Ted Simon is best known as the author of Jupiter’s Travels, one of the most influential motorcycle travel books ever written. Robert Pirsig’s Zen and the Art of Motorcycle Maintenance is another book that has long held a strange place in motorcycling culture: widely known, often recommended, and perhaps just as often left unfinished. In this conversation, Ted talks about finally reading Pirsig’s famous book and why it matters to him in a way listeners might not expect. Is it really a motorcycle book? Why has it stayed in the minds of riders for so many years? And what does motorcycle maintenance mean when the machine beneath you is not just a symbol, but the thing that determines whether the journey continues? What begins with one famous motorcycle book soon opens into Ted’s own memories of travel, breakdowns, repair, and the very practical reality of keeping a journey alive when there is no easy answer and no one else to do the work.

Lala Barlow was working in musical theatre in Melbourne, Australia, when the pandemic brought the industry to a halt. Drawn to motorcycles, mountains, and Patagonia, she spent years preparing for a solo motorcycle journey through South America, including a four-month shakedown ride across Australia. Lala shares what it takes to plan a major adventure, travel alone in unfamiliar countries, manage fear and uncertainty, and ride through Peru, Bolivia, Argentina, Chile, and Patagonia. A conversation about preparation, perseverance, and turning a dream into reality.