Freedom to the Form

AirMail Flights and Barnstorming in Today’s Silicon Valley

“What you got yourself there is a Cloud Snail!”

A young imagination is less encumbered by form, turning power plants into animals.

The words of my daughter echo Antoine de Saint-Exupéry’s Little Prince, who used the drawing of a snake that ate an elephant to determine whether an adult was enlightened. If they saw a hat, the Little Prince didn’t trust them.

I work at a venture firm and make a living looking for the enlightened, toggling between a life just north of the Big Sur coast and the so-called Silicon Valley. I fly “the mails,” as Saint-Exupéry did, using an old fabric-wrapped plane to deliver handwritten letters and offer “Bay Tours” to young engineers whose ideas we hope to back.

Saint-Exupéry documented the lives of daring pilots setting up early mail routes through the Andes and against the mistral winds of North Africa. His employer, La Post, was the technological envy of the world, pioneering overnight delivery that in its day was as revolutionary as Amazon or SpaceX is today.

Saint-Exupéry had a disdain for bureaucrats, an ethos held in golden matrimony between tech innovators and the venture capitalists that back them. So I fly, looking for the next generation to replace those whose gates I storm.

Lest we take this all too seriously, best to remember that to be a pilot, to aspire as an investor or even a father, is still to be tethered nonetheless to “the forms.” As my Zen teacher says, “It’s still a thing; an identity, a narrative.” Watching the twin stacks of Moss Landing poke through the marine layer, my daughter reminds me of the “formless” and the potentiality to be unbounded by form.

“Between our attachments, there is freedom” my teacher says. Freedom from these forms is liberating. As pilots, from up above, things at least make more sense, why a river leads to a port and port to a city. A practical kind of enlightenment you might say.

I’ve given a lot of people their first flight. Seeing things as they are, from the air, is fundamentally optimistic. People tell me it’s transcendent because it allows them to see the day-to-day rat race in a different way. The transcendence of seeing your neighborhood or your city from six thousand feet is the spiritual opposite of living in forms.

“But beware the great matter!” my teacher reminds. A life commuting by bush plane is just a thinly veiled version of form. It feels free, but it is no less encumbered. By story, by narrative.

How to tell the difference? Look for the feelings! To live is to feel. To fly is to feel. The Formless, always unbounded, is the Cloud Snail, or The Little Prince moving his chair for an eternal sunset.

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Peterson Conway

Peterson Conway is a pilot, writer and headhunter. He builds the early teams of companies commonly associated with the so-called PayPal mafia. He's the son of a professional smuggler and a Mormon school teacher. From them he learned to tell stories, write about people and live at the intersection of big ideas, talent and crazed persistence. Conway lives in San Francisco but spend summers flying off a dirt airstrip in Idaho. As a back-country bush pilot, he likes the metaphor of delivering special people to hard to reach places.

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