In the fall of 1987, as a freshman, I sat in the car outside St. Mary’s High School in Annapolis, MD, getting ready for football tryouts. I played in the local weighted class football leagues that, at the time, defined what level you played, and now I was about to go play with the “big boys.” I was scared and nervous and was coming up with all kinds of reasons why I should not do the tryouts. Was I good enough? What if I didn’t make the team? How would I feel about my self-worth? There were so many reasons I was looking for not to go to tryouts. I didn’t want to fail. I was unknowingly about to learn one of the first of many profound lessons of my life. It wasn’t a lesson from a decorated coach or a seasoned player; it came from my stepdad, a silent pillar of strength until that pivotal moment. His simple yet profound encouragement, “Come on, let’s go in,” was the nudge I needed to step out of the car and into a journey that would shape my high school years and my understanding of leadership, influence, and taking risks.

The Power of Encouragement

That day, my stepdad taught me the first lesson of leadership: the power of encouragement. In leadership, it’s often believed that one must undertake grand gestures to inspire or motivate. Yet, here was a lesson in the strength of quiet support, a reminder that leadership is not always about loud declarations but often about gentle nudges toward growth and resilience. He was so confident in me, more so than I was in myself.

Empathetic Leadership

Empathy is at the core of recognizing and embracing vulnerability in others. My stepdad’s suggestion to go inside wasn’t just about getting me to try out for football; it was an acknowledgment of my fears and an assurance that those fears were seen and understood. Despite me not saying a word – my stepdad looked at my body language and my eyes, and all the things I didn’t say spoke volumes. By encouraging me then, he demonstrated empathetic leadership—showing compassion and understanding for my situation without needing it explicitly stated.

Embracing Vulnerability

Sitting in that parking lot, wrestling with fear and doubt, I was experiencing a moment of vulnerability that all leaders face. It taught me that embracing vulnerability is not a weakness but a bridge to connect with others more authentically. It’s a strength that allows leaders to show that it’s OK to be scared and not have “all the answers,” but it’s not OK to let that fear prevent us from moving forward and seeking out others who can complement our weaknesses with their strengths.

The Impact of Taking Action

Taking that first step into the gymnasium was a leap into the unknown. It’s a reminder that action is a critical component of success. We can spend endless time planning, hand-wringing, and strategizing, but without action, those plans remain just that—plans. Leadership involves moving forward, making decisions, and sometimes, taking risks.

The Unseen Ripple of Our Actions

Reflecting on that moment and the path it set me on, I consider the unintended leadership lesson imparted by my stepdad. His encouragement was a small act, yet it had a ripple effect on my life, illustrating that leadership often unfolds in unexpected moments. This silent form of leadership—being present and supportive in the passenger seat of someone’s life—can have a profound impact. It’s a testament to the power of our actions, however small, in shaping the lives of those around us.


The Lasting Impact of Everyday Leadership

This story is a call to recognize and embrace the everyday opportunities for leadership that life presents to us. It’s about understanding that our most minor actions can inspire courage, motivate perseverance, and encourage others to step forward in their journeys. As leaders, we can create positive change, not always through grand gestures but through our everyday interactions.

Reflecting on What Could Have Been

I often wonder, what if I had never stepped out of that car? What path would my life have taken? Would I have chosen West Virginia University, joined the military, or joined the Ranger Regiment? What risks would I not have taken in life if I had never been encouraged to try out for football that fall day? It’s a question that underscores the importance of seizing opportunities, however daunting they may seem. The second and third-order effects of our choices can shape our lives in ways we could hardly imagine at the time.


As I look back on that day in 1987, gratitude fills me for the lesson learned in the parking lot of St. Mary’s High School. It was more than just about trying out for football; it was about learning to overcome fear, to embrace the possibility of failure, and to recognize the power of encouragement. These leadership lessons have guided me through my life and career, lessons that will inspire others to take their first step forward, no matter how daunting it may seem, and to reach out to those who inspired you and thank them.


Written by

Dave Taylor, CEO LDR Leadership