Skip the small talk
Imagine a party. At the beginning, the host tells the attendees there are only two rules for the evening:
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 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.