To Be a Leader of Systems

Picture with me, if you will, the absurdity of finding yourself swimming in the middle of the ocean. First think about the ocean and how deep and infinitely vast it is; then about how improbable it is to even fully grasp the notion of how large the ocean is, of how deep it is, of how wide it is; think about how there is so much of it we will never know, and so much we can never know.

Let that sink in, deeply and fully.

Now, as a person who sees systems, who intuits chaos, who can grasp these concepts of swirling infinities, you have to sit with the uncomfortable idea that if you were to find yourself stranded in the middle of the ocean, it is a death sentence of all but certainty. This might be fine if it were just you; after all, life happens, you know? Sometimes things are bizarre, sometimes luck just runs out. However, I’ve often noticed that people who become known for seeing systems often become in charge of them. In other words, you’re probably a leader–either by name, by identity, or by purpose.

But to be a leader is to understand that you’ll find yourself stranded in the middle of the ocean one day. Not just you, but everyone you lead. And you’ll need to chart a course. In the ever-changing winds, the ever-shifting tides, the unknown weather, and with an inability to see up or down or basically anywhere except a few minutes away. You won’t have the time to find your bearings even if you could. Yet, somehow, in this sea of swirling and infinite complexities and probabilities, in the midst of incalculable odds, you will find yourself needing to have simultaneously several different things:

Firstly, you need to hold in your head the knowledge that you will probably–no, almost certainly–fail. You will need to hold that uncomfortableness in your heart and carry it with you always. Never to share, but always to hold. Ground yourself in the impossibilities of what you’ll attempt, lest your hubris lead you to ruin.

Secondly, you will need to hold firm and irrationally deep conviction. Unshakable. Unshatterable. Conviction that you will succeed. This is the conviction that you have to share, that you have to use to lead people along with you, that you have to embody fully and without reservation. Because you have to keep going. You must keep faith. Up until the very last stroke. Up until the very last moment. Going past the moments beyond when you thought you could go. To succeed often requires–and always demands–of you to embrace the utterly insane notion that you cannot fail.

Thirdly, you will need to prepare and make ready everyone around you. Because to fail as a leader is not when you conviction and go down the wrong path. To fail as a leader is when you do not prepare people for when that inevitable failure happens. This will feel in uncomfortable contrast to the necessary conviction that you cannot fail. Unfortunately, leadership is defined by contradictions. You, as a leader, have to hold these unresolvable contradictions together. There is no reconciling them. There is no addressing that cognitive dissonance. Your only path will be to hold that storm of of disquiet in yourself, even as it slowly anguishes you.

If there ever was a trick to this, it cannot be described simply. But if I were to try, I would say that the trick is–I think–to learn how to dance in the rain. Plant gardens you will never grow. Prepare futures you will never see. Create victories you will never celebrate. Build memories you will never recall. Tell stories that will never be heard. Hear sorrows that will never be healed.

Lead people with kindness and empathy towards impossibilities; not because you can make them possible, but because you know both that you can and cannot. Smile at the chaos and laugh at the sworling vortex of insanity. Pick out the pinpricks of light buried inside that encompass what humans find worth living and weave them together. That tapestry is the cloth, fixed atop your mast of conviction, that you will use to sail your way through the seas of entropy.

Above all: Feel deeply, live fully, lead truly, hold empathy, and inside your heart the intellectual humility required to be able to see the beauty in the chaos. Oh, and learn to dance in the rain.