Getting Comfortable with Fear: Lessons from the Slopes

About ten years ago, I attended The Fear Workshop led by Mermer Blakeslee, author of A Conversation with Fear and a highly accomplished ski instructor with over thirty years of experience.

I started skiing in my twenties, and my goal was to move beyond the intermediate doldrums. As a cautious risk-taker, I tended to avoid steeper slopes until I was absolutely sure I could descend safely without injury. I signed up for Blakeslee’s workshop because I wanted to stop avoiding and start enjoying intermediate and advanced slopes with confidence.

The women-only seminar spanned three days, combining off-the-slope discussions with on-slope practice. Blakeslee opened with a powerful statement:

Fear is a critical component of an imaginative, creative, and interesting life.
— Mermer Blakeslee

I took a deep breath as her words resonated. Where would we be if we never took risks? That realization was worth the workshop. Fear isn’t my enemy—it’s my companion, guiding me toward growth. I needed to learn how to communicate with fear with kindness, not resistance.

This is where self-compassion plays a crucial role. Our culture tends to glorify positivity and frown upon vulnerability. No one wants to be seen as weak or fearful. But Blakeslee reassured us that fear is natural. In that space, we had permission to acknowledge it without judgment.

Blakeslee described two types of risk-takers:

  • Jane skis beautifully but avoids challenging terrain unless pushed. She wants to ensure she can navigate the slope skillfully and safely.

  • Fred charges down the hill regardless of his ability level and relies on sheer momentum.

These archetypes, inspired by people Blakeslee taught, reflect common approaches to risk. Unsurprisingly, Jane’s approach is often associated with women and Fred’s with men. I recognized myself in Jane—carefully analyzing risk and striving for certainty before taking the plunge.

Throughout the workshop, we practiced techniques to handle challenging terrain. One moment stands out: as I faced my yikes zone—a narrow, steep trail—I hit an icy patch and slid toward a tree. Panic surged. Instinctively, I tried to sit on my skis, desperate to ground myself. However, my instructor calmly reminded me to breathe and take it one turn at a time. Slowly, I executed a single, deliberate turn. Then another. Instead of fixating on the intimidating slope ahead, I focused solely on the next manageable step. This strategy—narrowing the focus and lowering the task—became my key to overcoming fear.

I felt an incredible sense of accomplishment as I reached the bottom and looked back at what I had conquered. My comfort zone had expanded. More importantly, I now had a strategy to make future challenges safer and more manageable.

Applying Smart Risk-Taking to Life

What defines a smart risk? How do we make it safe? Risk inherently involves uncertainty and potential setbacks. But smart risks are those that move us toward our goals and aspirations. In the workplace, this might mean:

  • Sharing an unpopular perspective in a meeting.

  • Volunteering for a challenging new assignment.

  • Tackling uncomfortable tasks like networking or delegating.

To make risk-taking feel safer, we can adopt the same approach I learned on the slopes:

  • Be self-compassionate—acknowledge your fear without judgment.

  • Start small—begin with a trusted ally or a low-stakes environment.

  • Adapt your approach based on your natural risk-taking style.

Two Steps to Smart Risk-Taking:

  1. Recognize your risk-taking style—Are you more like Jane or Fred?

  2. Develop a tailored strategy—Jane benefits from breaking the challenge into manageable steps, while Fred may need to pause and assess before diving in. Consider what approach suits the specific situation best.

What is your mindset around risk? What fear is lurking that you’re ready to face? How can you calm yourself, narrow your focus, and create a sense of safety as you step forward?

Perhaps, in embracing the discomfort, you’ll even find yourself enjoying the ride.

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