Ask Questions in a Different Way to Zero in on Your Motivations

I have a physical coming up and in order to prepare for it, I am doing nothing that I would ordinarily do.I take decent care of myself, but in preparation I have cut out all fats, began weighing myself daily and have increased my efforts to maintain calm. I am not doing this because I intend to change my lifestyle, so I must have some other reason for doing so.

I was talking with someone who has a lot of money, does not want their kids to get very much of it, is not charitably inclined and hardly spends anything on themselves. They called because they wanted to know whether we might be able to generate a better return than they were currently getting. Why?

There has to be some reason that people who are so disconnected from their money want more of it. Maybe it's because money represents safety, but they could live for another 1,000 years and not spend it. Maybe it's because having a pile of money means that they can do anything they want, but they don't want anything. I couldn't figure it out, and after we talked about it, neither could they.

I realize through trying to temporarily perfect my health habits and through the interaction with the person described above, that in order to better understand our money decisions, we need to make it Opposite Day.

Before you automatically say no to your kids' request for money, say yes in your head first — and then try to understand where the no is coming from. If you are prone to always saying yes to your kids, reverse it in your head, and try to determine your reason.

If you are not feeling valued at your job, figure out what you are missing and why you want it so bad. Then ask yourself how you would feel about the job if you felt recognized.

Use opposite thinking with all the money decisions where you feel stuck. This is helpful because we generally see only the things that support our positions, which makes it hard to remember how we initially formed them.

When I evaluate my physical strategy, I want to be perceived as healthy without making real changes to ensure my good health. Instead, I can ask myself how healthy do I really want to be and then make decisions aligned with that. My blood work may not be quite so good, but I suspect that quart of ice cream will more than make up for it.

Related: Regret Is Not a Helpful Planning Tool When It Comes to Your Finances