Workin' for the Man every night and day

So here's a question that's been coming up a lot lately: How do you define personal success?
For most of my life I defined success only in terms of career. A high-paying job, and therefore money in the bank and the ability to buy stuff, meant one person was more successful than another. That's why I went back to school and got a degree: education was supposed to increase the odds of getting a high-paying job. That's how I was raised. My mom sacrificed a lot to pay the bills, and in exchange I learned that work, sometimes, is the most important thing in the world. Work is what pays the bills, after all. Who cares if you're happy? That's why it's called work. "Welcome to the real world," as my mom's husband used to say.
The other reason I went back to school: my boyfriend at the time was working on a master's in architecture. His best friends were all working on doctorates. Some of them were globally-renowned scholars. All of them were extremely bright, enterprising, and "successful." Then there was me, with my laser-printed film school diploma, working 50 hours a week for a wage that toed the poverty line. I told my boyfriend that I felt "beneath" him and his friends. I wasn't on their "level." He told me that was silly, education doesn't necessarily equal intelligence... but that's the kind of thing you can only truly say after you've been to school, know what I mean? So I went back to school, because I didn't want to be beneath them.
Then H. entered the picture, and his worldview is so different from mine. He doesn't care about money or status or being "equal" with anyone. He doesn't feel the need to put on a show, or pretend to be something he's not. I can't necessarily say he's happy all the time, but it feels like he knows who he is. The other day a friend of ours described him as "just a completely genuine person." They said it was so refreshing to be around someone who wasn't pompous or loud or arrogant, someone who wasn't putting on a show or trying to attract attention.
Maybe this is the lesson I need to learn. I mean, I know my outlook has to change. I've graduated into one of the worst economies in years. Despite what the government says, people are losing jobs left and right. Professionals are taking jobs they're seriously over-qualified for, at drastic pay cuts, just to keep working. I mean, when I apply for a job, I'm competing against people with 10 or sometimes even 20 years more experience than me. It makes sense that people rarely call me back. If I define my life according to my title, or my bank balance, I'm always going to be unsatisfied. And if I set off in blind pursuit of titles and bank balances, ignoring the other parts of life, I might get rich... but I'll also lose all the things that make life what it is.
So I'm redefining the word "success." I still want "a job, a good job, one that satisfies my artistic needs" as the drunk guy says in Sid & Nancy. But a job isn't a LIFE, you know?
If you knew when you were going to die, what would you have to achieve in order to honestly say you lived well?