Fly The Friendly Skies

The truth is, I’m not actually afraid of heights … I’m afraid of falling from heights.

This may seem like a minor distinction, but it’s the reason why I have no problem inside an airplane, glass elevator or shaky gondola (a great name for a band), but break into a cold sweat (literally) when stepping out onto a fifth floor balcony.

And so it was with some confidence that I quickly and eagerly said yes when my brother-in-law Neale invited me along on a glider (AKA, “sailplane”) ride this past weekend.

Neale flies a “tow plane” at the airport in Stow, Vermont on Sundays and we happened to be up there for a visit.

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The gliding procedure is very straightforward:

  1. You squeeze into the backseat of the glider with your 16-year-old son, Jonathan.
  1. A pilot named Bill sits directly in front of you.
  1. Neale sits in a tow plane that is attached to the glider with a 200-foot long rope.
  1. Neale throttles the whatever and we’re up in the air in seconds.
  1. When we get to 3,500 feet, Bill releases the rope and Neale’s gone in a flash, leaving us to float along on our own.

In a word: Thrilling.

I count it among my top ten life experiences, somewhere in-between the afternoon I spent alone with Ben Stiller and the time I sat in for the drummer of a band at a crowded bar in my twenties.

But you know what was the most interesting part of our ride? It was watching Neale’s plane flying in front of us, during the ten minutes or so before he let us go.

It’s a perspective I’d never seen before; not in person or even in a movie. You’re very close to the tow plane; but you’re not inside it and it’s not flying by. Instead, it’s just kind of bobbing around in front of you.

And bobbing is the key word. It kept going up and down and rolling side to side. Generally moving in the right direction, but by no means a straight, steady line as I had always assumed.

People who’ve never worked for themselves often make this same erroneous assumption about running a business: They think it will be a steady climb, when in fact, it’s anything but.

In my experience, it goes something like this:

Up … up … down … sidewayssssss … up … more up … down … down … what the … maybe I should get a job again … oh look, leveling off … AMAZING! … sideways the other way … AAArrrrggggg!!! …. down … UP … UP … what the hell just happened?

And that’s all before lunchtime.

My point is simply this: It’s September, the time when we all get serious again and “go for it.” Nothing wrong with that; I intend to do the same.

Just remember, no matter how long you’ve been at it, it’s never a straight shot and there’s always a lot of bobbing. And even if you have a couple (or several) bad months in a row, it’s to be expected. It doesn’t mean you’re failing.

As they say in flight school (I’m assuming), no matter what appears to be going wrong, don’t forget to keep flying the plane.

P.S. For a bird’s eye view of Bill, Jonathan and me buzzing a fire tower, check out this short video here.


Discussion questions

  1. How do you manage the emotional ups and downs of running your business?
  1. Do you think Ben Stiller tells people about the time he spent an afternoon alone with me?
  1. Me neither.

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