Profiles in Courage: The product managers who removed Apple's headphone jack

“It really comes down to one word: courage. The courage to move on and do something better for all of us.” – Apple executive Phil Schiller, on why the company removed the headphone jack from the iPhone 7

The boys were down in the conference room, huddled around the design spec for the iPhone 7.

“I feel like we’re about to take Hamburger Hill,” the Manager said, tears welling up in his eyes. He made $450,000 a year and drove a Prius and everyone respected him. “It will take guts. But we’ve got guts. Don’t we?”

He was the bravest among us, having served several disastrous tours — on the Lisa, on the Newton, on 6 different redesigns of iTunes.

He was accustomed to crashing in flames — not literally, of course, because the Prius was a reliable, sensible sedan.

But still, he had courage. He knew that certain moments in history called for courage, like D-Day, and the raid on Osama bin Laden’s compound, and other incidents similar to a product design meeting for a forthcoming smartphone.

Failure was a possibility, and he knew what it meant to have something blow up in his face — metaphorically, I mean. He wasn’t, like, in the military.

But we had to do it, because none of these other bastards were going to do anything about the 3.5mm headphone jack standard. Not Samsung, not HTC, not BlackBerry, if that still existed.

They all lacked the swagger, the self-assurance—the courage.

We felt courageous—like firefighters storming into a flaming building, or like a very brave dog chasing a squirrel into the neighbor’s yard. Each day we wore the Apple uniform—an untucked Polo shirt, a dry-cleaned pair of Levis jeans—with pride.

The mood in the room was tense. The Manager was a gruff man, lacking the usual social graces of a software engineer. Gunfire was sounding all around us, because someone was watching Black Hawk Down in an adjoining office.

The office refrigerator had recently run out of both almond milk and Vitasoy. Morale was low.

Finally, one guy on our team—I’ll call him Martinez—lost it, and said we should turn back, replace the headphone jack, play it safe.

“No, dammit! We must have courage!” the Manager cried, banging his fist down on the table so hard it knocked over my carton of boxed water.

And that settled it. I called for a janitor to come wipe up my boxed water spill, and we headed off to do the bravest thing any of us had ever done.

We marched behind our Manager with pride. The stakes were high: If our mission failed, we could be fired, or, worse, forced to work on Find My Friends.

Just outside of Phil Schiller’s office, we stopped. There was no turning back now. We looked at each other, and we knew that there was a good chance we would die. Not for several decades, of course, given our demographics and annual income. But still: Someday we would be dead.

Yet we strode into the office with our heads held high, because we knew that when that fateful day came, when we met our Eternal Maker, we would be eulogized for our bravery, for our courage, in the face of a headphone jack crisis.

The rest, as you know, is history. I never saw the Manager again: He left Apple a few days later to open a couples SoulCycle retreat on Maui. But I will never forget his courage. Nor will the world.

Ernest Hemingway once wrote that “Courage is grace under pressure.” What he really meant, I think, is that courage is replacing one port on a smartphone with another port.

At least, during my days in the trenches at Apple, that’s how it felt.