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Ask HN: Living overseas with a profitable online business
113 points by SteveC on Oct 3, 2010 | hide | past | favorite | 95 comments
I am a UK citizen with a profitable online business. I have no real responsibilities other than that and I would like to try living in a few different countries for a while before I have to settle in one place. My web business means I can work from anywhere as long as I have an Internet connection. Has anyone here in a similar situation tried this? What sort of hurdles did you face with visas? How was tax handled? Did earning your money online make things easier or complicate matters?



I've done it for a couple of years (5 in all), from the Netherlands to Canada.

It cost an arm and a leg, but I wouldn't have missed it for the world.

As for taxes, the rule in my case was that as soon as I spent more than half a year per year in the one country that one became the one where I paid my taxes.

I did create a corporation in Canada in order to have a bigger footprint and to help with the immigration process. Eventually moved back to Europe because the immigration process seemed to take for ever (of course, two weeks after letting everybody go and moving back to Europe we received permission to become landed immigrants).

I wouldn't do it again with the same country, but really, it was a very nice time.

If an opportunity presents itself to move abroad again I'll probably take it (as long as it is not the USA or Canada).

Nothing broadens your horizons and teaches you stuff than moving to different places on the planet.

Asia in 2013? Who knows ;)

Earning money online made stuff considerably easier, it meant that no matter how rotten the local economy was there was always food on the table and transportation.

Health insurance is different per country so you'd better check in to that in serious detail before you make your move, there can be all kinds of limitations and liabilities if you mess that up.


But, I keep hearing and reading all of these "horror stories" about people waiting up to even TEN YEARS for immigration applications to get approval, particularly in Canada. The minimum I've read has always been over a year's wait, which still seems really long to me in this age of instant gratification.

Did you just go to those places as a visitor and lived there while applying for a more permanent residency or did you do a temporary work visa or something else?

These questions coming from an American wanting to immigrate to Canada as a first choice, but is seriously looking at S and SE Asia as well.


Ten years is not that bad actually, I can point you to a family that has been living there for 30 years and they still don't have their status.

As for the process, there are different 'routes', I picked the entrepreneur/investor route through the Buffalo office, I was / am fairly well connected and in spite of all that (and employing a bunch of people and some major investments).

My visum was a temporary work permit until landed immigrant status would be given but I never reached that stage.

Canadian immigration usually was quite ok when dealing with them at the airport (once every two weeks for two years), but I've had my frustrating encounters too, with hours of waiting to be sent on my way within 2 minutes of it being 'my turn'. Road crossings were a mixed bag, sometimes no problem at all, sometimes a big hassle when someone decided to pretend they're guarding Canada from all those Dutch terrorists they've been having lately.

We ended up going back because we had had enough of it. The schools in the area where we lived (rural Northern Ontario) didn't help either and the weather is simply brutal out there.

But again, I do not regret having done this, it gave me a completely new perspective on life and living.


There's an absolute ton of info to be had by trawling through the wiki and forums of British Expats:

http://britishexpats.com/forum/forumdisplay.php?f=33

Last I checked it was taking around 9 months if you could make your skillset fit in to one of their priority job classes where Canada is experiencing skill shortages. It's much quicker to get a temporary work permit if you can find an employer to sponsor you, and then apply for residency once you're here (which is what i'm doing).


this is very good insightful experience.. I am also thinking to work from one remote village where basic needs like electricity and internet available..

Enjoy the lively weather, nice friendly community surrounded by. As you raised, health insurance that is one very important thing to consider. In some part of world, the health facility are not upto the mark. So in case of need, there may be some issue. Except that it is wonderful to work where ever you wish to.


Can you advice a good place to check health insurance in serious detail? I would appreciate that.


It seems to me all the answers so far make it look far more complicated than what it actually is.

What I've done is just travel as tourist staying in each country around 3 months.

When I "lived" in Chile I just took weekend 'visa vacations' to Argentina and had my stay extended for another 90 days.

Nothing changed in terms of taxes for me, since I never really become resident of another country.

Earning money online definitely makes things easier since you never have to be paid as a local in whatever country you are at, therefore, not working there illegally or anything like that.

I am not sure how much money your online business makes you, but I usually aim for developing countries, where you can easily live on US $800 - $1200 tops a month. Like bradleyjoyce said I would recommend Latin America. I've lived/traveled/worked in Colombia, Chile, Peru, Argentina, Mexico.

Also, very important, make sure you have someone reliable back home that can help you deal with administrative/misc., stuff like depositing a check, receiving important mail, faxing stuff, and the sort of things you may not be able to do online.


This is great advice. I've done something similar and found that after about 2 months you can get a flavour of what life in that country would be like. It's a fantastic thing to do, and it will completely change your perspective on life in the UK!

It's incredibly important to have someone you can trust to take care of admin issues at home if you're gone a while though. My parents helped me out, but a lawyer or accountant will also work - but cost you a fortune. Possibly you can hire a temporary admin assistant, but make sure you trust that person to look after everything while you're gone; you never know what will happen.

The only problem that I've found has been getting a reliable internet connection for a couple of months at a time - if you have to work on sensitive things or you want to work on things for a long time, you don't want to work from public hotspots. I'd love to get some advice for that situation myself.


You make a deal with the a really nice internet cafe with a good connection. All the kids speaking in a foreign language going crazy over video games might be distracting (especially when school comes out o_O), but it's like a rentable AC office with a good connection and cheap drinks and snacks.

Or can rent a apartment that comes with it's own landline internet connection. The landlords can set it up in their name for you and it would be part of your rent.


You can usually find furnished apartments/room with internet included. In Buenos Aires and in Chile I found mine through craigslist.

Santiago: ~USD$250/mo all inclusive (with flatmates) Buenos Aires: ~USD$480/mo all inclusive Studio


Cool. My problem has been finding a room for two months with an internet connection - often there's a minimum period. It's not so bad if you like living with people, but if you live alone...

The idea about the net cafe is a nice one though - maybe I'll try that next time! :-)


This can work in some places, like South America, but not in others, like Europe. In Europe you get a 90-day tourist visa within a 6-month period, so if you stay for 90 days you must leave for and stay out of Europe for another 90 days before you can return to get a new tourist visa.


How did you like living in Peru? I've thought about getting an apartment there for a short while and work on developing my business.


I can recommend Ecuador. I am currently living on the beach in luxurious apartment with see view, swimming pool, safe gated community , 2Mbit internet connection for $900. All done through AirBnb


Peru is beautiful, but I'm not a fan of Lima's weather (think seattle). So for travel+fun I'd recommend just landing in Lima and going elsewhere in the mountains. If I did not have to recruit engineers, meet entrepreneurs or do biz dev, I'd def. stay in Cusco for a while.

The food and transportation is very affordable, and really really cheap if you don't go to the touristy restaurants and instead head to el mercado (marketplace). You can get a full meal with soup, drink and dessert for like US$.60-$1

Now, if you want to meet fellow hackers/entrepreneurs and recruit incredible talent, check out http://limavalley.com the startup/tech community in Peru.


The domain name seems to be wrong or expired.


You are right (I know my comment is old) but just in case,here is the correct url http://lima-valley.com/


I've been doing that for a few years now, first working in Japan, then living for some time in Malaysia, Thailand and China before deciding on settling here for some time..

For Japan, I was working there for a Japanese company so it's a bit different...

For visas in Malaysia and Thailand, I just switched between both countries for 2-3 months at a time (but stayed more in Malaysia), so I didn't need a visa for such a short time (as a french citizen). Since, my official country of residence at the time was france, I didn't have to pay any taxes. One word of caution, after one year of doing that it started becoming harder to get in Malaysia... So, it's not a long term solution...

For China, I've been here under a business visa. According to Chinese law, as long as I'm not a permanent resident (stayed more than 5 years with less than 90 days each year out of the country), I don't have to pay taxes on income outside of China.

Regarding health care, I'm using this insurance www.aplusii.com It's aimed at expats, costs 300 euros/months for me and my wife and covers us everywhere in the world except US and Canada (and then it does cover us there in case of accidents). I found them through a broker and would recommend you to consult one just to make sure you are covered in case of problems.

To keep costs low, it's a good idea to try and rent apartments for at least one month in each location instead of going to hotels. You get a better view of how people actually live there and it's much cheaper.

You can contact me if you have any questions (or decide to drop by in Shanghai), my email is in my profile.


> Since, my official country of residence at the time was france, I didn't have to pay any taxes.

I'm sorry, but I have hard time believing that. Since you were still a resident of France I'm sure you have to pay some tax to France in some shape or form.


Being a resident and being a tax resident are two completely different things. There are a few Asian countries (I believe Thailand) is one where you only pay tax on income if you're classified as a permanent resident. If you're on something like a 90 day business visa then Thai tax laws don't apply.

Contrast that with somewhere like the UK where you're deemed a tax resident only if you've been resident in the country for >= 178 days in the financial year (regardless of visa status). Combine the two scenarios, carefully managed, you can greatly reduce the amount of tax you pay.

It cuts both ways though. Somewhere like Australia which has a different tax year to the UK and it's possible to incur a tax liability in both the UK and Australia. You'd need to submit a return in both places, thankfully they have a tax treaty with each other to avoid paying double but you'll still need to submit returns to both.

But back to the OP, it's exactly this kind of approach wealthy individuals use to avoid paying taxes. Claim tax residence in a country that only wants your money if you're actually living there, live somewhere else that only wants your money if you're earning it in that country.


US is rare in that it declares the right to tax its citizens' income wherever they live. Most countries don't do that.


This article is pretty interesting: http://www.reddit.com/r/IAmA/comments/aejc4/i_work_through_a...

"I started freelancing in LAMP development 7 years ago. 4 years ago I started taking camping trips around my own country (Australia) & working via Wifi/3G. I soon started making little overseas trips, which got bigger & bigger. In November 2008 I sold my stuff & 'left'; I haven't been home since. I usually work 1 hour/day thanks to the weaker currencies of most places I visit. In richer countries, I work 2-3 hours. 3G modems & hotel WiFi keep me connected, an Australian SkypeIn # forwards to the mobile of whatever country I'm in at the time, Skype lets me call clients when necessary. I'm currently in Nepal having just got out of Tibet. I'm trying to get from Singapore to London without any planes (southern route --> SE-Asia->China->(Tibet)->Nepal->India->Pakistan->Iran->Turkey->Europe). AMA."


I just recently moved from the US, where my own company is based, to France, where my wife is from. I am still learning about the complications, but I can tell you of some of the challenges I've already dealt with:

Currency exchange: rates fluctuate on a regular basis and that makes budgeting a challenge. Sometimes you win and sometimes you lose depending on how the currencies move.

Insurance: health insurance by a provider that is outside your country of residence is going to result in some hurdles. You'll have to pay close attention to what your providers rules are for coverage outside of your country.

Visas: as long as you only stay long enough to stay qualified as a visitor then visas are probably going to be a non-issue. Once you exceed the amount of time allowed as a visitor then you have to deal with that countries rules for visas and they differ from country to country.

Cash, check and credit: acceptance of credit cards and checks in foreign countries will very. Banks tend to charge fees for withdrawing money in other countries so be prepared to eat those fees. Often it is easiest to just use cash, so take enough to get started and have a plan on how to get more while you're there, i.e. figure out where the cash machines are, if they accept your cards and what the fees are.

Tax: IANAL nor am I an accountant or tax specialist and I am not sure how it works in the UK. Having said that, the US is a bit odd in that they tax their citizens worldwide, so no matter where I live I will have to pay US taxes. If I am a resident in another country then I'll likely have to pay taxes there as well and then try to get a credit in the US for taxes paid overseas. It's still early for me on this one so I'm not sure exactly how taxes will pay out.

I hope this helps. Basically my suggestion is retain your UK residence and take extended "vacations" in countries you want to visit - it'll be a lot less of a hassle then trying to immigrate.


While the US will tax you as long as you are a citizen, you can take a credit for any foreign taxes that you already paid on the same income, which should prevent double taxing unless you happen to be in a very low tax country. If you had some kind of business setup to collect the income in the foreign country you could probably keep a lot of profits in the business and not claim much income for yourself, but it is something you'd probably want to talk about with an accountant and is probably different in the UK (I love UK tax forms by the way, so simple compared to ours!)

As for actual experience, I had a great time in Buenos Aires. You get 90 days visitor visa with a US passport and there is a good size population of ex-pats that take a weekend trip to Uruguay when they get close to 90 days, turn around and get another 90. A bunch of them make some cash teaching English and keep it all under the table, which I don't really recommend (I mean they still get you on VAT, but you don't want to mess with any laws in a foreign country if you can help it), but it isn't a bad place to be.


I hope this helps. Basically my suggestion is retain your UK residence and take extended "vacations" in countries you want to visit - it'll be a lot less of a hassle then trying to immigrate.

You will want to be very, very careful with that. I'm neither a lawyer nor an accountant, but the tax rules for US citizens are very different from pretty much everyone else. Tax authorities will generally not be happy if you try to pay no tax locally and send it all home. The rule is typically that you pay tax where you spend the most number of days of that tax year. No idea what happens when tax years for natural persons don't overlap (UK has April-April, many countries have calendar years) - in my case I didn't earn any money in the interim so it wasn't an issue.

Within the EU, you'll probably need to register your new residence as the, or one of the company's offices where its business is conducted. You don't need to register it as a business of that country, though, unless you're a sole trader. Any salary or dividends you pay yourself will usually be subject to local taxes, social security, health insurance and possibly other fees. Your accountant(s) will need to tell you where the business pays tax on its profits.

You may also require a permit for operating a business in that country. I did (UK citizen, located in Austria), and although software development is usually not regulated in the way the medical, legal and other professions are, I did require a certificate of any record on the UK Police National Computer, or rather lack of any record. This took almost 2 months and cost 10 pounds. I managed to sweet-talk the bureaucrat in Austria into not requiring an official translation, but the rule is that you do - this will add extra cost and time.

You may also require a residence permit, even within the EU. That too tends to be a mere formality, but usually they want proof of earning enough to sustain yourself. Not a problem if you're a UK limited company, you'll be used to your income being a matter of public record anyway. I didn't need this in Vienna, but a German friend in another State (Lower Austria) got an unpleasant visit from the immigration police.

UK->EU specific, but: you can forget your E111 for anything but emergencies. You'll probably be forced to get local health insurance (in Austria they write to you and bill you as soon as you register the business) anyway.

Hopefully, you'll encounter less hassle - Austria is exceptionally hostile towards the self employed, and taxes are insane.


For almost every set of countries in the 'matrix of possibilities' there is a tax treaty in place these days, your local tax office should be able to tell you quite a bit about the situation once you've settled on a country of your choice.


"You will want to be very, very careful with that."

You're right. You probably want to find a good tax attorney or accountant that is well-versed in the tax laws and treaties of any and all countries you plan on spending time in, especially if you plan on doing business locally.


My understanding is that under EU treaties, EU countries are obliged to treat companies formed in other countries the same as local companies, i.e. the government can't discriminate against you for having a company registered somewhere else.

Indeed many EU startups are officially headquartered in the UK even if they're based elsewhere in Europe for the favourable legal and tax implications.


[deleted]


This won't affect you if it's literally just a short vacation or even a business trip[1]. However, even if primary residence is only de-facto (generally, more than half a year spent at that location) you will probably be on the hook for tax. So beware of that 27-week holiday or business trip.

[1] exception: if you actually take payment in that location, e.g. selling stuff at a trade show, you need to register the business at the location you're visiting for that time as you are now operating from that country for VAT purposes. Ugh! VAT is a whole new can of worms anyway.


So what's the situation if you spend 3 months in 4 different countries each?


Ask an accountant. I suspect you'll be more or less free to choose your primary residence as long as you actually maintain an address there. But seriously, with any of these things it's best to talk to someone who knows the ins and outs of the tax laws of the countries you're visiting.


I would totally agree with the "extended" vacations it's going to give you less grief then trying to understand tax law in every country. Plus proving to your home country your really living abroad.


Sorry, refusing to understand local tax law, or refusing to pay someone who understands it is terrible advice. Ignorance is not a valid defense.


Part of understanding may also be understanding what you can 'get away with'. That sounds bad, but may well be a fact of life in some places, especially if you're not really invested in staying there for the long haul.


Yes, absolutely. This may be as simple as periodically leaving the country for short trips, but you have to know.


So if your a citizen of the UK and your earning income online to your UK business what does concern does say Guatemala have on your money if your living there on a tourist visa. No money is being created locally. You going to start a new business in every port you land on? Do you pay taxes to the local government when you go on vacation?


There is a difference between a vacation or business trip and residence. Many countries will treat you as resident if you stay there for more than half of the tax year, regardless of whether you say it's a holiday. It's quite possible that some don't, but you'd better know for sure.


The optimal solution in that case is to have your UK company earn the money and pay you a stipend on which you pay local taxes if UK taxes for corporations are more favorable than in the place where you live.

But really, you should consult an accountant or tax advisor for hard information after you have decided on a country to go to and for how long you intend to be there.

As a rule, < 3 months -> no problem, > 6 months = residence, in between, gray area, leaning towards 'extended holiday'.


Since last May I've been spending increasing amounts of time in Perú doing just that. Recently I've finally made the move more "permanent" as I've rented a house here in Lima and plan on staying a least a year.

The easiest way to go about it is to maintain your permanent residence in your home country and enter new countries as a tourist/visitor.

This officially means that you can't "work" in the country you are visiting. However, as long as your clients are not local and you get paid to your bank account in your home country, you should be ok.

I would highly recommend you review your tax situation for your country, and especially the country you will be visiting if you want to stay longer than their tourist/visitor visa allows.

I'm going through all this myself and have started blogging about it at http://expatentrepreneur.tv ... A lot of other people blog about the expat digital lifestyle. One I enjoy reading is http://exilelifestyle.com and he has links to quite a few others.

I highly recommend South America to you... it has a fast-growing tech/startup community (Chile, Brasil, Argentina, Peru) and there are tons of expats as well.

If you make it to Peru feel free to look me up!


Don't try working from Brazil; I tried doing it, but I just spend the whole year going out, partying and the beach. Never got any work done, but was the best year of my life.


Or you can go to a place in Brazil where there is no Beach ;-) Just curious, where in Brazil you went?


Rio de Janeiro. Highly recommended :)


Check out expat forums--there are a whole host of countries (largely Latin American) where you can live there on a tourist visa; every 90 days you take a weekend trip to a neighboring country and get a new tourist visa. Since you have an online business you won't be working in the local economy so work authorizations and the like won't be a problem.

Also, these countries tend to be really cheap. I know a woman who lived off of blog revenue in Costa Rica; mostly affiliate links to online gambling, which isn't feasible ever since the US government outlawed online gambling.


Another good source is online poker forums. The biggest is 2+2. Plenty of card players have moved abroad and play remotely.

http://forumserver.twoplustwo.com/92/travel/


Could you recommend some expat forums, actually?


Well you can start a corporation in singapore, panama, labuan or others. All foreign income not repatriated to singapore (i.e, it goes in a bank account in HK instead of singapore) is tax free. Panama corporations do have any tax in all income not derived from Panama. Labuan (in Malaysia) has an other low tax structure.

To avoid UK (and Canadian) residents doing a run around on their tax system with these corporations, any corporation who's 'top management' is majority run by residents in the UK (or in the UK) is taxed as if it is a UK corporation. Since your going to be away from the UK, you can remove your UK resident status (you have to do this properly, they can get you with things like still being registered to the NHS or having a residence in the UK still that isn't purely investment property, etc, etc). Once you loose your UK residence (you still stay as a UK citizen forever, your just not resident) your corporation will not have that tax status in the UK, and you do not have to pay taxes to the UK for your worldwide personal income. I don't know how it works when you move around in the EU, it can be different.

You can then travel the world as a resident of nowhere and be mostly tax free, with the majority of your income staying in your corporation, and drawing a living expenses income from the corporation. How you want to structure that income (being a corporate expense or personal income), and report it to the country your currently in depends on you and what your doing. It being an online business of you and your laptop, practically you'll not get any problems from working online on whatever tourist visa your using, since it's virtually undetectable and you don't really have to interact with their economy locally. Especially if it is only for one or two visa stays and a developing country. How you deal with that is up to you.

If you are going to plan which countries your going to, getting a tourist visa before you leave at an embassy in the UK will be useful, since you can get extra long visa stays vs the stamps you get arriving in the airport. For example you could get a triple entry tourist visa from thailand for free which would get you 3x2month stays in thailand. Your not going to get that from a embassy anywhere near thailand, but somewhere far like the UK would be a lot more likely.

For health insurance you can try to get an annual international travel insurance policy if you want to be covered.

I am not a lawyer and you should do your own research, but I hope this helps.


Tunisia (My country) may be a good place for you. When re-searching on how to start my own company, I found out that non-residents can easily form a company over the Internet and submit all papers (even without being here). Taxes are 10% but if you sign before 2011, you'll pay no taxes for 10 years.

Here's the website in question: http://www.tunisianindustry.nat.tn/en/home.asp It's in English and has lot of useful information. There is a section for online services and they'll answer your email within 24/48 hours. The cost is $100 or so, to form the company.

Life in Tunisia is good but not that cheap. You'll also miss your reliable Internet connection (though Water/Electricity are a lot reliable). The weather and food are good. Public services sucks, so you'll need your own car (for example), private medical care, ...


Tunisia (Few facts from wikipedia)

Northernmost country of Africa Official Language: Arab Second Language: French Population(1st july 2009) : 10.3 million (appox)

Tunisia has an authoritarian regime in the guise of a procedural democracy led by Zine El Abidine Ben Ali, who has governed as President since 1987 and has systematically diminished freedom of press and political pluralism while keeping appearances of democracy.

It also has one of Africa and the Middle East's highest per-capita GDPs (PPP)


I agree that other people here are making this more complicated than it has to be. Just go from one place to another on a tourist visa for the country you are visiting. Continue to pay takes in your home country and keep your work on the down low in the country you are visiting. You would probably be walking (if not crossing) some thin lines in regards to laws against working while on a tourist visa but I doubt you would have to worry about getting caught.

The only thing I have really found difficult is dealing with payment issues. Moving money in its many forms can be a pain. This is a big subject which is highly personalized for each person, so I won't get into it here. Just make sure you have a plan a, b and c for getting access to money and contacting your family when problems appear.


I'm quite in the same position like you (web business), I tried to go to the US for one year, but the visa progress is hell, too over one year to first tell us it is going to be ok, later revoking it. The US visa system is seriously broken. Other than that issues, I think its a great idea.


    The US visa system is seriously broken.
Seems like it from here too.

If I were the OP I'd stick to the EU, Australia or New Zealand (both of which have fairly liberal immigration policies, especially for UK citizens).


If I found myself in your shoes, i'd probably be planning an itinerary with one of the round the world tickets offered by the various airline alliances. They're really good value and allow you to see a heck of a lot of the world. And keep in mind you can use the round the world ticket to get to, say, Hong Kong (I love it there - recommended) and then use local budget airlines to hop between South East Asian countries over a few months, and then continue on with your round the world ticket to Australia or elsewhere.

The round the world ticket more or less forces you to keep moving as it'll only be valid for 12 months, and so you should be able to get by by just using tourist visas in each country. After a year of hopping around the world you'll be in a position to know whether you want to keep being a nomad, or if there was somewhere you visited that you'd like to go back to a little more permanently.

(Keep in mind that if you turn up to pretty much any country and say you intend to stay for 1 or 3 months as a tourist they'll want to know that you can support yourself - have your bank statements handy!)

But, yeah: go travel. Do it now before you start putting down roots. I once bought a round the world ticket to do 12 months of backpacking. 14 years on and i'm on my fourth country that i've 'permanently' settled in, with a fair bit of traveling thrown in along the way.


Absolutely don't buy a RTW ticket.

Definitely go around the world, but do it by purchasing a single one-way ticket. Travel overland as much as you can and when you hit the end of a continent, buy another one-way ticket to the next.

There's nothing worse than having a date on a calendar. It will mess up your trip over and over again, even if it's months in the future. Avoid dates at all costs. Get to the first place and let things work themselves out from there.

I've done 3 laps now, and the only regrets I've ever had have been things skipped to catch a flight or meet somebody at a fixed time/place.


RTW tickets are cost effective. You can usually pay some extra money to massage the dates, and it'll probably still be cheaper than buying tons of tickets (at least when I bought one... not sure how the prices have changes since)


Cost isn't what you're maximizing though. Sure, RTW ticket will run you $1500, whereas three one-way tickets will cost upwards of $2000, but compared to the $12k you'll spend all in, it's just not worth the constraint it places on you.

As an example, five years ago I started a trip that would start on the beach in Thailand, then go up through China and follow the Silk Road across to Turkey. 3 months in, I ended up detouring down to Australia to do a couple month's surfing with a girl who I'd eventually follow back to England and marry.

Had I booked, say, a flight from home from Istanbul ahead of time, I might not have wanted to blow it off and follow that girl who I'd only known for a month.

Traveling is all about freedom to do whatever you want with absolutely zero constraints. Keep that in mind before you buy a piece of paper that forces you to be anywhere at a given time. Even if that anywhere is "Asia" and the given time is "Sometime in the next six months". It's still a constraint, and it will still mess things up.


Yeah, exactly. When I had my RTW ticket you were buying a certain number of miles, a certain number of stops, and 12 months to get back to where you started. You had to book an itinerary when you started, but were free to change it as you went along...

It's waaaay cheaper than buying a series of one way tickets, assuming you make it around half way in to your itinerary (and there's nothing to say you have to use the last leg to take you home - abandon the ticket if going home somehow means your traveling will finish forever).


Costwise this kind of depends on where you're going... overland bus travel in Asia is much cheaper than, say, taking a train domestically in Germany.

But I totally agree on the schedule part. Every time I've booked in advance something has come up that has made me have to change plans, and I've regretted it. Buy one-way tickets and no more than a month in advance.


Have you been travelling alone or with a friend / girlfriend / wife?

I want to do this as well, but the biggest question for me seems to be who to go with or going alone (and then just trying to meet people everywhere)?


Initially, it was just me. Every once in a while I'd manage to convince a friend to fly out and tag along for a few weeks, thus putting one of those dreaded dates on the calendar, but in a good way. Along the way, I picked up a partner who was doing pretty much the same thing. We've scaled back the traveling a bit recently, but I did manage to drag her around South America for 7 months this year.

I'd recommend going by yourself if you have the choice. You just plain meet more people that way, and you don't run the risk of killing off a perfectly good friendship. On the road, you'll notice the same pattern a lot of times: two English girls who have been traveling together for a couple months and have clearly tired of each other's company but are too polite to suggest they go their separate ways. They're miserable, neither one getting to do what they really want, and forced to eat every meal together even though they've already exhausted all the conversation they could ever come up with. Sit down at their table and you'll instantly have two new friends.

Another benefit of traveling alone is that even as an introvert you'll periodically go into "emergency survival social mode" where you realize you haven't spoken to anybody in four days and you need to make some friends Right Now. And you will. It's as simple as walking up to any random gringo and asking "where are you from?"


Don't feel like you can't take more air tickets for short haul trips! What is a better use of your time, a 10 hour bus ride for $25 or a 1 hour flight for $50?


Depends on why you're travelling. Ten hours of seeing the countries you're in might be more gratifying than two hours of being treated like a dangerous animal at an airport and one hour of biting your knees in a plane.


I'm a fellow Brit and I've been running my web biz whilst travelling for about 5 years and totally reccomend that you do it. The visa's taxes, and banking thing can be tricky and is always changing but once you've made the jump it only gets easier. I have been running my online businesses whilst travelling around South East Asia and it totally rocks. mostly renting places in Thailand as a base (and once you have an address you can get a local bank account and other stuff) then because of the different visa rules you have to leave the country every 2-3 months anyway which I like as it sort of forces me to travel more and discover the other places around South East Asia that also support theis lifestyle, Bali, The Phlippines, Malaysia, Singapore, even places that are lesser developed like Laos still have solid internet connections and it is possiable anywhere. The obvious massive bonus is how far our britsh pound goes whilst living in these places. Still having an address (a famliy member or friend)in the uk is real handy also. So you are sort of registered as living in the Uk but travel alot. Then you can keep you existing english banks going. The biggest tip I can offer is buy the plane ticket and everything else will fall into place.


I'm doing this right now with my new wife, although our online business (lanyrd.com) isn't exactly profitable yet.

We're UK citizens, and we've made sure our company has a registered address in the UK (with our accountant). We'll pay all taxes in the UK - as far as the world is concerned, we're working on our UK business while travelling. We're doing everything on tourist visas since we're not performing any work for foreign companies etc.

Our accountant advised us that paying tax in the UK would be a great deal easier than trying to figure out how to pay it in foreign countries. Get a good accountant!

We've been travelling for 106 days now, through France, Spain, Morocco and now Egypt. Every single place we have stayed has had WiFi, though occasionally a little flakey. Working and travelling actually go very well together - we'll work in the morning, explore in the afternoon, then maybe work more in the evening. Makes it much less likely you'll over-work and burn yourself out as well.


(Thankfully, I am not a lawyer, but I've lived outside the USA for all but 30 months from age 18 to 31. This is not legal advice.)

For US citizens, you need to be aware of a lot of additional regulations -- US citizens are taxed globally, and if you make more than the $6k or so minimum, you must file a return every year. You have a certain exemption (approximately $95k now) on your income, so if you make less than $95k per year, you don't owe any tax, but must still file.

If you are in a location which has its own taxation, you may need to pay, and then use a tax treaty with the US to deduct foreign taxes paid, avoiding double taxation.

Basically, if you have substantial income or assets, you should use an international tax attorney to handle these matters for you. Only an attorney has attorney-client privilege, and your average US tax preparer (or even worse, H+R Block or something) has no clue whatsoever. If you make <$95k/yr and have pretty much just regular taxes, and are not subject to foreign tax (due to traveling on tourist visas and not really establishing yourself), you can probably file yourself -- you don't have a whole lot of deductions, etc., so it's actually fairly straightforward. If you have your own business, it becomes really complex, and I'd really go the tax attorney route.

There are lots of weird and non-intuitive special case rules built into the tax code, such as a restriction on "controlled foreign corporations", where >50% or so of the equity is owned by US persons, and are then subject to lots of extra US reporting requirements. This prevents a lot of the naive "keep all income in the corporation, pay yourself a trivial salary, expense all your personal expenses through the corporation" schemes, but also complicates legitimate foreign businesses owned by Americans. This is the kind of stuff you want the tax attorney for.

Right now I am personally stuck outside the US for the rest of 2010 due to taxes -- I worked in Iraq until August, making more than $95k, and thus it is a net savings for me of about $20k in taxes by remaining outside the US for the rest of the year, thus keeping my 330 days out of 365 out of the US, than it would be to return to the US. I have 6 days left in the US this year, which I might use for YC interview if I apply.

I plan to do my next startup in the US (maybe in tax-advantaged TX or WA vs. CA, but possibly just in the default of Palo Alto); taxes are annoying, but living outside the US is even more annoying.


Don't know about UK, but in Canada one can stop paying taxes once all "domestic ties" are severed. This means closing all bank accounts, disconnecting all phones and selling the car and the real estate (or alternatively leasing it out for a long term). Even after all this is done, the tax agency (CRA) will not assume you to be a non-resident if you do not stay out of the country for at least 2 years. So it is a hassle. Can't just lock the house, hop on the plane and spend a year travelling.

Btw, the best thing to do for you at this point would be to talk to the tax planning advisor. Pick a big accounting firm with lots of experience and in one hour you will know if you want to do I or not.


Is it really 2 years? You can't speed it up in any way?


The way I understand it is if you come back for residency in less than two years, CRA may have some questions.


But if you don't, and register those 2 tax years as non-resident then it would be fine?


That's my understanding, yes. Talk to a tax lawyer though - KPMG, E&Y or similar. No cheap, but it's money well spent if you are planning an "escape".


I've looked into this myself to some depth and also have some friends based over in Asia and Sydney doing exactly what you are intending, from my conversations with them the most overriding issue they have complained about is the weakness of the pound, especially in Aus where it has gone from 2.5AUD/£ to about 1.6AUD/£ in a little over 14months.

That being said thats really the only grumble I hear, the quality of life (weather especially!) seems to outweigh these issues.

Some useful links...

http://everything-everywhere.com/

http://locationindependent.com/


As someone on the other end of that trade, living in AUD while earning USD has been incredibly difficult in the last two years, and it's not going to get any better anytime soon.

The irony is I passed on buying a flat in London because I was worried the AUD would get weaker and I wouldn't be able to afford the repayments.


There are bunches of blogs from those that do this as a lifestyle. Thailand is a pretty popular spot for digital expats.

http://thrillingheroics.com/about


I second that. Firsthand.

Life is generally very cheap here. Overall, you will feel like walking on eggs for the two first years but after that things will be just fine. Culturally, you will need to be able to handle huge alignments.

Honestly, there are ups and downs to this but you will feel alive like never before (this is a general statement about living abroad).

I would advise contacting a good lawyer to help you handle the whole immigration hell (yes, it is). In the IT business there are some shortcuts agreements with the government that can help. I can give you a good pointer on this.

More generally, if you can afford it; do it by all means.


Could you specify if you moved, or are you a native over there? Also, is it possible that you write something more on the "pointers with the government?"


I move here two years and a half ago. I was working for an NGO specialized in ICT and after working for a while in France (my native country) I was proposed to work in Thailand on a clinic computerization project.

Now, I'm simply being employed by a company doing OpenERP customization and implementation. I do have plans/ideas for startup-like businesses (I suppose I'm a bit conservative as far as business is concerned but, eh, I'm French..). I don't personally start a business because I don't have the economic resource to do so. I do plan however to check the water some time soon.

For the pointers, I meant a good lawyer with extensive knowledge of the processes involved in relocating/establishing a business here:

    http://www.wissenandco.com/
The shortcut I was referring to is called BOI. It's an agreement which eases much of the immigration process. They are especially looking for companies working in the software business and you'll get bonus points if you're doing opensource as the ad-hoc ministry is currently very interested in opensource.

I guess I should have mentioned all that in the first place.

@ivanstojic I read your HN profile and before you ask, there is room for consultancy here. Also, NGOs are very interested in ICT consultants and I know a guy who, with the right mix of connections and experience, makes in 6 months enough to live for a year. Networking is the key.


I have a UK business and we decided with my wife to travel around the world. We could have saved a lot on our taxes by claiming non-residency etc. but in the end we didn't. We set our business virtual office as our home and all our mail goes there. So far we are having time of our life, travelled 3 months in USA & Canada and currently in Ecuador.

The difficulties we have are: - troubles with virtual offce - if you decide for virtual office choose carefuly - its very frustrating if you need to change the address while being abroad - time to actually do any work - there is so much to see in the world and having motivation to keep building your business is tough

Things we thought we would have difficulty but they are fine: - internet connection - all around USA & Canada we had wifi everywhere + I bought Verizon mobile internet + ATT data package for iPhone and so wired 24/7 . Also, in South AMerica - Ecuador, you can buy prepaid mobile internet for good price and its reliable - I thought the business will suffer but so far its doing better than before and it probably helped me to realize that if I want to grow my business - I need to hire good people and trust them to do a good job. - pretending you are in UK - I thought I will have hard time in getting new business / contracts signed - but other companies don't mind - in fact I signed biggest clients while being in a campsite in mountains of Canada. all contracts can be Fedexed etc.. no problem at all


I'm currently living in Thailand (remote programmer) and it's a great country to do these kinds of things from. When it comes to the visa situation here it's kind of difficult, I have a Thai wife which kind of takes care of that for me, otherwise your best option is probably getting a student visa. The internet connection is not the fastest (max 100k/s to the EU/US) but it's very stable even out here in the jungle.


Seconding the stability of the Internet. The speed is indeed not that fast, but when I lived there it was very stable and there were never any problems accessing the American and European parts of the Internet.


As far as tax goes, it differs a lot from country to country, at least with the UK, you don't have to pay their taxes if you are mostly in another country.

In some countries, merely visiting them for a holiday while being in charge of a business abroad is considered taxable.


I'm currently in Phnom Penh (Cambodia) doing this and it's working out extremely well. Extended visas are easy to get (note: pay the extra $5 on entry and get a business visa if you want to extend). Love the people and the place.


I've been considering an arrangement like this too, only I've heard a number of stories about people who kept taking "weekend" trips to renew their 90 day visas only to one day not be able to re-enter the country. I've overstayed an EU visa and no one seemed to care (I was traveling so much between EU countries that I honestly wasn't even thinking about it) but if you overstay somewhere like Singapore you can literally get caned. I'd look into countries where there are easier ways to get >90 day tourist visas, like Cambodia or Hong Kong.


I've been living abroad since 2007, living in Italy, Spain, Argentina, Brazil, India, Colombia and Mexico. I'm a US citizen. For US citizens interested in working on their business, you should know this: if you live outside of the US for 330 days in any 365-day period, you can deduct 100% of the taxes on your income, up to $91,400...

So I lived in India and Italy and Mexico/Colombia for the last year, earning in dollars, spending in rupees and pesos. For americans who have their own web business, it's something to think about....


this is good tax saving tips :) staying in home country (may be india in your case) with us citizenship still enjoying the monetary benefit of USA.


As a British Citizen Hong Kong is perhaps an idea, six month entry stamp no hassle. Perhaps buying a shelf company there, I think personal income tax is 15%? I know most taxes there are fairly low. If you do check out Lamma Island as a potential place to stay.

Otherwise, Cambodia is a pretty good shout, 1 year business visa costs about $300 (multientry) (no paperwork). That's the best visa I know of in Asia.


I have no experience with this myself, but I did read this article on the BBC's site earlier today about being an expat in Uruguay: http://www.bbc.co.uk/news/world-latin-america-11397130

Apparently, as long as you can prove a monthly income of at least $650, you can get a visa to stay.


I have been doing the same thing since 2001. In the UK, USA, Italy, Australia, switzerland. I am now in southern california I am a us citizen but if you are a foreigner you can easily and within 2 months buy yourself a place in the USA by getting a E2 Visa - Invest $120K in your own viable business (investments include your salary) and you are in!


I've done this since the 90's (I mean, not continuously). Your ATM card works anywhere; as long as you can keep everything at your bank at home working online or through the mail, travel on a tourist visa and work as you go. Pay your taxes at home.

There's nothing like it. You can't really understand a place in less than a year.


Don't be concerned with immigration issues for a while and leave your business registration and taxation status in the UK.

Sort out all the paperwork if or when you decide to settle down...in the meantime stay nimble, have fun and travel.


Visa processing made easy at http://www.visanow.com/resources/visadirectory/Visa_Director...


This link is actually quite useful. Down-voting must be some sort of a knee-jerk reaction mistaking this for a spam.


Head over to Asia, you can get your Visa really easily, then extend your visa over there by just crossing the border and returning again.

The cost of living is low and the atmosphere is great.


How do you guys deal with re-imaging a laptop in case the old one was lost? Do you keep an image online somewhere?


Try and have most data in the cloud (dropbox/live mesh/Amazon s3) and applications with cloud storage (google docs/basecamp/pivotal tracker).

I do carry a Windows 7 install disc and a 2.5" USB drive with all the various apps I need. (I code for .Net, so do require quite a few installed applications)

Total loss of a laptop while travelling would be a pain, but not insurmountable. Worse would be to lose the install media, but that's recoverable through MSDN, so given a day or two, would be up and running once more.

Would recommend having a virtual machine accessible from anywhere that you can fall back to if needed. That's saved my bacon a couple of times.


Don't forget that as a UK citizen you can live anywhere in Europe without a visa.


Could you be more specific about your online business?




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