“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.

I was finishing up a coveted rotational position on Wall Street and had the option to transfer overseas or to a new department within the bank. The world was my oyster, yet I felt deeply conflicted by the decision I faced. Do I continue on this finance track or forge a new path?

My first boss and mentor had a mantra I still use today: “Let’s do the math, shall we?” First, I crunched the numbers. If I left, I would certainly be taking a significant pay cut. How long could I live on the savings I had squirreled away before needing a new job? What salary would I need to enjoy a comfortable lifestyle? And most importantly, where was I willing to make sacrifices?

Next, I evaluated all the qualitative considerations — including my mental and physical health, along with my overall happiness.

After weighing all the factors, I asked myself what’s the worst case scenario? Would I die or be forced to live off ramen? (Side Note: That's usually my litmus test for draconian situations...). The likelihood of this occurrence was very slim -- I told myself if I can't find a suitable employer and make zero friends, I will have spent a few thousand dollars to move halfway across the country and back. New York will always be there. And if I didn’t go, I’d always wonder, “What If?” It’s a calculated risk I was willing to take. So I walked away from the hustle and bustle of my New York life and haven’t regretted it for a minute.

Nearly eight years later, I’ve made countless choices both big (starting a consulting company) and small (is there room left in my budget to splurge for extra guac?) in my professional and personal life — and every time I crunch the numbers and calculate the risk. It’s more of an art than a science, requiring a healthy mix of data and gut.

As you’ll quickly learn, I’m a self-proclaimed numbers nerd (I do honestly geek out over Excel pivot tables, but more on that later...). I’ve built a practice around helping creative business owners better understand their data and make smarter, more informed decisions. Whether it’s evaluating the success of a new business endeavor, figuring out how to be more efficient with your time, or if it makes sense to move across the country on a whim, we're all making calculated risks every day. Before we jump head-first into a decision, my first response is always, “Let’s do the math, shall we?”