I spent two decades as a network/pc tech and a systems administrator. When the time came to look around again, I was depressed by the thought of going through the job search, rolling the dice, settling in, performing triage and rebuilding, and then waiting to see how much management would allow to be done right in the long run. In my mind, it was the prospect of going somewhere else, doing the same things again, and spinning my wheels for a few years while I discovered which ways I'd be thwarted this time.
For background, I started off in the military (US Navy) and then transitioned to military/defense contractor (NAVSEA), then to civilian government contractor (USAID/STATE), and then I went corporate. I worked for a law firm, mistook the frying pan for the fire and jumped into the fire, went to work in a drug lab (a pre-clinical drug-development facility), was treated worse than the lab animals, found a K Street (Washington, DC) law firm with a casual dress code, and went back to working for lawyers. After about 5 years, I realized it was time to leave, and I no longer had much interest. Absent a carte-blanche startup opportunity, I walked away. Not the American Beauty deal, but I got 18 months of COBRA paid for, and continuing retirement plan contributions for the same term.
I bought the farm. Mortgaged my house, bought a 10-acre farm in West Virginia, and renovated. When complete, I sold the old house and decamped. Now, I grow peppers and make hot sauce. I keep bees and pack honey. I do what I want, when I want, and I answer to me. The farm's paid for, living expenses are minimal, and my retirement funds are intact. I'm a packrat, and I have a lifetime of collected stuff that's easily sold on eBay as needed. Even with medical expenses, I still have a positive cash flow.
There are many ways to do it. One of the easiest is to flee the big city for the middle of nowhere. My new place cost 1/4 of the old one, the new house is 20% bigger, and I have 80x more land. The trick may be funding the transition. I was lucky, my old house was paid for and I could borrow against it so the new place wouldn't have a mortgage.