It's a weird feeling to walk out of a store with a bag full of stuff and realize you have no idea how much any of it cost. Whenever that happens I think of that minor scandal when the nation found out the Clintons(?) didn't know the price of a gallon of milk.
I see not having to know prices as one of the best perks of being decently well off. I've had to count every penny when I was younger, and look for cheaper alternatives, and defer purchases, and it made money one of the big stressful things in my life.
Eventually arning enough that I could stop thinking about it other than checking my balance now and again was far more liberating than any of the subsequent improvements in my finances.
But I would like to add to it. Not only is it emotionally liberating to be better off, but it actually frees you up practically as well. Like you said: count pennies, look for cheap alternatives, defer purchases. If I wanted to buy something when I was younger, I would save money for a year, then spend hours/days/weeks comparing prices, waiting for deals, etc. This lingered deep in me, and I had a hard time shaking it as an adult. It's only recently that I can decide to buy something, have a quick look at what's good and where it's cheapest, and then buy it.
I never want to go the other direction and purely equate time with money, but to some extent any of the meaningless time I spent worrying about money I now can make money, and when I don't feel like it, I can have time off, without worrying.
Sorry for the rant, but what I really wanted to get to is: Having money means having time and energy to learn more ~= making more money.
I remember a quote about the best part of wealth being that you never feel like you need to cheat another person.
I can't google the source of it (you get some really weird results about rich men cheating, or being cheated on) but it always stuck with me as something to be grateful for every day.
Obviously, some rich people however, never got the memo.
Seriously. Probably the biggest mentality shift I had was when I stopped looking at receipts/prices. At this point, the only prices I ever pay attention to are travel ones (hotels/airfare).
