From Caddy to Cadi

“Yes, there are two paths you can go by, but in the long run, there’s still time to change the road you’re on.”  Stairway to Heaven - Led Zeppelin

For most of my life I have wage war against authority. I have made most of my life’s decisions based on my own set of values. What could be seen as a life based on high standards and virtue in many instances was simply a case of me telling the world “You can’t tell me what to do”. I have gone through life unable to travel on the traditional paths toward the prescribed successes that most do. It has been a struggle, often not based on principal but more on my inability to compromise or to follow orders I deemed illogical from those I did not respect. Through the lens of honest introspection, I can recall many instances of confrontation that I am proud of the stance I took. However, there are almost as many times that I look back upon with complete consternation as they were merely positions taken solely based on immature defiance.

For the most part my life has been a journey taken not on the main roads where most travel and achieve but instead in the jungles and swamps that most purposely avoid. I have maintained my independence from authority and construct by stumbling down many paths; most of which headed for either a place I would discover as unwanted or a disaster that I would have to endure and then recover from. I did make a couple trips to the main road upon invitation only to be disinvited once my wayward travels were discovered by those who had originally dangled inclusion. My existence has been unconventional in so many ways; my work life is just one of them. When I describe what I do and what have done to live and pay my bills, people often comment on how much they envy my freedom. I always reply in the same fashion, “Yes, I have the freedom to do as I want which also gives life to the possibility of starvation.”

My first real job was as a caddy at a private golf course. Carrying the golf bag, cleaning the clubs, raking the sand traps, and replacing divots were the physical parts of the job. But the most important service a good caddy was expected to provide was course navigation. That meant always knowing the location of your player’s ball and its proximity to the hole. On the night before my first day as a caddy my brother, who was one of the premier caddies at the club, gave me a map of the course which included distances from specific landmarks on every hole. He told me to keep the map to myself and just give the yardages when asked to do so from my player. This singular tool along with my knowledge as a golfer created opportunities for me to help my player navigate the course and thus made me much more valuable as a caddy. This first job provided me with a small but important first taste of independence. The money that I earned eliminated one step from the supervision process of my parents in that I still had to ask permission to do certain things, but I no longer had to secure its financing. This small differentiating factor was the beginning of what would become the overriding force in almost all my interactions, namely the need to be independent and the abhorrence and mistrust of all forms of authority.

As an adult, except for my time in commercial construction and as a small business manager, I have always been independently employed. For the past thirty years there has never been a regular paycheck for me. I have had a successful personal training business and while I have predominantly worked in the field of fitness, I have always done other things as well. I have built furniture for clients, outdoor structures, and designed and managed home remodels. Outside of my independent work activities there have been moments in my life when I have been forced by circumstances to take on little menial jobs to augment my income and meet my financial responsibilities. My first, second little job, was working at a grocery store. At 4am I would rise and go to work before heading to my real job working in construction. I was tasked with shoveling the ice in the meat department, sweeping and mopping the store floor, straightening up the lunchroom and cleaning the bathroom. Years later, when I made my decision to have my own personal training business I was once again forced to take on other work while I built up my clientele. During this time, I decided to make extra money by nude modeling for art students. I would stand for hours naked in front of different art classes.

The recent pandemic destroyed my Personal Training business and as it stretched out from weeks to months to years my savings began to disappear. One day when I returned from a small construction project, I looked out the window of my truck at my Cadillac parked across the garage. I knew that I either had to sell the car or it had to become a source of income. Since I liked the car and, to be honest, was too proud to give it up I decided that my new little job would be as a Lyft driver. Once again at 4am, before I start my regular day, I rise. But now instead of shoveling ice or standing in the middle of a room naked I drive people around for a few hours. I no longer have a simple map as when I was a caddy. The navigation system directs me where to find the person in need of a ride and then it tells me how to get them where they want to go. My passengers do not care where I have been or where I am going; they just want me to get them to their destination as soon as possible.

During low moments in the past, I would shake my head as I cleaned the grocery store bathroom and privately complain to myself; “I have a college degree I should not be scrubbing a urinal”. Later when I was standing naked in the middle of a group of art students, I remember being glad that I didn’t have to explain to my mother how I was making money. However, on most days I would just do my job while dreaming about the goals I was trying to achieve. Driving people around is no different. I sometimes dwell on my wrong turns or the transgressions that closed doors of opportunity. I feel sorry for myself and while immersed in self-pity I curse the fact that someone did not help me navigate to a better life. But those days are rare and I have come to the realization that my life from “Caddy to Cadi” is not an abject failure but a very powerful navigational tool. In my Personal Coaching practice and my writing, I now use the eclectic nature of my experiences and the knowledge they have afforded me as a source of directional help for those who feel either emotionally or physically stranded. Ironically, the wandering nature of my life and the diversity of my experiences have brought to a place where I no longer need a map as I did as a Caddy or now in my Cadi to help guide my clients to a better physical and mental state; I am the map.

CoachingBill Sheppard