As more and more people are freelancing these days (whether it was their own choice or not), an increasing number are also realizing that doing so from New York City, San Francisco, or any other expensive city doesn’t really make sense. I’m among the group of so-called “digital nomads” who has been location-independent for over a year now, saving money and having a great time by traveling all over Asia instead of a more expensive lifestyle in the States.

It’s definitely true that you can actually live on far less in many parts of the world, even in hotels and short-term apartments, but actually running your own freelance “business” isn’t quite as easy as it might first seem. Getting paid a First World rate while partying on Third World prices really can be a great way to get yourself started as an independent professional, as long as you take things like the following into account.

1. Acquire skills and clients before you leave

I’ve seen many people on travel messageboards who plan to take on this lifestyle, and some of them reckon they can save up a bit of cash, quit their fulltime job, and then head out on the road before picking up freelance work. This is (almost always) a mistake. Not only is the freelance market more crowded than you realize, and wages for services probably lower than you realize, but living on the road will be very disorienting at first, making it a tough time to find new work.

Yes, there are always loads of jobs on offer on eLance, oDesk, and even on Craigslist all over the world, but competition for them is so fierce that you are likely to make very little when you take your “admin time” into account. I recently posted a gig for a logo for a website for US$30 and within 3 hours I’d received 33 applications, including many who tried to undercut their competition by taking a lower price. Add in all that time applying for jobs and learning the specs from ones you get, and it’s a tough life regardless of where you are living.

For these reasons, and some others below, you are far better off establishing yourself as a freelancer long before you put your stuff in storage. Do it for 6 months while you are winding down your job, or work like crazy if you are already unemployed, and then set out once you have some steady clients or regular work.
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We’ve finally reached the era where it’s possible to travel around the world indefinitely and support yourself with a good lifestyle as long as you have a skill that can be performed with a laptop and an internet connection. Increasing numbers of “digital nomads” are roaming the planet and doing quite well financially as they combine travel with work, but of course it takes planning and discipline to really pull it off properly.

As someone who’s been traveling and working from a laptop all over Asia for the past 15 months straight I’ve learned about much of the good and bad with this lifestyle. It’s definitely not for everyone, and some who try get frustrated far sooner than they expected, but there’s a growing community of more or less permanent travelers out there who’ve traded a home address for a series of hotels, hostels, and short-term apartment rentals in some of the world’s most fascinating cities.

Let’s start out on a positive note, with five of the best things about working while roaming the planet.

1. Travel as long as you wish

Most of the people living this life were those who became addicted to travel and were only home long enough to save up for their next big trip. Now, with decent internet speeds in much of the world, including in many countries where hotel rooms and meals are far cheaper than a regular life in North America or Europe, it’s literally possible to travel as long as you want.

Obviously it’s important to spend most of your time in places that are within your budget based on how much you are earning, but it can also be shocking how much luxury you can get for as little as US$1,000 a month in a city like Chiang Mai, Thailand, where basic hotel rooms start at around US$5 per night. If you are a programmer or designer who can make US$50 an hour or more and can get a steady flow of gigs, you can skip around the globe to just about anywhere, even working well under 40 hours per week.

2. Pace yourself with sights

Anyone who has traveled for more than a month or so at a time can tell you that even sightseeing can get quite monotonous after a while. There are few things less inspiring than trying to admire the 19th most impressive Buddhist temple you’ve seen in the past month. Working while traveling actually helps refresh your desire to explore further.

Even setting aside 20 or 30 hours per week as work time leaves plenty of time to enjoy your new surroundings, while adding a pleasant rhythm to your schedule. There can also be times when you have a big project and want to concentrate on it as much as possible for days, weeks, or even months at a time. When you are finished you’ll be ready to move on, with a nice bump in your bank account at the same time.

3. Live like a local

Going from one urban hotel to another can be exhausting after a month or two, so most digital nomads mix in occasional rentals of apartments for a month or two along the way. It’s very nice not having to adapt your schedule to a hotel’s housekeeping regimen, and it lets you experience cities in a whole new way at the same time.

Tourist districts often have the best nightlife and the most opportunities to meet other travelers, expats, and other English speakers, but they also tend to be quite insulated from the normal life in any given city. When you are staying for a month or more in your own place you’ll shop at the local markets and meet your neighbors, which adds a whole new and very pleasant dimension to your understanding of that city.

4. Save money with increased flexibility

If you can work literally anywhere in the world that has an internet connection, then you’ll discover that you can save quite a bit of money by exploiting this flexibility. For example, let’s say you are staying near one of the beaches in Kerala, India, and you’ve decided you want to head next to Kuala Lumpur, Malaysia. A one-way ticket might be US$400 if you go this weekend, but only US$220 if you go three weeks from now taking advantage of an Air Asia fare sale, so you stay put until then.

And it’s not just flights that change prices dramatically depending on the timing. Many areas have peak holiday periods for hotel prices and then drop down to low-season rates immediately after. You can often avoid high season hotel rates and get great weather at the same time if you time things right.

5. Choose your climate

Speaking of weather, one of the more magical things about traveling long-term is that you can literally choose the climate you are in the mood for at any time of year. Tired of the cool weather and gray skies in January? Look out for a cheap ticket to Buenos Aires or Bali and put that smile back on your face.

In fact, since many of the cheapest and most plugged-in countries in the world are just north of the equator in south Asia, there’s a better chance that you’ll be getting tired of the heat and relentless sunshine rather than of the cold. Needless to say, the more money you are able to earn, the more options you’ll have open to you, and that sort of motivation can also greatly help your freelance career move forward.