Sounds like you've never tried this freedom that you speak of. I've been doing the 3 things on your list for the better part of 10 years now, and I've never been wealthy.
3. Living on the road is no more expensive than living anywhere else. Less usually, since there's no rent or car payment involved. I can live large in Thailand for $500/month.
2. Living on the beach, I once calculated that I needed to bill one day per month to break even. Anything above that went into savings. That leaves 29 days a month to do whatever you like.
1. During those 29 days per month, I work for either a.) myself or b.) nobody. Maybe once a year I'll take a short contract, pull in 20k or whatever, and repeat for another year.
And that's just the level of effort needed for subsistence. Any money earned above that goes straight in to the "retirement" fund, in quotes because frankly I consider myself retired today.
Aren't you extremely wealthy compared to the average Thai?
It sounds interesting for someone in your kind of situation, but there's a lot of assumptions that are not universals: being fairly rich (or having skills worth a lot) off the start, being limited to cheap countries (the parent poster talked about going around the world, which sounds a lot more expensive than and quite different from staying on a beach in Thailand), having skills that can be applied via teleworking and short contracts, etc.
When you return "home", wherever that may be, do you find yourself treated distantly by friends and family? My sister did the world traveling thing for years and though she did send postcards - we found it hard to share the same feeling of excitement for her travels as she did. She is back home now and starting her own family.
"Living on the road is no more expensive than living anywhere else. Less usually, since there's no rent or car payment involved. I can live large in Thailand for $500/month."
When I say "travel", I mean living in other countries for extended periods of time, which as you pointed out, is cheaper than living in many cities in the US.
" Any money earned above that goes straight in to the "retirement" fund, in quotes because frankly I consider myself retired today."
so..are you wealthy or not? It sounds like you are agreeing with me.
3. Living on the road is no more expensive than living anywhere else. Less usually, since there's no rent or car payment involved. I can live large in Thailand for $500/month.
2. Living on the beach, I once calculated that I needed to bill one day per month to break even. Anything above that went into savings. That leaves 29 days a month to do whatever you like.
1. During those 29 days per month, I work for either a.) myself or b.) nobody. Maybe once a year I'll take a short contract, pull in 20k or whatever, and repeat for another year.
And that's just the level of effort needed for subsistence. Any money earned above that goes straight in to the "retirement" fund, in quotes because frankly I consider myself retired today.