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:

• Establish an interest-bearing fund with some of the money, with the idea of supplementing my income with it. Ultimately the goal here is to replace my income entirely, but not quickly. I want to ease into this and not make drastic lifestyle changes that would clue people in, or fuck me up in the head.
• Establish a fund to pay for my parents’ mortgage. Like I said, they’re not rich. I don’t want to just give them money - in fact, I’m pretty sure that would have awful repercussions - but I want to let them keep a little more of what they earn, and covering their mortgage would do it. I’d tell them I’ve come into a little extra from “work” and that I want to use it to make their lives easier.
• Slowly start upgrading my living situation. Find a larger - but still modest - house to move into, while keeping the existing one as a rental unit. Otherwise, don’t change the way I live very much.
• Figure out a way to ease my kids into the idea that we’re better off now, without ever using the word “rich” at first. I don’t want them to end up like the spoiled kids of other wealthy parents - hence the need to keep lifestyle upgrades modest. “Better off” should mean “Dad has enough money to retire young,” not “we’re moving to a 10,000 square-foot mansion on the French Riviera.”
• Finally, establish the Qu’est-ce que c’est Charity Foundation, dedicated to funding homeless shelters, feeding the hungry, protecting LGBTQ+ youth, and fighting climate change. Making our lives easier is meaningless unless there’s a good world to live them in.

Yeah. I think that’s about it.