My Favorite Destinations, Part III

When small talk gives way to deeper conversations, a world of thoughtful insight reveals itself. Penetrating through questions about where one works and lives, opportunities to know someone more deeply start with simple, but profound questions.

“What travel destination changed the course of your life?”

Nine little words strung together with a real chance to know someone. At the best dinner parties or conversations over drinks at a bar, questions such as this have been served. It is one of my favorite questions to answer and it is something I am always happy to investigate in a new way.

As a kid growing up in rural Oklahoma, I often dreamed of a life in a larger city. I would daydream and create a world vastly different from my own. Those fantasies shared some common themes. I always pictured a fantastically decorated apartment in a walkable neighborhood. I dreamed about walking to work each morning, catching a train downtown, and working in an office tower at a job I really loved. Every night, I would return home to my neighborhood filled with local restaurants, bars, and shops. In my 12-year-old mind, this felt like the perfect scenario.

I did not know it at the time, but I was dreaming of Chicago. On three separate occasions, I have visited the Windy City. Each visit to Chicago has been transformational…