Since this thread didn’t really take off, I’ll ask a more general question.
Of those of you who, at some point in your life, got fed up with your stable, good-paying, and otherwise superfically desirable (or at least comfortable) job and/or lifestyle, what gave you the intiative to change and how did you stay motivated? By change I mean go back to school, start a new career, start your own business, et cetera.
And how’s that working out for you? 
Stranger
I am in the process of opening my own business because when all this nastiness in Iraq got started I was working for a French company in a VERY Redneck enviroment and (oddly enough) things slowed WAY down, after a long period of unemployment I had to take a job that sucked (things are a little better now, but in my industry the next “bust” (no, the bad kind) is always coming and I am scared.
Unclviny
I moved to another city when it became apparent that I needed to make a big change,
You could always join The French Foreign Legion.
Help support French imperialism in Africa,
I have just started back to night school, to get my master’s in library science. I’ve been in magazine publishing for 20-some years and not only am I sick to death of it, but I’ve aged myself out of the business. A friend in L.A. who is doing the same thing suggested it to me and I thought, “Damn—why didn’t I think of this five years ago?!”
So this “career-change” thing is slow, very expensive, exhausting, annoying (I really resent bad teachers and poorly written textbooks now, more so than I did my first time in college!), and will take three years, I should live so long.
And after I get my master’s, I hardly expect the libraries to be lined up at my door with job offers.
I was laid off.
Since I was in the process of buying a house in Washington, I rather abruptly left L.A. It’s not working out well. I got a job that paid half of what I was making, and I was laid off from that job in December. With the other problems I’m having in my life right now, I’m selling off my stuff. I think that having less stuff will give me piece of mind.
On the upside, there’s a guy in Bellingham who is interested in collaborating on a film or two. I don’t think this would have happened in L.A.
kniz: After losing my fiancée, I semi-jokingly said I should join the Foreign Legion.
I’ve casually followed your posts for the last few weeks, and I’m sorry things are working out so poorly for you. Hang in there.
With regard to “stuff”, I find myself in the same position. I have a motorcycle that I never ride (courtesy of an ex-roommate), and various other odds & ends that I just…don’t need. Nothing big really–I’ve had a rule that I don’t own any piece of furniture or appliance that I can’t carry, and I’ve mostly followed it–but I still worry about having too much stuff. Of course, I also have a terrible and mostly irrationaly fear of being homeless again and don’t want anything I can’t easily and cheaply store. I should really get rid of this stuff.
Eve, I’ve been advised by several people over the years that I should be a writer, journalist, et cetera, and while I’ve more-than-occasionally considered writing a novel or screenplay (or at least completing and sending off a short), I run in terror from the magazine publishing industry. It seems like a very trendy, fickle, cuthroat business, and trying to make a living as a freelance magazine writer seems to be like bailing water into your boat. I’ve known a couple of people who are in library science and though the pay isn’t great–actually, it’s pretty mediocre–they really loved their jobs. Being surrounded by, and participating in the classification and dissimenation of knowledge just feeds one’s intellectual passions. Good luck with it.
Stranger
Yep, that pretty much sums it up. You know the scenes in Patsy’s magazine in AbFab? I swear, they were not even exaggerating. It’s fun and glamorous and exciting when you’re young (I’m talking about the glossy mags, not the industry, trade publications, where I’ve also worked), but by the time you hit 40 you’re dead meat, and all the little 20-something Eve Harringtons are clambering up the ladder past you.
I have enough stress in my life. All I want is a room somewhere, far away from from the cold night air—with one enormous chair . . .
I have two motorcycles. One has a lot of sentimental value, and the other is freakin’ hot! I’ve barely ridden them, since it’s often raining up here. Still, I’m keeping them.
Good rule. The appliances I have came with the house. I don’t have a couch, and the chair I’m using came with the house. The problem is I have too much ‘stuff’. I have lots of toys that I bought because I thought they were neat. It would be nice if I had a place to display them, but I don’t. And I can’t bear to part with my books. I wish I had more shelves, since there are times when I want to refer to one or re-read tme. But most of my stuff is stuff that I don’t need anymore. I’ll slowly get rid of it.
I’ll take a shot at your OP, but I don’t know that my “changes” were quite as radical as what you are looking for. However, I can also relate the story of a friend from high school that may be more to what you’re looking for.
For me:
Leaving my first job and moving to a new location (where I didn’t know anybody), but same basic career. My first job was in the (SF) bay area. And after a number of years there, I got to the point of considering buying a place. This was at the height of the silicon valley boom, so housing was ridiculous (only to get even more ridiculous). I read this interesting article in the paper that described how, because silicon valley had boomed so quickly, that at best, all the modifications to the all the freeways could only play “catch up”. That they would never be “on top” of the situation. This, plus the housing prices, convinced me to leave the area. I had gone to school in San Diego, so I was familiar with how nice the weather is. And I ended up finding a new job there, and relocating. Absolutely no regrets. As a side note, having been completely burned out from my last project, I ended up taking almost a year off to find this new location and job. It was a bit longer than I had hoped, but now consider myself lucky to have been able to take that time.
Leaving job #2 to job #3. Both jobs #1 and #2 were with defense contractors. And though the work was always interesting, and I got to do some cool travel with them, I could see the belt-tightening going on with defense spending in the early 80’s. So I made a deliberate decision to get into the commercial world (there is a tendency to be pigeon-holed into defense work that can be tough to break out of). Absolutely no regrets.
My friend’s story:
This good friend of mine from junior high school, had this desire to become a dentist. But when he got to Berkeley, he was struggling so badly with a number of his classes, he changed direction and ended up as a mechanical engineer (something he was also mildly interested in). He, too, landed a first job with a big defense contractor. And though he made a good living, after a couple years, it really became a grind. He was not really enjoying it, and started to feel “stuck”. At a party of some mutual friends, he met up with an old school friend from Berkeley. Like my friend, this guy also changed majors after having struggled, and ended up as something other than what he had originally set out for. BUT this friend, like my friend, realized that he was not enjoying life, and pretty much chucked it all to return to school and pursue his original career.
This inspired my friend to do the same. And though it was a financial burden (his new wife ended up supporting them in this meager student housing), he quit his job and entered dental school. He graduated, and now has his own practice (he started out joining a practice, and then left to go out on his own). Absolutely no regrets, and he’s loving life.
I guess if I were to give any advice, it would be to try to get a handle on what is important to you. For me, living in a location where I can do the things I like to do (hiking, rock climbing, etc.) was important for me. My work and career are important, but are not as high a priority for me. That’s not true for all people, though.
I enlisted. It squared me away in ways that I desperately needed. 14 years later, I’m still at it, and still learning new things, seeing new places. It was a great decison, despite the hardships.
I hear you. I try to filter through the books and toss stuff I won’t re-read…but then I end up re-reading, and…you know how it goes.
I don’t own any furniture (other than a table of my grandfather’s) that I’d worry about missing. But sometimes I think I should buy a few more/nicer things just so I don’t look like I’m fleeing from justice; it’s kind of embarassing to have people over and have not enough seating. 
Or maybe I should just go with the Bedouin-style of decorating; a few cushions, some curtains, a firepit in the middle of the floor, dancing girls all around…
I could get used to that.
Stranger
I left everything and everyone I knew behind, and moved to Florida from Canada, got married and started all over from zero, at age 38. It’s easily the best thing that’s ever happened to me. I felt like I was stuck in an awful rut in Canada. Here, I’ve been allowed to make of myself what I could, and I’m doing very well. It’s great that it has worked out so well on its own, because I have to make my new life here work, no screw-ups. The alternative is going back up to Canada in disgrace, and I can’t ever let that happen. So, lucky for me, it isn’t a struggle to stay here and be successful, at least anymore. It was a good move for all the right reasons.
I left my prestigious-sounding and occasionally interesting position of 7 years with a Fortune 500 company. Why did I do it? I was stressed to the max, and the job was eating my body and my mind. I had tendonitis in both elbows that couldn’t get better because of my job, plus eczema all over my hands (stress is my trigger). To describe the stress level in my department, it was not uncommon for myself and others in my department to periodically break down in tears at our desks. But the breaking point was a panic attack I had after 4th of July weekend, thinking I would have to face another week of my job.
I knew I had to cut and run, today not tomorrow. I took a temporary job on my best friend’s horse farm (moving across the country to do so, leaving behind my SO). I had loose plans to move overseas (still being finalized) so I knew what the next step would be. In the meantime, my eczema is gone, the plantar warts I had been treating with no sucess spontaneously erased themselves, I’ve lost weight, and my elbows feel great. All in all, I couldn’t be happier with my descision.
My conversion from atheism to Christianity was an enormous and sudden change in my worldview. That might not be what you’re looking for, and I’ve told the story before, so I won’t bother you with the details. But still, it was a remarkable change that I never saw coming.
I also started a company. It did well, but I regret terribly that I incorporated. It was not necessary in my case, despite advice to the contrary. Killing a corporation is like slaying a dragon.