I once read an article that argued that the difference between people who aren't good with money and those that are comes down to how they perceive it.
"There's an old Yiddish saying that people regard money one of three ways: as blood, to nourish; as semen, to create, or as shit to be thrown away."
- Julia Phillips, You'll Never Eat Lunch In This Town Again
I think it's simpler than you think. I think it's a scarcity mentality. I think that if you have the option to spend more money on something you're less pissed off at the people who exercise their options differently. I think that if you've already got your money earmarked for things you need rather than things you want, you resent anything that people want but don't need.
I've been mixing reality television for like twelve years now. That means twelve years of listening to people talk candidly about how they'd spend their prize money if they win. I'd say 3/4ths of them start with "pay off debt." If your view of a sweepstakes is as a way to return to zero, you have a damaged relationship with money.
And I don't think that's your fault. I think Western society is one where consumption is celebrated, where resources are limited and there is absolutely zero fucking sympathy for the people who can't catch a break.
Wanna see the worst commercial in the world?
These are Millennials. They're spending all their money on avocado toast. Fortunately Wells Fargo will give them a nice, stern,'free financial health conversation' to make them feel bad enough to eat cold, sauceless pasta in the dark.
Freeze-frame on their savings account. They've got $12k in the bank, "100%" of their down-payment on a house. Which considering they're buying from a pirogi truck means they're either buying a used single-wide 90 minutes from where they dine or the food scene in rural Kentucky is far more eclectic than we've been led to believe.
The question you want to have is "how do you spend money?" and I think for far, far too many people, the answer is "stop tormenting me with your thought experiments."