when you buy a leather jacket, don't go for a pilot-style jacket, they scream midlife-crisis.
go for something chique, like
http://www.belstaff.com
i think, when you're in a midlife-crisis, you shouldn't sit in a pub and be frustrated, but you should live your life and enjoy it. so waste some money on things you like, but don't think about the money, doesn't matter. just buy yourself what you always wanted to have.
a lot of people say: oh look at this guy, bought himself a sportscar, what a midlife-douche. but the truth is: the men who buy stuff like a sportscar won't feel empty inside, they just re-discovered the fun in life.
(since you're only 33, you could still start to go after awepittance's idea but bang girls from like 18-22)