Great Questions

Great Questions

This is my intentional effort to learn and craft outstanding questions. The most effective people often ask the best questions. The most recently added questions are at the top. ”It’s a great thing to be rich in unanswered questions.” - Paul Graham
If plastic flowers were indistinguishable from real flowers, would you give them to someone on a first date?

Eric Markowitz

Sep 3, 2026 6:45 PM
What are the scarcest things in the world? (click to open)

Aug 25, 2026 8:27 PM
What are the most powerful words in the English language? (click to open)

Aug 25, 2026 8:25 PM
If you could change one thing, what would it be?

Debra Niewald

Aug 25, 2026 8:13 PM
What wants to emerge?

Debra Niewald

Aug 25, 2026 8:12 PM
What is the most important thing that happened today?

Jun 12, 2026 7:09 PM
Do you believe people can change?

Apr 9, 2026 8:16 PM
What was the last big thing you changed your mind about?

Apr 9, 2026 8:16 PM
What will you never learn if you only use the tools of language and logic?

Jan 27, 2026 7:40 PM
What are you becoming?

Sep 29, 2025 12:40 PM
If someone watched you for a week, would they believe you are serious about your goals?

Aug 10, 2025 6:41 PM
What do you want to be doing in the last decade of your life?

Peter Attia

Jul 8, 2025 7:48 AM
What increases in value as wealth approaches infinity?

May 22, 2025 12:03 AM
What increases in value as information approaches infinity?

May 5, 2025 8:48 PM
Are your best days ahead of you, or behind you?

Apr 16, 2025 7:05 PM
Are you treating life like the dress rehearsal or the show?

Mar 26, 2025 1:41 AM
Where is it wise to compress complexity?

Mar 18, 2025 7:01 PM
What is the most obvious thing to do right now?

Mar 18, 2025 1:31 PM
What experiences would I need to have to believe what you believe?

Mar 17, 2025 11:28 AM
What would you do if you could hire a tireless genius for $20 per month?

Feb 28, 2025 6:49 PM
What would you do if you had 10x the agency you have?

Jan 30, 2025 6:42 PM
What’s the best way to think about being helpful to you?

Nov 20, 2024 3:19 AM
How can I serve you well?

Nov 20, 2024 3:19 AM
What have you recently subtracted from your life?

Jun 20, 2024 3:52 PM
Why did we mock religion, only to mimic it?

Freya India

Jun 6, 2024 4:04 PM
What knowledge work can be converted into tokens?

May 15, 2024 10:31 AM
What led you to take this meeting?

Jesse Pujji

May 6, 2024 12:27 PM
Take a few minutes and think about something you are an expert in…then explain it to me.

Apr 28, 2024 11:48 AM
When you’re told that something is impossible, is that the end of the conversation, or does that start a second dialogue in your mind?

Eric Weinstein

Jan 29, 2024 1:43 PM
If you could have the answer to any one question, what question would you want the answer to?

Max Grev

Dec 14, 2023 3:03 AM
If you could take a year off to work on something that probably wouldn't be important but would be really interesting, what would it be?

Max Grev

Dec 14, 2023 3:03 AM
What's the last thing you crossed off your bucket list?

Max Grev

Dec 14, 2023 3:02 AM
What have you been thinking about lately?

Daniel Rhodes

Dec 14, 2023 3:01 AM
Did anything happen last week that you're still thinking about?

Varadh Jain

Dec 14, 2023 3:00 AM
What are you getting most excited about right now?

Sahil Bloom

Dec 14, 2023 3:00 AM
What gifts will I leave for unborn generations to come?

Patrick O’Shaughnessy

x.com
Dec 3, 2023 3:13 PM
What do you consider to be your finest hour?

Oct 31, 2023 12:10 AM
It’s impossible to please everyone. The question is: are you disappointing the right people?

Adam Grant

Oct 16, 2023 9:01 PM
Who has deceived thee so oft as thyself?

Oct 2, 2023 2:46 PM
If someone talked to you the way you talk to yourself, would you be friends with them?

Sep 10, 2023 2:44 AM
What do you spend an unreasonable amount of time doing?

David Perell

twitter.com
Aug 12, 2023 2:35 PM
Who is good at <skill> despite being poorly built for it?

Aug 11, 2023 6:16 PM
If you were required to dispose of all but one asset, what would you keep?

Aug 11, 2023 5:45 PM
For someone who is outside your field, what would they find most surprising about your field?

Jul 29, 2023 3:22 PM
How have you evolved? Show me.

Sam Hinkie

Jul 20, 2023 3:19 PM
Regardless of what they do or produce, who do you know that has the highest quality bar?

Patrick O’Shaugnessy

Jul 20, 2023 2:33 PM
What is the return on time for <item>?

Jul 19, 2023 6:17 PM
What is the outlook AND what is the predictability of the outlook?

Jul 19, 2023 6:15 PM
What has surprised you about <topic>?

Peter Kaufman

Jul 19, 2023 6:15 PM
How do you measure yourself?

Jul 19, 2023 6:15 PM