A few weeks ago, I shared why autumn is my favorite time of the year. Last week, I recounted my first memorable biking experience—a steep learning curve filled with challenges that ultimately ignited a lifelong passion. That passion led to a highlight of my summer: a memorable ride in the Virgin Islands with Sir Richard Branson.
Beyond personal memories, autumn marks another cherished event—the timing of our annual mountain bike trip. This isn’t your average gathering. It’s a unique assembly of founders, thought leaders, and remarkable individuals who not only share a love for mountain biking but also a deep desire for personal growth. Every year, we push each other to become better—not just in the way we ride, but in how we approach life. The progress we make on the trails mirrors the growth we seek in every area of our lives.
Plato defined the original four virtues: justice, wisdom, courage, and temperance. Of them all, I believe courage is the cornerstone. Courage is the precursor to action, the force that propels us forward when the outcome is uncertain. It’s the sweet spot between cowardice and recklessness, where meaningful growth occurs. Without courage, we can’t gain wisdom, achieve temperance, or pursue justice. Courage enables us to step out of our comfort zones and unlock our full potential.
In entrepreneurship, as in life, courage is the driving force that enables us to evolve. You may have heard that courage means “feeling the fear and doing it anyway.” Courage grows like a muscle—the more you exercise it, the stronger it becomes. It’s only when we step into the unknown, when things are uncomfortable, that courage comes into play. As entrepreneurs, we intuitively know that the unknown is where opportunity lies.
In my book Start Up Santa I explain how courage builds momentum through a cycle I call the courage flywheel. It starts with curiosity—the desire to explore new ideas and possibilities. That curiosity sparks creativity, enabling us to imagine and wonder about what could be. However, until we embrace the courage to try, it remains simply an idea—a fantasy that cannot materialize. We have to be willing to try in order to release an idea’s true potential.
When we do try, we are often met with resistance and challenges. We enter into the build-measure-learn cycle, where we make mistakes and fail, but do so understanding that this is necessary for progress. Overcoming these challenges builds our character, which in turn strengthens our confidence. And with confidence, we’re ready to embrace curiosity once again, beginning the cycle anew.
Mountain biking is a perfect analogy for this. To improve, we must constantly challenge our limitations, stepping beyond the familiar and into the uncomfortable. That is exactly what I experienced a year ago in Squamish on a steep granite slab that truly tested my limits.
After feeling reckless and out of control on the first day of the trip, I paused to regroup. By the third day, I had regained my confidence, which is when I stood at the top of the slab. Initially, I was hesitant and decided it was too much. Then, I watched my buddy Mike ride it effortlessly, proving it was possible. At that moment, I had to make a choice. I asked myself, after this trip, will I say: “I’m glad I did” or “I wish I had.” I chose courage.
This brings me to the second crucial point when it comes to expanding your comfort zone—who you surround yourself with matters. You want people who will push you to be your best. As you’ve probably heard, “You are the average of the five people you spend the most time with.” It is important to audit your relationships and ensure you surround yourself with people who do not envy you, but rather help you reveal your true possibilities and potential. This holds true in every area of your life. In the words of Jim Rohn, "In life, you may not be able to do all you find out, but make sure you find out all you can do."
Discovering what you can do is about expanding your comfort zone, and this is only possible if we surround ourselves with the right people and embrace the courage to try.
My newfound skills have created new potential, and the photos you see above are truly priceless. More importantly, all of this was forged while investing time with amazing people who bring out my best and in the process creating meaningful and magical memories that will last a lifetime.
As you reflect, ask yourself:
- What untapped potential lies dormant within you, waiting for the spark of courage?
- Who are the people you need to surround yourself with to uncover those possibilities?
- What bold action would you take if you knew you couldn’t fail?
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