43 Thought Provoking Prompts that Changed my Life

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.

  1. 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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