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How Facing My Fear of Failure Changed My Worldview

After years of leading wellness retreats, one woman finally turns inward to do some deep personal work, including confronting her own insecurities, so she can truly encourage others to do the same.

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There’s a common misconception that retreat leaders, especially ones who are advocating wellness advice, have it all figured out. I’m here to tell you that in my seven years leading all-women running and wellness retreats in some of the most beautiful destinations on the planet, I’ve certainly experienced times where I’ve choked and not been fully present. In those instances, I’ve been too mentally and physically exhausted from the retreat preparation or so overtaken by self-doubt that I didn’t honestly and effectively communicate my ideas about mindful running and wellness with my guests.

As the retreat leader, I experience the journey too, maybe even more so, since the event’s success largely depends on my ability to fully show up and lead the group through seven days of consecutive running, learning, growing, and sharing. My intent with every retreat is to create a supportive space for runners to challenge themselves in new ways. I was forgetting, however, to create enough room for myself to evolve, too. If I wanted my business to succeed, I had to be willing to do the internal work to overcome my own fears and insecurities and step into the role I felt called to fulfill.

Last year, I enlisted the help of friend, yoga teacher, retreat leader and life coach Kristen Stuart to be my guide through this deeply personal work. The irony is that the lessons I needed to learn and implement in my own life were the very same ones I wanted for my guests. I ask retreat guests to be vulnerable, honest, and examine what’s in their hearts and let those values steer them toward the best choices and actions for them. But before I could ask them to do that, I had to do it for myself.

First step was admitting that I’m a workaholic. I possess the kind of single-minded focus and stubbornness that has let me run 100 miles in a day or pull off consecutive 12-hour nonstop workdays. But in the past, I’ve paid a high price for such productivity in the form of severe fatigue and burnout from which it took me months to recover.


Related: Am I Just Really Tired or Do I Have Adrenal Fatigue?


“What would happen if you softened your focus just a tiny bit?” asked Kristen during one of our coaching sessions.

“I’m afraid I’d drop the ball, forget an important detail, disappoint a client or miss an important deadline,” I said. “I don’t want to make any mistakes because I don’t want to fail and I have no one helping me. It’s all on me to make things happen.”
“But the irony is that your fear of failure and of what others think of you is what’s keeping you spinning in circles and always on the brink of burning out,” she said.

This made sense and yet I didn’t know how to change it. Being an entrepreneur isn’t supposed to be easy. It’s typical to feel like you’re in a constant struggle. Insecurity and anxiety are par for the course, right?

Wisely, Kristen’s answer was no. “You can—and should—thrive in your role as a retreat leader,” she said. “Come from a place of trust and authenticity, and you’ll find the experience energizing rather than anxiety-filled and depleting.”

In the months that followed, I used daily meditation, journaling, yoga, and energy exercises like EFT (tapping) to integrate these lessons, break old thoughts and belief patterns, and thereby make way for a new mindset and sense of confidence.

By the time I stood on the clifftop overlooking the Mediterranean Sea at last month’s Costa Brava Running + Wellness Retreat in Spain, I felt a rare sense of peace and contentment. I turned to meet the gaze of the eight women standing before me in a semi-circle, waiting for me to lead them through a series of running exercises that would help them more easily navigate the undulating coastal trail ahead.

Rather than choking on the usual fear of saying something foolish or being overcome with nerves, I returned their gaze, feeling nothing but utter gratitude and respect. I was grateful for their trust in me and had never felt more ready, capable and willing to support them on their journey. And amazingly, the absence of fear and doubt opened space for lightness, fun, and playfulness for the entire group that lasted the entire week.

A few miles into our run, the trail popped out onto a remote rocky beach, surrounded on all sides by sheer cliffs. A small, dome-shaped building that looked like a converted boathouse was its only man-made structure. Large wooden double doors flung open to reveal cozy living quarters inside. The divine smell of warm chocolate came wafting out of this humble home.

“Bon día, Kiko!” said Pablo, our Catalan running guide to its apparent occupant. A sun-baked, pot-bellied older gentleman waved his hand, beckoning us inside. He handed out plastic tumblers and pointed to a pot of the stove. Kiko didn’t speak English, but obviously had something to share. He spooned a small serving of melted chocolate—too rich to call it chocolate milk—into each cup. It coated my mouth and delighted my taste buds with a gooey goodness like I’ve never had back home.

He then motioned to a piece of driftwood hanging from the ceiling. Countless tiny pieces of folded, colorful paper had been tied to its thin branches, giving it a Christmas tree-like appearance. Undoubtedly these had been placed there by travelers from all over the world tramping past his beach shack. He muttered instructions to Pablo, who translated for us. “Kiko says you’re to write down something you wish for, then tie to the tree. Only one rule: you can’t wish for material stuff,” said Pablo.

I waited for everyone to finish attaching their wishes before writing my own. There were so many things I wanted to wish for: Continued good health for my family, more travel, business success … but then I realized there was one thing in particular: I wish to never stop challenging myself to grow, experience new things and trust more.

Throughout the rest of the retreat, our tight-knit group shared deep conversations, delicious meals laughing fits, and great wisdom. I listened closely to their stories, questions, ambitions, and ideas, and could relate to so much of what they shared. I learned as much from them as I hope they learned from me. While the retreat is now over, my personal work is only just beginning. It will continue to evolve and step up to the challenge with each retreat that I lead. I can’t wait to see where it takes me next.

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