While many people strive for financial success, few know where to begin.

Unfortunately, there isn’t a formula or ready-made solution. You have to understand yourself –what motivates you, what causes you to stumble, and what you value most – in order to lay out a plan to reach your definition of success. Financial success is what you want it to be.

The following 36 questions are meant to help you understand your priorities, pitfalls, and dreams so you can begin to lay out a financial plan to reach your definition of success.

  1. What’s your financial guilty pleasure?
  2. What vices do you have that cost you more than $10 per week?
  3. Do you prefer to buy name-brand or generic?
  4. Do you buy lottery tickets?
  5. What is the largest discretionary purchase you made in the last year, and would you buy it again?
  6. What is your typical budget for a night out?
  7. Are you a saver or a spender?
  8. How many credit cards do you have, and how many have an outstanding balance?
  9. How do you define “need” and “want”?
  10. What constitutes a financial emergency?
  11. How often do you have to throw away spoiled food?
  12. What percentage of your income do you save?
  13. How long can you live off your emergency fund?
  14. Would you be willing to drive a few extra miles to save a couple cents per gallon on gas?
  15. What skills do you have that could be turned into a side hustle?
  16. Would you be willing to ask, “Do you want fries with that?” to make ends meet?
  17. Do you live to work or work to live?
  18. If you could undo one major purchase in your life, what would it be, and why?
  19. What did your parents teach you about money?
  20. Which is more important: job satisfaction or income?
  21. Would you steal to feed your family?
  22. If your house was on fire, what one possession would you try to save?
  23. What salary do you have to earn to feel successful?
  24. How much money do you have to have to feel wealthy?
  25. If you could trade everything you own for debt freedom, would you do it?
  26. If you were suddenly given a million dollars, how would you spend the money?
  27. If you won the lottery, would you want other people to know?
  28. What is your dream vacation?
  29. Would you rather have a nice house or a nice car?
  30. What is your plan to fund your retirement?
  31. What one money lesson will you teach your children?
  32. How would your life be different if you were wealthy?
  33. If money were no object, where would you live, what car would you drive, and what house would you live in?
  34. How much money do you have to have before you feel comfortable to retire?
  35. Do you want to retire early?
  36. If you could donate $1 million to any charity, which charity would it be and why?

Bonus: Do you use Tiller to manage your finances?

Whether you are just starting out on your financial journey or you’ve been religiously sticking to a plan for decades, remember that success doesn’t happen overnight. Even Warren Buffett, the third wealthiest man in the world, didn’t achieve his first billion until he was 56 years old.

Ansley Fender
Author

Business financial consultant, personal finance coach, tax preparer, mother, spreadsheet nerd.

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