Note: In many cultures, you would be considered a huge jackass for asking these questions out loud.
1. How much money do you spend each month?
2. Where does it go?
3. Where do you want it to go?
4. Are you rich?
5. What does rich mean to you?
6. Hey, how’d you pay for that iPhone?
7. How much do you automatically save each month?
8. Why’d you pull your money out of the stock market?
9. You’re always thinking about cutting down on spending. Ever thought about earning more money?
10. OMFG, are you REALLY planning to buy a house for the tax deduction?
11. If your employer has a 401(k) match, do you max it out?
12. Then pay off debt, invest in your Roth IRA, and — if you still have money left over — max out your 401(k)?
13. Once your money is in those different accounts, have you invested it according to some simple rules of asset allocation?
14. In the next ten years, you’ll have to pay for a wedding, new car, have kids, take vacations, etc. How much are you saving each month for those things? (In last week’s Scrooge Strategy tip, I showed how to do this tactically, along with a pre-built spreadsheet.)
15. 6 months ago, if I had told you the stock market would be on sale for 50% off, would you have invested more, less, or pulled all your money out?
16. You’re always complaining about money, but have you read even one book on personal finance?
17. When was the last time you said “no” when someone asked you to do something that involved spending money?
18. How do your friends handle their money, and how do you think it affects you?
19. What’s the one thing you could do today to start getting rich?
20. Why haven’t you already done it?
[Update]: Download a PDF version of these questions for easier sharing.
Forewarmed is forearmed: join my Private List for real-world money advice
Nobody’s perfect (and we all make mistakes) but all of the financial challenges above ARE avoidable. I’ve helped thousands of readers navigate these situations and lead richer lives. If you want more posts like today’s, join my free Private List.
Each week, you’ll get never-before-seen advice on:
- Preparing for life’s financial challenges BEFORE they arrive
- Using systems and automation to grow your money automatically
- Earning more money with skills you already possess
- Much, much more