I've started asking people a few questions about money to get some conversations going:
1. If you had "all the money in the world" — not literally, but all you wanted — what would you change about your life? (If anything?)
Some people have been telling me they'd like to spend less time doing paid work, though interestingly, not so they could do what we think of as leisure activities. People wanted to spend more time with small children or do volunteer work, which is probably wise. Being idly rich gets old fast. Others pointed to a few chores like laundry and doing dishes that they'd like to offload. One added that she'd like to always fly first class.
What's interesting to me is that, except for the big philanthropic goals people listed (which would require a lot of money, like "curing HIV" or "making Texas A&M the number one university in the world") many of the others would take more earthbound sums. For instance, most of us don't travel that often. Four first class flights per year would add several extra thousand dollars to each ticket, but we are talking a few thousand, not millions. And the fun part is that once you started buying business/first class tickets on a regular basis, you'd start getting upgraded on short, not-full flights. For free! Fun stuff. A housekeeper who came three times a week for four hours each time would run about $20/hour (building in payroll taxes). So that's $240 a week, or $12,000 per year. As for getting a different job that required less time but still paid well, if this was a long term financial goal, it could probably be done. It would require some research and training and networking, but we live in a varied economy. There are a lot of jobs out there.
2. Even if you did have all the money in the world (not literally, but all you wanted), what would you not spend money on?
I was flipping through Vogue the other day, and found some pages with a retrospective of the late Alexander McQueen's most avant garde work. I know, much of the fashion is conceptual. But there was a dress that was a grotesque version of the female body, made of the same material as prosthetic limbs, with a bit of horsehair at the bottom. No matter how much money I had, I would never want that dress. I felt the same way about some of the art in the galleries I once visited in Sedona, Arizona. How can something so cheesy be so expensive?
Anyway, I'm sure you can come up with a list too. The point of these questions is to remind us that money is a choice. When it comes to money, many of us operate under once principle: there is never enough. But by asking what we'd do and not do if we didn't have to think about it, we can clarify what matters (and doesn't matter) to us, and start thinking about ways to change our lives to move closer to certain goals.