April 1, 2017 – Departing Chicago

April 1st, 2017 – It was time to embark on an adventure I had envisioned two years earlier when I first threw my leg over a bike. Or was my first backpacking expedition the catalyst to my ’round-the-country roadtrip? Perhaps my nostalgia for the types of video games that allowed me to explore vast expanses riddled with hidden treasures evolved into a craving to do the same in the natural world? Maybe it was a sort of guilt built during my years prior as a Global Marketing Manager traveling to several countries and exploring their inspiring landscapes that made me yearn to explore my own for the first time…(insert “First World problems” comment here).Most likely, it was an amalgamation of everything, a pot of existential angst that had been patiently simmering as I casually added key ingredients and essential spices, eventually coming to a rolling boil in the months leading up to liftoff.Very little planning went into this venture. Rather, I simply loaded up my backpack with the wisdom I had acquired from previous expeditions, and armored my temperament with the faith that I can improvise my way down the road ahead. Over the course of several months, this wisdom and temperament would be thoroughly tested.
But alas, as of (September 1st?) my adventure has come to an end. In order to see as much as possible without constraining myself to an agenda, I embarked with a singular vision: To touch the eastern, southern, western, and northern-most points of the continental US, as well as ride through Boston, Miami, San Diego, and Seattle – the cities in the country’s furthest corners.