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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22 thoughts on “Fly The Friendly Skies

  1. Lew

    Hi Michael,
    To your comment about “As they say in flight school (I’m assuming)”: Yes, this is exactly what they say. I am a pilot, so I know. The cardinal rule of flying is: Aviate, Navigate, Communicate. In that order.

    No matter what, you ALWAYS fly the plane first. Then, figure out where you are and where you’re going. And only then do you communicate with Air Traffic Control.

    So, that’s the model. Now, write a nice analogy for how that should apply in your solo business!

    Cheers, and have a swell holiday weekend!

    1. Michael Katz Post author

      Laura, Michelle and Jen!

      OK, here’s the Ben Stiller connection. My dad was friendly with his parents. I was visiting my parents in NYC for a few days and they were all getting together at a studio where stiller and meara were recording some radio commercials. I went because I wanted to meet the two of them. I ended up sitting there all afternoon waiting for it to be over with their then 15 (?) year old son Ben. I was probably 21. I had no interest in some dorky teenager and he had nothing to say to me, so it was a very uneventful few hours!

      1. Jen Carsen

        This is fantastic. I can’t believe this story hasn’t yet made it into one of your newsletters, perhaps with some re-created dialogue:

        Ben: I plan to make many movies and become wildly successful in Hollywood, just like my parents.
        Michael: Beat it, kid–you bother me.

        1. Michael Katz Post author

          All I remember was that he was your typical, sullen high school kid with a big backpack who sat in the corner with headphones and his winter coat on the entire time. And that his parents were kind of bummed that he was interested in showbiz because the likelihood of success is so small!

  2. Charles Alexander

    1. I try not to get too excited with a new contract or too low when I lose one. And I yell at my laptop a lot.
    2. That’s all he could talk that I spent an afternoon with him.
    3. Oh, Ben Stiller. I was thinking of one of the Wilson brothers.

  3. Meryl K Evans

    1. Like this:

    2. Of course! Oh wait … you mean the one in “Night at the Museum?” Son of Anne Meara and Jerry Stiller of Seinfeld? Christine Taylor, his wife, one of the kids in “Brady Bunch Movie?” With family like that … gonna be tough to top it 🙂

    3. Me neither.

    And inquiring minds wanna know (Laura, too) … how did you spend an afternoon with Ben Stiller?

  4. Mark Wayland

    You had me at “Southern Hemispherians, feel free to smirk politely.”
    I can’t tell you how many posts/ newsletters/ emails I get from large so-called international organizations who believe that everyone is experiencing end of summer/ start of autumn.

    It can’t be that difficult to be simply inclusive.


    1. Michael Katz Post author

      Hello Mark!

      Yes, it’s the time of year where I always think about moving way south. Enjoy your turn in the sun and let’s definitely connect again in May!

  5. Jessica Hoelzel

    This was timely Michael, thank you. Being a solo-preneur is a bumpy ride, especially when managing motherhood alongside of it. With two kids out of three back in school, I’m looking forward to starting anew and smoothing some things out this September!

  6. Tara

    So very true about the ups and downs, wanting to go back to a steady job, and what other people often think.
    I’ve always wanted to fill in for a bass guitarist. One day….


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