How I Learned the System from the Inside

I had walked away from tennis in 1981 when I chose to play football at West Point instead. That decision felt final at the time. A decade later, the game found its way back into my life. Not through ambition or planning. Through circumstance. A professional situation ended abruptly and left me with something unusual: time, a significant severance, and no immediate need to explain what came next.

I started playing tennis again because it steadied me. There was no vision attached to it. No sense that it would lead anywhere. It was familiar, physical, honest. For a while, that was enough. Then an opportunity surfaced to volunteer as an assistant coach at my old high school. I said yes without overthinking it. What I found surprised me. I loved being on court with kids. Not selling. Not positioning. Just teaching and paying attention. Watching them struggle and improve in small ways that never show up in rankings or records. Coaching, at its best, is relational work long before it is technical work.

That experience led to George Meacham, who had been both my English teacher and tennis coach at Lexington High School years earlier. George knew me in more than one context, which mattered when he mentioned an opening for a summer tennis pro position at the Annisquam Yacht Club in Gloucester, Massachusetts. I was offered the position. Awarded still feels like the more accurate word.

I spent two summers at Annisquam as the tennis pro. The setting was traditional. The expectations were clear. The relationships mattered. By the end of the second summer, I knew something important had settled. I wanted to pursue tennis as a career, not casually, but seriously. At the same time, I became what you might call an insider. I was elected Second Vice President of USTA New England Eastern Massachusetts division. I became Chairman of Community Development for all of USTA New England. I served on the sectional board. These were not ceremonial roles. They involved meetings, decisions, budgets, and strategy. I was exposed to how the system thought about itself and how it justified its choices.

A man named Mark Beede within USTA New England took an interest in mentoring me. Mark was thoughtful, strategic, and generous with his time. At one point, he asked me a question that stayed with me longer than he likely intended. He asked whether I thought the road to the presidency of USTA nationally ran through community development. I was not sure. I answered honestly that I did not know. What I did know was that community was where I wanted to make a difference.

In 1993, I attended the USTA National Tennis Teachers Conference in New York City. At some point during the event, I and two other coaches, Don Johnson and Andre St. James, decided we had enough of the politics and took off for the afternoon to volunteer at the Harlem Junior Tennis Program. That moment probably told me more about my priorities than any committee assignment could have. The real work was happening on courts in Harlem, not in conference rooms in midtown Manhattan.

When I decided tennis would be my full time work, and that I wanted it to be performance tennis, I took a job at Sportsmen's Tennis Club in Boston. Sportsmen's had history. I had read about it in the Boston Globe. I had seen television ads featuring Bud Collins. What I found was a program that had fallen on hard times. Many of the kids who had once been its strength had scattered to other programs across New England. A small group found their way into my orbit. The Crichlow brothers. Timi Solomon. Others. At the same time, I was teaching Jessica Engel when a conflict arose with one of the more established pros in the region. I was teaching open stance forehands. He told Jessica's father that she could not work with anyone I was working with because the open stance was too radical, too reckless, too wrong.

Time has a way of resolving those arguments without conversation. But at the moment, the resistance was real. I was early enough to be suspect and late enough to be inconvenient.

Eventually, I realized that if I wanted to be taken seriously in the larger conversation about performance tennis, I could not remain in New England. The weather alone made year round development difficult. More importantly, the conversations that shaped opinion and opportunity were happening elsewhere. I moved to Georgia. I left family and familiarity because I believed proximity mattered. I wanted to be in the rooms where people talked about eleven year olds with potential, where ideas circulated before they became doctrine.

What I did not anticipate was how quickly my prior experience would be reset. When I approached USTA Southern, I was redirected to the Georgia district and placed on the Minority Participation Committee. A committee designed less to shape policy than to absorb frustration. A place where people could speak freely without being given authority to act. This was despite having served as Director of Community Development at the sectional level. Despite having been a sectional board member. Despite having held officer roles. None of that transferred. I was starting over in a role with little influence and no clear path forward.

That moment marked the beginning of a long relationship with the establishment that I can only describe as complicated. Not because I disliked institutions. I had seen what they could enable when aligned properly. But I was now close enough to see how often alignment was accidental rather than intentional. How ladders existed, but only for certain narratives. How good ideas could be welcomed rhetorically while being structurally sidelined. How the system rewarded compliance over clarity.

Over the next thirty five years, I watched patterns repeat. Coaches burning out quietly. Parents blaming themselves for confusion that should have been anticipated. Players disappearing without anyone tracking where they went or why. I remember one particular player who showed real promise at twelve. By fourteen, he was gone from competitive tennis entirely. His parents stopped returning calls. No one in the system asked what happened. He simply moved from the active roster to the category of kids who "didn't want it enough." That was the standard explanation. It required no investigation and assigned no responsibility. Officials rotating out. Directors turning over. The system studied who survived and ignored who did not.

I also watched coaches begin learning sideways. Not from official curricula. Not from federations. From books outside the sport. From late night phone calls with other coaches. From conversations in parking lots and hotel lobbies. I lived this myself during my years in Georgia and North Carolina from 1993 to 2008. A group of us would gather at each other's facilities on weekends. Atlanta to Augusta to Columbia to Fayetteville to Birmingham and beyond. We brought our players. We watched each other coach. We gave feedback without positioning or politics. It was collegial, and over time we learned to trust each other without hesitation. That informal network taught me more about actual coaching than any certification course I ever completed. I had entered those years believing that better technical knowledge would make me a better coach. I left them understanding that better judgment about when to apply what I knew mattered far more than accumulating more information.

These coaches borrowed language from psychology, leadership, literature, even fiction, because those fields had better words for what they were actually experiencing. Journey. Failure. Identity. Meaning. Performance became a metaphor rather than a destination for many of them. It stopped meaning winning or rankings. It started meaning the capacity to keep developing under pressure while maintaining joy in the work itself.

Judgment, I came to understand, was the real skill. And judgment cannot be downloaded from a certification course. It develops through exposure to uncertainty, reflection, and comparison. Through hearing someone else say they thought the same thing and here is what they learned the hard way. Those exchanges rarely happened in sanctioned spaces because sanctioned spaces rewarded certainty. Questions became risky. Doubt became a liability. The gap between what coaches said publicly and what they believed privately widened until that gap became the real work environment for anyone who stayed long enough to see the pattern.

What was missing was not expertise. It was architecture. Places where insight could circulate without penalty. Where coaches could compare experiences rather than defend philosophies. Where parents could talk without performing confidence they did not feel. Where the people who left were studied as carefully as the people who stayed.

I did not leave the system. I stopped waiting for it to lead. There is a difference.

What I build now exists because of what I saw then. I trust proximity over titles because proximity is where understanding actually forms. I trust pattern recognition over compliance because patterns reveal what compliance obscures. I trust sideways learning because it is how judgment actually develops in complex systems where official answers arrive too slowly or not at all. Institutions matter. They create containers and distribute resources. But they are rarely where understanding originates. They are where understanding gets codified after it has already proven itself elsewhere, usually in places the institution did not design and cannot fully control.

I learned the system from the inside. I learned its strengths and its blind spots. Most importantly, I learned where learning actually happens. And it is almost never where the org chart says it should be. That is not cynicism. It is pattern recognition from someone who spent decades close enough to see what works and what only appears to work when you are not paying close enough attention.