Aigeus, awesome post. Sorry, I don’t have a good answer for you. In fact, I’m in a very similar situation, and am searching for the answer myself.
I'm 35 and a corporate lawyer with a large law firm. I dislike my job for a variety of reasons, and the only reason I go to work every day is to collect a paycheck. The upside is that I am in a good place financially. I'm debt free and have assets (mostly stocks and bonds) worth roughly $350k. The downside is that I know this is not what I want to do with my life, and every day that goes by I feel like I'm just wasting my precious time in the rat race.
My plan is to move on in the first or second quarter of next year. At that point my warchest will probably be up to $450k. I'm single and am not tied to any particular place, so I have a bit of freedom. The problem is that I have no idea what to do next. I begin to feel anxious if I feel like I'm not working towards a goal or doing something engaging, so I need to figure out a plan.
I enjoy creative activities that involve building things or solving problems. When I was in college, back when the internet was just blasting off, I enjoyed designing websites. I could log hours in front of the computer, sometimes forgetting to eat or even use the restroom, working on projects in early versions of Flash and Dreamweaver. I sometimes get this feeling in my legal work. For example I (somewhat) enjoy drafting custom contracts that meet the needs of a particular transaction. The problem is that there is so much other bullshit that you have to put up with, especially in a law firm setting. I am generally more of a thoughtful introvert than an aggressive go-getter lawyer-type, so I don't see myself succeeding in this environment, or enjoying my life even if I do succeed.
These are the options I'm considering:
1. Regional firm - I could move to a smaller market (like my hometown in South Texas) and try and join a regional firm. I think with a regional firm I might be exposed to more of a variety of hopefully interesting projects and generally enjoy a less-stressful career as a lawyer. I could use this as a stepping stone to something in-house for a local company, or to solo practice. I think this is the conservative option. Less likely to substantially increase my happiness, but not a bad move career-wise.
2. Government Work - I could try and find an interesting public sector job, such as working as a prosecutor or public defender or city attorney. I would take a huge pay cut, but I might be able to get fired up and passionate about the work. Also, I don't have any litigation experience, so I could expand my legal skill-set. The downside of this option is that there's a huge risk that I will not enjoy the work. At the end of the day it may probably end up as just another tedious, and lesser-paid, slog that requires dealing with asshole lawyers all day.
3. Solo Practitioner - I could try and set up my own small shop in a smaller market, maybe work out of my house and try and attract clients on eLance. I think this is a good way to maintain freedom and flexibility. Assuming I get any business, I could only take on matters that are interesting to me, and pursue other projects on the side.
4. Non-law - I could try and find something else I enjoy, outside of the law. This is the option that most intrigues me, but is also the most intimidating. I have no idea where to begin. Real estate, web/graphic design, non-profit work, teaching, FBI agent (fuck yeah!)...someone mentioned home inspection. These all sound like they might be interesting fields, and there are probably a ton of other options that could work. Where do I start?
Maybe a combination of option 3 and option 4 is where it's at. What would you do if you were in my shoes?