Life Aboard: Leap of Faith

How did flying hang gliders lead me to life aboard a cruising yacht and writing this column? Indulge me for a minute.

Standing on a grassy slope, which gently falls away to an 800-foot vertical cliff is risky enough, but being willing to run as fast as you can down that slope would seem crazy to many. Yet this is where I found myself as a young man learning to fly hang gliders. The first lesson in flying is that if you want to learn to fly you have to leave the security of the ground beneath your feet, to literally run away from the safety of the earth and trust the wings above.

Fast-forward 30 years, when I found myself firmly planted in a career, with a house and all of the other trappings of success; the young man inside of me had not lost the thirst for adventure. Now, what would it feel like if I walked away from all that I believed gave me safety and security? I found myself thinking of my first cliff launch. If I wanted to experience something new, I had to run from the safety of my current life and trust that I would be OK.

So it was at the top of my career, I chose to sell a successful business and step off into the unknown. When friends and colleagues heard I was leaving, they wished me happiness, with many saying they wished they could do the same. Most said something like: “Financially I could leave, but I don’t know what I would do with my time if I didn’t work.” My thought upon hearing this was always sadness for them, that they had nothing else in their lives besides work.

I didn’t know exactly what life after my career was going to look like, but I knew there was more out there besides what I was doing. In pondering this, I recalled an article in the Baltimore Sun I had read years before that gave me hope. A reporter interviewed five people who were successfully enjoying their post-career lives and the interesting thing this group had in common, was all of them were happily engaged in some activity they had no experience with or exposure to in their earlier lives. The lesson here seemed to be you had to free yourself of what you were doing in order to see any other possibilities.

My wife Dori and I knew we loved spending time on a boat and that we enjoyed traveling, so building a long-distance cruising boat to enjoy when we left our careers seemed like a logical step. What we couldn’t have envisioned was the writing, teaching, consulting and photography work that would emerge along with this life aboard. To have developed a second career, pairing a lifestyle we love with the rewarding aspects we get from sharing this life with others, is far more fulfilling than we ever could have imagined.

Leaving a long-held career felt like standing on the edge of that cliff all over again, with the same thrill, uncertainty and fear of leaving behind the familiar. But just as stepping off into the unknown taught me to soar, so too has the decision to leave the structured life of a career and embrace a new chapter. Boating, much like flying, has become both the means and metaphor for this transition. There is an inherent sense of freedom in untethering yourself from the daily grind, in casting off into uncharted waters and trusting that the journey ahead will be rewarding.

For us, our life aboard offers a sense of adventure and self-reliance—navigating unfamiliar routes, weathering storms and enjoying the serenity we feel when we’re aboard. It mirrors the process of redefining life after work: the challenges, the unpredictability and the freedom to chart our own course.

For me, boating became more than a pastime—it was the perfect avenue for discovering there was life beyond work. I found purpose in learning, teaching and sharing that lifestyle with others, proving that stepping away from a successful career doesn’t have to be an end, but rather the beginning of a different kind of success—one filled with adventure, joy and self-discovery.

This article originally appeared in the December 2024 issue of Power & Motoryacht magazine.

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Source: https://www.powerandmotoryacht.com/column/life-aboard-leap-of-faith