Feel miserable working in a cubicle or living in a boring town? The Internet has revolutionized the term ‘work’ today, bringing new opportunities and employment that didn’t exist until recently.

For many, the Internet is an opportunity to combine work and traveling the world. The term ‘digital nomad’ is frequently overused and often simply means hacking around in cheap accommodation with a small level of income to keep you going. But, there are some folks out there who have shown that you can combine a career with the freedom to travel on your own schedule.

To cut through the garbage, we caught up with seven bona fide location independent workers and business owners about what they do, how they do it, and what steps others aspiring to follow them can take.

Read on for more.

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Image via wavebreakmedia / Shutterstock

7 ‘digital nomads’

This is the story of 7 ‘digital nomads’.

1. Matthew Kepnes, Nomadic Matt

Can you briefly explain what you do for a living, how it all began and where you are based?

I’m a travel writer who runs a blog called Nomadic Matt that teaches people how to travel on a budget. I started the blog in 2008 after 18 months overseas. I had originally intended to make the blog an online resume for freelance work but it developed a life of its own and here I am today. I am based in NYC.

Can you describe a typical day in your life?

When I am home, I try to wake up early, go to the gym, answer emails, work all day, then out with friends at night. When I am on the road, I work in the morning, head out sightseeing for the day, then work again in the early evening before going out for dinner and drinks.

What is the coolest place/most fun thing that you’ve done in the past year?

Last December, I went to southern Africa for three weeks. It was an incredible trip.

Tell us something that will make us green with envy about your setup?

I can work from anywhere in the world I want.

What are some of the drawbacks about living/working as you do?

There are drawbacks to everything. When you are always on the road, it’s hard to get into routines and build habits. Dating is tough because you are never in one place long enough to form a connection and before you know it, it’s time to go again!

Do you have plans to switch back and lead a more regular life in the future?

I don’t know what the future holds but for the next couple of years, I’m happy doing what I am doing.

What advice do you have for people who are tired of the regular 9-5 job routine and want more independence and freedom to travel?

If you want to travel more, go do it. You’ll work until you’re dead so taking some time off for a bit to travel is perfectly fine – I’ve seen couples, families, and seniors do it. If that’s not realistic, try to negotiate with your boss a four day work week and take short trips around your area in the three days you have off. Travel doesn’t have to be about going some place exotic, just someplace new and I bet there are many “new” places near you!

You can find Matt on Twitter: @nomadicmatt

Images via Nomadic Matt

Can you briefly explain what you do for a living, how it all began and where you are based?

I often joke that I eat soup for a living, but that is essentially where my career has gone in the last few years. I was a corporate lawyer for more than five years in New York and quit to travel for what I thought would be one year around the world. I started a blog, Legal Nomads, to keep family and friends apprised of my whereabouts, and shared the stories and misadventures from my travels.

As the site grew, I began to receive offers for freelance writing and figured ‘why not see where it goes?’ I decided to keep the site ad-free (it still is) and in 2010, I moved it from blogger to WordPress. I started to build a routine that involved winters writing and eating in Asia and summers in North America, speaking at conferences and doing consulting work for social media.

In the last few years, my focus has shifted toward food — specifically street food — as a great lens to fully explore a new place. I wrote a book last year about how to do so called The Food Traveler’s Handbook, and I’m starting up small group food walks in Saigon, Vietnam, from January.

Essentially, it is a life built around learning through food on one hand, and social media consulting work on the other. Very satisfying, and very delicious.

Can you describe a typical day in your life?

It honestly depends on where I am living at the time. In Saigon, my days involve writing interspersed with lots of soup. Nighttimes will regularly house conference calls to North America — with the 12 hour time difference to EST, it’s often the best time to connect with clients. When none are scheduled, I will meet up with friends for a meal or snails and beer on the street.

In North America, I’m often moving from place to place so my routine is less fixed.

What is the coolest place/most fun thing that you’ve done in the past year?

I had a great year, but the highlight was quite recent, when I took my mum to Rajasthan for her birthday. We hadn’t travelled together in decades and it was truly rewarding to be able to do so. Not only did we eat our way through Rajasthan, but she also came to hear me speak at a conference in Bangkok, which went a long way toward explaining a bit more of what I do. She also got to meet others who were living a location independent lifestyle — perhaps now she can explain it to the rest of my family!

Image: Fried balls of mung bean flour, called daal motth in India

Tell us something that will make us green with envy about your setup?

I truly wake up every day thankful that I’ve been able to build a life around the things I love. I am still admitted as a lawyer — having a worst case scenario is a good thing, after all — but thus far I enjoy what I do too much to contemplate a return to the law.

What are some of the drawbacks about living/working as you do?

The uncertainty of where you will be in several months time, the flexibility that can sometimes overwhelm when any option is available, staying healthy when you put your body under stress by moving around frequently, rarely having the people you love in one place (since you aren’t in one place either). None of these outweigh the positives just yet!

Image: Ranakpur, a Jain temple outside of Udaipur in India

What advice do you have for people who are tired of the regular 9-5 job routine and want more independence and freedom to travel?

There are a few ways to look at it: one is to move into a sector where the job will involve travel, be it teaching or consulting work or engineering. Another is to keep developing skills that would be useful (mobile app developer, Web designer, etc) from anywhere.

It’s not a calming choice to walk away from what you grow up being told is normal, but at the same time if you are excited enough about that flexibility to build life on terms you find compelling, the latter is a very rewarding option.

You can find Jodi on Twitter: @legalnomads

Images via Legalnomads

3. Stuart McDonald, Travel Fish

Can you briefly explain what you do for a living, how it all began and where are you based?

I run Travelfish.org, a travel-planning website that covers much of Southeast Asia. [Stuart’s wife] Samantha and I launched the site in 2004.

Sam is a journalist and I’d previously written a couple of guidebooks, then learned enough Web programming to get myself in trouble. We then borrowed $5,000 off my parents and combined our skill sets to create what began as a website covering a few of our favourite places in Thailand.

Today, with 17 writers across the region, Travelfish.org is arguably the largest independent travel planning website dedicated solely to this region.

We’re currently based in Bali, Indonesia, but have in the past run Travelfish from Bangkok, Phnom Penh and Jakarta.

Can you describe a typical day in your life?

I have two lives. My home life, which is broadly comparable to an office gig, and my on the road life, when I’m, well, on the road.

At home, I’m generally up by 5:00 am checking the site and email, faffing about on Twitter and so on. Once the kids are out the door to school I’m pretty much locked in my mancave upstairs where I could be doing anything from coding to writing to managing ads and so on. Twitter and Analytics are on the side screen all the time. I have a 15-minute nap around 1:00 pm and then work through into the evening… I’m generally fading by 8:00 pm.

On the road, I tend to inspect stuff (be it hotels/sights/whatever) in the morning and late afternoon and write them up in the middle of the day and/or evening. While on the road I make heavy use of Instagram — it’s a great way to broadcast interesting things to do.

Early morning and late evening are dedicated to keeping on top of what I manage to spend 10 hours a day at home on. Yes, when working at home work will take all the time you give it.

What is the coolest place/most fun thing that you’ve done in the past year?

In July, I learned to dive in the Togean Islands in Sulawesi (written up in this iBook). Having a one-on-one tutor with not another dive group for dozens of kilometers in fantastic conditions was very cool.

Better still? There was just about no Internet.

Tell us something that will make us green with envy about your setup?

I can run most of the business from my iPhone, though in practice I normally use my laptop. This gives me a tremendous amount of flexibility, so it’s easy to jump on my bicycle, ride down to the beach 10 minutes away and work away to the background thunder of surf.

What are some of the drawbacks about living/working as you do?

Work takes all you give it and having the discipline to close the laptop and go for a swim with the kids is, well, after nine long years, still a discipline I’m yet to perfect. I travel a lot — generally on three to four week slots (I’m in Burma for a month right now, for example) — and I do miss my family terribly while away. I still love the travel of course, and I do love what I do, but having kids does change things considerably.

Also, being able to run the business from a phone means you’ve really always got your business with you — in your shirt pocket. There is a significant downside to that and a true holiday generally requires me to get somewhere with no Internet connectivity (like the Togeans mentioned above).

Image: Stuart hard at work “researching” snorkelling spots off the coast of Bali

Do you have plans to switch back and lead a more regular life in the future?

No.

What advice do you have for people who are tired of the regular 9-5 job routine and want more independence and freedom to travel?

Careful what you wish for. Tossing the PC and a cubicle for a laptop and a tan makes for a sexy $25 ebook headline — but in practice it’s no panacea.

There are significant lifestyle costs to pursuing this style of living, not least that in many cases you’ll be working far more than you would have been back in the cubicle, in a far less productive manner and often in a less than ideal work environment.

But, when that all gets me down, I get on my bike and ride down to the beach to watch the surf.

You can find Stuart on Twitter: @travelfish

Images via Travelfish

4. Dan Andrews, Tropical MBA

Can you briefly explain what you do for a living, how it all began and where you are based?

I currently write and podcast about business and travel at TropicalMBA.com. That started as a place for me to share my thoughts about the business I was building — an ecommerce business I started in late 2007 that makes products like cat furniture and portable bars.

The blog has since evolved into a community for digital nomads and location independent entrepreneurs to network with each other.

Can you describe a typical day in your life?

My schedule revolves around preserving my creative time. I generally wake up around 8:00 and work to 11:00 or noon on creative stuff, then I’ll head out for lunch with with friends or while listening to an audio book. I spend a lot of time walking around, listening to books, and meeting friends at cafes.

Early afternoons are for paperwork, email, and phone calls. In the evenings I’ll take a run and do some exercise and meet with friends for dinner and drinks. About every three weeks I get the itch to take a trip somewhere and end up wondering around for a few weeks with a wacky schedule.

What is the coolest place/most fun thing that you’ve done in the past year?

One of the highlights of 2013 for me was flying to Prague to give a talk at Rob Walling and Mike Taber’s Microconf. I’ve never been asked to speak at an event before so that was an honor and a challenge, and buzzing into a great European city for a week to meet some great people was the kind of thing that I could only fantasize about when I started my career in business.

Tell us something that will make us green with envy about your setup?

For me the biggest luxury is time, and thanks to the business, I have a lot of it to spend doing the things I love like hanging out with friends, reading books, and just bumming around and exploring.

Image: Dan at Cloud 29 bar in Bangkok, Thailand

What are some of the drawbacks about living/working as you do?

To be honest it’s such a privilege to have the opportunity to travel and see the world that I can’t bring myself to complain about it.

Do you have plans to switch back and lead a more regular life in the future?

No way. There’s nothing wrong with a more regular life, but I lived one of those for a long time and don’t feel any need to go back :)

What advice do you have for people who are tired of the regular 9-5 job routine and want more independence and freedom to travel?

What worked for me was changing my social networks. When I started spending time with people who were getting things done, I not only could see how to get similar results for myself, but I had a network of people to support me as I went through the process of growing a business. It took me half a decade to build my business, it would have been tough to go it alone.

You can find Dan on Twitter: @TropicalMBA

Images via Dan Andrews

Can you briefly explain what you do for a living, how it all began and where you are based?

I move to a new country every four months based on the votes of my readers.

It’s a strange kind of lifestyle, and it started when I found myself living a version of the ‘American Dream’ out in LA, professionally and financially successful, but in a rut psychologically, philosophically, intellectually, and in most of the other ways that matter most.

I needed a change, and after a whole lot of shifts and adjustments, I found myself with a blog and not much else: everything that wouldn’t fit into a carry-on bag was sold or given away. I’ve been traveling full-time ever since (over four years now).

Most of my income comes from my books, essays, and other projects these days.

I’m hanging around Reykjavik, Iceland through the winter, but I’ll be tallying the votes in February, so at that point I could end up anywhere (and as I write this I’m in Marrakech, Morocco, on a food tour with a chef friend).

Can you describe a typical day in your life?

I actually can’t, but not for lack of wanting to.

Since I started traveling this way, there isn’t really a typical day. There are certain habits I’ve stuck with fairly consistently — workouts and writing habits and the like — but I don’t do them at the same time every day, in the same way, etc.

Habits are actually quite terrible for my type of lifestyle, I find. Anything too rigid keeps me from being able to roll with the punches and pounce on opportunities as they arrive, so I have a whole lot of goals (stay healthy, always be writing), but I don’t get dogmatic about how to reach them. This gives me the ability to stay malleable and adjust and adapt each day to whatever circumstances I find myself in upon waking up.

What is the coolest place/most fun thing that you’ve done in the past year?

That’s a tricky question — I actually really geek out over things like publishing new books and meeting new people and learning new things about the places I’m living, so every day is riddled with excitement and crazy joy.

It was a lot of fun setting up a permanent office for Asymmetrical Press (an indie publishing company I founded with a couple of minimalists in Missoula, Montana) earlier in the year.

I took some time off from international travel to live in that relatively small town for several months between book tours and absolutely fell in love with it. It’s also a thrill getting to work with such talented people (the aforementioned co-founders, and the authors we’re honored to publish alongside our own work).

Image: Colin with his business partners

Tell us something that will make us green with envy about your setup?

I can go anywhere I want at any time, and so long as I can hop on the net every once in a while, I can continue to do my work (work that I love) from wherever I land. I work for myself, so I make all the decisions (creative and otherwise) about what I do and how I do it, and I have an absolutely amazing audience of readers who are encouraging and wonderful and make even the tricky aspects of my lifestyle incredibly easy and enjoyable in lots of ways

Also: everything I own fits comfortably on my back, so it takes me 10 minutes, tops, to pack and get ready to leave; last-minute trips couldn’t be easier.

What are some of the drawbacks about living/working as you do?

Everything is non-standard, from the way you fill out paperwork, to the way you deal with family and holidays, to the way you manage relationships and bank accounts. It’s awesome if you don’t mind blazing trails with everything you do, but sometimes you just kind of wish someone else would have done it first and written an instruction guide for you to follow (or a series of them).

Image: Colin engaging in some fake hitchhiking while in New Zealand

Do you have plans to switch back and lead a more regular life in the future?

Not really. I mean, anything could happen, and if something better comes along (better in terms of allowing me greater freedom, the ability to learn and experience new things constantly, and a superior method for meeting and surrounding myself with the kinds of people I want to spend my time with) I’ll be all over it. But at the moment this is the absolute best lifestyle I can possibly thing of. It’s perfect for what I want, and I’ll stick with it unless my priorities change or it’s replaced by something that suits my needs even better.

What advice do you have for people who are tired of the regular 9-5 job routine and want more independence and freedom to travel?

If you really want to travel, you can always make it happen: it’s just a matter of sacrificing something (or many somethings) to do so.

Before you spend your life savings hitting the road, though, make sure you know why you want to do it, and identify the best means of making it work, and how to perpetuate it (if applicable).

You may also find, while deep-diving into your motivations, that you don’t want travel specifically: you want novelty and new experiences and the like. You can start achieving those things immediately, without leaving your hometown. Do so.

Whatever the case may be, though, start working on it immediately, or you’ll keep putting it off.

You can find Colin on Twitter: @Colinismyname

Images via Colin Wright

6. Natalie Sisson, The Suitcase Entrepreneur

Can you briefly explain what you do for a living, how it all began and where you are based?

I’m Natalie Sisson, an author and world traveler who is on a mission to ensure entrepreneurs create freedom in business and adventure in life.

Through my blog (Suitcase Entrepreneur), podcast, videos, digital products, coaching and workshops, I help them get really clear on their ideal lifestyle and business, and then show them how to achieve this by building their personal brand and using social media, online tools and outsourcing.

I run my own business from my laptop and a smartphone and live out of my suitcase, traveling the world and going on adventures. The world is my home.

Can you describe a typical day in your life?

No day is typical in my life but I’ve learned that true freedom comes from being disciplined. So while I can’t set myself up with a daily routine, I can make sure I prioritize getting in my exercise and gratitudes first thing, enjoying my fave meal of the day – breakfast — while working through my three most important actions of the day.

I have a virtual global team now so that I can focus on what I do best which is spreading the message and ethos of the Suitcase Entrepreneur community through writing, podcasting, videos and online engagement, marketing and more.

Depending on where I’m traveling and time I have available I’m either producing content, planning new offerings, coaching clients, doing interviews, analyzing and optimizing my business plans, engaging and marketing online, or working on empowering my team. This is usually mixed in exploring new places, hanging out in cool cafes, playing Ultimate Frisbee or training for an event like my upcoming Quarter Ironman.

What is the coolest place/most fun thing that you’ve done in the past year?

The coolest thing I’ve done in the last year was crowdfund, write and self-publish my book, The Suitcase Entrepreneur.

I have always wanted to write and publish a real book and wrote this one in Malaysia, Borneo, Phlippines, Germany and England, as well as on many flights and in airports, cars and trains. I went on a book tour before it was even published and once it was too, and more importantly gained a whole new community of supporters and people who’s lives I’ve been honored to make an impact on.

Aside from traveling to 18 countries, I spent the first four months of the year tripping around South East Asia, running my business, hanging out with Orangutans and Pygmy elephants and playing in way too many fun Ultimate Frisbee tournaments.

Tell us something that will make us green with envy about your setup?

I feel pretty damn lucky to have a business I love and the ability to choose freedom. So I guess it’s the fact that I can work from anywhere, wake up when I want, work on what I want and from where I want, and spend time doing what I love every day.

What are some of the drawbacks about living/working as you do?

Constantly being on the move can start to wear thin, especially when you travel as much as I have this year. Packing up yet again and leaving a place you’ve really fallen for, or having to say farewell to new friends and connections you’ve just started bonding with can sometimes be hard.

Not having a place to call home or keep a little bit of stuff — I do think that deep down we all need a base so I’m working on having something in 2014 that fits that description. Ideally I’d have a base in Europe, North America and New Zealand (my homeland).

Do you have plans to switch back and lead a more regular life in the future?

Yes, I think my days of constant adventure will start to slow and in a few years time I will invest in a few places I can have as my base, and share with friends and family. 2014 will be my year of focus: on my business and spending more time in fewer places – so I’ll see how that fits.

It’s also going to be about spending more time with my friends and people I admire and having deeper, longer lasting experiences – like retreats, events, and community building.

What advice do you have for people who are tired of the regular 9-5 job routine and want more independence and freedom to travel?

Invest in your future now and make the change you need to live your best life. I can’t tell you how many people I talk to, advise, mentor and coach who are afraid of living their dream. Sometimes it pains me to see them make excuses for not taking action or to let limiting beliefs overpower their natural talents and gifts.

We only have one life, and the Universe rewards bravery — so get to it!

You can find Natalie on Twitter: @nataliesisson

Images via Natalie Sisson

7. Adrianna Tan, Me Launch Pretty One Day

Can you briefly explain what you do for a living, how it all began and where you are based?

I work with technology startups that want to come to Asia. Through my business — Me Launch Pretty One Day — I help launch them in various Asian cities.

Having worked in tech for a couple of years now in various capacities, this was something that I loved doing the most, and it just so happened that I’ve had the ability to turn this into a business.

I’m based in Singapore most days but travel regionally around Southeast and South Asian cities for work and leisure.

Can you describe a typical day in your life?

The main decision for me to make is where I work from, most days. I move around: from my home office to a number of co-working spaces to the bars and cafés that I like.

I set up calls or meetings when necessary. Checking in with the client is important to make sure we are on the same page and so that we can track our progress.

My work is usually carried out in phases. The actual work involved depends on the territory I am working on, the task at hand (e.g. help my clients with legal or infrastructural setup, run workshops and events, or get a localized version of their site or app up and running).

This week my daily schedule involves setting up workshops in five Asian cities and then actually executing them. It’s a bit different everyday, which is why I love what I do. There is a lot of writing: copy, press releases, emails; a lot of talking: workshops, events, meetings. A lot of moving around too, whether it is intra-city, inter-city or international.

What is the coolest place/most fun thing that you’ve done in the past year?

In September this year I decided to try to do more “activism” in some of the causes I am passionate about.

One of the projects is Culture Kitchen, a food and art project that aims to bring Singaporeans and our immigrant communities closer to each other. I had the first Kitchen on 22 September, and it served up a South Asian version of biryani together with a Singaporean interpretation of the same dish.

We invited 150 people: Singaporeans and expats, visitors and residents, and also 70 migrant workers from India and Bangladesh. The idea was to bring unlikely dinner companions together so as to kick start greater dialogue and understanding. It’s a small step.

Tell us something that will make us green with envy about your setup?

While many people think that working in this way means you are sitting in your underpants working on your laptop at a beach, that isn’t always the case. [Ed: I didn’t get that memo!] Although it certainly can be and there’s no one to stop you from doing so. [Ed: Oh, that’s ok then.]

For me what’s more important is the ability to define the work that I want to take on. If a project is boring or if someone is an asshole, I have a bit more agency to do something about it than if I was working a regular gig.

What are some of the drawbacks about living/working as you do?

You never stop hustling. This can be a big plus — it certainly is for me because I love it. But you never really stop or switch off.

It can also be difficult to make more normal arrangements in other aspects of daily life. For example, I could never sign on to even a four-week course in something, anything. I can’t guarantee that I can be in one place every Monday. My schedule is up in the air and spontaneous and any kinds of classes or packages: yoga, gym, guitar lessons, anything time-specific is quite difficult for me.

Do you have plans to switch back and lead a more regular life in the future?

No.

I don’t really know what regular means in any case. When I was in university my job on the side was to be a roving photojournalist — and I found that life makes sense only in this way for me. Although I had to learn the hard way to at least get the basics right so that this lifestyle works for me.

What advice do you have for people who are tired of the regular 9-5 job routine and want more independence and freedom to travel?

Be very sure you are an independent self-starting person who will get up and do stuff even when your circumstances change. If you need an environment (an office) or a schedule (working hours) or other people (a boss) to be the factors that matter when it comes to work, then you should probably think quite hard about making the plunge.

Also, it really is just an illusion that having this independence and ability to travel is the best thing ever. You only see the best bits of other people doing it.

When I was doing travel writing I think I worked a whole lot harder, and definitely wasn’t traveling the fun way you’re thinking of.

You can find Adrianna on Twitter: @skinnylatte

Images via Adrianna Tan

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