The Summit

A short story about an after-hours lesson in leadership

It was the end of the second night at our annual CEO summit. The trip’s last cocktail hour was winding down, and people began to say their goodbyes and make their way to their rooms.

Turning to look out the back of the southern-style cottage, I spotted him—a CEO I deeply respected, one of the best we’d ever had in our portfolio—sitting in a rocking chair on the porch, quietly nursing a drink. He was alone.

I hesitated, then walked over, drink in hand, grateful for the chance to get away from the thinning crowd.

“Mind if I join you?” I asked.

He glanced up, gave a small smile, and gestured to the empty rocker beside him. “Not at all.”

We settled into a comfortable silence. The night was cool, and the moonlight played off the rustling leaves in the dense woods stretching out beyond the porch. He looked out at the trees, his face calm but intent, as if reconnecting with an old memory.

“Been a good summit,” he said, still looking out into the woods. “Good to see this group again.”

“Yeah, it has been,” I agreed. “I always learn something new at these things.”

He nodded absently, gaze still focused somewhere in the darkness beyond. He spoke. “You know, we’ve worked on a few projects together, but we’ve never really talked about your path…How you ended up in this line of work.”

He let the question linger, eyes flicking back to me for a moment before drifting back to the trees.

I took a sip of my drink, letting the answer take its shape. “It’s been a winding path. On paper, it was sales, then business school, then consulting, then this. But along the way, I did a bunch of stuff that feels like it prepared me for this latest thing. It’s the weirdest job I’ve ever loved. I don’t know if I’ll do it forever, but for now… I like it. I’m good at it. It feels like I’m in the right place, doing the right thing, at least for right now. And that feels good.”

He nodded slowly, smiling slightly as his gaze settled back on the trees. He seemed… comfortable. Centered. Like someone savoring a moment of physical stillness after a hard day of manual labor. He spoke again. “Ever think about running one of these companies yourself?”

“Only every day,” I said, quickly, with a smile. “I think I’ll always have that itch. Like I need to prove I can do it, if for nothing else than a kind of… I don’t know what to call it. A kind of… love of the game?”

That got a smile, but he didn’t look at me. Instead, his gaze stayed fixed on the woods. I followed his eyeline. It was a nice night. The nearly-full moon filtered through the trees, casting sharp shadows over a sandy path that cut through clusters of ferns and taller palms, their thick fronds shifting quietly like the dark edge of a moving wall. The air smelled like salt and damp earth, and clumps of Spanish moss hung draped over the branches like wisps of smoke frozen in midair. The woods felt both hypnotic and closed-off. Alluring, but impenetrable.

“I know what you mean,” he said softly, almost to himself. He repeated the line. “I do know what you mean.”

We both drank slowly, taking in the moonlit forest wall. I broke the silence. “Hey, can I ask you something?”

“Shoot.”

“I’ve been thinking a lot about my job and our companies. About what I can do to help our teams get to where they need to go.” I said. “And… I don’t know. I just keep coming back to this one big idea—that we don’t finish enough things.”

His eyebrows lifted, a subtle interest sparking in his eyes. For the first time in a while, he turned his eyes back to me, breaking his connection with the woods. Without speaking, he invited me to continue.

“I see it all the time,” I continued. “We start doing the right thing, but almost never finish it. The team creates an Ideal Customer Profile, but they never get around to building the actual list. They train their teams, but never write down what they really expect from them. They send out the metrics to us, the investors, but don’t talk about the numbers when we’re not there. They have great ideas, but then… they… I don’t know. They pull back.”

He leaned back in his chair, gaze flicking back to the trees. “Yeah, I get it.” He smiled, exhaled slowly. “And I have some thoughts.”

I motioned with a welcoming gesture, my hand sweeping from his direction to the trees, indicating that no one else was there to listen in. “Please.” I said.

He took a small sip, then began speaking as he sat back and rocked his chair gently. “Ideas aren’t the problem. Ideas are cheap. Ideas are safe. Ideas are standing on the edge of the battlefield and pointing out where the fight might end up being. There’s no risk in that. There’s no risk in saying, ‘Hey, maybe we should try this out.’ Because if that thing fails, you still have cover. It was just an idea, after all.”

He rocked forward, setting his feet solidly on the plank porch floor, eyes narrowing, still on the woods. “But leading? Leading is something different. Leading is putting yourself out there. Leading is saying, ‘This is the way.’ That’s vulnerable. When you lead, you’re taking a stand. And you’re putting yourself on the hook to deliver.”

He paused, eyes still searching the darkness, then turned back to me with a kind of quietly-satisfied pride, like he’d just put words to something he’d been feeling but had never articulated.

“People, on average, don’t like that. They want to hedge. They want credit for the idea without the responsibility that comes with it. They want to feel bold without actually being bold. So they share the idea, and then they stop short.”

He took a deep breath, gaze steady on the woods now, almost daring it. “But that’s not leadership. Leadership is risk. It’s risk of rejection. It’s risk of failure. It’s saying, ‘This might not work, but I’m going to lead you through it anyway.’ And that risk is what builds trust and respect—because your team sees you’re not just proposing something safe… something easy. They see you stepping out there with them.”

He paused, took another sip, and leaned back in his chair.

“Leading isn’t about having good ideas. It’s about having the courage to act on your ideas. To commit. Anyone can say, ‘I know what to do.’ Knowing what to do is easy. Only a leader can say, ‘This is what we’re doing. And I’m going to help you make it happen. Follow me.’”

I felt an involuntary grin forming. He was nailing it. He was good.

“Cheers,” I said, raising my glass. “To knowing what to do… and to making it happen. Two very, very different things.”

He paused, smiled, clinked his glass with mine. “Hey, that’s good. Gonna steal that one.”

I laughed, leaning back in my chair. “Please do.”

A minute passed. He stood up then, slow and deliberate, recognizing when the conversation had naturally run its course. He nodded toward the woods, as if acknowledging something unsaid, then turned back to me.

“Good talk,” he said, clapping me lightly on the shoulder. “I’ll see you around.”

I watched him walk inside, the outer door of the cottage closing with a soft metallic click, leaving me alone on the porch.

I leaned back in my rocking chair. The path through the trees, illuminated by the moon, was clearer now. Winding, uneven, but so clearly there. The woods, the path—all of it felt closer. More alive. More inviting. Like a quiet suggestion to step off the porch and into the night.

But not tonight. Tonight, I was fine where I was.

I took a breath, savoring the afterglow of the conversation.

Like I said: I always learn something new at these things.