Posted for my recall. Taken from The Simple Dollar, which is public domain.
1. What five things do you most truly love doing? Think of things that you both enjoy in the moment and also enjoy looking back on later. Do any of these cost money?
2. What five things that you do regularly do you truly hate doing? You hate thinking about them and doing them in every way. Are these in any way worth the reward you get for doing them?
3. What things are preventing you from doing more of the things you love and less of the things you hate? How can you remove those obstacles?
4. When was the last time you felt guilty about an expenditure? Why did you feel guilty about it?
5. What would you do if you went to work tomorrow and your boss handed you a pink slip? Get as specific as you possibly can. What could you do right now to make that less of a shock?
6. What five people (besides yourself) do you care for most in the world? Do they know this? What could you do to show them that you feel this way? Does your reaction involve money? Does it need to involve money?
7. Have you ever been in a situation where you felt powerless about your spending, almost as if something else was in control of it? Why did you feel that way? What do you feel was driving that spending?
8. Can you think of five ways you attempted to control your spending? Did they work or not? If they didn’t, can you remember the exact moment when you realized you were losing that battle?
9. Do you remember a time in your life where you weren’t concerned about money? What specifically changed between then and now? Is the difference between the two mostly “stuff”?
10. Can you name all of the individuals and organizations that you owe money to, and roughly how much you owe and what the interest is? Which one is dragging on you the most? Why does it drag on you?
11. Where do you want to be in one year? Describe your life in as much detail as you can. Can you name five actions you can take in the next week to lead you to that goal?
12. Where do you want to be in five years? Describe your life in as much detail as you can. Can you name five actions you can take in the next week to lead you to that goal?
13. Do you actually ever want to retire in the traditional sense? If not, what do you want to be doing with your life at the typical retirement age?
14. How much do you actually earn for each hour you work? Don’t just divide your salary by the number of days you work and the number of hours you work each day. Subtract out the cost of commuting, clothes, social events for work, eating out, taxes, and other such expenses, and add in the hours you spend commuting, attending conferences and meetings, working late, and so on. That dollar amount is the exact value you put on an hour of your time - your true hourly wage.
15. Once you know that exact value, what else could you be doing to put that much in your pocket, particularly work that leaves you feeling more fulfilled and happy?
16. What would happen to those around you if you walked out of your house and were hit by a Mack truck and killed? What would happen to those around you if you walked out of your house and were hit by a Mack truck and put into a long-term coma? What could you do differently to cover those bases?
17. Think of ten childhood memories about money. Do these memories point to a healthy relationship with money (saving and planning for the future) or an unhealthy relationship (spend, spend, spend!)?
18. When was the last time you bought something primarily to impress someone else? Did it work? Did you ever buy anything to impress someone and had it completely fail to work?
19. When was the last time you bought something that was completely unnecessary? When you look back on it, do you feel happy about that purchase? Do you feel happy about earlier frivolous purchases? If some make you feel happy and others don’t, what’s the difference between the two groups?
20. When you sit down and send out your bills for the month, are you left feeling good or bad after doing this task? Why? Is there anything you can do to change that perspective?
