1. the Dynamo. Love your job. Do something interesting, get expert at it, rock around the clock. Examples: Herb Simon, Cal Newport, anyone who works at a nonprofit. Sometimes these people are academics or doctors. They're always driven.
Upsides: you're Making A Difference. It's widely socially accepted. If you're an expert, you probably won't have trouble making money. The hours you're at work are wonderful.
Downsides: work might consume your life. Family and friends will require some effort. Unless you really work on developing your attention, mindfulness, and compassion, you might become a one-dimensional scatterbrained pencilhead. Also, the academic life is not easy.
2. the New Rich. Examples: Tim Ferriss, Chris Guillebeau, any number of bloggers and internet businessmen. Make some money somehow. Do it using the least effort possible. (beat the system a bit maybe.) Now that you have enough money to survive comfortably, spend the rest of your time pursuing any passion you want.
Upsides: how does this not sound great? This, not the 40-hours-for-40-years grind, is the standard of the new world. You still get to be your own boss. Making A Difference is overrated anyway.
Downsides: other people might try to drag you down. It's not as easy as it sounds. The hours you spend at work might be crummy. You might wonder why you're selling Pokemon Beanie Babies instead of Making A Difference. You have to keep up your personal development in your free time, because what is life if you're not somehow learning?
3. the Mercenary. Examples: a couple friends I won't name b/c y'know the internet. Travel around, get a job, make some money, quit your job, live for a while, when you're out of money get another job.
Upsides: as a softwareman, this is totally feasible. It's like plan #2 except when you're not working, you're totally not working.
Downsides: you might spend your life implementing a points-and-badges system for someone's social Web 2.0 AJAX mobile local foursquare twitter blatz. You have to lie to others because not liking your job is generally socially frowned upon. If you start to take it too seriously, you may have to lie to yourself to stay sane.
4. the Monk. Examples: some travel bloggers I guess? Oh and maybe the Buddha but that was like 2600 years ago. Whether you actually become a monk or just start wandering for a long time is up to you. This is always a remote possibility that I will probably never have the guts to actually pull off.
Downsides: don't be an idiot. (honestly. I don't mean this sarcastically. It's a legit choice, at least for a while. But you'd have to take extra care not to be an idiot.)
5. other kinds of specialized lives. Like say you're a lawyer; you'll undoubtedly have different paths than this. Or a field linguist or a veterinarian or whatever.
6. the 40x40. Put in your 40-hour work week for 40 years. Make a lot of money doing something you don't like. Get a gold watch when you retire.
Anyway, there is no great wisdom here besides that I like to organize things and give them names. I'm trying out Career Plan #1 right now; I feel like I could definitely hit it in the academic world. If it doesn't work out, let's give 2, 3, or 4 a try. I wonder if there are any big categories I'm missing.