Scott Monty - Strategic Communications & Leadership Advisor

Scott Monty - Strategic Communications & Leadership Advisor


A Woodland Road with Travelers by Jan Brueghel the Elder, 1607 (public domain - Metropolitan Museum of Art)

“We, at the height, are ready to decline.
There is a tide in the affairs of men
Which, taken at the flood, leads on to fortune;
Omitted, all the voyage of their life
Is bound in shadows and in miseries.
On such a full sea are we now afloat;
And we must take the current when it serves
Or lose our ventures.”

   — William Shakespeare, 1599

In Friday’s edition of Timeless & Timely (“The Choices We Make”), one of the timeless links was to Robert Frost’s poem “The Road Not Taken.”

And I promised to follow up on that with some additional thoughts.

It’s probably his best-known poem, having inspired so many other creative outputs from others: books, commercials, episode titles for a dozen TV shows… In fact, it may be the best-known American poem of all time.

It begins:

“Two roads diverged in a yellow wood,
And sorry I could not travel both”


And concludes with the iconic lines:

“I took the one less traveled by,
And that has made all the difference.”


But when making a reference to the point of this poem, most people get it wrong.

Our initial instinct is to view this poem as a celebration of individualism — of making a conscious choice and going in a direction that others might not.

But if you read it again, one road isn’t less traveled. Frost writes:

“I took the other, as just as fair,” and “the passing there / Had worn them really about the same.”

So the narrator knew that both paths were comparable. And he simply chose one of them, as it looked just as good as the other.

There has to be some reassurance in that. When we make a choice down an unknown path, we warmly welcome any clue that can provide more certainty.

And there’s always the temptation, after we’ve made our choice, to convince others that we knew what we were doing all along.

This is exactly what happens in the poem.

Look again: when Frost writes:

“I shall be telling this with a sigh
Somewhere ages and ages hence,”

He’s saying that one day in the future, he’ll be recounting this moment in time — what will he do then?

He’ll tell everyone:

“Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.”


So this isn’t really about making an uninformed choice; it’s about how we concoct stories to make a narrative about our choices.

Or put another way, it’s how we look back at a situation and romanticize it a bit. Or justify our decision. Or infuse it with details, embellished with larger figures and more expansive descriptions that we didn’t notice when we were in the moment.


Don’t you think it’s reasonable to believe there were embellishments and improvements along Frost’s way?

Of course there were. I mean, who’s going to want to read or listen to a poem about a guy who comes to two grassy paths and just picks one at random?

So in that respect, yes, it’s about choices. But it’s also about the choice to tell a story in a certain way. And each of us faces that every day as we choose to create our own narrative or a message for a brand or company.

As storytellers, we choose which details are essential to include, and which are superfluous to the story. In doing so, we capture the imagination and attention of the people we’re trying to reach, whether they’re in a room with us or in front of a screen somewhere.

The conditions in which we do this are ever-changing: room size, platforms, moods, competing priorities, staff…

And so elements of our narrative change accordingly. But always leading on to something better.

And if we’re reassured in our decision while telling our stories, all the better.

Thanks, and I’ll see you on the internet.

👉 Premium Members receive an additional related essay, plus curated links, stories, and audio and book recommendations every other Friday. And the latest feature: regular Office Hours every week to explore a topic together.

Join the club by signing up below: