The Art of Business Road Trip

Illustration by Hugh Macleod

Let others lead small lives, but not you. Let others argue over small things, but not you. Let others cry over small hurts, but not you. Let others leave their future in someone else’s hand, but not you.

- Jim Rohn

Lifestyle Entrepreneurship

I am a lifestyle entrepreneur. I punched out of the military and subsequently left corporate America so I could have the freedom to pursue those interests that were demoted in importance while working for “The Man”. I chose (and still choose) to work on remarkable projects and with remarkable and inspiring people instead of grinding away each day in an effort to amass a fortune that may someday allow me to do what I want. I don’t put off until “retirement” the adventure that life serves up in the present.

When I set out on my own several years ago, my goal was to establish a business that complemented my desires to travel and explore, to participate in endurance sports and to help others pursue their dreams. I needed a business infrastructure that provided the flexibility to live, play and work anywhere and at any time I chose. I spent months researching and testing business systems and business models until I found a combination that met my goals of flexibility and profitability.

The Summer Adventure

I put my business systems to the test by traveling a lot and make it a point to set out on some sort of extended adventure every summer. One of my missions during these summer adventures is to take a mental step back from the day-to-day rigors of life and entrepreneurship, to take stock of and be thankful for the abundance in my life, and to re-focus my priorities for the coming months. I also use these trips as opportunities to push past my perceived limitations and demolish any imaginary ceilings that may be holding me back.

The Road Show Starts on September 7th

This summer will be no different. On Tuesday, September 7th, I will be leaving my home base in Seattle for a month and heading to the East Coast, Central America, the Caribbean and South America. To make it more interesting, I will not be checking any luggage and will be traveling with only a carry-on bag. My office will be my laptop and wherever I am sitting at the time; my running routes will be in the jungles of Costa Rica, the mountains of Columbia, and the beaches of Aruba, among others; and my commute will be via boat, plane, bus and horseback.

So why am I mentioning all of this? I would like for you to join me on this adventure. There will be challenges, business and travel lessons learned and funny stories, and I would like to share and discuss them with you. My goal is to demonstrate that you can travel the world, pursue your interests and earn money at the same time. You don’t need to sit in cubicle for the next 30+ years to earn the right to follow your dreams. Those dreams are there for the taking right now.

In the end, a meaningful life is the only life that is worth living.