Great questions
Big thinking questions
What do I spend a silly amount of money on? How might I scratch my own itch?
What if I did the opposite for 48 hours?
What would I do/have/be if I had $10 million? What’s my real TMI?
What are the worst things that could happen? Could I get back here?
If I could only work 2 hours per week on my business, what would I do?
What if I
Dream big questions:
‘What would I be like/spend my time doing if all my current major problems had been solved?’
‘What are the things I say I value but don’t act as if I value, and what would my life feel like on inside if I actually acted as if I valued those things?’
‘What am I afraid of doing, and what would my life be like if I wasn’t afraid of
52-Brilliant-Questions
Most of the time, “What should I do with my life?” is a terrible question. “What should I do with this tennis serve?” “What should I do with this line at Starbucks?” “What should I do with this traffic jam?” “How should I respond to the anger I feel welling up in my chest?” These are better questions. Excellence is the next five minutes,
... See moreTimothy Ferriss • Tribe of Mentors: Short Life Advice from the Best in the World

End-of-year work retro questions:
Do I Know What’s Most Important To My Boss In The Upcoming Year? Does My Team?
What’s The Most Impactful Piece Of Feedback I Got This Year? Did I Give Clear Feedback As A Manager?