Developing as a Leader: A Trilogy

While writing this article I reached out to a colleague, Hilleary Hoskinson, and he affirmed my intuition regarding having too many themes in one article. As I reflect on his intelligence, I am drawn to the Greek Myths which all contain wisdom, excitement, humanness, privilege, sorrow, deep learning and the opportunity for one’s soul to grow. I’ve divided the article into three short vignettes, all telling stories containing learning and values, which provide the foundation and framework for my coaching practice. 

My years have been filled with the privilege of being a father and cause me to reflect on how many sons out there have a challenge when it comes to crafting their own identity and forging their own path. The shadow of one’s father includes many loving attributes but it also requires separation, finding one’s own self. This finding one’s self is not about measuring-up to one’s father. It is about discovering your dreams, not the dreams you think you are “obligated” to fulfill. It’s simple, but not easy. It’s a journey. I will now provide a very brief look into my own story.

Part One: A Privileged Youth and Its Challenges

Growing-up as the son of an Army Colonel and the grandson of an Army General, my mind was painted by adventurous exploits by two men that I deemed larger than life. I was deeply loved by both of them. My dad was one of the founding fathers of the 82nd Airborne Division, a West Point football player, a commando and fought all of WWII and the Korean War as a combat officer with General Ridgway. My grandfather was an orphan, went to college at 13, graduated when he was 17, ran off to the Spanish American War and became the second highest ranking General in the US Army. His father and President Roosevelt signed my father’s diploma from West Point, Class of 1940.

I had the privilege of spending my formative years, ages 9-14 living at West Point where my father served as the Athletic Director. During these years I met many historic people. I sat with President Kennedy at the Army/Navy football game and questioned him, “Why are you sitting on the Army side, weren’t you a Naval officer?” He answered me, “Doug, I am sitting on the Army side, because it is required of me as President, don’t worry, I will move to the Navy side at halftime.” This was a thrill visiting with the President and it was part of being my father’s son. My father and I would also visit the Waldorf Towers where we would visit with General McArthur, where his first question to me was always the same, “How is your grandfather?” I was immersed in a life of military service, devotion to country, competition as the underlying girder and interacting with men who most people read about in history books. To this day I am deeply and emotionally moved, watching fellow Americans interact with their emotions when they visitWest Point…Duty, Honor, Country. 

I soon went off to college, where I attended Stanford University. I took pride in leadership roles, becoming the president of my fraternity, one of the founding fathers of the Stanford Ice Hockey Club, playing on two Championship Rose Bowl football teams, while also trying to excel academically. I was deep in a world-view based on competition. Glory was attached to winning and shame was attached to losing. Unbeknownst to me I was living my life trying to be somebody. Deep in my psyche I felt ashamed that I wasn’t good enough. I am very dyslexic and the academic world of “memorize and regurgitate” was a constant reminder of not being good enough. I am a very slow reader and can’t remember much of what I read, so sometimes I felt as though I was drowning under waves of overwhelming text, from the countless amount of books and articles I had to analyze. I am however extremely intuitive and during those undergraduate years I was drawn to how people learn. While I really wanted to be a teacher, I knew I wouldn’t last a month in a traditional school system, because of my “revolutionary” views about helping people “learn how to learn” rather than simply being taught. 

During my senior year at Stanford, I met two wonderful guys, Mike Clark and Mike McClellan, working as a bartender in one of their restaurants. They backed/mentored me in business and helped feed my voracious appetite for the practical learning of all aspects, real estate, the construction of restaurants and as well as operations.

By 24 I became a business owner, and craved any fragment of knowledge I could get my hands on, that contained vital details concerning any thing business related. More victories! I was also briefly married in my mid-twenties. However, my framework of perfection and my walled-off feelings contributed heavily to going our separate ways. Again, this binary perspective allowed little to no reflection regarding the complexity of my emotions. If my emotions challenged my being, I ran from them.

 Life began to change; I didn’t realize things were changing until I was around 30. The recession hit, the restaurants struggled and I thought the businesses declining meant I was a bad person, a failure and a loser. I ran from these feelings and numbed the feelings as much as possible. The shame of failure felt like death. I was Icarus flying higher and higher trying to defy the realities of the sun.