Those moments when you spend money are the ones that shape your attitude toward money.
Rather than “I have to spend this money”, it should be “I get to spend this money.”
Don’t spend to maintain your lifestyle. That’s feeding an addiction. Spend to make the world better. Give money to charity.
Don’t pay rent to avoid being homeless. Pay it because now you get to come inside and keep your stuff there for another month.
Otherwise, it doesn’t matter how much money you have. You’ll get used to it and then that will become the new normal.
You’re already in the top 1% of richest people who’ve ever lived. But, you’re used to it, so you don’t notice it.
The problem is that there’s a monster you keep feeding who’s never satisfied.
You have to stop feeding it.
(Alternatively, you could just keep increasing the amount of money you have. Up up up up up. Like Jeff Bezos. Until you’re literally in a rocket going up into space.)
Don’t pay rent just because rent’s due today. That’s the problem. Instead, pay because you have a great appreciation for what will happen if you don’t pay, and so you’re paying to change those specific things.
It’s too hard to change your habit all at once just by telling yourself to think differently about why you’re paying.
Read that again carefully, because that’s what all the self-help gurus will tell you to do. But, it’s stupid advice.
Instead, change it going forward.
Spend one dollar today on something that’s purely optional but values-driven.
Then, over the years in the future, you can feed that habit until it overtakes the other one.
Right now, you have an aversion to spending money, which means you also have an aversion to making money.
That’s because the only reason you’re trying to make money is to feed the monster, which you hate doing.
(Disclaimer: this all just occurred to me in the shower today. It seems right, but I haven’t tested it. Any accusations of charlatanism will be dealt with swiftly and without mercy.)