I took the time to craft a response to a FB expat forum post about any regrets making the move, that best explains how I view the decision, and actually, pretty much every choice I make these days.
“You really need to decide whether you want the remainder of your life to be exhilarating, or mundane. Really determine which you prefer. If mundane, keep doing what you're doing and wait for death. If exhilarating, understand that fear of jumping into the water is normal, and is a prerequisite to exhilaration, which will usually carry with it risk. The only certainty is death, and what you do between now, and when the grim reaper's hand taps you on your shoulder, is up to you. The only life you get can be spent in innumerable ways, and you get to determine which best suits you.
I retired and moved out of the States 17 years ago. Since then I started a design and construction business, a restaurant business, a winemaking business, and a thriving publishing and writing business (11 years ago, and shifted over 4 million books and been on the front page of the WSJ). I've never been happier. Friends come to visit and are envious of my lifestyle and freedom. I have zero remorse for charting the course I've taken, and my only regret is not doing so 27 or 37 years ago.
Most lead lives of quiet desperation, per Thoreau. But it isn't a requisite. You can elect to have an exhilarating life. First step is understanding that fear of doing so is normal and healthy. Second is to hone in on what really excites you, what wakes you up in the morning with a sense of optimism and possibility, and do it. The desire to avoid change is a fool's errand. Life, by definition, IS change. Use your time wisely. And buy Expat Secrets of Mexico on Amazon - that's my shameless plug - you may find it quite helpful in figuring out a lot of what is involved in selecting a spot that matches your aspirations, and in removing some of the fear that comes from not having answers to valid questions.
Good luck. There are no wrong answers to this one, just roads less traveled.
You know, you have it right. Only live once (I think) Everything changes anyway. How you can manage all your businesses plus writing, etc., is impressive.
After first visiting Thailand in 1983, I moved here in 1994. About 14 years living and working in Bangkok, and then 15 years up-country Thailand where my wife was born. Slap bang in the middle of Indochina.
Small village, 100 houses, surrounded by Jasmine rice fields, and friendly and helpful farmers. The way things used to be growing up in Ol' Blighty in the late fifties and early sixties. During these crazy times, I'm really grateful for where I am