Challenging Money Questions

Did you know?

Due to coin flips, George Washington still makes decisions to this day.

Below are some challenging money questions.

1. You come across a large inheritance left to you in a distant relative’s will. However, you discover that the money was acquired through illegal means. Do you accept the inheritance or report it to the authorities?
2. You own a business and have the opportunity to significantly increase prices on a product in high demand, potentially exploiting customers during a crisis. Do you raise the prices or keep them fair?
3. As a high-ranking executive, you have the power to make decisions that could maximize profits but harm the environment or exploit workers. Do you prioritize financial gains or act responsibly?
4. You have the choice to donate a large sum of money to a charity that aligns with your values or invest the money to potentially generate larger financial returns. Do you prioritize philanthropy or personal gain?
5. You hold a position where you can favor certain business partners or investments that could benefit you financially, but it may not be in the best interest of your company or stakeholders. Do you prioritize personal gain or act in the company’s best interest?
6. Would you rather have a million dollars or the ability to travel anywhere for free?
7. If you were given $10 million, would you still work for your current company?
8. Would you rather have a 10% raise or the ability to work from home one day a week?
9. Would you rather have the ability to double any money you touch but lose half of your memories, or retain all your memories but live on a fixed income for life?
10. Would you rather have a guaranteed income for life or the ability to turn your passion into a lucrative career?
11. If you could only spend money on one thing for the rest of your life, what would it be?
12. If you could go back in time and change one financial decision, what would it be?
13. Would you rather be able to retire at 40 but have to live in a small studio apartment for the rest of your life or work until 65 but be able to afford a luxurious mansion?
14. Would you rather have the ability to invest in any stock or asset and be guaranteed to make a profit or be able to eliminate all your debts instantly, but never be able to invest again?
15. Would you rather have a guaranteed inheritance of $500,000 but have to take care of a family member with a disability for the rest of your life or have no inheritance but be able to pursue your passion without any financial burden?
16. Would you rather live without internet for a year or live on a strict budget of $100 per month for all expenses for six months?
17. Would you rather invest all your savings in a risky startup that could either fail or make you a millionaire or keep your money in a savings account with minimal interest?
18. Would you rather have your credit card debt forgiven but never be able to use a credit card again or pay double the interest on your current debt but keep using credit cards?
19. Would you rather legally change your name to a corporate brand of your choice for a $100,000 sponsorship or remain with your current name but pay a $10,000 fine?
20. Would you rather have all your purchases be public knowledge or never be able to purchase anything online again?
21. Would you rather live in a small studio apartment in a desirable location for free or own a large mansion in a remote area but have to pay $10,000 per month in mortgage payments?
22. How would you make a trillion dollars?
23. How would you trade a $1 to everyone in earth
24. You just won 1 billion in the lottery? what do you do with it?
25. What’s the craziest thing you’ve ever splurged on?
26. What’s the most creative way you’ve ever saved or made money?
27. What’s the craziest financial risk you’ve ever taken? 
28. If you could go back in time and give your younger self one piece of financial advice, what would it be? 
29. What’s the worst financial advice you’ve ever received?
30. What’s the most ridiculous thing you’ve ever lied about to avoid spending money?
31. Imagine you’re a billionaire tasked with spending $1 million in 24 hours without keeping anything for yourself. How would you spend it?
32. If you could invent a new form of currency, what would it be made of and what would you call it?
33. If you could only use one type of currency for the rest of your life (real or fictional), what would it be and why?
34. You’ve been given the opportunity to be the first person to colonize Mars, but you have to pay for the entire mission yourself. How would you raise the funds?
35. Would you rather win $1 million or have the ability to never pay taxes again?
36. If you could invent a new financial product, what would it be and how would it work?
37. What financial rule would you create if you were in charge of the world economy for a day? 
38. Would you rather always get a 50% discount on everything you buy or always make 50% more income?
39. What’s the most unusual job you would do for a million dollars?
40. If you could only use one form of payment for the rest of your life (cash, card, or digital), which one would you choose and why?
41. If you had to live without one common financial service (banking, credit cards, online payments) which one would you give up and how would you adapt?
42. You’ve been given the power to solve one global financial issue. Which one do you tackle and how?
43. If you could start a charity, what would its mission be and how would you raise funds for it?
44. You’re offered a book that contains the financial future of yourself and everyone you know. Do you read it?
45. If you could create a “financial utopia,” what would be its three foundational rules?
46. You’re given the chance to teach a mandatory class on personal finance to high school students. What’s the most important lesson you’d want to impart?
47. What are your most valuable items that you could barter with someone if the currency collapses?
48. How would you spend your time if your basic needs where met?
49. If you could hire someone to do any household chore for you forever, which chore would you choose?
50. If you received a $100,000 windfall, how would you allocate it between spending, saving, investing, etc.
51. What’s one purchase you regret and one you’re really glad you made?
52. What’s one thing you spend too much money on that you should cut back?
53. What’s one thing money can’t buy that you wish it could?
54. How has social media and influencer culture impacted your spending habits?
55. What’s the most unethical thing you’d do if it made you extremely wealthy?
56. Would you rather be wealthy and miserable or broke but truly happy?
57. How have your cultural traditions and values shaped your relationship with money?
58. If you lost all your money and possessions, what non-material things would you be most grateful for?
59. How important is generational wealth and leaving an inheritance to your values?
60. What’s one thing money can’t buy that you wish it could?
61. How have your spiritual or religious beliefs influenced your views on money?
62. What’s your biggest financial fear or insecurity about the future?
63. Would you rather have financial security or perfect health?
64. How would you use money to make the biggest impact in your community?
65. If you could automate one aspect of your financial life, what would it be?
66. What’s one financial trend you’re currently interested in or following?