Planning and Some Thoughts

The Art of Planning… and Letting Go

Planning a long road trip has turned out to be more involved than I first expected. It’s easy to say, “Let’s go!”—but quite another thing to sit down with a notebook and actually map out an itinerary.

The internet is an invaluable resource, but there’s something irreplaceable about holding real maps and travel books in your hands. Thank goodness for the CAA and their fantastic collection of detailed maps, as well as the ever-reliable TripTik planner. Sadly, TripTik will be phased out this November—another casualty of the digital age.

The deeper I dive into the history of old Route 66, the more fascinated I become. Growing up on the works of John Steinbeck and the haunting Depression-era photography of Dorothea Lange, I’ve long been drawn to the allure of the Mother Road. It’s a journey of dreams, resilience, and discovery—one I’ve always longed to experience firsthand.

It’s interesting to reflect on the influences that shape us. Not fleeting pop culture figures, but those who create profound, thought-provoking works that leave a lasting impression. Media trends may pull us in different directions—I’m not immune—but it’s the timeless voices of writers, photographers, and artists that truly resonate.

In my own career, I’ve been deeply influenced by figures like Steinbeck, Lange, Eddie Adams, Bernie Boston, Robert Capa, Margaret Bourke-White, and Farley Mowat. Their work not only shaped my perspective but also taught me to see the world through different lenses—both figuratively and literally.

That brings me to an important realization: one of the biggest pitfalls in trip planning is overplanning. Too much structure can strip a journey of its magic. Preparation is essential, of course, but the most memorable moments often come from spontaneity.

So, with maps in hand and research done, it’s time to loosen the grip on planning. The best adventures come when we allow space for the unexpected. Let’s throw caution—within reason—to the wind and embrace the thrill of exploration.