The Road to Reinvention

“You can’t reach for anything new if your hands are still full of yesterday’s junk.”

~ Louise Smith

In our 20s, my wife and I were young and poor, scraping by with big dreams and a tiny budget. We had just enough in our financial plan for one car, not two. Then, out of the blue, a guy I knew was selling his 1978 Yamaha 650 motorcycle for a really great price. It was sleek and black,  whispering tempted freedom to my adventurer heart and low-priced kindness to my bank account. So, we went from one vehicle to two, and I learned how to ride, frightened and uncertain at first but was soon flying down the road with the wind at my back. It seems that just about everything connected to owning a motorcycle is cheaper than a car. You can pick up a used motorbike for a lot less than a used car, insurance is dirt cheap, and motorcycles get great gas mileage. Heck, even common maintenance is cheaper because much of it can be done with a few wrenches in your own garage.

I rode that bike to work and back for several years until we moved from Colorado to Indiana and we got another car. Our little family was growing, so it just didn’t make sense to keep the bike, no matter how much I enjoyed the ride. We became a two-car family. I became a four-door dad with a 9-to-5 job and, well, settled into domestic life. I traded motorcycle adventures for bedtime stories and dance rehearsals but every so often, I still thought about how it felt to be on that bike and the thrill of the open road.

Fast forward from my mid-20s to my mid-50s. In 2024, after wrapping up another summer theater camp in the Rockies, I found myself on the familiar road home, contemplating the next stage of life. The drive stretched over three days, with two of my daughters traveling alongside me. They slept most of the way—understandable, given the exhausting pace of theater camp—leaving me with long, quiet hours behind the wheel and plenty of time to reflect.

In the previous 15 or more years, my summers had been devoted to teaching theater camp, each vacation shaped by rehearsals, performances, and the energy of young actors. But as the miles rolled by, I realized that I was ready for a change, uncertain what could possibly surpass the experiences I’d had, but certain that something new was needed. As we made our way across I-80, we passed several motorcycle riders, each one stirring memories and igniting my curiosity. I watched them for hours, studying their freedom and the unique rhythm of their journey. By the time we pulled into the driveway three days later, I knew exactly what I wanted to do next: buy a used motorcycle and start riding again. The moment the idea entered my mind, it was settled. All that remained was to find the right bike.

The day I bought her, at the dealership. "Harriet," my 2015 Harley-Davidson Street 500.

From the moment I laid eyes on her, a week later, I knew that this 2015 Harley-Davidson Street 500 was destined to be mine. She was just right—not too big, not too small, striking that perfect balance between approachability and excitement. With her stunning, understated color, she radiated beauty without ever veering into flashiness. For me, she was the ideal “restarter” ride. In the span of the year that followed, I racked up roughly 7000 miles on Harriet, carving out new routes and stirring old feelings. That might sound like a lot of miles to some (Google tells me 3000 miles/year is pretty average) and not nearly enough to others. But for me, it meant meaningful commutes through the city to work, fun errands around town, and two epic journeys: one to St. Louis and back for work, and a three-week solo ride to Colorado and home again. Harriet truly was the perfect companion for a man rediscovering the joy of the open road, eager to embrace fresh adventures.

In that year, I think squeezed every last drop of adventure out of Harriet, at least for me. Somewhere on a gravel-strewn Nebraska back road, as I made my way home across the heart of America, it struck me…just as I’d once taken a leap toward something new, it was time for another step forward. I’d grown as far as I could with Harriet. So, when I got back, I started searching for a bigger bike and prepared Harriet for her next chapter too. I gave her a thorough cleaning, polished every inch, fixed up a few things, and made sure she was ready to show a new rider what true freedom felt like.

Offers trickled in all autumn long from interested buyers, but none felt quite right. I passed on them, trusting the universe to send the right home when the time was right. While money played a part (the plan has always been to sell each bike to fund the next) it was never the driving force. I was determined to find a rider and a home worthy of everything Harriet had given me. She deserved it. After all those miles, all that discovery and joy, I wanted her next chapter to be as rich and rewarding as ours had been and as meaningful as mine was going to be next.

In November, a couple from Wisconsin came to meet Harriet. Both were seasoned riders, with a stable full of bikes (mostly Harleys), and the wife had recently fallen for the Street 500 after riding one in a motorcycle riding course. It was the perfect bike for them and the perfect home for Harriet. A few weeks later, they returned, trailer in tow, ready to whisk Harriet off, eager for fresh adventures once winter finally gives way to warm, sunlit roads. I had no doubt she was headed toward exactly the right kind of journey.

In relationships, careers, and hobbies, I think we can’t be afraid of new journeys, adventures, and experiences. As well, it takes immense courage to know when it’s time to stretch oneself into next journeys, adventures, and experiences. I’m not very good at being or feeling settled. I’m constantly excited and energized to find another gear, seek out new sights and sounds, and feel new feelings. There’s an awful lot of roads, small towns, old bridges, and horizons to discover. I want to see them all. No kidding. I’m not sure there’s enough life left to see as much of the planet on two wheels as I’d like, but I plan to try. Here’s to always chasing what’s around the next bend and having the courage to believe we’re worth going there and remaining determined to being there.

Whether taking a first step into the unknown or letting go of the current to take the next step, the road to reinvention is worth every mile.

My 2012 Kawasaki Vulcan 900 Classic LT. Little bit bigger in all ways and extraordinarily comfortable and fun to ride. Here, I took her on my first work trip to Madison, WI for a video shoot and back home again to Chicagoland.