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I'm absolutely fine with your lifestyle and understand your happiness, but you have to realize that the 3 assumptions it's based on, that you have to be "young, healthy, and single", are all highly mutable.

Which is why I'm doing this now that I can :)

So you are not "never have to work again rich" through software? If you have to work on small projects to sustain your lifestyle, that is working. Work is work even if you like it. But thanks for sharing.

This is not quite on point. But thanks for sharing.

Right over my head. Woosh... My pleasure.

Nice, that a toss-away handle is getting you off.

All new accounts are not toss away accounts. Every account is new one day... Why don't you explain why my first comment is off point. The Ask HN question was "Did you get "never have to work again rich" through software?" gregschlom's answer was "Yes", then he goes on to explain how he plans to work on small projects to support his lifestyle. How is he "never have to work again rich" if he has to work again? It looks like his comment was edited, so maybe the provenance is lost on this little misunderstanding. But I'd like you to explain your snipe at me.

I know some people who live down in Costa Rica and have done that. There's basically two ways to get "rich" in this way: make lots of money, or reduce costs radically. They're not mutually exclusive-- you could basically plot a graph of cost and income/savings where a certain colored-in portion of the graph would be "freedom".

Do you tuck away some retirement savings, or at least rainy-day money?

Not now as I'm living off my savings anyway, but usually yes.

You ever listen to the "Travel Like A Boss" podcast? This is a show about location independent entrepreneurs who mostly do drop-shipping. A lot of them live in and around South East Asia and are from the U.S. It's a lifestyle that wasn't possible until the mid-2000s. These guys make $1000 a month from this online stores yet they live like kings in these low-rent countries. For me it's one of the most interesting sociological developments of the 21st century.

My wife and I live like this in SE Asia. I run a small company, but don't really do a lot now. SE Asia is amazingly affordable.

I was able to keep my US salary, but we live much better here.

This is an awesome lifestyle, however, it's not a lifestyle where you would "never have to work again" as it "only" allows you to travel. However, if at any point in time you want to do something outside of travel, you couldn't do it such as starting a family/sending your kids to college/anything that would require financial independence.

How much savings did you have when you started this.

I'd rather not share publicly (maybe it's just my european mindset, I know americans are supposed to be more open about this) but feel free to email me if you want

How easy is it to find places to rent is these locations? Through Airbnb and such it seems you end up paying quite a high monthly rent.

As someone more or less in the OPs situation (greg), you stay in a hostel for a few days while looking at local ads or knocking on doors. If someone doesn't have a room or apt, they likely will take you to a neighbor who does.

I've lived for many, many months on what people back home (US) spend on food per month. To do this, you might have to lower standards a little and increase the importance of having new experiences. If I wasn't struggling financially for various reasons, but making a very average "US office job" salary while abroad, I'd have lived like a king in the countries I've lived in. As is, I've lived in what I'd consider interesting locations and been in interesting situations, never at risk of going hungry but, frankly, always worried about it. In my early 30s, I'm now rethinking my lifestyle a bit but don't regret what I've lived.

>knocking on doors

Specific doors, or you just approach families and ask them if they or someone else is looking for a lodger?

I'm considering doing long stay travel this winter, and want to figure out some logistics beforehand. I was thinking of renting airbnb for a few days, then looking for something with these characteristics:

  * Private (could be attached to a family residence)
  * Meals cooked
  * Cleaning and laundry handled
  * Not terribly expensive. I speak the local languages of the places I plan to travel to, which should help.

Any experience finding that kind of accommodation, or do you know how you'd look for that kind of place if you had more money?

Not specific doors, just in areas I think I'd like to live. Getting all those characteristics in one place at the same time might be shooting too high but it's possible, I suppose. Finding a place to stay/rent, then talking with the people you're renting from or neighbors, you might have a better chance of hooking up the rest, even from a single person (ie, one person who cooks meals, will do cleaning and laundry). If the people who rent have a cleaning person, you could start your inquiry there.

As for my experience finding everything you're looking for in one place/with one family, I've done that but it was more about lucking out and finding nice people (they didn't even charge for "one more mouth to feed" or laundry). But those items don't need to be expensive at all if from a third party, especially if you're headed to a developing nation (or one hit hard by a crisis, like where I am, in Portugal).

As a side note, in general, the farther you venture from the best spot in the city, the cheaper it gets (and the more authentic your day-to-day experience when compared to the "average Joe") and the likelihood of better hospitality increases.

But in the areas you want to live, you just knock at a variety of doors. They're not places that have advertised?

In Cuba I found a lot of places that offered all of the above, but they're a special case where you need a license to rent to foreigners. That's a good idea about getting a house and then contracting out for work.

How do you deal with trust in those cases?

"They're not places that have advertised?" Correct, some of my best results were from just talking to people about finding a place, knocking on doors, etc.

Trust is tough cause in one case I had rented a room which included a separate kitchen and bathroom/shower (reasonable for the price I was paying, $150). Well, the renter put another person in my room at one point, charging that person the same as me and therefore making double on the same space. In another case, the renter told me I didn't prepay him at the start of the month (something I swear I did) and I had no proof that I did so I ended up probably paying twice ($90 rent, so…). In both cases, I moved out soon after.

The lesson being that sometimes you're going to get worked over (because you're a foreigner) and you just have to take it in stride and move on. The important thing is to be clear, to get written and signed receipts if need be, and to learn to say no if things start to sound fishy or not close to what you expected. Also don't pay ahead, try to keep everything current so that if you do need to move somewhere else, you won't be out of luck because you decided to make things easy and just pay a few months in advance.

>Correct, some of my best results were from just talking to people about finding a place, knocking on doors, etc.

That's the benefit of doing the hostel thing and talking with people that have been where you're going. Some will say what's in your LP and some might have other suggestions. The staff as well -- they might have friends in another city or tell you where they stay, bc it's cheaper for them, and maybe hook you up.

There's also the AirBnB w/o paying: couchsurfing.org - which has been around a while.

personlurking mentioned Portugal - it's been a while but when I was in the Algarve during a summer trip there tended to be some little old ladies always letting their places out. They looked quite nice and, if you were staying a week or more, were reasonably priced. Even better if you find some companions.

exactly what I do :)