The Day I Realized I’d Been Channeling Socrates All Along

In January 2020, during a filmed interview about tennis, I said something that seemed ordinary at the time but later turned out to matter more than I knew.

“My favorite historical figure is Socrates,” I said. “I’d love to have his ability to ask questions that make people look at their own thoughts and beliefs—to help them change through conversation instead of instruction.”

Then I went back to talking about tennis.

Four years later, when I reread that transcript, it stopped me cold. That line contained the seed of everything I’ve built since—from my coaching philosophy to The Alcott Dilemma and Communiplasticity Solutions. I just hadn’t recognized it yet.

I’d called myself a “mad scientist” that day. I said I’d always treated young players as experiments. “It was never a cookie-cutter approach,” I explained. “What’s best for you right now might not be what’s best for you two years from now, so we try things on.”

I wasn’t using educational theory then. I was describing intuition—the sense that every learner’s wiring is different, and the only way to find the right input is through testing. Some tests failed; others produced breakthroughs. Over time, I realized the real experiment wasn’t technical. It was cognitive.

The more I asked players questions instead of giving instructions, the more they developed self-awareness. I remember working with Cory Ann early in her training and asking simple questions instead of correcting her stroke. The first time she explained what she saw rather than what she did, I knew she’d crossed into real understanding. That shift—seeing herself think—became the benchmark for progress.

That’s when the court stopped being only a playing surface. It became a small version of the philosophical marketplace, a space where questions did the teaching.

I also noticed how the nature of those questions changed with age. With beginners, mine were true-false or A-B. As players matured, they became multiple choice, then open-ended. I said in that interview, “As they get older, I start leaving things open-ended—the kind of things you think of as essay questions.”

That line described a structure I’d been following instinctively. Thinking matures by the evolution of questions. I was unknowingly building a framework that mirrored the stages of reasoning itself.

Reading Bronson Alcott years later felt like discovering an ancestor—which made sense, since I’d grown up walking past his house in Concord without knowing why it mattered. His Records of a School described children reasoning through dialogue, the teacher acting as midwife to their thoughts. The parallels were uncanny. He was doing in a parlor what I’d been trying to do on a court.

The connection forced a larger realization. Teaching—whether in a classroom or on a baseline—is less about transferring skill than about designing conditions where discovery can happen. I began describing coaching as architecture. The work is to build an environment where ideas move freely and where learners sense what’s true through their own perception.

When you think of coaching as architecture, communication becomes the building material. Every phrase either opens space or closes it. A rigid message breaks; an adaptive one bends. That insight eventually became communiplasticity—the ability to adjust communication to fit another person’s way of processing information.

I didn’t arrive at it through theory. I found it through repetition, by noticing what kinds of conversations produced growth and what kinds stopped it.

As my focus shifted from one-to-one coaching to system design, I began to wonder whether this kind of individualized dialogue could ever scale. Socrates reached a handful of students. Alcott reached a few dozen. Both depended on intimacy and attention. Could that level of precision expand without losing its soul?

That question led me toward technology. If a system can recognize a learner’s cognitive pattern, maybe it can adapt its language just as a good teacher would. The goal isn’t to replace human mentors but to extend their reach—to preserve the spirit of the conversation while multiplying its audience. In a sense, it’s about giving Socrates infrastructure, or what I sometimes call giving him a megaphone without losing the whisper.

The 2020 transcript reads differently now. What once felt like casual answers were early sketches of ideas that later shaped my entire framework. When I said I wanted to be Socrates, I was naming the core of my work without realizing it: learning as conversation.

The pattern runs through every phase—Socrates questioning in the agora, Alcott in his Concord classroom, me decades later on a sun-baked Texas court. Different settings, same experiment. Each of us testing the belief that transformation begins with a question demanding self-examination.

It’s easy to miss this while you’re in it. For years I thought my craft was about mechanics and measurable progress. Only later did I see that everything pointed back to inquiry—the art of asking at the right depth and resisting the urge to answer too soon.

Now the challenge is structural rather than philosophical. How do we keep that conversational integrity as AI enters the learning process? My hope is that technology can amplify a teacher’s precision without flattening the human texture that gives learning meaning. The risk, of course, is the opposite: that efficiency will replace nuance.

Still, I keep returning to the same image—Socrates whispering in a crowd. The task is to make sure more people can hear the whisper clearly.

When I look back at that old interview, I no longer see a coach explaining his method. I see a moment when instinct spoke ahead of understanding. The years since have been about catching up to what instinct already knew: the art of teaching—whether through conversation, sport, or software—is helping people see themselves thinking.

It just took a few decades, and one old philosopher, to help me name it.