The Flak Jacket
A True Story of Leadership, Being a Dad, and the Cost of Being Right
This story is based on real events from my life several years ago. I have changed the names and titles of the individuals involved to protect their privacy. I spent years thinking leadership was about having the right answers, only to learn – painfully – that it is actually about being strong enough to hear the hard questions.
There was a specific kind of silence that fell over a boardroom in Cabo. It was different from the silence in Chicago or New York. In Cabo, the silence was heavy, underlined by the indifference of the ocean crashing a few hundred yards away and the hum of aggressive air conditioning trying to keep twenty high-net-worth individuals from sweating through their linen shirts.
We were at an offsite. Five stars, ocean view, spouses attending “activities”. The setting was designed to foster “alignment” and “vision,” but mostly it just raised the stakes. When you are arguing about the future of a company while your wife is having margaritas with the CEO’s husband by the pool, the professional and the personal don’t just blur; they collide.
I was there as the Chief Strategy Officer. My job, on paper, was to make sense out of chaos. From the Naval Academy, where order is survival, to my years as a systems engineer, my career has been built on a simple premise: I find the signal in the noise. I fix the mess.
Jim P., our CEO, was in fine form. Jim was brilliant – a visionary in the truest, most exhausting sense of the word. But he was also rude and derisive, and he had a memory that selectively deleted the contributions of everyone else in the room.
We were deep in a session about transformation targets. Jim was tearing into the VP of Product, a good man who was currently stuttering over a roadmap. Jim didn’t just disagree; he dismantled.
“It’s lazy thinking,” Jim snapped, tossing the report onto the mahogany table. “It’s small.”
The room flinched. This was my cue. I stepped in, not because I wanted to, but because it was a reflex. It was the muscle memory of someone who has spent a decade smoothing over rough edges.
“I think the point Jim is making,” I said, keeping my voice low and even, “is that the model needs to match the market opportunity. If we look at the systems view...”
I rephrased Jim’s insult into a strategy. I turned his derision into a “challenge.” The tension in the room dissipated. The VP shot me a grateful look. I felt a familiar, tired satisfaction. I had stopped the bleeding. I had kept the machine running.
That evening, during the cocktail reception, I found myself standing next to P.G.
P.G. was a board member and a celebrated Fintech CEO. He was tall, careful, and moved with the slow, deliberate gravity of a planet. He was politically astute, warm, and often seemed indecisive only because he listened more than he spoke.
I was holding a drink, watching the sun go down, expecting a nod of approval for how I handled the afternoon session.
“You’re very good at that, Meer,” P.G. said, looking out at the Pacific.
“At what?” I asked.
“Translation,” he said. He turned to face me. His eyes were kind, which made what came next worse. “But you aren’t helping him. You’re his flak jacket. You absorb the shrapnel so he never feels the impact of his own behavior. And frankly, it makes the rest of us trust you less. We need a Chief Strategy Officer, not an enabler.”
The air left my lungs.
My chest tightened. It was a physical blow. The heat started at the back of my neck and crawled up to the tips of my ears, hot and prickly. My pulse hammered in my throat.
The instinct to fight was immediate and violent. I wanted to debate him. I wanted to tell him that without me, Jim would have fired half the executive team by lunch. I wanted to list the three crises I had averted just this week. I am the only reason this works, I thought, the indignation rising like bile.
But I froze. Because the look in P.G.’s eyes wasn’t hostile. It was disappointed. And that disappointment triggered a memory from three weeks prior, twenty-five hundred miles away, in a dark car on a rainy Thursday.
I was driving my sixteen-year-old daughter, Sam, to a friend’s house. The windshield wipers were swiping back and forth, keeping time with the uncomfortable silence in the cabin.
Sam was smart, sharp, and at that time, deep in that phase where I was less of a Dad and more of an obstacle. We had been arguing about her schedule – she was overcommitted, stressed, and dropping balls.
“You just need a schedule,” I had told her, frustration leaking into my voice. “If we map out the week, prioritize the big rocks...”
She had turned to look out the window. “Dad, stop.”
“I’m trying to help you win back your time, Sam.”
“No, you’re trying to fix me,” she said, her voice quiet. “You treat me like I’m one of your projects. You’re always managing me. You never just... hear me. You just want to get to the solution so you can stop listening.”
At the time, I had dismissed it. I told myself she was just tired. I told myself I was the responsible one, the one with the answers.
But standing on that terrace in Cabo, with P.G.’s words hanging in the humid air, the two moments snapped together.
You’re managing.
You’re an enabler.
You’re not listening.
The common denominator was me.
I realized I approach relationships the way I approach systems engineering. I look for friction, and I try to eliminate it. I look for noise, and I try to filter it. But people aren’t systems. When you “manage” a CEO’s rudeness, you aren’t fixing it; you’re hiding it. When you “manage” a daughter’s stress, you aren’t relieving it; you’re invalidating it.
I looked at P.G. I forced myself to take a breath. Tongue to the roof of the mouth. Uncurl the fists. Let the adrenaline crest and fall.
I didn’t have a clever comeback. I didn’t have a strategy.
“You’re right,” I said. My voice sounded rough.
P.G. didn’t smile, but he nodded. He didn’t offer a platitude. He just let the truth sit there between us, heavy and real.
“So,” I asked, “what does it look like if I stop translating?”
“It looks messy,” P.G. said. “It looks like Jim having to clean up his own messes. And it looks like you risking his anger to save his leadership.”
Later that night, I went back to our room. My wife, Rani, was packing. We were flying out the next morning. The room was a disaster of suitcases and clothes, the debris of a week of forced socialization.
I sat on the edge of the bed. I watched her fold a silk scarf with precise, angry movements.
“You’ve been checking emails for the last hour,” she said, not looking up.
“I’m just closing out some threads,” I said automatically. “Clearing the deck for travel.”
She stopped folding. “Meer, you’re here, but you’re not here. You’re always optimizing the next hour. You’re always in “strategy mode”, never present.”
Three strikes.
I looked at her. I looked at the chaos of the suitcase. The old Meer would have explained the importance of the emails. The old Meer would have pointed out that my work paid for this trip. The old Meer would have been right, and he would have been alone.
I put the phone on the nightstand. Face down.
“You’re right,” I said.
Rani looked at me, surprised. I usually have a rebuttal. I usually have a checklist in my head explaining why I am correct.
“P.G. kicked my ass tonight,” I admitted. “And Sam kicked it three weeks ago. And you’re kicking it now. I think... I think I’ve stopped knowing the difference between leading people and handling them.”
Rani sat down next to me. The anger in her shoulders dropped an inch. “So what’s the strategy, Strategy Officer?”
“I don’t have one,” I said. “I’m just going to sit here.”
She leaned her head on my shoulder. It wasn’t a movie moment. The AC was too loud, and I was terrified about what would happen when I stopped being the “fixer” for Jim. I didn’t know how to do it yet.
But sitting there, in the quiet, felt like a start.
Growth, I am learning, isn’t about acquiring a new skill. It’s about shedding an old defense. It’s about realizing that the armor you built to survive the Naval Academy or the corporate ladder is too heavy to wear at the dinner table.
It turns out, you can be right about the system, and wrong about the human. And the only way to fix that isn’t to think harder. It is to stop, listen, and let the hard truth change you.
I hope you enjoyed the story.
Enjoy your loved ones and the rest of your day!
And thank you for spending some of it with me.
Warm regards,
Adi