I started this as a response to the "how to keep productive" question, but I'll try to address the other questions people have been asking in the thread later on.
We also have the issue of taking some period of time to get back into the productive zone. What we do is spend the visa limit time in each country. For americans in the UK that is 6 months, for instance. So we rented an apartment for 6 months. In the Shengen zone (most of europe) it is 3 months, and last year we spent 2.5 months in berlin.
In both cases we spent most of the time working a normal lifestyle %90 of the time. After our 2.5 months in berlin we spent a couple weeks traveling as tourists (that's where the other 0.5 months went.)
I figure 2 weeks on either side of a relocation are not going to be productive, so might as well spend half of that time, or so, doing tourist stuff. By having such great breaks regularly, we are recharged and I think more productive when we are working.
The weird thing is, indoors, the only thing foreign really is the outlets... so it feels like we're still in the USA, but then you step outdoors and the language, accents and architecture are completely different. So you can "travel" across the globe every day. It is really hard to explain that feeling but it is pretty powerful.
Taxes & Visas-- As far as governments are concerned we're tourists. We present ourselves this way and we get tourist visas. However, for most visas "tourist" and "business" visas are essentially the same. We don't work in any country in the sense that we don't have a job, we don't participate in their employment schemes. We're taxed like americans (the US taxes your income no matter where it is earned).
As I mentioned we're doing a startup. (We did one and we're just in the process of pivoting so what the new one is at this point is a little vague.) I don't feel out of the technology scene at all-- I have all the same connections I did before we left, except that I can't go to local unconferneces, but I didn't really get much out of them.
There is one conference that I miss that is done in the USA only, but we started buying the videos for it. Spending hundreds of dollars on conference videos sounds expensive, but it is cheap compared to actually going there (Even from within the USA). I don't really miss the networking opportunities-- and we're now networking with a real international network. EG: we network with the locals wherever we are.
The technology scene really is global.
This is a big one. This inhibits a lot of people. However, if you've got an income from your work, and savings to get by in the USA, you can get buy longer when you're traveling. Even traveling in expensive first world places like europe, right now, we're able to live on the budget we were living on in the USA. Overall, we're actually spending a bit less, and we spend a lot less when we are living in lower cost places (even places in eastern europe, which are "expensive" compared to southeast asia, are cheep.)
So, we could have remained in the USA, and spent the same amount of money. I don't think we would have gotten any more work done, and we would have had a lot less fun. Plus, as our product is global, better understanding of other countries helps.
Health insurance: We have the health insurance we had in the USA. It covers us globally. There are specific health insurance plans that cover long term travelers and we might switch, we just haven't done so yet.
Neither of us are under 30, nor are we over 50.
Crazy? You hear a lot of people who knock this idea. Lots of people say "I'd love to do that but I've got responsibilities" or the equivalent.
That's fine... just don't presume we're not doing serious work, we aren't doing a "real" startup or anything lie that. These days startups often have employees spread around the globe... we don't have to carry the whole company with us.
I think people thinks this is harder than it is. Or maybe for some people the idea of living out of a backpack is tough.
Personally, I relish the challenge!
Between my laptop, camera, and assorted stuff, I've got about 7 pounds of clothes etc, and 10 pounds of electronics gear. Every time we-repack, we actually shed some unnecessary stuff. It is a process... but I love it.
Whenever you decide to start a company with your partner, you're making a big commitment. You're taking risk of future reward in exchange for giving up immediate high salary (but horribly no-fun corporate jobs.) Previously we'd done the corporate jobs and the startup thing, and it was time for us to do our own startup.
For anyone out there considering doing what we're doing, the budget is what matters. If you can do this for the same cost of living, or less, than living in the USA, then why not do it?
What I didn't talk about is how much income we're currently making. And I didn't mention whether we were profitable or not, or whether we've passed the income we would have been making if we'd stayed in our corporate jobs. I don't want to go into that, because it isn't really useful for anyone considering this, as you have to make your own determination, but I feel safe in saying that I expect to live more comfortably in "retirement" than I would have if I hadn't done this startup.
Finally, I'm not sure what retirement is, really. I took a long break before, and travelled, and within a week of being on the road I was exploring ideas for starting a company. I had set aside 6 months for myself, didn't have to do anything (and when I came back, I got a job quickly, with the interviewers seeing my "employment gap" as something to be jealous of.) I don't expect I will ever stop working.
But, in my "later years" I do plan to travel more luxuriously.
We missed the date by a year-- exactly the year it took us to get ready for this.
Takes a lot of time to get rid of a couple decades of accumulated junk. That's one of the bigger inhibitions. We didn't put anything but a couple small boxes in storage with friends, we got rid of everything.
Sort of our "burning the ships" moment, but also, the thing is, it was mostly unnecessary.
Like in fight club - we thought we had the sofa thing covered. Forget that. There will be more sofas in the future.
Here are some warnings, learned through experience:
As a foreigner you will often be treated as a second class citizen. That may or may not matter much, depending on where you go, what you do, whether you speak the language, and how many quality contacts you have in your host country.
I found it disheartening but eye opening just how poorly I was treated sometimes just because I wasn't a native, didn't speak the language, or was just being a respectful tourist.
Dealing with the bureaucracy in foreign countries when you're not a native could be a nightmare. It's even worse when you don't speak the language.
Again, speaking the language is also really important if you want to have natives as friends. Far too often expats socialize within a cocoon of other expats. And it's very easy to become very isolated in a foreign land, especially if you're not naturally very social and outgoing.
Flying and various other mechanics of travel might seem fun when you first start, but they'll become routine and maybe even onerous before too long -- especially with the ever increasing hassles of going through security and customs.
As a native in your own country you can frequently get away with a lot of things and talk your way out of many situations that you can't when you're a foreigner.
Foreigners and tourists often get taken advantage of because they don't know the rules, because they're afraid of getting kicked out of the country, and because they get little sympathy from some natives who look at them as nothing more than walking cash machines.
Of course, sometimes foreigners can get away with stuff that natives can't.. especially in the realm of social faux-pas, where a foreigner can be forgiven for being ignorant of local customs. But even here, not everyone is equally tolerant.
That said, I've benefited greatly from travel. It's been a very educational and mind-opening experience. Through it I've met many wonderful people and seen and experienced things I could not have imagined had I stayed in my home country my whole life.
I definitely encourage everyone to travel. But doing so long-term takes a special kind of person who's able to put up with a lot of inconvenience, hassle, and insecurity that you just wouldn't need to deal with if you'd just stayed home. (Of course this last bit wouldn't apply if "home" is some war-torn or economically depressed place compared to the countries you're traveling to.)
Some of the other companies we've heard about are mentioned in this article, but we don't have experience with them:
Sorry, I can't give a definitive answer on the solution, but this is an area where we're still learning.