Robert Frost’s “The Road Not Taken” Applied to Leadership

The American poet Robert Frost is lauded as one of America’s greatest modern poetic talents. During his life, he won the Pulitzer Prize for Poetry not only one, but four times (1924, 1931, 1937, and 1943).[1] Regarding Robert Frost, Blog - Robert Frost - Road Not Taken President John F. Kennedy said, “He has bequeathed his nation a body of imperishable verse from which Americans will forever gain joy and understanding.”[2]

In order for a poem to be considered literary, it must teach and have broad application across numerous professions, disciplines, life styles, and living situations. Numerous people from various backgrounds should be able to learn something from the poem about themselves and the lives they lead.

Frost’s poem titled “The Road Not Taken” has been used to help teach spiritual, ethical, and social principles. I would like to apply it to the subject of leadership. If you have never had the opportunity to read the poem in its entirety, I have included it at the end of this article in order for you to appreciate it as a whole. In order to help you see this poem through the lens of leadership, I will take the poem one stanza (paragraph) at a time and apply the topic of leadership to Frost’s writing. Following is the first stanza:

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;

Numerous organizations task only executive-level leaders with developing the long-term strategic direction and strategic vision of their division or department. As leaders develop and revise a strategic direction for their areas of responsibility, their research will likely leave them to decide between at least two different directions, or foci. Some leaders will have to decide between three or more strategic directions. Such decisions can be extremely difficult, even when their research uncovered really good, accurate, and timely information and data. Multiple paths may look promising; however, those leaders that are armed with the best, most up-to-date information available to them can see only so far down each path before it either bends or is covered by undergrowth and becomes invisible.

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,

Time and again, leaders will discover that their research will point them down a path that has been taken before, either by another department in their organization, or by a competing organization in their industry. Why does this happen? Because one particular strategy is applicable in multiple settings and situations. The cliché, “if it ain’t broke, don’t fix it,” applies to strategies like this.

Research may uncover another way to accomplish a strategy—a path that is “grassy and want[s] wear.” Paths like these don’t experience much travel. The reasons are many and varied, but may include simple facts, like:

The ROI has never been determined
Few organizations that walk the path experience success
Many organizations that walked the path were able to work within the parameters of success and growth dictated by the path

Any one of these points may tempt a leader to walk his or her department down a well-worn path. But the strategic leader will ask one simple question of each one of these points: Why? Why has the ROI never been determined? Why do few organizations experience success when they walk that particular path? Why do many organizations fail to work within the parameters of success and growth determined by that path? If you as the leader cannot find the answers to these questions, branch out and have your people help you find the answers. The answers are out there somewhere. They will likely jump at the opportunity to help their you, their leader, make a strategic decision that will benefit the department or organization as a whole.

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.

After finding the answers to the above questions, and probably more, the leader, with the help of others, can determine that a not-often-trod path is the most appropriate strategic route to take. In the beginning, you may look down one path or another as far as you can and see that there are even more signs of disuse, more “leaves no step has trodden black.” Before walking new paths, many leaders have a feeling that if it doesn’t work, they can come back and go down the well-worn path they have always walked. But because they sense the potential hidden along the new path, they have a feeling that, “knowing how way leads on to way, / doubt . . . [they will] ever come back” to the old path. And that is okay. Given this, new paths will likely yield opportunities for innovation and change that will not allow departments and organizations to go back to how they were before. Look at what Steve Jobs did for Apple after developing and introducing the iPod, iPhone, and iPad to the world. There is no way Apple could ever, or would ever want, to go back to their old way of doing things.

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.

Only after the passage of time will a leader know if the path they chose was the correct one or not. Apple released the first generation iPod on October 23, 2001. Now, over ten years, and many iPod generations and several i-products later, Steve Jobs could, if he were still alive, sit back and say, “I made the right strategic decision.”

What about you and your department or organization? Even if you aren’t a department or organization leader, what can you do to apply “The Road Not Taken” to your areas of responsibility?

Taking a new strategic direction on can be scary and nerve racking. But “Somewhere ages and ages hence,” you may be able to look back on that ultimate decision and say, “that has made all the difference.”

The Road Not Taken[3]


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;	5

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,	10

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.	15

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.	20