In 2008, I started traveling. It just sort of happened, but three general things sparked this pursuit: I met a girl, no one would hire me, and the world called me in a way that I could not ignore. There I am above at the time - a 29 year old college senior with a massive bottled water and hair.
Growing up, I had not been many places, but I was deeply curious about the world. I had a thesis at the time that you could learn about a place, read about a place, and immerse yourself in the culture of a place from afar, BUT, as a studious pursuit you would never truly FEEL a place until you stepped off the plane at that place. This is true. You don't ever GET it, unless you go.
In January of 2008, I rang in the new year studying abroad in Central America, met my wife Kristin, and together we decided that travel is an important and foundational element of life. We made a conscious decision to elevate it above most other things. If we had kids, we would find a way. If we had work, we would find a way. No matter the circumstance, we would find a way.
We designed our life around travel.
In 2008, we took a small month long trip to Europe, and I wrote a newsletter about it, including a two page screed on a sandwich I had eaten on a beach in Tarifa, Spain.
In 2009, we went to Asia, and that is when it really happened. I started a blog called goboogo and wrote about our travels throughout Asia that summer. That blog was a modest success, at its peak getting nearly 10k views per day (years later). We paid for all of our travel through day-trading the market. We also lived with my grandparents which kept obligations low. We had made sacrifices to support a life of travel.
Stepping off the plane in Hong Kong that summer, the first time, changed my life completely. I felt a pull down an entirely different path - in a two roads diverged in a wood style. A trip can change your life. Towards the end of that trip late one night, in the rainforests of Borneo, with glowing insects lighting up the trees like Christmas in July, I decided three things: I would marry this girl, I would be back on the road as soon as possible, and I would never ever stop traveling and visit every country in the world. What else is out there I thought.
When we returned to the states, we went to Montana, followed by Mexico, followed by Italy, followed by Egypt. After that, we booked a flight to Vietnam for another summer (2010) tour of Asia. That summer, we returned to Hong Kong, visited Myanmar, dove in Sulawesi, and did a bunch of other awesome stuff throughout Southeast Asia and Indonesia.
I was approached to write for AOL as a travel writer. I still remember that night I got the email at a shitty hotel in Kuala Lumpur, thinking " I can do this for a living?" This was back before the days of influencers and the landscape we have today. It was a break. I think I got paid something like $100 per post and got many trips paid for outright. My writing was read by millions of people, and I believe I was the most read travel writer in the world in 2011 - one of my posts was even read by two million people.
Condensing all of this into a few paragraphs belies the true story in its excitement, conflicts, etc, but that is what happened in a mechanical way. I accidentally became a travel writer, did it for two years, and moved on.
From there, we kept traveling. In 2011, Kristin and I got married with 70 of our closest friends and family in St. Croix. We spent that summer in the middle east and South Asia.
We moved to Indiana for business school that fall. That is another path - none of it happens without travel. I built a business, sold it - all this crazy shit happened to someone who spent 10 years working on his undergrad degree that no one would ever hire. Travel elevated me.
In Summer 2012, I took an internship at Delta Air Lines in marketing. This meant we could travel internationally for basically free. We flew nearly 100k miles that summer and visited 13 countries. We used to have our dog Lou choose between two pieces of lunch meat to determine where we would fly - Paris or Buenos Aires, Grand Cayman or Zurich, etc. It was that extra.
The trips began to increase in frequency as for the first time ever, people began to pay me to do things, and those same people also owned a fleet of planes. In 2013, I took a full time jab in Revenue Management at Delta Air Lines. In 2014, we welcomed Harper into our family. She was in Paris by 4 months old. China and Japan before 2. Harper is now 4 and has been to 22 countries. Her brother is not far behind her, he was one of the youngest shoppers at the Long Jing tea markets of Hangzhou at 3 months old. After all, if we had kids, we would find a way. We have had kids (three), and we have always found a way.
I am going to skip the parading out of epic journeys that have happened in between, but I will say we never slowed down. Travel has always been the foundation.
Now, about 11 years after starting the journey, I have the good fortune of looking back at my thesis and knowing it was right. Travel changed my life. I was nothing, and it developed me. It made me better and faster and smarter and gave me perspective, which is my single most cherished personal development. In 11 years, I have visited 100 countries and that shit is engraved into my being. No one can ever take it.
There is an exercise I like to do as an entrepreneur. It is an exercise that manifests itself on occasion in introspective action films as the main character is factored down into his/her most essential parts. I ask myself, if you take away everything - money, network, degrees, friends, home, everything - you are left with just experiences and perspective. I only invest in things that pass that test; I want to add to that "experiences and perspective" balance sheet daily, but more importantly at a decade level as well. I believe most investments we make in ourselves have to happen over a long period of time to be truly sustainable and life changing. That is travel for me - a decade in, so far so good. I am ready to double down.
So travel, it started out as a count - how many countries could I visit. It has evolved from there as that has become less and less important. But, it is still an element behind where I go and a quantifiable travel barometer. So here I am in Grand Cayman, country number 100. Life is good.