The Exit Strategy

How did I get here?

I don’t mean “how did I end up in a coffee shop writing a blog post?”  I know I took the bus to get here.

No, rather, the question at hand goes something like this.

How did I – a small town prairie boy from Canada – end up being a regular in a coffee shop in Tokyo writing yet another travel blog post?

My journey started exactly six months ago – and over that time, I know many people have had questions about the path I’ve taken.  I chose to not share much over that time because so many pieces of this puzzle (my trip) hinged on me living up to contractual obligations which have now come to a conclusion.

Today, however, I feel not only able, but ready to share a bit more of my story.  It’s strange for me to talk about myself this way.  But I share all of this as a way to join the conversation with those who (even for a minute) have considered long-term travel as a goal.

What’s stopping you?  How do you get to your freedom?  What is your exit strategy?


My first spark of interest in long-term travel came at around age 24.  I’d spend many Friday nights after a long week of work with a glass (or three) of wine, surfing the web, devouring stories from backpackers who’d blog of their adventures.  I felt like a kid reading Davy Crockett, and I, too, wanted to go explore.  However, the travel bug was at odds with my career ambitions.

I’d known forever that working in radio and television was what I wanted to do with my life.  As a child, I constantly stole my mother’s wooden spoons because they’d make great “microphones.”  Cardboard boxes became TV cameras.  In high school, I jumped at the chance to become a jack of all trades at the local community cable channel.   In college, I learned the finer points of my craft. And then, I put my nose to the grindstone for nearly 15 years working in news, programming, management, and ultimately as a morning radio co-host.

I was doing a job I loved – a job I worked my whole life toward.  Travel, I concluded, would have to be deferred to some other point in life – when the timing was better, my ambitions had been satisfied, and my bank account was big enough.  Or, so I thought.

*   *   *

The goofiness of the following picture needs some explanation.

Producing and hosting morning radio isn’t for the timid.  You wake up as the bars close.  You get in to work as the rest of the world is hitting their REM cycle.  You’re performing at your peak when everyone else is cleaning the crust of sleep from their eyes.  Coffee – it turns out – is a magic elixir which helps make the job a lot easier.

While I’d wait for the lunchroom Keurig to brew my first cup of the morning, I’d kill time by setting up my iPhone to snap a photo.  I’d dress it up with stickers, then send off to Chris (who was just finishing his day at work in Tokyo).  It gave him a chuckle after a long day at his job, and it helped spark my creativity to start the morning.

Lack of sleep + the lonnnng wait for coffee leads one to be creative at 3:30 in the morning.

The guy in this photo doesn’t know it yet, but five hours after taking this picture, he’ll learn he doesn’t have to show up for work the next morning. Or the morning after. Or ever again.

Minutes after the May 12th morning show ended, I found myself sitting in a conference room which I had been in many times before for what I found out would be my final meeting.  One item was on the agenda – the end of my nearly 12 year career with a company that I had grown up in.

It’s always a “tough conversation” to tell someone they’re not part of the team going forward.  I know – I’ve had to have those conversations as a manager and, (as little as the person getting sacked cares) it sucks for the person giving the news as much as it sucks for the person getting the news.

Ultimately, I knew nothing I said or did could change what was happening to me.  I could only control how I reacted to it.  I stayed composed, professional and mature while accepting my new reality.  There would be more than enough time to privately (as is appropriate) deal with the Kübler-Ross “five stages of grief.”  I expressed my appreciation for the opportunities and experiences I had during my time with the company.  This was only business – nothing personal.

I walked out of the radio station for the final time and got in my car.  I should have been a blubbering mess, mortified of my new employment status, terrified of what comes next.  But, I wasn’t.  A wave of calm swept over me.  I felt an eerie sense of clarity – and I think I know why.

Like all of us, I’d sometimes find myself slipping off in to a daydream about how life might have been different had I explored what was behind door number 2 in the choices I encountered through my career.  Specifically, I’d often think of how I was always taking the road of career advancement – staying loyal to one organization – rather than exploring my suppressed wanderlust.

Daydreaming and the Internet are a potent pair.  It turns out you can research anything, including the road less travelled.  And I had done just that – for many hours over many years.

Buried in my web browser at home was a folder labelled – for lack of a better title – Exit Strategy.  Inside, I’d store snippets of the web which piqued my curiosity on the topic of travel and self-improvement.  I’d often click the link I’d saved for an online “round the world ticket” calculator – just to see how much money I needed to live my vagabonding dream.

Inevitably, my daydreaming would become a strategic planning session with windows upon windows of Excel spreadsheets and calendars open, planning a trip I had no intention on taking.  At least, not just yet.  I’d snap back to reality, close it all down, and pour myself in to focusing on my career (until the next time I opened the folder.)

I think having some sort of vision for what a life without broadcasting would look like helped take the edge off the news of my termination.  It lifted a weight off my shoulders.  I’d invested time thinking about all the things I wanted to do but couldn’t because I didn’t have the time or resources.  Now, a blank slate was staring at me, and I was a wee bit scared that I actually might do it.  I actually might stuff my life in to a backpack and go travel!

*   *   *

As the day continued, I shared the news of my departure with the people closest to me.  I was calm and collected about the whole situation.  That concerned some people.  My best friend Justin thought I was in shock.  My parents were much more emotional about what happened than I was.  I didn’t run at the mouth about my long unexplored wanderlust, because saying it makes it more real.  This news would be more than enough for everyone around me to digest, let alone announcing my intention to “get up and go.”

Chris (who didn’t believe me at first when I told him about what happened, thinking I was pulling a late April Fool’s prank) sent me a link later that night to the podcast hosted by Tim Ferriss (The Four Hour Workweek).  Knowing my predisposition to long-term travel, and being one of the few people who didn’t need me to tell them that I was already thinking a travel adventure might be in the cards, he pointed me toward a recent episode titled “How to Earn Your Freedom.”  In it, Ferriss shared an excerpt from the book Vagabonding by Rolf Potts (a seminal book in Ferriss’ own life).  In it, Potts spoke to the notion that the only thing keeping people who want to go exploring from doing it was their own inhibitions.

Vagabonding is about gaining the courage to loosen your grip on the so-called certainties of this world.  Vagabonding is about refusing to exile travel to some other, seemingly more appropriate, time of your life.  Vagabonding is about taking control of your circumstances instead of passively waiting for them to decide your fate.

At first, I felt like an imposter as every second of the podcast ticked by.

“I didn’t earn my freedom,” I thought.  “I just got kicked to the curb.  How is that earning anything?  The decision was made for me.”

However, the more I thought about my situation, the more I realized the opportunity was staring me in the face.  I couldn’t ignore it anymore – I had been handed my freedom.  Was I going to suppress my travel desires like I had so many times before, or would I take advantage of the groundwork I laid with my Exit Strategy?

With a library of reading I’d done on the topic, a deep-rooted wanderlust which wouldn’t stop itching, and now affirmation from someone as successful as Tim Ferriss that it wasn’t crazy to leave everything behind to go exploring, I decided to seize the opportunity.  The timing was not of my choosing, but that didn’t matter.  I had been given my freedom, and I needed to do something with it.

*   *   *

I could never understand how people in the movies run to the airport and just jump on an airplane.  Real life is so much more complicated.   The only thing stopping me from setting off to tour the world the next morning was four months of some of the hardest work I’d have to do in my life.

I sold some of my bigger belongings (because nobody wants to haul a sofa or IKEA entertainment centre around).  I gave up my apartment and moved in with my parents to save money.  I ultimately said “goodbye” to a lifestyle I’d grown accustomed to, and started to plan my journey.

Six months later – here I am, sitting in a coffee shop in Tokyo, actually living out my Exit Strategy.  I’m using the skills I honed during my career to write stories, produce videos, and record podcasts to tell the tale of my trip.  And, I’m starting to think about the destinations which come next, along with ways I can work remotely (putting some of those skills to use in other ways) to earn cash and keep this adventure going as long as possible (and necessary).

What is most important half a year later is that I don’t regret the decision I made.  Not for a single minute.

*   *   *

Now, if you’re reading all of this and are muttering “bullshit” under your breath with each paragraph break, I get it.  I’m sure some think I’m being overly rosy about everything that has happened, and what you really want to hear is that it’s not all rainbows and butterflies.

This is not easy.  I’ll give you that.  I’m as far outside my comfort zone as I’ve ever been.  But as an important mentor in my life once told me, you’re not growing if you’re not uncomfortable.  For example, booking my first set of plane tickets was scary.  However, doing so ensured I’d never again have to daydream about living out of a backpack.

As I mentioned earlier, I found my own way of dealing with the classic “five stages of grief” everyone experiences with a loss – denial, anger, bargaining, depression (albeit not the clinical kind in my case), and ultimately acceptance that what I was for 12 years was not ended by me handing in a letter of resignation, but by someone telling me I was off the team.  It’s not easy news to hear.  But, after seeing how so many others in my industry had dealt with getting cut in angry, bitter, unhealthy ways, I promised myself long ago that I would never handle it that way.  Life is too short to be pissed off all the time.  Instead, I concentrated on pushing forward and seizing the moment.

*   *   *

I’d long thought about what I’d do when the planets would align and I’d get my shot to go out and see the world.  I never imagined it would happen the way it did.  But, I’m a firm believer that as much as guys like Tim Ferriss and Rolf Potts say we need to earn our freedom, sometimes (often), we can’t control the schedule.  When the opportunities arise, we need to be in the right frame of mind to see what is staring at us as a blank slate – a chance of a lifetime.

If you are presented a with a crossroad, are you ready to handle it?  What’s your exit strategy?  Having one will change the way you look at life’s surprises.  And if you don’t have one, there’s never a better time than now to start to think about what you’d do with the opportunity.

4 thoughts on “The Exit Strategy”

  1. Good for you for having the courage to follow your dreams. You took a setback and turned it into a launch pad for your life adventure. Bravo!! Miss listening to you on the radio, but this is even better!!

  2. I had wondered about your thinking and your plan-this is a pretty cool outcome! I am really enjoying your journey, personal and physical. Carry on Vagabond Boy!


  3. I’m a great believer in things happening for a reason. This is a prime example of it! The catalyst for our travel adventure began when I walked out of a job I hated. I felt a little bit bad about it, but mainly I was ready and walking out was the right thing to do. I had a song by Jamie T going round in my head whenever I doubted my choice, the lyrics are:
    You were always meant to walk out that job
    You keep stopping
    Should tell your girl more often
    That loving is all about doors unlocking
    Now you’re certain ’nuff near a man free
    With a buddy holly hiccup on a karaoke
    Tweedle on the needle,
    man you adjust the thread
    Great granddaddy fought in Gallipoli
    The only of his friends not shot down dead

    That kept me focused! All the best to you and enjoy your journey.

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