‘I have more money than I know what to do with’: I’m a single millionaire with no heirs and don’t like spending. What’s wrong with me?

Dear Quentin,

My problem is that I don’t know how to spend money in a way that helps me enjoy myself or makes my life better or more comfortable. I can afford to spend more than I do — in fact, I could buy just about anything I want — but I have great difficulty actually spending money. I struggle to find things that truly meet my expectations.

A couple of issues come up repeatedly: