I don't think it's that people with money NEVER stress about spending money - it's a matter of degree. Most software engineers are good earners by US standards, and as such, going to the water park for $40 doesn't really register. Buying a $1 soda isn't even worth thinking about. However, buying a $20,000 car would certainly lead to some thoughts like "Can I afford this? What won't I be buying because of this car?" The advantage that a good income provides is that you're not stressing about daily purchases - not that you stress about nothing at all.
This is exactly it. Practically everyone has some legitimate financial concerns but when your financial concerns get to the point that every single purchase feels like it's effecting your bottom line in a meaningful way is when there's an extra layer of stress on your day-to-day thinking.
I find having a good income just brings on the stress of ensuring that you are saving enough for when you no longer have a good income, and so that $1 soda is still a mental hurdle, even if you can easily afford it.
I've found that automating my finances make a lot of those stresses go away.
I don't have to worry about accidentally overspending in my checking account and not being able to pay my bills because my bills are paid from a separate account, and they're all on auto-pay.
Likewise, my savings and retirement investments are automated and I just know that enough is going there. I have a checking account, which is labeled "Spending" and that's what I use to buy groceries, etc. It doesn't matter that it's literally dwindled down to almost $0 a couple times a month because my bills and investments are automatically managed.
My wife and I lived pretty poor for the first 3 years of our marriage, and only the last couple years have I been earning enough to be able to "set-it-and-forget-it" with my finances. The reduction in stress is HUGE, though. Earning more money definitely allows you to spend your time thinking about things that don't cause such stress.
Interesting perspective, but I feel like the stress comes from the idea that you can never have enough saved. Even if you schedule a certain percentage of your income to be saved automatically, what if you need that percentage + N in the future? You are ultimately limited by your income, but within those confines, if you squander a $1 now, you won't have that $1 to fall back on in the future.
