity’s greatest achievement?
- What’s your favorite story? Real or fictional.
- The University of Chicago abolished its football team and heavily deemphasized sports in the 1930s. Was this a good idea?
- In which area of life do you have the best taste? (Follow-up: why aren’t you spending more time in that area?)
This list takes questions and inspiration from many sources. Chief among them are Lama’s list, and All Souls examination papers. I plan on updating the list often and linking to sources as I remember them.