The Will O’Leary Rule

Mark O'Brien
5 min readAug 6, 2019

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This is not the real Will O’Leary, and he doesn’t play him on TV.

During the years I spent toiling for an advertising agency, the ego of the high-flying gentleman who owned the establishment fancied charter flights. In fact, to impress an adolescent nephew, Il Grande Formaggio once chartered a jet to fly us to a meeting in Cleveland, took the nephew on the flight, and had the cabbie who drove us from the airport to the meeting drop the nephew off at the Rock and Roll Hall of Fame. Le Gros Fromage had to replace his entire hat collection after that momentous trip.

Will Mick and Keith be there today?

Most times, though, he chartered small prop planes at a local airstrip. One such charter, booked in the dearth of commercial flights available in the immediate aftermath of 9/11, took us to Richmond to meet with a prospect. The small plane sufficed: It’s less important to impress a prospect than it is to convince your teenage nephew you’re The Man.

A Tangent

Two things are true of me: (1) I fall asleep readily on planes, frequently being out like a light before being airborne. (2) I disdain seat belts, on planes, in cars, anywhere. Aside from the fact that they make me uncomfortable, I once witnessed an event that solidified my anti-restraint stance:

Driving south on I-91 in Connecticut with my two then-young sons in the car, a station wagon in the left lane and a sedan in the middle lane attempted to switch lanes with each other at the same time. Recognizing their tactical error simultaneously before they collided, the drivers of the cars jerked their respective steering wheels.

Not good.

The driver in the sedan in the middle lane veered violently but safely into the right lane. The driver in the station wagon, the suspension of which responded as if it were manufactured of old bed springs and marshmallows, yanked her steering wheel hard left toward the median. The car responded by barrel-rolling off the highway and onto the grassy median between the north- and south-bound lanes of traffic.

As the car rolled across the median, the driver-side door was thrown open by centrifugal force, ejecting the driver upward, directly perpendicular to the ground, as the car rolled away beneath her. She landed safely and unharmed in the grass on the median as the car continued to roll, across the median and onto the other side of the highway, at which point it was struck by a north-bound tractor-trailer rig and pretty much disintegrated. Lesson learned.

Back to Our Story

At any rate, we undertook our flight to Richmond heedless of the fact that there were violent thunderstorms the length of the Eastern Seaboard. In my characteristic state of oblivion, I was comatose before the plane’s three wheels ever pried themselves free from the tarmac.

At one point during the flight, the plane was rocked so violently — percussion from a thunderclap? a wind shear? generic aviatic turbulence? — my belt-less body was hurled upward (or the plane was hurled downward) causing me to wallop my noggin on the ceiling of the cabin … and even waking me up.

Ooh, that smarts.

I put my hands to my head, making a quick check of my scalp to ascertain whether I’d suffered a laceration. I found a decent sized mouse on the top of my coconut, but no broken skin or blood. (If I hadn’t whacked my thick, Irish skull, I might have been killed … or worse.)

I also made a quick check of my shorts to make sure I was still sanitary. Then I decided it might be prudent to panic. At the very least, it seemed as if a simmering terror might not be completely out of line.

But before panicking or surrendering to stark terror, I looked forward to the young dude in the cockpit. He was cool as a cuke. While this might have qualified as rank rationalization, been a textbook example of wishful thinking, or been tantamount to a furtive search for the silver lining in a septic tank, I arrived at what seemed at the time to be two fairly sensible conclusions:

  1. The young dude in the cockpit knew a hell of a lot more about flying that plane than I did.
  2. If he wasn’t rattled, let alone terrified, there was no reason for me to be.

Denouement

When we were safely grounded in Richmond, I went up to the cockpit, congratulated the young dude on his aeronautical acumen, thanked him for his grace under what I took to be a completely new spin on atmospheric pressure, shook his hand, and asked him his name.

“Will O’Leary,” he said matter-of-factly, without artifice or self-consciousness.

And, so, was the Will O’Leary Rule born. (The Will O’Leary rule is alternatively known as WWWD — What Would Will Do?)

Reality? What reality?

Now, any time I’m on the verge of any calamity, catastrophe, or cataclysm, I look for one person who appears to be fully composed — or blissfully ignorant. I don’t care. I don’t attempt to judge the person’s cognitive acuity. I don’t look for signs of sentience. I don’t check for vital signs. I just take comfort and go back to sleep.

No worries. No seat belt.

Thank you, Will.

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Mark O'Brien
Mark O'Brien

Written by Mark O'Brien

Trust yourself. Question everything. Settle for nothing. Conform to as little as possible. Write relentlessly. And never quit.

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