The Road Less Traveled

Jeff Cunningham
The Extraordinary Lives Project
4 min readMar 12, 2021

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Yogi Berra famously said, “when there is a fork in the road — take it.” The American poet Robert Frost somewhat the same thing, “Two roads diverged in a wood, and I — I took the one less traveled by, And that has made all the difference. I’ll try to explain why the befuddled baseball catcher and the Nobel Prize-winning poet said the same thing.

Berra was a well-known barroom philosopher prone to grammatical inventiveness that left people bewildered while nodding their heads. “It’s so crowded no one goes there anymore” is illogical yet requires no explanation. If listeners laughed at his malaprops, Berra cackled all the way to the bank. He was the third highest-paid ballplayer on the Yankee team because when he saw the fork in the road, he took it.

If you look back on your life, you’ll see, perhaps inadvertently, that you have taken many forks in the road yourself. Some worked out. Others are detours that one hopes will lead somewhere. Give it time. I left college without finishing my degree and spent many evenings in my thirties writing a final thesis. Some forks lead to oblivion, and you need to turn back and start over.

While Berra would never call his idea a ‘thesis,’ it mirrored the meaning of Robert Frost’s poem, “The Road Not Taken.” He wrote the poem in 1916 at age 42. According to the Paris Review, “The signature phrases of “The Road Not Taken” have appeared in advertisements for Mentos, Nicorette, during the Super Bowl and in more than four hundred books and is arguably the most popular of the 20th century.” The poem also inspired M. Scott Peck’s massive international bestseller, The Road Less Traveled. Phyllis Theroux of the Washington Post said, “was not just a book, but a spontaneous act of generosity.”

A careful observer will say something is not right here.

Is the poem the road less traveled or the road not taken? Those are two interesting but dissimilar ideas like tigers or lions. The answer is that Peck borrowed his title from the end of the poem, “I took the road less traveled, and that has made all the difference.” His meaning is different from the title Frost used, and it goes to the heart of the thesis about why some people get to have extraordinary lives. Because I owned the house where Robert Frost liked to spend his Christmases, I feel obligated to explain his poem and why it inspired this introduction.

The home at Crow Island, Massachusetts, where Frost spent his Christmas

Frost hated Christmas as much as Scrooge. He was not as much “bah, humbug,” as he was fastidious about whom he spent his time with. There was only one person whose company he could stand for an evening, as he said in another poem, “Hyde Cox, the Laird of Crow Island where I spend Christmas would be an island if not for an isthmus.”

The prior owner of my stately, Crow Island in Manchester by the Sea, MA, was a wealthy literary bon vivant who liked to ride on the back of the garbage trucks in his spare time. I never had a chance to meet him as I bought the home from his estate. He was the latest private owner of Andrew Wyeth paintings, having discovered the artist as a young man, and became a close friend. His famed literary salons were held in the living room, which I converted into a large dining room, where he had such a keen ear he would recognize different labels recording of Mozart. If you are a Dartmouth graduate, he donated all his possessions to the college, including my $6 million purchase of the home.

Frost and Cox made a Laurel and Hardy couple. One was short and spare, the other large and curvy if not rotund, and as the Scotch poured forth into their glass, their cynicism filled the room. In this way, they celebrated Christmas night every year, smoking unfiltered cigarettes to their heart’s content while scoffing at materialistic fools who didn’t know better. The oxymoron may have been lost on the two of them, either due to consumption or confusion. But what was really going on was they took a different path, and for them, it made all the difference. Had Yogi Berra been present as Cox refilled Frost’s glass, I am sure he would say how great it was they all took the fork in the road.

It is why I believe Frost was not talking about what he might have missed in life. After all, he was still in his forties: “Yet knowing how way leads on to way, I doubted if I should ever come back. I shall be telling this with a sigh Somewhere ages and ages hence.” His last line is “I took the road less traveled by,” suggesting we should try the new and try it now, which happens to be Extraordinary Habit #2, to take our best shot to be somebody. If it doesn’t work, we can always head back again. Nothing comes closer to describing the process that turns life from ordinary into extraordinary.

The Road Not Taken

Two roads diverged in a yellow wood,

And sorry I could not travel both

And be one traveler, long I stood

And looked down one as far as I could

To where it bent in the undergrowth;

Then took the other, as just as fair,

And having perhaps the better claim,

Because it was grassy and wanted wear;

Though as for that the passing there

Had worn them really about the same,

And both that morning equally lay

In leaves no step had trodden black.

Oh, I kept the first for another day!

Yet knowing how way leads on to way,

I doubted if I should ever come back.

I shall be telling this with a sigh

Somewhere ages and ages hence:

Two roads diverged in a wood, and I —

I took the one less traveled by,

And that has made all the difference.

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