Sometime in the 1970's my family packed all their belongings into a used station wagon and drove from Chicago to Flagstaff. One of my earliest and most iconic memories is the sight of the Sears Tower receding in the distance though our rear windshield, vanishing along with good friends and family as we left the only world I knew for a completely unknown future in the west.

Thinking about it today, I can't adequately express the astonishment I feel at my dad's decision to move west. He left a guaranteed career path offering enormous prestige for a two-man practice in basically the middle of nowhere. But—he says by way of explanation—he loved the mountains and there was a ski area.

Over time, growing up in Flagstaff, the word 'Chicago' became synonymous in my family with a dark alternate reality, a cautionary tale of what might have been had my dad not made the bold decision to relocate his family. Crime, pollution, the rat race, the soul-crushing flatlands of the midwest—we'd escaped it all by the grace of God and my father's determination to give us a better life.

It's a nice story—but it's not the whole story. Truth is, as I've gotten older I've come to a much broader understanding of what we left behind in Chicago, good and bad. And though I can never know, I can't help wondering what my life would have looked like if we'd stayed. This July I flew to Chicago with my family for a wedding. We've still got roots back east, and if you follow them, they go back a long, long way—blood relatives, multi-generational friends of the family, all of it a vast tapestry of connection that we gave up when we moved.

As for the city itself: it's awesome!

To my adult eyes Chicago offers a stunning convergence of geography, people, infrastructure, and architecture. To the north of the city are quiet tree-lined streets that exist as if plucked directly from my childhood memories. At the city's heart is density at its finest—diversity, choice, opportunity, energy. You could argue Chicago is a more beautiful and livable version of Manhattan—especially when you're cruising Lake Michigan just off Navy Pier at sunset.

Does that mean I'm going to move back? Probably not. There is no ski area, after all. But I don't see my family's departure from Chicago as an escape anymore. I see it as a change, trading one kind of life for another. To be honest I wish I could have both. Maybe that keeps me from fully inhabiting either world, maybe that keeps me where I am today.

But it's who I am: a child of two very different places, and an adult who's always trying to find a balance between them.

— July 26, 2012

Andy Lewicky is the author and creator of SierraDescents