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.

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.

What is it like when you return home?

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.

Apparently, when asked how he does it, the brother quipped, "Most people are too stupid to be poor."

No, for the chance of complete freedom later.

I suppose I could live in a cardboard box on the side of the road and quit my job, but I don't think it would be a very nice existence.

Having enough money to quit your job, buy a nice house, support a family, and travel is the ultimate freedom. You don't have to answer to anyone.

You may be happy with much less, and that's your choice. This is my definition of freedom. It's also why I am working on my own company.

The money isn't even the point. If I could get all of the above for free, I would do it (who wouldn't?). It's what the money provides.

Ahh, but there's the rub. What good is a nice house and a family if you live at the office and devote every waking moment to your startup?

I think those things are nice too. My point is that there are a lot of people who have a house, a loving family, and travel, who are not rich. If that is really your goal, sacrificing your happiness, health and sanity in pursuit of FU startup money is a pretty circuitous way of attaining it.

You don't need to devote every waking moment to a startup to be successful. I devote lots of my time right now only because I am also working a day job. Once I am making enough money and I quit my job, I could easily run it during the day.

I value my free time more than anything. If I was just going to trade in one office slave job for another, I wouldn't even bother.

I would also rather spend my life working on my own projects than be forced to make someone else rich. Have you ever had to implement ridiculous features or work until 10 o'clock (unpaid) because your manager or boss decided at the last minute that something needed to be changed?

"I think those things are nice too. My point is that there are a lot of people who have a house, a loving family, and travel, who are not rich."

What is "rich" to you? It's a relative term.

"If that is really your goal, sacrificing your happiness, health and sanity in pursuit of FU startup money is a pretty circuitous way of attaining it."

When did sanity come into the discussion? I love working on my business. Programming is a passion of mine. I am also pretty healthy. I exercise every day (biking, jogging, and/or lifting weights). I also sleep around 8 hours a night and try to eat a healthy diet.

It's also not a permanent sacrifice. It's only until things get to a level where I can hire other people and or quit my job. School is a 4+ year sacrifice. What's the difference?

I'm halfway through Harry Browne's "How I Found Freedom in an Unfree World" (recommended by someone on HN) and he has an interesting definition of freedom. Freedom is spending more time seeking pleasure than avoiding pain.

I'm paraphrasing, but I think that's the gist of his definition. Good book.

Very interesting definition. Thanks for sharing that.

It vaguely reminds me of Amartya Sen's Development as Freedom, in which he explores how the right to certain opportunities may be as essential to freedom as the right to property.

The connection may only be superficial, but that was a good book too. (Sen was a Nobel Prize winner.)

Negative freedom, freedom from having to do things you don't want, can be had by quitting your job and living in a cardboard box. Don't want to go to work? That's cool, you can just sit in your box, or go for a walk, or whatever.

Positive freedom, on the other hand, can really only be had in this society by accumulating money. If you want to buy a house, support a family and travel, then you need to have the cash to do so.

Of course, if you get enough money, then you can have both. The converse isn't true. But that's difficult to do, and it certainly is a gamble. I think you and the OP just have a different idea of where it's desirable to be on the continuum from -ve to +ve.

When has it ever not been? In pre-modern society people still used some for of currency to obtain things. You could technically live a "free" life without money, but your existence would be even worse than it is now.