Lots of wisdom here, Wil.
In 2010, I went through a similar event and actually sold my telecom/hosting provider for similar change. I thought I’d just live that “passive income dream” from there, live on a beach, maybe SEO a few small content sites. 10 days later, someone from my previous life contacted me asking for help and it spiraled into the agency that I run now.
We’re pre-programmed to chase that carrot in this society but when you get it- that alone is surprisingly hollow. In that first venture, I had a few partners. Our office was in a pretty small town. They’d rotate out new sports cars every month or two and it began to feel alienating from “normal people”. Just like you, here, I’ve since made it a conscious effort not to be an opulent douchebag just because I could.
Since, starting fresh was the best thing that ever happened to me. It was needed. Maybe it will be at some point for you as well. But I’m betting that’s only true if you’re prepared to jump into doing something else great.