Train Rides & Cocoons

Sweeping his finger across the classroom, my professor issued a searing indictment: “The reason you all are here in law school, and not across the street in business school, is because you are risk averse.”

I don’t know about my classmates, but I was guilty as charged. And my professor’s observation has haunted me since. I had many reasons for going to law school, but unfortunately, among them weren’t bravery or adventure. I wasn’t there because I wanted to practice law. Rather, I was there because I was too afraid to figure out what I really ought to be doing in life.

The irony, of course, is that by avoiding risk, I was boarding a very long and expensive train ride from which only risk would save me.

Six years and beaucoup bucks in student loan payments later, I walked into the managing partner’s office at my firm and put in my notice.

Was I leaving for another firm? No. Where was I going? I had no idea.

These answers were highly unsatisfactory and extremely confusing to him, and, quite frankly, to me as well. Although I was terrified by my decision, the one thing I did know for certain is that I couldn’t spend another day of my life doing that. Having enjoyed the safety of classrooms and offices all my life, I awakened in my 30s miserable and in a panic, realizing that if I didn’t act, my train was destined for unfulfillment. So, rather than continuing on, I decided to shed my cocoon of caution tape for once, and eject myself from the ride and off a financial cliff into a million unknowns.

The sense of relief was immediate. Having felt like I had been swimming upstream all my life, I turned tail and suddenly found myself carried effortlessly downstream, with all of the small and big things in life seemingly heading my way for once. With inertia in my favor, I threw myself headlong into my creative interests and miraculously emerged in an immensely gratifying career as a photographer and writer. Whether by luck or as a reward for my leap of faith, the universe had caught me. But during that free-fall, I learned an important lesson: to fear regret more than risk. It makes the payoffs taller and the disappointments shorter.

What has followed is a decade of magnificent adventures. I’ve had the privilege of working with some of the most creative and ambitious people in the hospitality industry, including at Blackberry Farm and Blackberry Mountain. And I’ve discovered that it’s a field littered with stories like mine – of pushing the boundaries of comfort, overcoming fears and sometimes, making daring and difficult leaps.

For Joel Werner, executive chef of the Firetower at Blackberry Mountain, joining the Blackberry team required a huge sacrifice. He was working as a chef in Cincinnati but realized that he needed to expose himself to a different level of cooking and service. Foregoing the opportunity of becoming the head chef of a restaurant in his hometown, he instead took a demotion and accepted a position as a line cook at The Barn at Blackberry Farm®.

In those early years, with his life still in Cincinnati, Joel would often drive the four-and-a-half hours each way on weekends to see family and friends. But his dedication to honing his craft paid off. He climbed the sous chef ladder, and when Blackberry Mountain opened, he was offered the helm at the Firetower.

The hospitality industry can be a pressure cooker, which is why so many within it love retreating into nature. Joel loves fly fishing, as do I. We’ve been out angling together in the Tennessee hills, and love swapping stories of sight fishing in the Florida flats. But whereas I am content to let nature simply be a beautiful backdrop for a pastime, for some, it presents challenges to overcome.

For Dr. Jill Beasley, who helps others focus on wellness as a neuropathic doctor at Blackberry Mountain, mountain biking is a way for her to practice mindfulness and humility. Navigating a downhill trail demands mental acuity, physical strength and balance. And she’s discovered that gravity not only tests the outer limits of her comfort, but, as she told me, also “keeps me in check when my ego outgrows my skill set.”

Jill’s confession gets to the heart of why I gravitate toward stories like these. Like my own journey, theirs are journeys of self-betterment, which require deep introspection, personal accountability and, above all, action.

Following an accident a decade ago, during which she was pinned upside down in her kayak, Cassidee Dabney, the executive chef of The Barn at Blackberry Farm®, was reluctant to get back on water. But, instead of letting her fear prevent her from doing something she loved, Cassidee recently reintroduced herself to kayaking and even forced herself to learn how to roll – a technique that requires her to flip herself underwater in her kayak, and then back up again. (If you didn’t see her self-deprecating videos on Instagram about this process, then you missed some of the most endearing and funny social media content produced in the last year.)

She told me that she’s not only doing it to overcome her own fears and equip herself with life-saving skills, but she’s also doing it for others: “I really think it’s important not to be a burden on my fellow paddlers.” But most importantly, Cassidee said, “It was something I needed to do alone.”

Indeed.

We all benefit from the charity and goodwill of others and, sometimes, luck. But there are some things in life that only we can do for ourselves. And when we do, we grow.