GO FOR IT!
The best times in life come from taking chances. Keep this in mind Joel, you can always return to the boring working world grind. You could always claim temporary insanity, whatever, but it will always be there.
How bad do you want to do this? Really, how bad?
If you have confidence in yourself and that you can support yourself (even if you have to be a beach bartender or something) you'll be able to experience real living without following someone else's time schedule.
If I had stayed at my decent paying, albeit, tedious and restrictive job I would have gone crazy with depression. I made the leap and will never, ever return to working for anyone else. I am now living my life exactly the way I want to. I'm a food writer who does web design on the side and last year I was wined and dined in France as part of my "work". Alain Ducasse's staff treated me like I was a celebrity (you should see my office, a computer sitting in my tiny little kitchen, ha ha). I never know what's going to happen next, but it's possible because I have time to pursue things most people chained to a 9-5 job can't do.
All kinds of things have been happening since I broke away from the traditional route. I get all kinds of gourmet treats sent to me from around the world, Businessweek did an article about me all because of an email I sent one of their columnists about one of her columns. I've dined with Madonna's family at their winery and am able to call her dad by his nickname.
It took a few years, but I make more money doing what I love than I ever could have at the airlines. And, I don't work full time, only when I want to. Just recently, I emailed Emeril Lagasse's editorial manager at Emerils.com. She invited me to become one of the regular feature writers. I'm sorry to brag, but I absolutely love what I do!
If I ever do another column or series of articles it will be to inspire others to go after a real life and quit the rat race. It's been the most fulfilling aspect of my life and I cringe when I hear the horror stories of mother's missing their kids first steps or people only living for the weekend.
Go for it, you won't regret it and you can always find work, you know that, don't you?
Good luck,
Anne
"When caught between two evils I generally pick the one I've never tried before." Mae West