I think the concept of "enjoying your money" is a pretty new one. I grew up in the 60's and 70's and airplane travel was for rich people, families shared one car, etc. etc. We weren't rich, so we didn't expect rich people things. I wasn't an adult, but from my viewpoint there wasn't a "but I deserve to have a daily cup of fancy coffee" equivalent.
I didn't work for 10 years when my kids were young. I was lucky to have the means to do so. I admit I enjoyed when I went back to work and we got cable tv, paid for some activities for the kids, took our first airplane vacation as a family, I got my first cell phone (back when you could still function without one,) we bought a second tv, etc. We didn't have those things on one income, but we did have retirement savings and an emergency fund. We weren't hurting financially, we just didn't have the "extras" and didn't expect them because we were making a choice. When our earnings went up, our choices could change.
I remember trying to explain to my kids why we couldn't afford a video game system. They said "x has one and they're on free lunch." (Kids used to know those things.) We explained that people make choices about how they spend what they have. A very hard concept - and one that is very key.
It was a shock to me when I went back to my college campus and there were coffee stands etc. all over. Back in my day, there was one coffee shop and basically only professors ate there because we all had the food plan cafeteria and didn't want to pay extra.
Life is organized differently now - but it's organized in a way that makes it easy to start to feel like extras are necessities. Thinking about it, it seems like we used to have 3 "classes" - poor, who couldn't afford necessities, middle class - who could afford necessities and sometimes extras, rich - who could afford whatever they wanted. Now we have another class of people who are just plain living beyond what they can afford -and those come from all three of the original classes. I'm not suggesting we all go back to a classest, "know your place" mentality - but if we don't understand the basic live within your means message, things get really screwy.
The other big thing that has changed is that the idea of investing and growing money used to be something only rich people did. Now, without pensions, most of us need to be investing - something we haven't had the mentality for and have failed miserably at. It used to be the poor spent money the minute they had it so it didn't disappear, the middle class used their money to live, and the rich used their money to grow money. Now all of a sudden all of us are supposed to be growing money and we don't know how to make that mentality change.