It only works if you live near some large body of water of course...
That way you're out of the office and in and out of everybody elses.
Doing contract jobs for a while is great way to use the same skillset that you already have (job qualifications matter a lot less when you're contracting then when you're being hired for some odd reason).
Your new 'interview' will be the 'pitch', where you sell yourself and what you can do.
Start with offering your services back to your old boss :)
Beware though, there is no safety net, no guaranteed paycheck. It's not for everybody but if you can handle the lack of security and you are somewhat business savvy you'll do fine.
You already have outside contracts to get you 'ramen profitable'. What are you waiting for?
Try something completely mad if you want to get out and interact with the world. What about moobile web development? Pull up next to the burger van at you local car boot sale, in your Mr. Webby trailer and offer 'By one, get one free' websites. IDK, just an idea.
Or, you could ditch your office job all together and find a day-to-day "work" activity that does help you feel more connected to the world.
If you can, then any place with a wireless network can be your office... (a good wireless network anyway).
I'm sure I stole this suggestion from someone else, so if you want credit feel free to take it.
While I agree that you shouldn't just pick teaching as your career on a whim, like so many other things in life, sometimes you just gotta try things out to see whether you're good at them and enjoy them. The hard part is moving along when you know you need to.
One of the things I'm examining is a position as a "sales engineer". I would go on the road and help sell, train users, teach, and evangelize the technology. I'd get to program a little (proof on concepts, demos, example apps, etc.) but not sit in an office all day long. Best of both worlds. Stay tuned...