Of course, I'd do all the obvious things, such as getting a bigger house, a newer car, and quitting work, but beyond that, I have no interest in an extravagant lifestyle—or at least that's what I tell myself.
By a bigger house, I mean one typical of upper-middle-class living. I've watched plenty of videos of people touring million-dollar mansions, and they all look too big, open, and sterile to me. I've seen cozier tiny homes than those. And by a newer car, I mean a 2017 model or so instead of the 2007 one I drive now.
Really, give me a nice cottage by the lake with some land and a big garage for all my tools and toys, and I'm all set. I much prefer the idea of "hidden wealth" over showing it off. I'm just kind of worried that I wouldn't be able to live up to my own expectations if push comes to shove, and there's really no way of testing that. Am I just kidding myself here?
I feel the same way about fame. Many people aspire to become successful YouTubers or such, but the idea of people recognizing me on the street sounds awful.
You should still recognize that you are in the top 2%, and are wealthy. Poorer people look at what other people are spending money on because it's unfair that so many people can't afford the basics. You have to look around to understand the situation. You sound like you don't other people looking at you... trying to downplay your weath as "well-to-do" or "upper middle class", which we all know are euphemisms. It's ridiculous that you would think of yourself as not wealthy, but also not think twice about a $1000 tab.