Apparently this is pretty common. We aren’t that good at predicting things that will make us happy or sad. There’s a great TED talk about this https://www.ted.com/talks/dan_gilbert_asks_why_are_we_happy/...
I think the problem I had was that when you have very little you are quite care free. You take chances and don’t worry about the consequences because you have little to lose and lots to gain. This feels good! But once you actually get somewhere you start to worry about stuff. What if I lose this money? What if I do the wrong thing and it all goes wrong. What should be a great position becomes scary and unstable.
Now would be a great time for some proper reflection about what you want from life that isn’t just about owning and buying stuff. You’ve bought your way out of that game now and it’s time to think about what’s really important to you. I also think Tony Robins is a genius for his ideas in this stuff.