My Story

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$185. That’s how much I spent on the plane ticket that changed my life.

I didn’t know it at the time but buying that plane ticket was the first in a string of actions that has helped me build a life.

More about that in a minute though.

Let’s flash back to December 16th, 2013…

Another flight…

This flight wasn’t life-changing but it was a MISERABLE way to end the best four months of my life.

I was five hours into American Airlines Flight 60 from Tokyo to Dallas. “Only six hours to go!”

I had just woken up from what can barely be called a “nap” (I can’t sleep on planes).

My head was pounding…my throat was sore.

Why did I get on this plane again?!

A small child in the seat in from of me stared through the crack between the seats with an evil grin.

He was mocking me. He knew something I didn’t. Children seem to have a way of knowing things don’t they?

What did this kid know?

This kid knew I had just caught the flu

For the first time in my life…

On a plane STUFFED with people…

From him.

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So there I found myself, trapped in a sea of people. Just half a day removed from the MOST AMAZING four months of my life.

I was headed home on a one-way ticket with an empty bank account and a pounding head.

Some way to end the trip of a lifetime huh?

Things couldn’t possibly get worse right?

A few weeks later, January 5th, 2014…

I was staring out the window at another dreary winter afternoon in Charleston, South Carolina.

This was the third day in a row I’d spent staring out that same window.

Before that I’d spent a long two weeks recovering from the flu I got from devil baby on that plane to Dallas.

But now here I was, day three of staring out the window wondering what I was going to do with my life.

Were my traveling days behind me?

I shuddered at the thought.

It was the 5th of January now and all of my friends and family were back to work. New Year’s Eve was well in the rear view.

Everyone had somewhere to go. Lives to live. New Year’s resolutions to keep.

Not me.

What the HELL was I doing?

I shifted in my seat and rolled the orange and black swirled bracelet around my wrist.

My friend Lauren bought it for me two months before in Siem Reap, Cambodia.

I hadn’t noticed it much over the final weeks of my trip. Too much was going on I guess.

Now for some reason it stood out like a sore thumb.

I asked myself again – out loud this time…

What the HELL am I doing?

Why the HELL did I come home?

I could still be slurping noodle soup street-side, telling travel stories on a starry beach, exploring temples, LIVING LIFE.

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Instead I was nearly dead broke with no plan and no job.

I gave the bracelet a hard tug. No use keeping it on. It’ll just remind me how I’ll never get that lifestyle back.

I grabbed my laptop off the desk and flipped it open.

It was time to look for a REAL JOB.

It was time to SETTLE DOWN.

I’d GOTTEN THE TRAVEL BUG OUT OF ME.

That’s what everyone kept telling me anyway.

As I started to type the URL of one of the major job search websites I felt a weight on my shoulders.

The weight I felt was the fear that I would NEVER be able to travel as much as I wanted to again.

I looked down at that bracelet again and made a promise to myself.

I was going to live a life of travel no matter what. I wouldn’t stop until I found a way.

There’s gotta be a better way…

I decided that day that I could never settle into the “real world.”

There was NO WAY I’d step foot in a cubicle again, HOPING my boss would give me a FEW DAYS OFF.

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Nope, I had to do something.

I needed a way to make money while I traveled.

Was it possible? I had no idea.

Cue father Google…

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I spent the next six or so hours scouring every blog article I could find that had anything to do with making money while you traveled.

And guess what? I found some good options…

Teaching English seemed like a good idea.

The problem? You were pretty much stuck in one place for at least a year. I wanted to MOVE!

What about a work visa in Australia? They have a program setup where you can work and travel for a full year.

Eh, its sounds nice but it’s not SUSTAINABLE.

Working at hostels? There are plenty of them all over the world and they always seem to be looking for help!

Great I’d do that for a few years and then have no skills to build a FUTURE FOR MYSELF.

And then I stumbled onto something interesting…

I found an article about a group of people making money online doing the things they’d normally do in their “day jobs.”

The only difference? They worked for themselves on a contract basis.

They were freelancers.

The author said people were hiring for ALL SORTS OF SKILLS.

He said the industry was growing like crazy with no signs of it slowing down.

I had to check it out.

I went to one of the popular freelancing sites the author recommended to have a look around.

What I found was at first INCREDIBLY exciting.

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There were literally thousands of jobs being posted.

I kept hitting refresh every few minutes and new jobs were being posted all the time!

I dove in a little further to see what kind of money these things were paying and my excitement went from a 10 to an 11!

But my freelance dreams were short-lived…

It was when I really dove down deep into the job postings that the reality set in.

There were jobs, sure. The problem I was faced with was…

There was a LOT of competition…

Not only was there a lot of competition, but almost all of it was coming from countries like India and the Philippines.

How was I supposed to compete with people who could live comfortably off of a few dollars a day!?

Just when I was about to give up I noticed something. Even though most of the freelancers were from overseas…

The majority of the jobs were being awarded to freelancers from the United States!

I quickly started scanning through the profiles of American freelancers to see the jobs they had been awarded.

About 90% of the applicants on those jobs came from low-cost countries.

That means that these American freelancers (and to be fair the UK and Australia had it’s fair share too) were regularly beating out low cost freelancers.

And here’s the kicker…

Because you could see all of the bid prices…the Americans were charging more…much more.

Despite charging sometimes double or triple the amount, the American freelancers were still winning 90% of the jobs.

This was it, my big break.

In retrospect what I did next was insane…

Remember that $185 plane ticket I told you changed my life? I bought it that day…

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I bought it right then and there on the heels of discovering what I thought was a freelance gold mine.

My one-way ticket to Cancun, Mexico left me with $771.95 to my name.

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I IMMEDIATELY panicked…

Now if you are reading this thinking that was probably a stupid move then I’d say you are right.

Very right.

So right, that I immediately realized I was in some serious trouble.

I had no income and had just wasted about 20% of the little money I had on a one-way plane ticket.

And what was my plan?

My “plan” was to spend the next month pouring all of my energy into starting a freelancing career that let me travel full-time.

The bad (obvious) news…

I certainly had the cards stacked against me. For starters:

  • I had never made a penny online before that day
  • I didn’t have any real marketable skills to make money with (I was wrong on this one, you won’t BELIEVE what people will pay you for)
  • I only had a month to prove I could make it work

The good news…

Here’s where I bet on myself.

For starters, I viewed the deadline (the flight) as a good thing.

Nothing like a little pressure to get your ass in gear.

The real kicker though was…

I knew there was NO WAY I could let my travel dreams go down the drain.

The pain I felt when I returned home from my 4-month trip in Southeast Asia was real.

It was one of the sharpest and hardest hitting pains I’d ever experienced.

I knew that I would do ANYTHING to not feel that pain again.

And guess what? Despite all of the odds, it worked!

Have you ever pictured yourself living in small suburb of Prague, shopping at the local market for your produce, sharing a pint with strangers who don’t speak your language after work, and then riding public transit to explore the city in the evenings?

I’m not talking about just visiting Prague. I’m talking about LIVING THERE.

How about exploring the mountains of Northern Spain on your lunch break in Oliana? Winding your way down streets filled with the sounds and smells of country life on the way back to your flat. Hell, can you imagine working with this view:

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That leap of faith I took that day in January 2014 allowed me to do those things and more.

Since I booked that ticket and took the leap of faith I’ve:

  • Spent 6 months slowly traveling and working my way across Southern Mexico, Guatemala, Nicaragua and Costa Rica
  • Spent 8 months living and working in Ho Chi Minh City, Vietnam
  • Used my flexibility to crash some travel friends’ wedding in Dublin, Ireland
  • Lived in or visited the Czech Republic, Spain, Australia, Thailand, Indonesia, Singapore, Panama
  • Spent time at home visiting family and friends

I’m not mentioning these things to brag here, what I’ve done isn’t groundbreaking…

Instead, I want to show you what freelancing can do for your life and your career.

  • It allowed me to live anywhere I want.
  • It allowed me to build a sustainable income.
  • It allowed me to have a life filled with travel.

Sure, there were some mistakes and hard times along the way…

Listen, this lifestyle isn’t perfect. It sure isn’t easy.

Just like anything you have to work at it.

I’ve made so many mistakes along the way that I wouldn’t wish on my worst enemy…

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but you know what? It was so worth it.

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