Making the Decision to Become Digital Nomads

Matt’s Journey – Inspiration, Move Me Brightly

I’ve always loved to travel.

When I was in high school I was a bit of an underachiever (‘so smart…if he would only apply himself,’ my teachers would say). In my junior year, my parents told me that if I made honor roll they would buy me a plane ticket to Europe and a Eurail pass.

I think I maybe shocked them when I made honor roll and had a hell of a summer backpacking around Europe!

When I was in college (go Hokies!) I was a total free spirit.

I did things ‘my way.’ Grew my hair, adopted a ferret, followed the Grateful Dead around the country seeing a total of 123 shows and paid for it by buying cheap beer in Canada and selling it at a 300% markup in Dead show parking lots across the US.

Matt in College

Then I graduated college, got a job, married my college sweetheart and had kids. I was a dad at 22…I didn’t do things ‘my way’ anymore!

Life happens.

I still had the wander bug, though. And have flown well over 2 million miles all over the world visiting over 50 countries for both work and pleasure.

When my marriage ended I fell back on my travel passion even more. My travel friends became my travel family. I even ended up marrying one of them: Lisa.

Today I am happily re-married and, as Lisa puts it, the conservative one in our relationship – even though I keep telling her that I was a hippie back in the day!

Somewhere on my body there is even a Grateful Dead tattoo to prove it – and not the ubiquitous Steal Your Face, but an homage to Lady With a Fan/Terrapin Station!

But in any case, here I am, finished raising kids well before 50 and ready to do things ‘my way’ again.

A couple years ago Lisa suggested we quit our jobs and travel the world for at least a year. She had a plan. She always does! 🙂

My primal first reaction was: YES! Immediately followed by: no freaking way that will ever happen.

But did I mention she had a plan…yeeeaaahhh..and that included getting me on board with the idea.

To that end she planned a 2-week trip to SE Asia: Laos, Cambodia and Thailand. Her mission was to get me acclimated to the idea of living a life of affordable luxury while seeing the world.

It worked.

I spoke with so many ex-pats and fellow travelers who were taking a break (either temporary or permanent) from the rat-race…and LOVING IT.

The only way I can describe it is like when a fever breaks: one second things seemed so dim and difficult and the next everything seemed so healthy and so possible.

Koh Samui

Pondering the Decision to Become Digital Nomads in Koh Samui

But we didn’t take this decision lightly. And so we decided to spend a year putting our lives and affairs in order.

There was a project at work I wanted to see to completion, Lisa had a contract for the year, we had to get in shape, and we had a condo to sell before we could make a go of it.

But that’s another story for another post – preparing to be digital nomads.

There was one promise that Lisa and I made to each other before we left: we would live a nomadic lifestyle traveling the world – but we would do so in an affordable upscale way. No hostels, no night busses. Plenty of 1 br apartments and business class flights!

Lisa’s Journey – I Actually Did it My Way

In December of my senior year in high school I received an acceptance letter from the University of Notre Dame.  In February my parents drove me to South Bend, Indiana to check it out. 

As we were walking through O’Shag Hall I noticed a large sign for the ‘London Program’ – a study abroad program.  Even today I can so clearly see the Beefeater in a crisp red uniform, his right foot in the air mid-march. 

I looked at my parents and said ‘I’m going to study abroad when I am a junior – I am going to go to London!’

There are a few reasons why this story is important:  

1) This is my first memory of making a specific travel goal.  Although I had always wanted to travel, until that day I had been a kid without a plan.

2) One time in high school my good friend Stephen called me from the plane phone on his way to California. I could have DIED of jealousy! That was as close as I’d gotten; I had never been on a plane – but I was determined to get on one.  And soon. (There were many reasons Stephen and I were besties in high school – but the fact that today he is a purser for an airline and lives in Paris pretty much tells the tale!)

3) In 4th grade when we had to list the states we’d been to, I was so jealous of my classmate JT who had been to 8 states. I had grown up in a small town in Pennsylvania…and standing on the campus of Notre Dame in northern Indiana was the farthest I’d ever been from where I grew up.  Now I was going to go to London.  I was sure of it.

4) My parents’ heads were already spinning at the prospect of my going to Notre Dame, so by throwing studying in London on top of that I may as well have told them ‘I’m going to study on the moon’…it must have seemed equally likely to them at the time.

Well, I did go to London my junior year. 

And my mom (who had also never been on a plane) and dad flew over and visited me while I was living in London. That will forever be one of the absolute best weeks of my life.  Of course, I didn’t stop there. 

I backpacked around Europe when the semester was over and left London a few days before Christmas a different person – I was now a traveler.  

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Me Studying in London During my Junior Year of College

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I Taught Myself to Drive a Stick-shift in this Car…on the Left Hand Side of the Road!

My Mom and Dad Visiting me in London During Study Abroad – My Dad Went All-In Sporting a Tweed Cap!

Every major decision that I’ve made in my life since then has been driven by one goal – to travel as much as possible.  I took a consulting job with Ernst & Young out of college so that I could travel around the country every week. 

After a 1.5 years of travel to client sites I was placed on a local project in Chicago…so I looked for a new job and moved on.  Having learned my lesson, from there on I let it be known at every job I accepted (I tended to move on every 18 months or so until I was about 30) that if I was put on a local project I would leave.  I was never put on a local project again.

For the next 13 years I traveled every single week all over the country and world.  On weekends I would do ‘alternative travel’ (flying somewhere besides home for the same or less cost, so that it is still expensable).  I learned that you could fly from Cleveland to London for a weekend for the same price as flying from Cleveland to Chicago (crazy but true), so I went to London a LOT that fall. 

Here is a link to some past travels that I blogged about.

Of course, travel is even more fun with friends, and for that I was lucky – I found my peeps on a website called Flyertalk ( www.flyertalk.com ), where people exchange tips and tricks on frequent flyer programs and travel.

Posters there set up ‘do’s’ to travel together – or at least meet up at interesting places around the world.  In July of 2002 I hopped on a plane to Seattle for my first do – a beer festival in Portland Oregon.    

Many Of The People In this Picture Are Lifelong Friends. And One Became My husband (yep, the guy with the goofy hat in the middle). 

Travel was my job, my hobby and my passion. But then, in January 2008, while relaxing on the beach in Rio de Janeiro (alternative travel!!), I read a book called ‘The 4 Hour Workweek’ by Tim Ferriss. It changed everything for me. 

In this book he describes the idea of the ‘New Rich’ who are not tied to an every day job. He makes it sound really easy to start a side business, quit your job and travel the world.  It isn’t.  I assure you. 

BUT – this book was life changing for me in that it made me look at the world differently.  It made me say ‘well, if other people can do it, I can do it: travel can be my whole life!’  It would take another 8 years before I would actually start a digital business, but the inspiration started there.

I started dating Matt in 2009 after a week-long trip to Russia where we realized that after 7 years of friendship, we just might be more than friends.  I was living in Chicago, working in Houston every week, and dating Matt in DC. 

After about 9 months of this I gave up my place in Chicago and moved to DC, and 6 months later I hopped off the partner track at Deloitte to work for myself – and I took on a local client – remember when I told my bosses I would quit if they put me on a local client?  Yeah…life changes when you fall in love.  Or does it?

I found that I had a lot more time on my hands than I had had traveling every week and meeting the demands of a Senior Manager at Deloitte.  I was bored. 

And so I made the decision that it was time to figure out how to actually become a digital nomad – a word that didn’t exist when I first read Tim Ferriss’ book in 2008, but that had becoming a thing thanks to technology and restless souls like us.  In case you didn’t catch on yet, when I make a decision to do something, it usually happens… 

So now my hobby and my passion are my life. And best of all I have a fellow traveler, best friend and amazing partner to share it all with!

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