I Was Always Watching

Daily Letter · Mindset Operating System · 8:42 PM

FIELD REPORT | I Was Always Watching

Growing up in Baltimore, I was constantly just watching lacrosse.

Not playing it yet, in a lot of those moments. Watching it. The varsity at St. Paul's, where I would eventually become a player myself but for years was just a kid on the sideline absorbing whatever I could. Summer league games my dad refereed — games that, looking back, I had no idea at the time were as stacked as they were. The Gait brothers. Tom Marechek. Dave Pietramala. Legends, walking around in shorts and t-shirts in the Baltimore humidity, treating a summer league game like it mattered, because to them it did.

I would go to Hopkins practices while my mom walked the track, and I would just watch. Not the drills exactly — the dynamics. The body language between coaches and players. The way a captain stood differently than a freshman. The specific quiet that fell over a group of grown men when a coach started talking and everyone actually listened. I never heard most of those conversations. I did not need to. You can learn an enormous amount about a team by watching how its people move around each other when nobody is saying anything at all.

And then there were the VHS tapes. I would record college lacrosse games — entire games, just to have them — so that I could go back later and rewind, pause, rewind again, trying to understand not just how players were moving but why. What made one player's footwork different from another's. What a great off-ball cut actually looked like in real time instead of in a highlight. I was reverse-engineering the game years before I had the vocabulary to explain what I was doing.

Phil Jackson wrote something in Eleven Rings that I did not read until much later in life, but that explains exactly what I think I was chasing on those sidelines and in front of that VCR as a kid. Basketball is a sport that involves the subtle interweaving of players at full speed to the point where they are thinking and moving as one. That is what I was watching for, without knowing that was the word for it. Not the goals. Not the highlight plays. The interweaving. The moments where five or six individuals stopped looking like individuals and started looking like one organism that happened to be wearing six different jerseys.

Jackson also wrote that the strength of the team is each individual member, and the strength of each individual member is the team. I watched that principle play out on a dusty summer league field before I ever had a name for it — guys who would go on to be Hall of Famers, treating a throwaway summer game with the same care they brought to a national championship, because their standard for themselves did not change depending on who was watching.

And there is a third line from that book that I think about constantly now that I am the one on the sideline with a whistle instead of a kid recording tapes. The sign of a great player is how much he elevates his colleagues' performance. That was true on every field and every practice I ever silently studied. The best players in the gym were rarely the loudest. They were the ones who made the four-on-four drill at 6 PM somehow better than it had any right to be, simply because of how they moved and who they made better by moving that way.

I am still watching, all these years later. Just from a different spot on the field now.

Eleven Rings is genuinely one of the best books I have ever read on leadership, teamwork, and what it actually takes to get a group of talented, ego-driven individuals to play for something bigger than themselves. If you have not picked it up, I cannot recommend it strongly enough — whether you have ever touched a basketball or not.

But there is a reason I am telling you all of this tonight instead of just leaving it as a nice memory about childhood and VHS tapes.

Because all of that watching — years of it, quiet and unglamorous and completely unnoticed by anyone except me — did not prepare me for what it would actually feel like the first time my own coach looked at me and decided I was not yet the player I thought I was.

There are moments in your life that last less than a second and somehow end up changing everything.

Mine happened on a rainy afternoon during my junior year of high school, when a routine pass climbed straight out of the top of my stick and sailed over everyone's head.

I will get there. But I need to take you back further first, because the pass was never really the story. The pass was just the moment everything that came before it finally became visible.

ACT I — Repetition Before Recognition

This is the part I think every parent reading this needs to hear most.

I was not cut. I was not behind. I was developing — and there is a difference between those two things that took me years to fully understand, and that I do not think gets said enough to the kids living through it in real time.

Freshman year was not about varsity. Sophomore year was not either. And here is what I want to be honest about — nobody panicked. Nobody complained. Nobody transferred. Nobody questioned the coaches or campaigned for more playing time on my behalf. There was no crisis to manage because there was no crisis. There was just the work. Two years of reps stacked quietly on top of other reps, accumulating into something that had no name yet and absolutely no audience watching it happen.

All those years of standing on sidelines watching the Gait brothers and Hopkins practices and rewinding VHS tapes — that was its own kind of repetition. Different muscles, same patience. I did not know it at the time, but I had already been training myself to wait for an opportunity long before I ever stepped foot on a varsity field.

Looking back now, we were not waiting for an opportunity.

We were preparing for one.

ACT II — The Promotion

Then it finally came. Varsity. Junior year. Second midfield line.

This should have felt like validation — the payoff for everything I had spent years quietly absorbing on sidelines and in front of a television, recording games nobody else cared to keep. Everyone around me thought I had finally arrived.

Instead, it felt like pressure.

I am going to admit something here that I do not think I have ever said out loud before. Everyone around me thought the coaches had finally seen what I could do. I secretly wondered if they had made a mistake.

I think more people live inside that exact sentence than will ever admit it. Parents wondering if they are actually qualified for the responsibility standing in front of them right now. Executives sitting in a promotion they are quietly convinced someone will eventually realize was a clerical error. Athletes standing on a field they spent years earning the right to play on, certain that any moment now everyone is going to figure out they do not belong there after all.

I was seventeen years old and already fluent in that particular kind of fear — the fear of being found out, dressed up as gratitude so nobody could see what it actually was.

ACT III — Playing Defense Against Failure

This is where the real lesson lives. Not defense in lacrosse. Defense against my own mind.

I was not trying to create. I was not trying to attack. I was not trying to win.

I was trying not to mess up.

That is a completely different game than the one everyone thinks they are watching from the sideline. Every possession became an audition instead of an opportunity. Every touch felt like a test I was one mistake away from failing publicly. Instead of creating, I was protecting. Instead of competing, I was surviving a season I had spent two years on the sideline earning the right to play in.

All of those years studying the game — the body language, the footwork, the interweaving Phil Jackson would later put into words for me — and somehow none of it had prepared me for the part where my own fear could quietly take over a body that knew exactly what to do if I would just let it.

ACT IV — Thin Ice

A few weeks before everything changed, my coach called me into his office before practice.

He did not raise his voice. He did not make it dramatic. He just told me the truth, plainly, the way the best coaches always do — the way I had watched coaches at Hopkins do it from the bleachers years earlier, before I ever understood why their players listened the way they did.

"Kyle, I'm not getting everything you're capable of. You're on thin ice. We need more."

That was it. No further explanation. No bullet points on what to fix. Just the sentence, sitting there in the room with both of us, doing exactly what it needed to do.

Looking back now, I do not think he was talking about one practice or one game. I think he was talking about the version of me that had been quietly showing up every single day for weeks — present in body, absent in everything that actually mattered.

ACT V — Rain

It was a rainy practice. The kind where everything moves a half-step slower and the ball feels heavier than it should.

We were running a simple offensive skeleton drill. No pressure. No defender. Just throw, catch, move the ball down the line — the most basic possible version of the game, the kind of drill where mistakes are not supposed to happen.

I caught the pass with my left hand. Switched to my right. As I released it, the ball climbed straight out of the top of my stick.

It sailed over everyone's heads and rolled onto the next field over.

Silence.

My coach turned around. He was not yelling. He did not need to be.

"That's enough."

Three words. Sometimes three words hurt more than thirty would have.

I knew before I even walked off the field. It was not the pass. It was everything that had come before it. The pass did not cost me the position. Months of tentative, protective, audition-style play had already done that quietly, one possession at a time. The pass simply confirmed, in front of everyone, what had been happening all along in private.

Walking toward the locker room that afternoon, I thought I had just lost my place on the team.

Looking back twenty years later, I had actually just found the beginning of my career.

That is where Letter 047 starts, tune in tomorrow night for what propelled me into where I am today with the game!

MINDSET OS

There is a massive difference between protecting your position, proving your worth, earning your spot, and creating something extraordinary.

One mindset shrinks you. The other expands you. Whether you are twelve years old, thirty-nine, or running a company — people can feel the difference before you say a single word about it.

Play through your hands, not your fears.

Young players almost always think a mistake like the one that ended my junior year start is mechanical — bad grip, bad footwork, bad timing. Most of the time the mechanics broke down because the mind got tight first. Loose hands come from a loose mind. Confident feet come from committed decisions. The body usually follows the belief, whether the belief is true or not.

Most people think confidence comes before performance.

I have found the opposite to be true. Confidence often arrives the moment your focus leaves yourself and lands on serving something bigger than you are.

I did not know it yet, standing in the rain that afternoon. But that shift — from protecting myself to serving the team — was already on its way to finding me, whether I was ready for it or not.

About the Author

Kyle Smedley is the founder of Harbor Lane Holdings, building at the intersection of sport, people, and capital.

Career stops include Events.com, Tourmaline Builders, Lombardi Contracting Corporation, and DPR Construction. Today he leads Atticus Lacrosse Company, working alongside Mad Dog Lacrosse and Ravenscroft School, and Harbor Lane Company, operating across real estate, private equity, and talent placement.

Field & Fathom goes out every night at 8:42 PM.

Reach out directly: [email protected]

Until tomorrow,

Kyle

Founder · Harbor Lane Holdings · Atticus Lacrosse Company

Field & Fathom · Harbor Lane Holdings · Daily

Busy executive. Packed calendar. An inbox that never empties.

Everyone is talking about AI agents. Every week brings another promise of an assistant that can do it all.

Catch is the real deal.

A smart, proactive AI admin agent focused solely on taking administrative work off your plate.

It schedules meetings, triages your inbox, drafts emails in your voice, resolves conflicts, sends follow-ups, and handles the countless small tasks that consume your day.

Available wherever you work — Gmail, Outlook, Slack, WhatsApp, and even over the phone.

No setup. No training. No learning curve.

Catch learns how you work, takes action when it's confident, and keeps things moving without constant supervision.

From swamped to sorted in seconds.

Get started with Catch and have your assistant ready before your next meeting.

Test Catch for free