My expererience kind of folds in with Art's. I'm about a decade younger so I'm more of the generation that was influenced by those who experienced the Depression. Everything I did had "security" in mind. I started out my real working days in law enforcement for the security that it brought regarding steady pay, no layoffs, some family security in pension and other public benefits. That doesn't mean that I didn't do foolish things and stick my neck out once in awhile. Risk is the prime rib of life.
I left LE to become a peddler, a seller of insurance products. Talk about a change. You eat only if you sell. But that was a motivator, to make me do what I needed to do to prosper. I didscovered that some risk taking and self motivation brought some rewards; more possessions and a better lifestyle.
But as I grew older I began to see that those folks that I thought were worthy of my envy, (I've never really envied anyone, actually, but I needed some kind of descriptive adjective) had many of the same problems that I did, sometimes evern more. I discovered that my possessions were not what they seemed. I learned that reaching a goal sometimes did not provide the satisfaction that I thought that it would. I came to understand the relativity of ones position. At some point one needs to look around and realize that one is really blessed in many ways, but we don't stop long enough to realize it.
I think that those folks who are the eternal optimists, always happy, successful, having many possessions often seem to get slapped in the face with reality. It seems that their fall is much longer and the landing much harder than for those folks who valued their families, their friends, who might be considered to have litte.
In my view, real happiness is more of a spiritual thing, fed and nurtured by a firm conviction in the fact that I am a unique created being, loved and looked after by my Creator. I stumbled across an Old Testament writing in the Book of Jeremiah that became one of my favorite sayings that when I'm blue about something, tends to buck me up. 17th Chapter, verses 5-8 if anyone is interested.
I think each person sort of gravitates toward what makes them content. Happiness is an elusive thing that none of us really caputres, imho. Like fairness, what the heck is happiness anyway? One man's castle is another man's prison. I know a guy who lives in a 5000 sq ft home with an indoor pool etc etc and 10 million bucks invested safely. But, he very rarely is able to get out of bed because of a serious back problem that is not fixable. Contentedness is a better place to be. It always allows the acceptance of what we have tempered by the knowledge that we could improve our lot if we really wanted to, but knowing that we really don't have to.
Just my $.02.