Do you daydream about quitting your job and traveling around the world? What about taking it a step further and building a location independent career, so you can live and work wherever you want to?

I can remember the first time someone labelled me a “digital nomad” on a major blog… Two-and-a-half years ago these were the words of Corbett Barr—back when his site was still called Free Pursuits. Corbett listed me among the top 10 Digital Nomads to Learn From, alongside Tim Ferriss and Rolf Potts—two truly incredible writers who inspired me to follow my own path in life—as well as huge A-list bloggers Chris Brogan and Mike Elgan, and big names in the travel blogosphere including Christine Gilbert from Almost Fearless and Chris Guillebeau of Art of Nonconformity fame.

I wasn’t quite sure what I thought of the label at first, although I was immensely honored to be among such incredible company. I was excited! Reading Tim Ferriss’ The 4-Hour Workweek and Rolf Potts’ Vagabonding had been a turning point in my life—those two books opened my eyes to whole new possibilities and put a fire under my ass to create a life of my own design, and try my hardest to enjoy every moment of it.

Not long after in late 2009, Jonathan Mead used me as a case study in his manifesto The Zero Hour Workweek, which played off of the ideas in Tim’s book, but took them even further to encourage people to build businesses that basically allow them to get paid to be themselves. Soon I was being interviewed about my live-and-work-anywhere lifestyle, and people started calling my story inspiring, and asking me about my travel experiences and advice for overcoming travel obstacles.

Sometimes I’m a bit embarrassed by the buzzwords (digital nomadlocation independent… and lifestyle design… there’s another one!) but eventually I embraced the title Corbett had bestowed upon me. Who’d have known that just two years later I’d be running a business course called Digital Nomad Academy with the help of Corbett himself and several other hugely successful remote-control entrepreneurs I look up to!

Like many people, sometimes I feel like the small (but growing) online niche we’re in is a bit too cliquey, too markety, and sometimes people get big egos, or they feel under pressure to maintain the appearance like they’ve got everything figured out and their lives are just so cool.

I know, because I’ve been there… but I’ll be the first to tell you, nobody has it all figured out. I’ve been broke as a joke many times along my journey, I’ve been stuck up a creek with no paddle many times on my travels, I’ve experienced immense business failures, I’ve been stabbed in the back, I’ve been discouraged. But, this is an incredible life we’ve all been given, and I’m grateful for the amazing adventures and obstacles I’ve experienced. I wouldn’t trade my experience for anything.

I’m even more thankful for the people around me who have helped fuel this adventure. It has its ups and downs for sure—I was defrauded and went through several down months. I wasn’t confident everything might not collapse at times. I took a break from blogging and let some of my friends use this platform to share their writing and their projects with you (I see no point writing unless I actually have something to say, but once I conquer the challenges laid out in front of me, maybe then I’ll have something of real value to share about them).

But despite the challenges of living an unconventional life, I have no plans to quit traveling, meeting new people, and having new experiences anytime soon, to stop experimenting with my own businesses, to ever go back to a 9-to-5 if I can avoid it, to move back home, or to stop blogging about this weird journey. Living life your own way, you will definitely be confronted with setbacks, and the journey will be more challenging than living according to someone else’s prescribed path. But it is absolutely, 100% worthwhile. 

Krabi tropical office

My girlfriend and I are fortunate to live for now in one of the most beautiful regions in the world, in a three-story townhouse surrounded by forests and beautiful limestone mountains, all for a fraction of what it would cost back in California.

Emily and I recently spent a week in Singapore, and it was the most fun I’ve had in months! We were trying to decide what country to visit for a renewed visa and I decided I really wanted to visit old friends there. She teases me that I can’t travel anywhere unless I know someone there, and when I thought about it, I realized it’s not far from the truth.

Undoubtedly when most people think about travel, they tend to think of places, monuments and landmarks like the Acropolis of Athens, the Roman Colosseum, the Eiffel Tower, London’s Big Ben, Bangkok’s reclining Buddha, Krabi’s mountaintop Buddhist temple, the Petronas Towers in Kuala Lumpur. Each of these are fantastic places I’ve been able to see on my travels. But what really has made my travels remarkable are the people I have met and the experiences I’ve shared with them.

I became very close with my French professor in high school, who was also a huge influence on me (as far as my interest in travel, culture, art, music and languages). The very first time I traveled outside the U.S. was a trip with some classmates to France, and what made it special was the wonderful family I lived with for a week on the Mediterranean coast in Cannes, as well as the time I spent with Mssr. Hodgins and my classmates wandering around Paris.

London is probably one of my top three favorite cities in the world to visit. Although I really enjoy wandering around on foot through London and sightseeing, it wasn’t the London Eye or the Houses of Parliament that kept me coming back… it was because I first traveled there on my own to visit my cousin Ian, who spent a year as an exchange student there, and it was the fun crowd of college students I got to know—James, the Toms, Sarah, Dav, Elaine, and many more—when I visited him for two weeks that made my experience so special.

I traveled to Spain for a three-week Christmas and New Year holiday with my friends Paul, Tim, and Ryan. Barcelona was a stunning city with great food, equaled by the gorgeous views and historical Old Town on Ibiza (and it’s nightlife), but what really made the trip special were the incredible friends we made—Meye and Barbara, two amazing women who took it upon themselves to show us all the best restaurants and pubs in town, introduced us to friends, showed us the parades and the local Catalans celebrations, and invited us into their homes for Christmas dinner!

Catalan friends Barcelona

Greece, Turkey, and Italy are infused with history, vibrant culture, and amazing sights (especially for someone who studied history at university) but what made my travels there special were the memories and time I spent bonding with family.

When I first arrived in Thailand, it was two Thai friends I met—Poon and Om—who spent three days driving me all around Phuket on their motorbike showing me the sights.

Bangkok is a huge metropolis with great nightlife, great food, a big flag on the backpacker trail. But what made it so much fun for me was the people. I got caught up there for a year and a half eating cheap street food all the time with Migration Mark, Joel, Ryan, May, Nalin, Bank, and Aum, going out partying, and running fun monthly mixer events and volunteering with Dwight Turner, Christina, Craig Gonzales, and others. I remember the first day Sean Ogle landed in Asia, and we went with my sister and my friends Chris, Ryan, and Nick to explore the ancient ruins and Buddhas at Ayutthaya, coworking with David Walsh and Derek Johanson, planning a TEDx conference with Rob, Greg, Andrew, Chris, Karla, Fluke, and more.

Sean Ogle Thailand Ayutthaya ruins

Travel puts me face-to-face with friends—many friends I’ve known for many years from school or work, but also many who I’ve met and become friends with through running my business online.

In Bangkok, mostly through Twitter and the Bangkok Tweetups that Dwight and I would put on, I also was able to meet in person with awesome bloggers Dan Andrews, Adam Baker, Benny “the Irish Polyglot” Lewis, Gary Arndt, Matt Goult, Jodi EttenbergJonny Gibaud, Marc Gold, Ross Hill, Kevin Revolinski, Wes Nations, Ryan Martin, Mark Powers, and many more.

Warning: I’ve linked to a lot of people in this post! But I want to share each and every one of them with you (I’m definitely missing more than a few, too) not to gloat… not because I’m some celebrity, but because I’ve been blessed to meet so many truly cool people from around the world—each of them working on their own unique, interesting things—and each of them has at some point or another in my travels made a profound impact on my journey in their own small way. Because of that, I do encourage you to check out each and every one of these folks and discover how they’re making the world a more interesting place. I owe it to them to share what they’re doing.

In Bali I met Kyle and Bessie Crum doing yoga in the rice paddies, Stuart McDonald eating ribs at Naughty Nuri’s, Jez Tryner for a drink, and spent time with my friends Jerm and Vie at their lovely condo.

In Kuala Lumpur I met Nomadic Matt Kepnes while wandering around hostels, Dwight and Mark and I met our travel buddy Agnes (who drove us at lightning speed at 11pm one night to see the cozy little town of Melaka, on a whim!) through Couchsurfing, and I met Hani Khaursar, Vishen Lakhiani, Brian Wong and others on a subsequent trip when I spoke at a conference.

Phnom Penh has been home to my two friends Brittany Sims and Caron Margarete who, along with some of Cambodia’s footballers showed me the town and made me feel right at home.

Here in Krabi, I spent considerable time climbing and beach partying with my friends Alicia, James, Vanessa, Peter, Jane & Toto, and I finally met in person with my blogger buddies Carlos Miceli, Colin Wright, Adventurous Kate McCulley, Backpacking Matt Kyhnn, and Shannon O’Donnell, who’ve all stopped by on their travels.

Colin Wright Carlos Ross Railay Beach Krabi

When I traveled back to the States this year, in Austin, I met up with Markus & Ashley, Nick Reese, Jenny Blake, Ridiculously Extraordinary Karol Gadja, Where is Jenny Leonard, Andy Drish, Andrew Norcross, Thursday Bram, Technomads Chris & Cherie, and many other good folks for a week of awesomeness while South by Southwest was on.

The San Francisco Bay Area is home to a host of inspiring folks like Ramit Sethi, Corbett Barr, Amber Zuckswert, Charlie Hoehn, Lorna Li, and serial entrepreneur Rajesh Setty (and I also had the pleasure of meeting Mr. Chris Ducker there, who usually plays an Englishman in the Philippines).

Los Angeles is or has been the stomping grounds of my very good friend Ryan, entrepreneur Jun Loayza, blogger Jonathan Mead, dating coach Jordan Harbinger, my friends Dariane Nabor, Laurenne Sala, and many other cool peoples.

In past trips to Singapore, I’ve met other cool nerds (like myself) Adrianna Tan, Ziqi Koey (who also just visited us here in Krabi!), Guyi Shen, and many more.

Singapore Marina Bay Sands

This trip, Emily and I had an incredibly fun time together…  we did all the touristy stuff: we walked all around the city on foot, stayed on the beautiful riverfront in Boat Quay, gorged ourselves on amazing delicious food from all around Southeast Asia and beyond, we hung out at the marina by night and took in all the city lights, wandered all around the big fancy new Marina Bay Sands resort and casino, went to a Salvador Dalí exhibit, to the cinema, briefly to a concert hall, and much more. But our time together there also reminded me that one of my biggest motivators is the people I get to share it with.

It was seeing my friend and singer Shimona Kee for her birthday and enjoying the hip young local music scene, having a lovely homemade dinner with Michelle at her impressive 16th-floor apartment, having a drink, a shisha and a catchup with my old friends John Berns and Martin, and getting to meet Derek Sivers in person (the very down-to-earth, engaging, but brilliant and wildly successful gentleman who founded CDBaby) to chat about travels, businesses, failures, and planting multiple flags (BTW you absolutely must watch this fascinating, short 8-part video series by Sivers). Getting to interact with, have fun with, learn from, and learn about all these fascinating people that are all doing their own interesting things—that’s what makes travel so much fun for me.

Running my business online has meant I’ve built friendships with people all around the world. Interacting with people through Twitter alone has connected me to dozens and dozens of new people that I’ve actually become real friends and done business with.

The point is, I’m just an average dude—but because of the way I choose to live my life, the way I run my business, and the way I reach out to connect with other people out there, I’ve had an extraordinary experience making new friends all around the world. The tools I’ve used to build an international network of friends and colleagues are also available to you.

Being location-independent, running a business online, and being on the move—living my life this way has opened many doors to people and experiences I wouldn’t have back in my “normal” life, that I would have never dreamed I’d have. My passion and what drives my journey is the interesting people I meet… making new friends and having fun new experiences with them, learning from them, and growing with them. Your interests, what drives you, and the life you want to have may look entirely different to mine, but whatever they are, there are millions of people you can connect with out there in this small little world of ours. The amazing journey I have had, like many others, is only an example of what anyone could do. You only need to start opening doors.

What journey are you on? What are the people, places, and experiences that have meant the most to you along your path?

If you found this interesting, and if you’re anything like me, click here to get some incredibly awesome (and completely free) stuff to add to your toolbox and learn more about my philosophy. You won’t regret it→