On The Road Not Taken and making peace with ambiguity
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.
I already know you can’t count the number of times you’ve heard these lines by Robert Frost quoted in high school English classes, on literal hikes, and maybe just by that one friend who can’t help but go for the nastiest-sounding flavor in the ice cream shop.
We quote these lines from Robert Frost’s "The Road Not Taken" all over the place. Usually when we do, it's to use them as unassailable proof that being different is always the objectively better option - and all because... *checks notes* a famous dude said so in a poem a hundred years ago?
But if you read the rest of the poem, you’ll see that the speaker isn’t actually convinced that there was ever any meaningful difference between two paths before him.
He checks both paths out to the best of his ability…
long I stood
And looked down one as far as I could
Picks one because he has to in order to move forward…
Then took the other, as just as fair,
Gives a half-hearted reason for why he took that path while also admitting that his reason is kind of made-up given how similar the path he chose was to to other one…
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same,
Considers going back to try the other one, but knows he can’t simply live life perpetually looking back and litigating every decision he’s ever made…
Oh, I kept the first for another day!
Yet knowing how way leads on to way,
I doubted if I should ever come back.
And finally, in those last famous lines, he rationalizes that his decision was the better one… not actually knowing if that was true.
The internal monologue in Frost's poem looks a lot like the one a lot of us as leaders and innovators will be familiar with as a new opportunity enters our awareness. When making big life or business decisions, we've trained ourselves to look for ways to reduce risk and ambiguity to the best of our ability before marching forward – which, of course, is often a smart thing to do. But it’s not such a good when that instinct starts to slows us down from making even very minor decisions that would amount to a ton of cumulative learning and progress over the long-term if we allowed ourselves to make them. It's also not such a good thing when it leads us to seek to eliminate all uncertainty before we move on a new experiment, a candid conversation, or anything else that lays beyond these forks in our path.
If you’ve seen my speak you may have heard me explore the concept of Imperfectionism. It’s a competency I believe all poets and innovative leaders alike should embrace, and it boils down to the belief that it is generally far better to make a dozen tiny decisions that are all slightly off than it would be to make one perfect decision in the same amount of time. In the context of the road not taken, then, Imperfectionism is about making peace with not knowing how things will go, or how things could have been.
The beautiful irony of "The Road Not Taken’s" famous lines is that because we assume that Frost said them with confidence, they give us a comfortable way rationalize our decisions not knowing how the other path would have been… which is exactly what Frost was creating for himself when he wrote them.
Maybe this post-hoc rationalization isn't such a bad thing if it enables us to make peace with our path and our commitment to walking it - twists, stumbles, and all.
So when faced with strategic uncertainty, with a tough conversation, rather than picking the path less traveled on principle, and instead of waiting for any and all ambiguity to clear from your vision completely, embrace that ambiguity as a core part of every decision you will ever make as a leader… and just walk forward.
It’ll make all the difference.