Serendipity vs. The Act of Will

Thinking through the opposing natural forces.

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What are the relative merits between, on the one hand, of being a master of serendipity and the opposite: making things happen for yourself that you want to have happen — of goal setting and producing desired results from a concerted act of will.

It is a rare skill to surf the natural energies of life, (of business, of relationships) — with deft grace and Zen-like acceptance. If the world gives you lemons, make lemonade. From my home I can watch “real” ocean surfers paddling out to put themselves in just the right position with respect to how things are moving around, being patient and watchful, and then knowing how to move themselves to capitalize on an unimaginably enormous surge of energy, leveraging it for their own purposes. You don’t control the wave. At best you just get to ride it, not to be afraid of its power, balancing on an unstable surface in motion, gliding wherever it’s going, and perhaps dropping off when you don’t want to go there…

Knowing when to let go. That seems to be key too. I have long been inspired by the simian locomotion called brachiation. Swinging through jungle canopies, new world monkeys let go of a branch and fly through the air, hoping to catch something safe on the other side. They’re built for it, not only with prehensile feet — feet that grab like hands — but prehensile tails. And yes, occasionally they actually miss and hit the ground. But not often.

Personally, I like this serendipity camp… and try to be a full-brachiator in my life. Watching the forces swirl, looking for a rising wave and enjoying a ride. Often this is manifested where two remarkably improbable events coincide, making an even more unlikely event suddenly feasible. There is an adage that what appears as “luck” is simply the union of preparation and opportunity. To me this is where entrepreneurship, like surfing, resides — those who look lucky are simply highly skilled, they put themselves in the right place, they are unafraid of trying multiple times and unafraid of failing… and they know how to wait…

To some being a master of serendipity looks like magic. We think it’s easy mostly because of a phenomenon called “survivorship bias” — where we only see the winners, and all the monkeys that fell to the ground disappear — and we are left with the false impression that all who play will win. To others, a trust in serendipity seems lazy, unfocused, and unambitious — as if you were adrift on an ocean, going wherever the winds might blow you. A vagabond, a drifter. But sailors can also tell you that regardless of where the wind blows, you can go wherever you set your sights.

And even gamblers, those people who roll dice and put their trust in the universe to deliver for them, tend to “fish their wish,” and try through an act of will to change the chaotic order towards their goal. Impossible, certainly — and yet when my dice “crap out” with an 11, I’ve been chided more than once that I wasn’t focusing

The twin killers of serendipity are inertia and fear. Inertia is the tendency to move because you’re moving, or stick because you’ve been stuck. The first law of thermodynamics is powerful on our molecules, and seduces all evolved humans to behave more from habit and less from instinct. We tend to do what we’ve always done. We settle into routines. We prefer familiarity. Similarly it is fear that keeps us in bad marriages (fear of loneliness) and out of start-up companies (fear of poverty), or more generally, a fear of the unknown –jumping from a dull stable job to an exciting risky one has such an unpredictable outcome, the uncertainty is unnerving. The devil you know is better than the devil you don’t. So people stay put, they don’t let go of vines until they have another vine firmly in hand. In the animal kingdom, this is known as semi-brachiation: old world monkeys and apes move this way. Clearly, we are evolved from them.

So this brings up the opposite lesson: to pick a goal, and drive toward it. You don’t improvise building the pyramids or painting the Sistine Chapel. Plan your work and work your plan. Persistence in the face of adversity. Sailors go where they set their sights through skill and work. They leverage the powers of the wind but aren’t a slave to them. They make the winds take them where they want to go. The adage that always motivated me here was “Success is largely a matter of hanging on after others have let go.”

I know many writers and they’ll tell you that as much of an artform as writing is, you cannot only write when you’re inspired. You’re not always inspired. When those magic forces coalesce and a great work is produced, it’s nothing short of spiritual — the writer often feels just a vessel for some creative product that seemed to come from somewhere other than their own mind. But professional writers will simply tell you that writing is a discipline, it’s work, and you do it every day whether you’re inspired or not. Writers write.

So where does that leave me? Am I a serendipity ninja? Floating through the decades in a practice of preparation — and watching for all the trajectories of opportunity, calculating subconsciously where to stand to catch the ball. Am I the architect of my future? Where fate cannot be trusted to get the right supplies and right workers aligned to build that wonderful edifice — where to the greatest degree, each detail must be worked out in advance, and built on plan. I feel both, and neither.

And what of love? Is it magic, effortless, transformative art? Powered by serendipity, of chance meetings and funny coincidences telling us to pay attention? Or is it work, of patience and understanding and frequent pain, with some far off goal that we must apply ourselves to. When is it time to let go? and what is the goal?

And so perhaps there is a lesson.
We plan. We dream and design our lives, and we work tirelessly to construct them… but we learn not to pound square pegs in round holes, we learn to notice resistance when it occurs, and to stop pushing: we are sensitive to the forces that even we cannot control, and when we feel the wind coming around from the other side, or the wave rising that would be foolish to imagine we could divert, we have to know how to let go of the vine, flex like a tree in a storm, and drift naked and unknowing into a future, draped only in confidence in ourselves, in our ultimate impotence, and simply try to enjoy the ride.

Written by

Living a creative life, a student of high magic, and hopefully growing wiser as I age. • Ex-Lucasfilm, Netflix, Adobe. • Here are my stories and photos.

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