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My dream is to be able to travel the world and have a new adventure every day. With the internet, every day I'm able to see this beautiful and unique world, but those are only photos. I want to experience those places and cultures.

There are some things, of course, I have to think about, and the one most important is income. How do I support myself while travelling the world? The first thing I think is What are my talents?

I'm a software engineer and love everything about software and the open source world. I'm a hard gamer and love to play a variety of games. I have very little experience with video and photo editing (Photoshop and After Effects), but the little I had with that, I enjoyed it. How can I make a decent salary writing software while travelling the world?

I've also thought about writing a blog about my day-to-day adventures, and maybe even making a Youtube channel with vlogs about my day-to-day adventures. If I were to do that, how successful do you think it would be? If it was, how well could that support me (or how much money do you think I can make)? I also thought about photography, and to take photos and to sell them online, if that's possible.

Of course, there are things that, as a normal citizen, I wouldn't have to pay like house payment (though I would be paying rent or for a hotel which may or may not be less), car payment (though I would rent cars when I needed to), home internet (I could use Wi-Fi at local shops if applicable), entertainment (most likely if I'm travelling the world, I will have less concern about what new movies or games are coming out), etc.

I make a pretty good salary and have GREAT benefits including health care, retirement, etc. For me, it would be hard to let go of those kind of things. Is it possible while travelling the world to get some sort of health care? I hate to sound negative, but what happens if I need surgery but can't afford it, could I not get health care? And how would I take care of my retirement? What happens when I'm old and decrepit and don't move around as well as now?

It's that time in my life where sitting behind a desk, 40 hours a week, 5 days a week just isn't cutting it. Has anybody here or anybody you know of attempted this? How successful were they?

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Related - Long term travel without being super wealthy –  Mark Mayo Mar 1 '13 at 23:22
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In a way you're asking if you could make a good living as a Hollywood actor. Of course some few people with the right skills and talents make many millions of dollars doing that, others never get their break, and many more end up somewhere in between. It's going to be the same following this dream. Is it possible? Yes. Will every person who tries to find a way to live well while traipsing the globe for years? Of course not. So there really is no "one right answer" to this question. If you want to follow your dream then go for it, but dreams are not guaranteed to come true. Life's a gamble. –  hippietrail Mar 2 '13 at 7:53
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I voted to close. The question is awesome, but it belongs on a forum, not on a qa platform. Similar question have also be closed. –  andra Mar 3 '13 at 11:34
    
This would be a great topic for our blog when we get it, or possibly for a chat room event. But it's subjective and has no "one right answer" so despite being very popular it's not a good question for Stack Exchange's Q&A format. –  hippietrail Mar 4 '13 at 23:35

6 Answers 6

up vote 40 down vote accepted

I do exactly this, and have done so for the past five years. I am a software developer (previously web, now iOS) doing contract work for customers in a range of countries. I live in about five or six countries each year, spending anywhere from a week to several months in each.

I've lived in Tokyo, Bangkok, Singapore, London, Rome, Prague, Sydney, Melbourne, Manila, Chiang Mai, Bali, Kuala Lumpur, and many more.

I'm currently on a full time contract as a senior developer for a company based in a country which I have never been to.

As others have said, there's no shortcuts. It's not often easy to get remote contract work, and the usual freelancing risks are often magnified. It's a risky lifestyle with regards to job security, so you'll need to make some mental changes, and be comfortable with living a bit more on the edge.

  • Build trust. Customers aren't going to want to take on an unknown worker in a far away country without first establishing a reasonable level of trust. Build strong business relationships with your clients.

  • If you're doing full time contracts, don't move too fast. Travelling sucks up days at a time, in airports, trains, etc. And settling into a new workspace in a new country can have unexpected complications (dodgy internet, etc) that can cause you to lose precious workdays. Plan on spending a minimum of a week in each place, unless you've set the time aside as holiday time.

  • Make sure you've booked and planned a decent length stay in each place that will provide you reliable internet, a work environment free of excessive distractions, and enough full work days to get the work done.

  • Keep your customers happy. The same goes for any contract work, but when you're living in countries in which you're not a legal resident, there's no safety net to catch you if you stuff up and lose an important client.

  • If you're only doing casual, part time work, staying in hostels is okay. But if you've got a big project that needs serious time commitment, hostels are not good. You will be surrounded by people who are on holiday, who will treat you like you are on holiday. Holidayers are the digital nomad's kryptonite - they suck up your precious work hours with casual conversation and temptations of day trips to interesting local sights.

  • Most of the time, book serviced apartments and hotels. You'll get a distractionless work environment with reliable internet. Hostels and budget hotels are a risk to your employment, and should be reserved for weeks you set aside as mostly holiday time.

  • For healthcare et al, you need travel insurance. You can usually buy travel insurance for up to 12 months, which gives you at least some safety net for the year ahead. Booking 12 months insurance is not much more expensive than booking 3 months, as most of the cost is built into a base rate, regardless of duration. Travel insurance will cover immediate medical costs, as well as theft of possessions, etc. Research it well and make sure the policy covers everything you need, and that you've understood the terms.

  • Don't bother with travel blogging or travel photography if you already have skills that fetch much higher pay (ie software development). Every backpacker with a camera and a laptop is trying to be a travel blogging photographer, and almost all of them are earning effectively nothing. Use the high paying skills you have, and earn a proper income.

  • You don't need to downgrade your lifestyle. Work hard for the right people doing the job that you know how to do well, and you will earn a full income. There's no need to walk the streets in dirty backpacker clothes looking like an extra from The Beach.

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Incredibly good advise! –  feklee Mar 2 '13 at 11:37
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@Zurechtweiser As to going back to the same house, I often go back to favourite serviced apartments in each city. I'll start planning my longer stays a couple of months ahead, to make sure I can book the best apartment. In each city I might have one or two favourite neighbourhoods, with maybe a couple of favourite apartments in each, and might chop and change between them each year depending on mood. –  sobri Mar 2 '13 at 15:58
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@Zurechtweiser For seeing holidayers in hostels when I'm working, that's never bothered me. Mostly because there's a tendency to see the backpacker experience as superficial and unappealing. They'll often be only staying in each place a couple of days, and won't get a chance to have the richer local experience that long term travellers have available to them. Hostels are fun and social, but backpackers are somewhat in a lesser league. Traveller snobbery, if you will :) –  sobri Mar 2 '13 at 16:07
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@feklee I try to get apartment buildings that have a gym. For me, back problems are highly correlated with physical fitness and core strength. Squats and deadlifts build strong back muscles, which protects me against back problems. That said, I do keep a sharp eye on the room photos on hotel websites, to make sure their chairs look at least passably good! –  sobri Mar 3 '13 at 3:52
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@feklee That's another reason why I tend to avoid hostels. In past years I've occasionally ended up working from bed, because the hostel didn't have adequate common areas. That's a very effective way to cause back pain. –  sobri Mar 3 '13 at 3:55

For most people trying what you propose, making money while traveling, is not possible. Luckily, there are plenty who prove this just a rule of thumb, not a hard law.

Yes, it's possible to make enough money from a vlog, a blog, photography, professional articles or travel advice. But it's very hard to get started, and no real shortcuts to make it big. From my experience, it's really almost always a bit of luck and a lot of persistence that make for success.

That said, if you're indeed a decent developer, going freelance will allow you to be quite mobile. Perhaps even mobile enough to travel a lot. But what then helps is an existing client base who are ok with not always, if ever, meeting you in person.

I travel 3-6 months out of the year and have lived in a dozen countries or so in the last 15 years, pretty much always project related. I'm a developer. So, I'm not too distant from the type of life you seem to be interested in. But also know that the first half dozen years were rather tough. I got out of a well paying job to earn virtually nothing for years. But, I also firmly believe in the end it was worth it.

Pretty much all the projects I get are through word of mouth, which seems to be often the case when you're a freelancer, whether you're on the go or not. In the end, I'd say that keeping your client base happy or finding new clients isn't much different whether you're on the road or not. That said, clients tend to be wary of working with providers who they can't see or call into their office once in a while. The only remedy for that, really, is to consistently deliver quality.

Indeed, health care expenses outside of the US are reasonable in many places. International health care plans that don't cover the US, but pretty much do cover the rest of the world are often reasonably enough priced. And worth the money, in case something goes horribly wrong.

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It seems that you, when you started, had the same goals as me. Travelling 3-6 months out of the years isn't too shabby. Do you have any pointers or tips? Anything you wish you could undo when you first started, or things you would have done differently? you can edit your original answers. Thanks! –  Rob Avery IV Mar 1 '13 at 19:31
    
I would say that beside luck, talent and skill are also important factors. You might get by with any one of these three but you'll do better with some of each. –  hippietrail Mar 2 '13 at 7:54
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@Rob: I don't really think there's an essential difference between being a freelancer who's on the road and one who isn't. The same caveats apply. If anything, you'd probably have to be even more reliable than when not traveling. –  MastaBaba Mar 2 '13 at 11:17

There is a term called digital nomad. This is someone who has no real home and is travelling and working using the internet.

As a software developer you can do a lot of work independently using oDesk or any other freelancer web site. Chiang Mai, Thailand is called the Mecca of digital nomads.

At least what I know it is inexpensive to get health insurance that covers travelling outside the US.

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W00T for Chiang Mai! :) –  MastaBaba Mar 1 '13 at 19:07

You may want to try Coworking. That's a way to get a workplace and to meet like-minded people from all over the world, many of them freelancers.

I am writing this, sitting in Coworking Las Palmas, which I found via deskwanted. Among my colleagues are other programmers (like me), a translator, a biologist (I believe), a serial entrepreneur, and architects.

Coworking spaces can also be useful to find clients. One of my current clients I have met at Loft to Work Madrid, other ones in Berlin at TheBusinessClass.Net and at Betahaus.

Often, I also work from public libraries. When using the Biblioteca Nacional de España in Madrid in 2011, I was pleasantly surprised to find a room with office chairs. It can't get much better than that!

Concerning accommodation, what has worked for me is Airbnb or similar for a week or two, then rent a furnished apartment or a room from a local. Coworking colleagues may help you. Personally, I don't like staying in hostels (too busy) or hotels (too sterile), and both are expensive compared to other options. You may also use Couchsurfing for the first days, which can give you good insight into local life.

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This is a great question. I travelled for a couple of years by bike, and I made some money from web development, photography, writing and teaching English. My favourite out of these would be teaching because it integrates you with the community. Working freelance websites is quite alienating. Being a digital nomad is the best way to be IMO, and it is also flavour of the moment. Flavour used to be just going, but now its going and doing it sustainably. Hence books like '100 startup' by chris guillebeau try to figure out how its possible. However, I would say and agree with others that its a lot of work. Guillebeau in his book says its much easier to start the business before you leave, and run it remotely than start it whilst on the road. Web store fronts are more popular than high street ones these days so there is no reason not to set up any kind of business this way. Like anything to do any of this successfully takes time and patience and hard work. good luck with it, and post back with your experiences.

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  1. Develop some course work that you can offer at nominal fees.
  2. Create slide shows of the places you are visiting
  3. Visit local schools/colleges to explore tutoring/slide shows.
  4. Before landing in a city, make some linked-in friends. They can tell you the tricks of surviving in their city as well as offer some professional contacts.
  5. Be prepared to live a very simple life away from the comfort++. I think this does not match with your basic requirement of decent salary.

These are my thoughts as someone who left a cozy job in India to start all over again in the United States as student. Good luck to you!

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This is unlikely to provide a decent income. Downvoted. –  Ankur Banerjee Mar 3 '13 at 12:15
    
I do agree. This is more saving up. –  Pixie May 20 at 11:00

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