CALCULATED RISK
Thoughts, ideas, and stories about business, life, and good decision-making.
On my last morning in Dubrovnik, I set my alarm for 5 AM. My Airbnb host told me the sunrise was even more spectacular than sunsets. As I watched the sun peak above the rugged mountains and illuminate the Adriatic Sea from my perch overlooking Old Town, it compelled me to chase the morning light through a Sunrise Serenity Series on Instagram…
For this European adventure, I intentionally made sure I had my lodging and flights arranged in advance (I would have suffered a mild panic attack otherwise), but as for my daily activities, I wanted the option to choose as I go. No “must-see lists” — just me waking up each day and deciding what I felt like doing.
One of my biggest anxieties around travel is that I’ll have an unsatisfying meal (sad, yet true)…
Walking is my favorite way to get acclimated to a new city. I’ve spent many enjoyable hours over the past week strolling through narrow cobblestone alleys, ancient walled cities, and bustling piazzas throughout Rome, Tuscany, and Dubrovnik.
In each of these different places, I keep coming back to two primary observations…
I’ve often dreamed of living abroad, even for a brief stint. The problem was, I couldn’t make the numbers work. If I was locked into an apartment in Chicago, it would be too expensive to float two rent payments while I gallivanted overseas and stuffed my face with fresh cheese. Plus what would I do with all my belongings?
I kept pushing off my timeline…
“I took a calculated risk.” That’s how my story begins. In July of 2011, I decided to pick up and move from New York City to Chicago without a job or an established network in place. I had only spent one cold, rainy weekend in The Windy City, but it seemed like a perfectly suitable place to call home. For many, this seemed like a wild idea, especially for a Type-A planner like me…
