We did the opposite, but twice.
Had money. Lost it (first dotcom crash)
Had money again. Lost it (second dotcom crash) - the day before we closed on the house we were buying.
We didnt live very differently when we had money from how we live without. We rarely ate out, and I very rarely bought anything for myself. The only thing I spent money on was books for the kids and for me, and I have to say that I still spend a fair amount on books - just can't break that habit.
My only regret is that we didnt cash in some of our fortune one day sooner so we didnt lose the house.......
Honestly, though, the only time I am sad that we don't have our $$s any more is during crises like Katrina. We still give what we can - but boy, I'd have loved to have had the money to do something really significant to help.