I remember it like it was yesterday, driving home from a friend’s house last Super Bowl Sunday, staring at a guy my age racing down the highway on a bike that looked as mean as it did fast. Why not me?
More than 10 years ago I took what many would call a traditional path after finishing college to begin my career in finance. As I spent the next decade working hard to establish a practice in financial consulting, I would often admire the stories of friends who had taken post-graduate adventures of the soul. I remember speaking to my girlfriend (who would later become my wife) several years ago about my master plan that upon my 35th birthday, I would bring to the office a backpack, hiking boots, and a debit card with $50,000 in savings to walk the earth on an aimless two-year journey of self-discovery. Reality and rational thought prevented this dream from ever materializing, but the thought of this journey would remain a tenant in the back of my mind.
I’m not sure exactly why, but seeing that motorcycle last Super Bowl Sunday flipped a switch. Now 33 years old, my life had reached a comfortable pace that was in need of a disruption. My mind began to race as I lay in bed that night. Where would I go? Which of my friends would have the ambition to join me? And most importantly…how the hell do I operate a motorcycle?
Fortunately, the motorcycle gods smiled upon me over the next several months. I was fortunate to find that Skip Fordyce Harley-Davidson provided the Rider’s Edge training course that was as comprehensive of a beginner’s course as I could find. Additionally, I found a similar kindred spirit in an old friend, Zach, who was looking to write the same chapter in his life. After meeting Jordan, he seemed more than willing to coach Zach and I into shortening the learning curve. After all, Zach and I had an ambitious departure date. While it was only March, our plan was to hit the road in June. Our itinerary would be to aimlessly roam the better part of the US for three weeks, visiting some of the most awe-inspiring towns, landmarks, and food joints that make up the fantastic fabric of this country. Even better, Jordan would be joining us as our epic journey of self-discovery would crescendo with a visit to one of the most notorious biker rallies in the South, the ROT Rally in Austin!
After ample research, Zach and I decided that we would go the Harley-Davidson route. There was something about doing this trip on a Harley. After months of accumulating the right gear, we were ready to make this dream a reality. I received many different reactions from various folks after mentioning our plans to take this trip, from “amazing” to “foolish” to my personal favorite “are you terminally ill?” I found that you learn a lot about people when you tell them that you are about to ride cross-country on a Harley that you just learned to ride three months ago. However entertaining the comments, I found a common thread in the wide-eyed glory with which this dream was received by the 30- to 50-something guys that felt the claustrophobia of life’s predictability. Far from dissatisfaction (I love you, honey), every guy’s life reaches a point when they begin to wonder when their Easy Rider/Into the Wild moment will come. For us, this was going to be it.