10/28/2026
What's the best money you've ever spent?
I don't mean the most expensive thing you've bought. Not the thing that got the most attention from other people.
I mean the single piece of spending that, upon reflection, genuinely offered you the most joy.
When most people actually pause to think about this, the answer typically isn't a thing. It's an experience. A trip with someone they love. A class that changed how they thought. A meal that became a memory.
Or, it's the wedding, the honeymoon, the surgery that fixed something painful, or the year of therapy that changed how they think about themselves.
The pattern is consistent enough to warrant close attention. The best spending of most people's lives tends to be relational, experiential, and (more often than not) surprisingly modest in terms of cost.
I love this question because it tells you, with very little ambiguity, what matters most to you.
Most people have never been asked to look for that pattern. They've been asked about goals, about risk tolerance, and timelines, but they've rarely (if ever) been asked what spending brought them the most joy.
It's a small question, but it's one of the most useful ones I know.
