Chasing Chapters: How Benjamin Alexander Measures a Life Well-Lived

Olympic skier Benjamin Alexander shares his unique approach to life, valuing rich experiences over singular achievements. From DJing to skiing at the Olympics, he’s filling his “book” with unforgettable chapters—and he’s just getting started.

For Benjamin Alexander, life isn't about following a single, predefined path. Instead, it's about creating a series of rich, diverse experiences, each worthy of its own chapter in the symbolic book of his life. In a recent interview, the former DJ and Jamaica's first-ever Olympic alpine skier shared his philosophy on living well. His approach is refreshingly different, focused on variety, adventure, and pursuing personal fulfillment rather than sticking to a single identity or career.

"I believe that on our deathbed, we want to have a book filled with all of these incredible chapters of things we've done," Alexander says. For many, a stable and consistent career—whether as a banker, doctor, or finance professional—is enough. And, as Alexander quickly points out, there's nothing wrong with that. However, for him, focusing on one role throughout life falls short of his desires. Instead, he envisions his life as an eclectic tapestry of experiences, each more adventurous than the last.

Alexander’s life already boasts some remarkable chapters. From his beginnings in Wellingborough, England, where he was raised by a Jamaican father and British mother, to his career as a globe-trotting DJ, he has never shied away from reinvention. After leaving a successful career in finance, Alexander spent years performing in some of the world’s most iconic venues and festivals, including the famed Burning Man in Nevada and Ibiza’s electrifying party scene. But even that wasn’t enough.

In 2016, a ski trip to Whistler, British Columbia, introduced Alexander to alpine skiing. This experience would transform his life yet again. His encounter with the sport led him to pursue a new and ambitious goal: qualifying for the Winter Olympics. By 2022, after only a few years of training, Alexander made history by representing Jamaica in the giant slalom event at the Beijing Winter Olympics. It was a monumental achievement, but it was just another chapter for Alexander.

As he reflects on his journey, Alexander acknowledges that he's only scratched the surface of what he wants to accomplish. "I want to have ten of these crazy stories, such as getting to the Olympics, moving to Asia, and living on the other side of the planet as a DJ," he says. He's already lived out three major chapters—DJ, Olympian, and Adventurer—but he's got "at least seven more to go."

For Alexander, measuring life well-lived isn't about how much money he makes or the accolades he receives. It's about the stories he can tell, the experiences that push him outside his comfort zone, and the memories that will one day fill the pages of his life's book. This mindset encourages an openness to new possibilities and a willingness to take risks, even when the odds are stacked against you.

Alexander's journey is a powerful reminder that life doesn't have to fit into a neat, tidy box. Whether pursuing a career, a passion, or an entirely new adventure, what matters most is writing your own chapters—and never stop turning the page. For Alexander, the story is far from over. He's already looking ahead to the next chapter, eager to see where his curiosity and ambition will take him next.