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Life Lessons from the Clipboard King

Sep 05, 2023 | Cole Ruth


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What do you do when you find yourself in uncharted waters? I asked my father, a former pilot and lifelong clipboard devotee. Here's what he said.

My father the pilot in his C-141 circa 1980.

I’ve been thinking about checklists lately. If you haven’t read The Checklist Manifesto, I highly recommend it. In this book, Atul Gawande, a surgeon, talks about how having checklists in the operating room and in commercial cockpits has drastically reduced the likelihood of error.

I start each day with a checklist, and I keep a few financial checklists on hand to send to clients – I have one for widows and one for divorcees, for example. These types of checklists are helpful for situations that others have been through before; they've left their cumulative wisdom behind like breadcrumbs for others to follow. But what do you do when there is no checklist for your situation? I decided to ask my dad.

My father was a pilot, first for the Air Force and then for the airlines until he retired. I’m not sure if all pilots implement checklists at home, but he does. In fact, I can’t recall a time in my life when he didn’t have a clipboard nearby and on this call I found out why: he has FIVE.

I reached him in North Dakota, on the edge of the Black Hills, where he and my mother were camping in their motor home. 

“I probably didn’t have checklists until I started flying,” he admitted. “I’ve always been an organized person but on my fist assignment, they made me a scheduler. I would never have been able to keep everything straight without a clipboard. 

“Since then I’ve always had at least three. The first is the red one. It contains the ‘musts dos’ – the things that have to happen TODAY or very soon. Like paying a bill, or taking a car in for an oil change because I’ve already driven it longer than I should have. The red list has to do with money and bills and responsibilities. The second checklist contains the stuff I can kick down the road a little. The third contains thing I can kick down the road further, and the fourth is stuff I can kick way down the road.

“I’ll tell you something. My father - your grandfather - never took notes. Ever. It didn’t concern him enough to get the first things done first. In 1979 he got one last shot at his dream. He had a car in the Indianapolis 500. I went with him and my brothers to the race. They managed not to finish last, but he had forgotten to safety wire the rear end oil plug. The nut came out and all the oil drained out in the first lap. If there was ever a case for a checklist in his life, it was then.”

Always bring lots of tools.

My father ranged off topic for a bit, talking about my uncles and cars. Then he circled back to my original question. “But you asked about what to do when you find yourself in a situation where none of your checklists apply. Your question is apropos. I don’t want to worry you, but we are at 5000 feet.” He paused to let that sink in.

For almost 20 years my mother has struggled with severe persistent asthma. In 2010 I took her 8,516 feet up on the Palm Springs Aerial Tramway and she started having trouble breathing before we got to the top. We got right into the line to take us back down, and I spent the interminable minutes worrying over when to call a life flight. Now she takes a portable nebulizer everywhere she goes.

“On our way up from 2000 feet yesterday, your mother charged her oxygenator,” my father continued. “But at 12:10 last night, the unit failed. It popped the GFI and ceased operating.”

Fortunately, my dad had just the right tools on board and an old computer charger that happened to match the oxygenator’s output signals: 19.5 volts. “The charger had a transformer, but a different tail, so I spent the next few hours changing the tail, and it worked!”

When I called, they had just come in from spending the day outside. My mom was fine, he said, and all was good. 

Keep your wings level and true

“But Dad,” I asked. What about the fifth clipboard?” 

“Do you remember the day your mother brought the tape measure out on the deck at the lake house?”

I nodded, though he could not see me through the phone. 

“It was a 90-inch tape measure. She extended it all the way and explained how we hope to live until age 90, so every inch is a year. When we held the tape measure out at age 64, we figured we had 20 inches left, if we were lucky. Now we’re in our 70s. We’re starting to see how fragile we are. Every moment is so important. And we’re a little anxious about the time going by too fast and not being ready for it. So the 5th checklist contains the things I want to do.”

My grandfather never got another shot at Indy. We do not always fully realize our dreams. But we can have the checklists to keep us on course for the life we want to live. What is the stuff that has to get done today? How many lists do we need to help us get to the items on the 5th one? 

My dad, again: “If you live long enough, you are bound to find yourself going through life on autopilot," my dad mused. "Maybe you achieved what you wanted to and you’re just coasting along, content. Then something unexpected happens, and you have the opportunity to see possibilities where you did not see them before. In those moments, I have rarely let uncertainty trouble me. To be clear, uncertainty in my world is defined as those things over which you have no control. When faced with uncertainty, I look for things I do have control over. Then I grab the bull by the horns and head in that direction.”