Eyes Turned Skyward

Words of investing wisdom that stand the test of time.

“Once you have tasted flight, you will forever walk the earth with your eyes turned skyward. For there you have been, and there you shall long to return.” - Leonardo da Vinci

When da Vinci wrote these lines - somewhere in the years bracketing the close of the fifteenth century, in a notebook kept in mirror-script against the prying eyes of his patrons - no man had ever flown. No man had ever seen the earth from above, nor known what it meant to be lifted from the ground and held there. The condition these sentences describes was, in the literal sense, unavailable to any human being alive on the planet.

Da Vinci was writing about a sensation that did not yet exist.

This is the strangeness one must hold steady in the mind when considering the words. They come from a man of Florentine streets and Milanese courts, whose entire bodily experience of altitude was confined to the towers of his city, the hills beyond it, and the few feet of separation between his standing height and the floor of his workshop. He had no aircraft. He had no balloons. He had no testimony from any man who had ever risen, because no such man had ever lived. He had only the birds outside his window, and the strange certainty that what they were doing was a state into which a human being could enter and from which, having entered, would never psychologically depart.

There is an almost prophetic feel to the statement. It is the prophecy of a man who understood that there exist experiences which, once tasted, reorganise the soul that has tasted them.

Four centuries would pass before the Wright brothers proved him correct in the literal sense. They had studied Leonardo’s work. They had also read the writings of every other man who had attempted what they aimed to do and failed. What they maintained above all else was a refusal to accept the consensus that heavier-than-air flight was impossible - a consensus held by the most distinguished scientists of their own century, including Lord Kelvin, who declared the question settled five years before Kitty Hawk. The bicycle mechanics from Dayton, Ohio, with no formal scientific training and a workshop full of bent metal and patched canvas, kept building, because the men who had given up were wrong and the man writing in mirror-script in 1490 was right.

When Wilbur first lifted off the sand on the seventeenth of December 1903, for twelve seconds, at an altitude that never exceeded ten feet, the world changed. And not just the world of aviation. Our understanding of what a human being is, what he can know, and what he can long for expanded. Leonardo’s prophecy was fulfilled in a single, juddering arc of motion above a North Carolina beach. And every man who flew afterward - every passenger in every metal tube humming above the clouds, every astronaut looking back at the curvature of the earth, every fighter pilot in his moment of speed - entered the condition da Vinci had named without ever knowing.

The condition is this: that having known something, the soul cannot un-know it. That having stood in a particular place, the man who stood there will spend the rest of his life unable to forget that the place exists. Leonardo understood, four hundred years before the experience was available to anyone, that flight would not be merely an act. It would be an altered state of being. The man who had tasted it would walk among other men, but his eyes would be turned skyward, because he knew what was there.

There is no investing essay here. There has never been an investing essay. There is only a story about what happens to a human being who has briefly inhabited a magnitude.

And yet.

There is a particular experience available to the investor - rare, unpredictable, and almost impossible to describe to those who have not yet lived it - which functions in exactly the way Leonardo described flight. It is the experience of having held, at the right size, for long enough, a single business that did what one suspected it might do.

The conventional language of finance has no adequate term for it. Words like “multibagger” or “tenbagger” describe the arithmetic without harnessing the experience. The arithmetic is the smaller part. What is altered, in the investor who has lived through such a return, is his understanding of what is actually being played for.

He has tasted flight. He has been in the air. And he will spend the remainder of his career - every analyst meeting, every stock screening exercise, every late night with a balance sheet, every position-sizing decision, every conversation with another investor - with his eyes turned skyward. Because he knows what is there. He knows what a single position, correctly identified and doggedly held, is capable of becoming. He cannot un-know it. The knowledge re-tunes everything that follows.

This is the condition Leonardo predicted. And it explains, in a way no spreadsheet ever can, why the patient and ruthless search for asymmetric returns must become the entire structure of a serious investing life. This search is not reliable and it is not comfortable. But the man who has flown knows that flying is the only thing worth doing, and the man who has held one of the great compounders through a stratospheric run knows the same.

The vast majority of his subsequent ideas will fail. Most of his concentrated bets will revert to the mean of mediocrity, or worse. He will be wrong, often, in front of people who notice. He will hold positions through drawdowns that would have shaken him before flight. He will refuse to sell at points where every financial model says he should. He will look, to many observers, faintly unhinged. He has been to a place where the air is different. He cannot pretend, having been there, that the air at ground level is sufficient.

The pre-flight investor cannot understand this. He looks at the ground game - the small steady gains, the diversified positions, the comfortable returns - and finds it perfectly satisfying, because he does not know what he is missing. He reads of investors who hold concentrated positions and assumes they are reckless. He cannot conceive that they have simply seen the curvature of the earth and refused, forever after, to walk with their eyes lowered.

This is the deeper meaning of asymmetric thinking. It is a state of altered consciousness available only to those who have lived through it - and they will spend the rest of their career attempting, with the discipline of a monk and the obsession of an artist, to find their way back to it.

Leonardo did not fly. He died without ever leaving the ground. But he understood the condition flight would produce in those who tasted it with such precision that, half a millennium later, his words apply to a domain he could not have anticipated, with a fidelity that suggests he had glimpsed something universal - that a magnitude, once experienced, becomes the only thrill worth seeking.

The investor who has not yet tasted flight should keep searching, because flight is what the search is for. The investor who has tasted it does not need to be told. He already walks with his eyes turned skyward. He has been there.

And there he shall long to return.

Stay still.

Win slow.

Theodore