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The Story of How I Became a Vagabonding Entrepreneur

As most of you know from reading my site or my free Digital Nomad 101 guide, I left California in November 2008 with a one-way ticket to Asia and no plans to return for at least a year.

My desire to travel abroad started as a bit of an escape—to start fresh somewhere new. I’d had a nasty breakup, found myself bored in my 9-to-5 office job, stagnating in my personal growth, followed by another messy relationship. I was ready for change.

I’d lived in my hometown for 24 years and I was ready for new scenery.

Like Neo in the Matrix, I didn’t know what it was, but always knew that there was something wrong with the world. I looked around at everyone tied to their cubicles, plugged into the Machine, slaving away chasing some “dream”, but really just feeding the System: a system that encourages the status quo, conformity, mediocrity, stagnation, and submission to the same groups that have always held power in our society.

But I digress…

How This Whole “Digital Nomad” Thing Started

I remember the EXACT moment I decided that I was going to follow MY intuition when it came to how I live my life, where I live it, and what I make of it.

Rather than waiting for retirement to do what I wanted with my life, I decided to quit wasting time going down the template life path and start working on doing the things I dreamed of doing NOW. Even if it means I fail a few times before succeeding.

It sounds so obvious once you start thinking differently than they tell you to think about your “career”, but technology now enables us to collaborate from opposite ends of the earth, and build 1-man businesses that span the globe on the internet. What many folks don’t realize is that means you’re no longer tied to one place, geographically.

Digital nomads are the savvy professionals who leverage technology to work from anywhere they want—from home, the coffee shop, on the beach, or from the other side of the world! With a laptop, an internet connection, and a little resourcefulness, you can hire assistants in India or the Philippines, manufacture in China, and sell products to customers on the opposite side of the earth!

From the time I was toying with the idea of sneaking my way into Stanford Graduate School of Business, I’d already built an online platform to share my ideas about business, technology, and social entrepreneurship. And with my growing web development business, I’d already worked with clients in Canada, Australia, France, and beyond. Why couldn’t I run my business from anywhere?

I was smart enough. I was good enough.

There were naysayers who said I’d fail… that I’d go broke and come home with my tail between my legs. I had many moments of doubt (and still do, that’s part of being an entrepreneur!)

But here I am still after more than 2 years, while they sit in their cubicles…

… living near my favorite beach in the world, working on my own creative projects, meeting tons of cool entrepreneurs and travelers, and free to go out for dinner and drinks with friends any night of the week!

Creating a business that I could run remotely from anywhere in the world has given me the freedom to choose: where I live, when I work, and it has enabled me free up more time to put into relationships, writing, volunteering, and many side hobby projects.

And being able to travel frequently and spend extensive time abroad (I’ve traveled to another 8 countries in the last two years) is perhaps the most impactful and meaningful facet of the lifestyle I’ve been able to create. I can’t imagine any better way to learn about yourself, your values, and worldview, than interacting extensively with a wide range of people who will show you their many different diverse cultures, traditions, values, religious beliefs, and more (not to mention their food and parties!)

I used to get emails from friends of friends, or referrals from my clients. People started to notice the way I was living my life.

Now I get hundreds of emails every month from people who are interested in traveling or moving to Asia, or who are striving to build their own freelance businesses so they can have more time freedom and location independence.

When I started, there wasn’t anyone in the trenches with wannabe Digital Nomads like me.

“Lifestyle design” has of course been around for ever. And as you all know, there was Tim Ferriss’ book The 4 Hour Workweek… which was a major wake up call for many of us. And there have been a lucky few who have been working “telecommuter” jobs for the last 15 or 20 years I suppose.

But the Digital Nomad lifestyle is really a paradigm shift. It’s still a new idea in the workplace, still in its infancy. At the time when I got my start, there was nobody out there to mentor me or supervise me or even to brainstorm with me when it came to actually taking my small business mobile.

There were no authorities on the subject who were accessible.

There were no training programs…

So I researched and read and taught myself along the way, taking bits of knowledge from business mentors, internet marketers, travel gurus, social media “experts”, remote workers, and more. And I actually became a part of the early Lifestyle Design/New Rich/Digital Nomad community that was just starting to grow (and still is growing).

My passion (and flat-out obsession at times) for living life on my own terms, and for helping others achieve the same freedom, is what kept me going, and keeps me going, even when things get tough.

In The End, After Tons of Work… All My Passion and Drive Has Worked . . And in a BIG Way.

Back when I began doing all of this (all alone, working until 5 in the morning, pull my hair out some nights) I never would have dreamed that…

• I would have a hugely successful blog—with an audience of thousands of worldly, ambitious readers—and that lets me connect with hundreds of brilliant online entrepreneurs, accomplished authors, and intriguing travelers from around the world in person!
• That I would have millionaire globetrotting clients, and customers on 5 continents!
• That I’d co-found a company (with friends, just for fun!) that would get us in the New York Times
• That my story would be featured in books, or that I’d be interviewed by ABC News or countless business & travel sites
• Or that I’d be speaking at (and helping organize) international business conferences
• Or be able to help underprivileged and orphaned children with my friends at In Search Of Sanuk

But In Addition to Being Humbled By the People I’m Able to Interact with Every Week and the Impact I’ve had, I’ve Also Been Fortunate to Have A Very Gratifying Lifestyle (My Friends Call It Amazing… I Just Enjoy Having Choices).

For example, I get to work FROM HOME (wherever that is this week) on the web with individuals all over the world, and know that I’m making real and meaningful connections with people (and that my interactions with clients and friends can create dramatic changes for the better).

I never would have dreamed that I’d get to set my own schedule (so I have more time to spend with friends, in relationships, and getting to know new business contacts).

And I never would have imagined that I would be able to jet set around so many beautiful destinations and stay in such luxury as I have at times… It doesn’t cost as much as you might think to live a rockstar lifestyle abroad, by making a few savvy choices and using a couple smart geo-arbitrage principles.

So Here’s What I’m Getting To… Here’s What I Feel Compelled To Do…

So here’s the deal. Things have changed since I got my start a few years ago.

There is a TON of demand from people who want to know how to build a business that lets them live like this, way more than I can keep up with (like a thousand times over). And with each passing day, there are also more and more people who are successfully DOING IT. There are a lot of bloggers talking about “lifestyle design” or “location independence” who are just locked up in their dorm rooms—who haven’t actually traveled anywhere, and whose only “business” is their blog, but in the last two years, I’ve gotten to know dozens of people who are REAL success stories, many of them in person. These folks are the real deal. So I feel that our community is being compelled to step up to the plate.

The time has come for a central place to gather all these successful Digital Nomad authorities in one place where those of you who need guidance and encouragement can learn from them directly.

It’s time for some of you to stop living vicariously through what you read here and elsewhere online…

… and I’m on a mission to bring many of my friends and several of the big names online together to take you by the hand and actually TAKE ACTION to move towards the life you want. In my heart of hearts, I want to empower every one of my readers to have the same freedom and choices that I have. I’ve wanted this for a long time. And this is way overdue.

It’s time for Digital Nomad Academy

Last week I asked if there were many aspiring digital nomads out there who’d be interested in my complimentary resources guide.

I’m a lazy procrastinator, and I didn’t want to make the thing if you guys didn’t want it… so I made an interest list to gauge the interest.

(If enough people joined the interest list, I promised you I’d compile the free guide).

Well… um… enough people joined.

I was blown away! Over 600 people signed up for the interest list, which resulted in well over 200 comments & survey responses from all across North America, and as far as Australia, Hong Kong, Sweden, Argentina and South Africa! I’ve been really humbled by the buzz surrounding the Digital Nomad 101 guide. I even got enthusiastic responses from authors Seth Godin, Rolf Potts, and Sam Carpenter, who I featured in the guide!

And there has been A LOT of interest in the coaching program that I talked about POTENTIALLY developing. So we’re doing it. DNA will become a reality in early 2011.

We’ve already secured commitments from some of the biggest Digital Nomads online to be faculty members at Digital Nomad Academy, and we’re in talks with several more. I’m going to bring as many of my friends as I can into this program to share their success stories, and so you can ask them your questions directly—a wide range of people from all different backgrounds, running different kinds of businesses, traveling and living in different countries.

AND we have an incredible curriculum we’ve spent a LONG time developing for you to go alongside the premium access to the experts. More on that later…

The Final Call

Starting tomorrow, only people on the Digital Nomad Academy early bird list will receive insider information on the upcoming coaching program and receive the free content we’re creating for you (If you’re on the list, you’ll get that free resources guide, and next I’m working on a case studies report, because that’s what many of you asked for).

(I’m not here to hard sell you, and some readers are only here to read my travel stories or my thoughts on web entrepreneurship, not because they want to live the same way I do… so I want to be considerate of them and make sure that they don’t get bombarded with information they don’t want or need).

So if you want to get the free resource guide, and the all the good stuff I’ve got coming your way, I highly suggest you join the Digital Nomad Academy early bird list below now:

Get on the DNA waiting list! Plus get our Digital Nomad Resources Guide and Case Studies Report absolutely FREE:

We hate spam just as much as you

That’s It For Now

Well, I’m off to figure out where I’m meeting my diver friends for New Year’s Eve barbecue tomorrow night!

But rest assured that if you’re on the DNA email list, I’ll be hooking you up with lots of great resources and information…

Have a GREAT New Year’s weekend, and remember to check back for your regularly-scheduled programming here next week!

–Cody McKibben
Dean, Digital Nomad Academy

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