Disclaimer: These prompts are not mine. I did not invent them. I have included the source of where I initially heard them. If that is not the original source, I apologize in advance.
If you want more, I expanded on each prompt here.
- Make a map of my failures indicating the rough date they occurred. Write beside each one what I learned.
2. What might I do to accomplish my 5-year goal in 6-months, if a gun was up against my head? (Tim Ferriss)
3. Who was the first person that told me about the career/job I am in? Have I had any similar discussions since?
4. Where in my life can I trade a short-term, incremental gain for a potential longer-term game-changing upside?
5. What is my third most unique strength?
6. What would make what I am doing right now easiest?
7. What do I spend a silly amount of money own? How might I scratch my itch? (Tim Ferriss)
8. What is the worst possible scenario if I take “x” action? What can I do to limit the downside? (Stoicism)
9. What would I do if I had $10 million but still had to work 40 hours a week? (Financial Samurai)
10. Will I choose make this a dead time or an alive time? (Ryan Holiday)
11. How might I build my non-work life around what I do in a way that lets me frame it as a source of greater meaning, joy, connection, and engagement or something that gives me freedom to do other things that provide those feelings? (Jonathan Fields)
12. If I could only work 2 hours per day on income producing activities, what would I focus on? (Tim Ferriss)
13. What is something that doesn’t make sense?
14. What is the least crowded channel into what I want to accomplish? (Noah Kagan)
15. What if the only way to add to my life was to subtract from it? What would be the first 1–2 things that I would remove?
16. Who are my top 7–10 digital mentors I most want to be like?
17. What is something I would miss if I no longer had it?
18. What is one relationship that I have let slip? What is the reason?
19. Do I enjoy what I am going to do today? If not, how long has the question been no? (Steve Jobs)
20. When was the last time I laughed at work?
21. When was the last time I participating in guilt-free play? (Charlie Hoehn)
22. If I had no fear today, what would I do? (Eleanor Roosevelt)
23. Who would be most upset if I quit/moved/tried this?
24. What is your biggest win in the last seven days?
25. If I was making my life into a movie, what scene would I make sure to add and what scene would I make sure to remove? (Donald Miller)
26. What is my most perceived weakness? How can I turn it into a strength? (Arnold Schwarzenegger)
27. If I had to instill one piece of advice in your own child’s mind, what advice would I give?
28. What is one closely held belief I have? When is the last time someone challenged it? (Marc Andreessen)
29. What blogs/books/articles do I read on the normal Saturday morning before any else wakes up? (Ramit Sethi)
30. What is something that I believe that none of my friends do?
31. Why do I want to be rich? What are the specific traits or things you will be able to do? Is there a way to have those now?
32. What are the 20% of things in my life that cause 80% of my anxiety?
33. Who is someone that I have not talked to in awhile that I am grateful for?
34. When I had the opportunity, did I choose courage over comfort?
35. Why am I doing what I am doing? Why? Why? Why? Why?
36. What has become more important to me in the last year and what has become less important?
37. Would my 15-year-old self be proud of who I am today?
38. What dream did I have to give up to get where I am?
39. What’s the best lesson my father ever taught me? (Cal Fussman)
40. What are some of the choices I have made that made me who I am t0day?
41. When did I learn a lesson the hard way?
42. What is something that I lost that I will never get back?
43. When did I last perform a random act of kindness?
Bonus: A quote, not a prompt, that always helps me clarify my thinking:
“[W]henever you find yourself on the side of the majority; it is time to pause and reflect.” — Mark Twain
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