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Born rich:
Much of my life would be extremely different. I grew up impoverished, because my dad is a musician and my mom is an artist. Neither profession is likely to lead to obscene wealth, and neither of them is good at handling money when it comes in. Add to that the fact that they're both hoarders to some degree, and... Well, my parents love me and they're kind people, but a little money might have made some things easier.
Sadly, with their mentalities, I think it might also have caused a lot of damage.
So in this alternate universe, I'm imagining my dad actually hitting the big-time. Mentioned alongside the likes of Tom Petty or Peter Gabriel or something (his musical tastes are eclectic, so I could see alternate-Dad getting rich with a wide variety of musical styles).
What would that mean for me? I'd have good haircuts and clean clothes that fit well growing up. I'd wear glasses that weren't taped together.
Presumably, I'd also have deeply problematic relationships with both of them. And I could see fame and fortune killing my dad early. (He's alive and healthy in this timeline, and I prefer it that way.)
Winning the lottery:
Hoo boy. I think at first, I'd be hesitant to change anything. I'd take the lump sum payment and just... sit on it. Sock it away until I can make all the arrangements I need to make with it. And I'd tell no one except my wife. Not even my kids at first.
I'd keep working while making arrangements, too.
Those arrangements would be:
Yeah. I think that's about it.
How very sensible and levelheaded. Most people I think would rush into buying a house and splashing out on luxuries without thinking how they should make that money last and work for them, and suddenly the money’s disappeared and they’re bankrupt.