I always feel very awkward regarding money. We don't know very many people with money and so I avoid talking about things we do/get. My degree is shite, but I landed some pretty nice jobs making good money off it due to experience. We've been fortunate, I cannot deny that. It doesn't hurt that we live in a low cost of living area and have no kids. We paid the house off last year at around 15 years, have no other debt, have retirement savings, have investments (although I suck at that and they are not doing so hot, wish I'd learned more about that over the years), have other properties as well. I started with pins back when they were dirt cheap for beat up ones. I didn't buy any more until I paid the house off. I bought a NiB recently, however unless a dream machine (that actually got fully released w/o the BS) came about, I doubt I would ever do that again. I'm not rich by any means, I am just well off. We are still mid 40's and I could probably quit and work at McDonalds part time if I didn't think I'd hate scrimping (and working at mcdonalds lol). I started my own company years ago out of necessity, and while I did alright, I have no desire to do so again as an actual job.
I know way too many people who died shortly after they retired and that thought really bothers me. Putting all that money away to never actually see it, not that everyone forgoes fun, but still.