May I join the “off-topic” discussion too? 
I’ve a few words. However, I don’t view this discussion as off-topic. ;D The Big Gundown’s theme is to follow your principles against the well-heeled status quo. So in a way, the way we handle our careers/work/goals is related to our principles and worldview.
A few of you mentioned about the futility of schooling - I completely agree. Much of today’s education is outrageously expensive for one, and not only does it not prepare you for life’s challenges, it can hardly help you get a job that pays well and gives you satisfaction. Perhaps, our post-industrial society upbringings are leading us to have too many expectations?
It wasn’t too long ago that our ancestors didn’t eat everyday, dealt with famines, plagues, wars, autocracies, and they didn’t have the luxury to ask for satisfaction. They just wanted to stay alive and overcome survival. Now it’s different. We have basic needs met (mostly) and the soul longs for more, I think.
I have degrees and I haven’t used them directly in my “career.” Our elders (at least mine) have really got it wrong - education doesn’t guarantee shit when it comes to jobs these days. If you throw a rock at someone on the street in the developed world, chances are he has 2 Masters degrees. It’s that common but uncommon in my elders’ generations where a high school grad is viewed as an asset and is guaranteed a job. I spent most of my 20s in and out of miserable jobs and dealing with general instability. I figured no one is going to give me opportunities, so I started my own thing. I try to keep it low-key and even most of my family doesn’t know. But when they say do what you love, I think it’s true. It doesn’t feel like torture. It gives life meaning. That is far more satisfying. Interestingly enough, it feels like the universe is finally agreeing with my choices, my thing is slowly developing.
Another factor, like Col mentioned, is luck. Whether luck and fortune are written into your fate, you won’t really know until it happens. I’m pretty lucky in the sense I never had to starve or have no one to bail me out, but I’ve also been unlucky in so many areas. I’ve known some well-to-do people and they are not any better in any way, just more lucky. And even the people we consider to be lucky or privileged may be privately miserable. It goes both ways. Perhaps, they envy the people with simpler lives. I’ve seen quite a bit of the poor, rich, and the middle’s lifestyles, and I’ve concluded ultimately everyone just wants to love and be loved ;D
But ultimately, I think guts and courage have a lot to do with success or feeling successful. Just like Corbett had the guts and courage to say no to the railroad baron, we also have to go beyond our comfort zones and risk high stakes sometimes. It takes courage to go for what you believe in.
Friendship, family, and feeling loved and valued are ultimately the only things that matter to us most, so don’t take career crap so seriously.
So… it’s not off-topic and this is about keeping The Big Gundown’s spirit alive!!! ;D