Book, bell and candle.
I don’t have any particular reason for invoking the exorcist’s essential field kit, except that perhaps I myself need to expel some little gremlins running around in my brain. As most of you know, I was recently laid off from my job at Workbench Law. It was pretty much the only firm/person I would even have considered working for. I have always had something of a love/hate relationship with law practice. On the one hand I never actually expected to practice law; the degree had more to do with getting the credentials necessary to be entrepreneurial and help others of the same bent. On the other hand, when I have been in lawyer mode, it’s been easy (to a limited extent) and fun (to a slightly greater extent). I completely understand why the job is gone (associates are dropping like flies, everywhere). But now I find myself contemplating a shingle for the first time ever.
The problem (and this is the enduring problem for young lawyers) is that while I am good at some things, I’m not battle-hardened in any specific and expensive way. I’m a newbie. I’m hecka talented, but that’s not enough to make me a good attorney for any schmoe who walks through the door. There are people I might be a good attorney for, but they live and work on the frontier. There is no stable law; the wind changes and all your little bits of paper fly up into the air. The big advances in thought are made by academics, who have both the time and the energy to try to frame the discourse about “how things oughta be.”
So naturally, as I was talking myself out of the notion of going solo this past week, I’ve had two very specific conversations about legal work. Paying legal work. Not “wahoo I can buy a vacation home” paying, but paying nonetheless. Enough to cover the costs of actively practicing law in 2009 (for me, these are fairly small – pretty much Quickbooks and bar dues). And more importantly, the jobs would simultaneously benefit the frontier population, the dreamers and creators and people with big ideas. My tribe.
So with due solemnity I am posting the question to the universe. If you’ve read this far you’re either a buddy or extremely bored. Either way, pony up some advice – how do I resolve the question of what to do?

Sounds like you should take the paying legal work! Even if it’s just enough to cover your costs right now it’s likely to lead to more paying work, and I think the fun factor should count for something.
Go for it.
I actually quit a long term, very stable job back in June because I couldn’t take it anymore, wanted to pursue my own projects/get involved in the PDX tech community, etc. – with mixed results. Ventures didn’t pan out, the economy (and the “savings” I had rolled into the stock market) evaporated, and I waaaaay overestimated what I could do.
Sounds bad? Well in the end, I had spent all of my capital and worked for 6 months building a business that ultimately hasn’t panned out – yet. And in many ways it was the best time of my working life in the last eleven years working in software. I learned a ton, met great people, made connections that are enduring, and thoroughly enjoyed making my own way. In the end I’ve returned to a longterm software contract, but it pays better, is much more flexible, and is a much simpler life than the job I left.
Ultimately what I’m saying is what my dad told me long ago: Leap and the net will appear. I didn’t exactly know what the net would eventually be, but there ’twas. I’m better off as a result, and know a LOT more about how I operate.
So there ya go. You’ll be more than fine if you give it a shot.
So it’s a month later. Did you figure out what you want to do when you grow up?
Enquiring minds are nosy and whatnot.