100 Questions To Ask Yourself If You Want To Reach Financial Independence

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Time For Self-Reflection: DaVinci’s 100 Questions

Michael Gelb has written a book called How to Think Like Leonardo da Vinci.

In the book, Gelb shares 7 principles that characterize the genius of da Vinci.

He also gives you exercises so that you can grow in these areas. The first principle is CuriositáItalian for an insatiable curiosity. 

And the corresponding exercise is called “100 Questions,” which helps you apply this curiosity to yourself. Here are the steps to this powerful exercise.

Step 1:

Set aside at least 45-60 minutes of quiet, uninterrupted time.

In your journal or notebook make a list of 100 questions. 

These questions can be anything you want, from “How can I make more money?” or “What is the meaning of life?”  to “Why do I have to work?” or “What’s for dinner?”

The only rule is that you have to do it all in one sitting.  Write whatever comes to mind, write quickly, and don’t judge the questions or worry if they’re good enough.

The first 10-20 questions will be easy, but then you might hit a wall like I did. 

Keep going. Don’t worry about repeating the same question or coming back to the same topics (this is actually an important part of the exercise to recognize themes in your mind).

The questions that come to you late in the process may be the most important.

Step 2:

Once you’ve finished with at least 100 questions, review your list and highlight the themes that have emerged. 

Did you write a lot about money? Your family? Your job? Vacation? Hobbies? Some of the themes will be familiar but others may be a revelation.

Step 3:

Again review your list of 100 questions and choose the 10 that seem most significant to you

Then rank these in importance from 1 to 10. Don’t worry about answering these questions right now.  The work of writing them and creating a list that you can go back to is all that’s important.

Power Questions:

Gelb calls your top 10 questions Power Questions. 

If you ponder and reflect on them they have the power to change your life for the better (and also the power to shake you up a bit, so be careful!).

I recommend writing down any of the power questions that resonate with you. Then just let them simmer in your mind for days.

Let them bubble up when you’re in the shower, when you wake in the morning, or when you’re driving your car.

Pondering these questions, like “How much money is enough for financial independence?” has been significant in my life.

My index investing journey, the blog you’re reading, and the coaching business where I teach students of FI are the results of pondering on this question!

Here’s My 100 Questions (All Right, It’s Only 85…)

1. Am I doing what I truly want to do in life?

2. Is the search for financial independence the reason to why I am so happy and motivated on my work?

3. How much money is enough for me to quit my job and not worry anymore?

4. Is $500K really enough for me to quit my job?

5. Will I get an inheritance? How much and eventually when will I get it? Should I calculate for it in my FIRE-number?

6. How long should I save for early retirement?

7. What should I study next?

8. Is it that important that I get a degree from the studies? Or is self studies just as good?

9. Is my life spent according to my values?

10. Should I work part-time now?

11. What would I do if I were working part-time?

12. Is my dream job to be an engineer?

13. Do I enter flow mode enough in my current work?

14. What would happen if I just tried to start my business now?

15. Why should I wait on starting a business until I’m financial independent?

16. Will I handle the risk by doing a business on my own?

17. Is the thing that I like with my corporate job that it gives me a secure amount of money every month?

18. Doesn’t a business have a much larger potential for bigger income?

19. Why am I always that afraid of the unknown? I’ll die in the end anyway.

20. What is the next step for me in life?

21. Why do I want to reach financial independence? I love to work on things.

22. When will we have our wedding?

23. When will we have our kids?

24. Is that what’s missing for me to be completely happy?

25. Will I be a great father?

26. Where should they grow up?

27. Will they be happy?

28. Is happiness a part of myself or can I recieve it from my surrounding environment?

29. Why do I think so much?

30. Do I want to become an investor?

31. Is investing in terms with my values in life?

32. Is the 4%-rule safe? What about 5-6%?

33. Will I stop thinking about security and money when I’m financial independent?

34. Should I quit my blog?

35. Is all the effort writing a blog worth it?

36. Do I write anything of value?

37. When will I try to write a book?

38. Will I ever feel like “succeeding” in life or is life a constant work in progress?

39. Will I ever get there? And when I get there, will I then think about a new goal (a new there)?

40. Will I ever be content? Why do I strive for more in all areas all the time?

41. Is it worth spending time on Twitter?

42. What is worth spending time on anyway?

43. Do I live a life with meaning?

44. When will I have time to read all the best books out there?

45. Is that my purpose with financial independence? Reading and sharing what I learn through the blog?

46. When will people see me as the person I am?

47. Is everybody just as interested in learning about their own personality as I am?

48. Do I live too much in the future?

49. Am I planning life too much?

50. Do I wake up early every day because I’m so curious about learning more?

51. Should I study philosophy or psychology?

52. Do I want to teach others about what I learn or do I like to keep it to myself?

53. Would I be a good teacher?

54. What is the meaning with life?

55. Should I become a lifestyle coach? Would I succeed?

56. Will I ever dare to try something without having the fear of failing?

57. What is the definition of rich? Am I really rich when my wants are few?

58. When will politicans introduce universal basic income for every citizen in the world?

59. Would a system with universal basic income work? Would more people explore their creative sides and start their own businesses?

60. Could the study of social economics be of interest for me?

61. I think I’m more interested in learning only for the sake of learning. Is it meaningless to just learn something without ever using to anything?

62. Why doesn’t it exist some kind of work where you just read and learn things all day? Is that the reason I want to become financial independent? So that I can spend time on doing this every day?

63. Is it possible to freeze time so that I can have the time to read all the books I want to read? A new book is published every second and it’s stressing me out.

64. What does my friends really think about me?

65. Am I well liked by my family?

66. Will I ever learn italian and live in Rome? If not now, when?

67. Would my wife and I like to live abroad, or would it only felt like an escape from the “real” world?

68. What is worth spending time on in life?

69. How much time should I spend with family/friends in a regular week?

70. How can I become financial independent faster? So that I can start living the life I truly want.

71. What is the life I truly want anyway?

72. Would people think I’m weird when I quit my job?

73. What is the one book I should read that finally let’s me understand what life is all about?

74. Should I watch LOST again? The flashbacks in that TV-series has deep insights in my opinion.

75. What would I do in life if money was no object? Will I find out when I’m financial independent?

76. Where can I meet similar INFJ-personalities that I can discuss with? Do they like to write as much as I do?

77. Is happiness only real when shared? Or can you experience that same happiness in solitude?

78. What is required for living the good life?

79. Will I be more content and happy by reading about it?

80. Will my inner curiosity about life ever disappear?

81. Could I save more money? Do I waste any money today?

82. Should I keep tracking my expenses? Or is it enough to register my income, how much I invest and how much I pay down on the mortgage.

83. Will life be any different when I’m financial independent, or is it merely an illusion?

84. Will my worries disappear when I have enough money?

85. How would I ideally spend my 24 hours everyday?

Route 2 FI’s 12 Power Questions

1. Will life be any different when I’m financial independent, or is it merely an illusion?

2. Why doesn’t it exist some kind of work where you just read and learn things all day? Is that the reason I want to become financial independent? So that I can spend time on doing this every day?

3. Will my inner curiosity about life ever disappear?

4. Will I ever be content? Why do I strive for more in all areas all the time?

5. Will I ever get there? And when I get there, will I then think about a new goal (a new there)?

6. What is the one book I should read that finally let’s me understand what life is all about?

7. Will my worries disappear when I have enough money?

8. Is the 4%-rule safe? What about 5-6%? 

9. Will I stop thinking about security and money when I’m financial independent?

10. Why should I wait on starting a business until I’m financial independent?

11. Is $500K really enough for me to quit my job?

12. Will I get an inheritance? How much and eventually when will I get it? Should I calculate for it in my FIRE-number?

This was a deep dive into my head and my thinking.

What is your power questions? Would love to hear from you!


Read all my posts in chronological order here: Archives


Have questions, comments or suggestions? I would love to help you with your FI-journey.

Feel free to reach out directly at @Route2FI on Twitter or email me at post@route2FI.com


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