By Maria Popova (themarginalian.org)

Some of the most difficult moments in life are moments of having to choose between two paths leading in opposite directions — to tell or not to tell, to leap or not to leap, to leave or not to leave — each rife with losses (even if they are necessary losses) the pain of which you will feel acutely and with gains which you are constitutionally unable to imagine.

You could do it rationally, applying Benjamin Franklin’s framework of weighing the pros and cons. You could do it emotionally, turning to people you trust to decide for you, abdicating responsibility for doing the right thing. You could concede the futility of free will and flip a coin. Still, that bifurcation of the soul remains because life, in all its irreducible complexity, is not something you can optimize the way you optimize a route for minimal traffic or maximal scenery. What makes those moments so difficult is the knowledge that there will never be a way of testing where the other path would have led — you only have the one life, lived.

But perhaps there is a third way — one based not on renunciation, which is at the heart of all binary choices, but on integration, which is the pulse-beat of possibility. A way to stop trudging the ground of forking paths and lift off into the sky of the possible.

Art by Marc Martin from We Are Starlings

That is what the Danish philosopher Søren Kierkegaard (May 5, 1813–November 11, 1855) explores in his 1843 masterwork Either/Or (public library). Long before Alan Watts admonished against the trap of thinking in terms of gain and loss, before George Saunders offered his lovely lens for living an unregretting life, Kierkegaard writes:

If you marry, you will regret it; if you do not marry, you will also regret it; if you marry or if you do not marry, you will regret both; whether you marry or you do not marry, you will regret both. Laugh at the world’s follies, you will regret it; weep over them, you will also regret it; if you laugh at the world’s follies or if you weep over them, you will regret both; whether you laugh at the world’s follies or you weep over them, you will regret both. Believe a girl, you will regret it; if you do not believe her, you will also regret it; if you believe a girl or you do not believe her, you will regret both; whether you believe a girl or you do not believe her, you will regret both. If you hang yourself, you will regret it; if you do not hang yourself, you will regret it; if you hang yourself or you do not hang yourself, you will regret both; whether you hang yourself or you do not hang yourself, you will regret both. This… is the sum of all practical wisdom.

[…]

Many people think [they are in the mode of eternity] when, having done the one or the other, they combine or mediate these opposites. But this is a misunderstanding, for the true eternity lies not behind either/or but ahead of it.

Kierkegaard considers the frame of mind necessary for living beyond either/or:

Were I to wish for anything I would not wish for wealth and power, but for the passion of the possible, that eye which everywhere, ever young, ever burning, sees possibility.

In no region of life is the tyranny of binaries more punitive and the passion for possibility more vital than in our closest relationships, which at their strongest and most nourishing must transcend the confines of binary categories, for any relationship on the level of the soul has elements of lover, parent, child, and friend, and suffers when subjected to either/or. And yet there are times in life when such relationships collide with the confines of practical reality, the reality in which binary choices must be made, and must shape-shift in order to survive.

Illustration by Maurice Sendak from a vintage ode to friendship by Janice May Udry

A century before Anne Morrow Lindbergh wrote so beautifully about embracing the mutability of intimate relationships, Kierkegaard considers what it takes to let a relationship change organically in order to feed the soul in a new way:

The same relationship can acquire significance again in another way… The experienced farmer now and then lets his land lie fallow; the theory of social prudence recommends the same. All things, no doubt, will return, but in another way; what has once been taken into rotation remains there but is varied through the mode of cultivation.

What a way to remember that mediating holding on and letting go is the art of trusting time, that everything is eventually recompensed, every effort of the heart eventually requited, though not always in the form you imagined or hoped for.