Chapter 1 — Mechanical Delay

I found out I was probably the father of five-year-old twins while standing on the cold marble floor of O’Hare, thirty-five minutes after cursing the flight delay I was certain would ruin my career.

I was forty-four, and I had made punctuality into something close to a religion.

I owned a small chain of boutique hotels — Miami, Charleston, Savannah, Key West — and that morning I was flying to Boston to close on a historic estate, the largest acquisition of my life.

I had come to the airport with two hours to spare, because I always came with two hours to spare.

And then the departure board flashed the word every traveler dreads: MECHANICAL DELAY.

I called my chief financial officer and told her to start the board meeting without me if she had to, that I would be there the moment they cleared the aircraft.

Then I went looking for a quiet corner away from the crowded gate, toward the floor-to-ceiling windows, and I opened my laptop, and I got through exactly two lines of a financial summary before my life divided cleanly into everything that came before that morning and everything that came after.

I have thought many times since about how close I came to never looking up.

Two lines further into that summary, and I’d have kept my head down until they called my flight.

Instead, a few yards away, something caught the edge of my eye, and I looked.

I have to explain, first, what a delay meant to a man like the one I was that morning, because it is the whole irony of my life.

I had built everything — the company, the reputation, the self — on the principle of never making anyone wait.

Punctuality was not a habit for me; it was a moral position, almost a form of contempt for people who couldn’t manage it.

A man who is on time, I believed, is a man who respects other people’s lives; a man who is late is a man who has decided his own time matters more than yours.

I had fired people, quietly, for a pattern of lateness.

I had ended a friendship, more or less, over a man who kept me waiting forty minutes at a restaurant and did not think it mattered.

And so when that board flashed MECHANICAL DELAY, I experienced it as a small personal catastrophe, a violation of the order I had imposed on my world at such cost — thirty-five stolen minutes that might, I told myself, unravel the biggest deal of my career.