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  • Writer's pictureSawyer Earwood, CEP

The Crossroads Exercise: A College Essay Exercise

"The Road Not Taken" by Robert Frost 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.

Perhaps one of the most widely recognized poems in recent history, Robert Frost’s "The Road Not Taken" has seared itself into our collective culture. The poem itself has reached such a level of popularity that one could argue it has formed its own subculture around decoding, explaining, and correcting frequent misinterpretations of the poem. While I am many things, I am not an English major and I’ll leave those debates to the academics. My purpose in broaching the subject of this poem is to point out how this poem and all of its interpretations (correct or not) can be a valuable asset to high school students when brainstorming college essay ideas.

Table of Contents:


Before we dive into the exercises, I think it’s important to look at the three frameworks we’ll be using to analyze Frost’s poem:

Framework #1: The Road Less Traveled

When I think about this poem, the first thing that comes to mind is the colloquial use of “the road less traveled.” On its surface, the phrase is simply referring to an artificial descriptor Frost uses to differentiate the two roads. However, in American culture “the road less traveled” carries significantly more baggage.

Maybe it’s America’s history of aggressive expansionism through the idea of manifest destiny, or perhaps the iconic image of a strapping, hunky archaeologist cutting his way through the jungle thicket to claim a gold idol. Regardless, I think American culture has placed an ideal upon “the road less traveled”. To “take the road less traveled” is to venture where few others have before, to carve one's own path, to discover, and ultimately to own the dual-belief of having agency over your choices and that exploring the unexplored is inherently beneficial.

It doesn’t take much effort to find some glaring flaws in this misinterpretation that has overshadowed the original interpretation of the poem:

  • Is there an inherent benefit to exploring the unexplored?

  • Is the unexplored truly unknown, or only unknown to the traveler?

  • Is discovery enough, or will there always be a push to claim, own, and conquer?

For our first framework, I want students to walk away thinking about choosing the road less traveled as an important turning point for their personal growth (academically, professionally, or personally).

Framework #2: The Road Not Taken

If you’ve ever studied Frost’s poem in an academic setting, one of the first lessons was likely about the difference between the popular misinterpretation of the poem and Frost’s original intent. Once again, I am not an expert on Frost or poetry, but here’s a quick amateur summary:

The intended interpretation has Frost reflecting back on his choice between taking two roads. Frost knows that he can only choose one road, and even acknowledges that his musings of returning to the alternate choice are not realistic. During the decision-making process, Frost makes it clear that he has no real reason for choosing one road over the other. After making the decision to choose the second road, Frost retroactively justifies his choice with surface-level details. As the poem reaches its conclusion, the audience is told that choosing the road “less traveled by…made all the difference.”

If the first framework of analyzing this poem emphasizes the importance or value of taking a less traveled path, then this second framework reveals that both roads are, for all intents and purposes, exactly the same. We cannot see the future and we can’t change the choices made in the past. Regardless of which road was chosen by Frost, his conclusion would be the same: he made a choice and it was part of a chain of decisions that led him to his current place in life. Therefore, the emphasis here is not on the road but rather on the ability to accept that a choice must be made and that choice must be lived with, regardless of the outcome. In this sense, Frost is reflecting back on an arbitrary choice and assigning meaning to it from a future perspective.

I reference this idea frequently when working with students during the college search. At the end of the day, most colleges in this country will provide an excellent education, but a college’s reputation or prestige does not guarantee success. An uninvolved C-student at Harvard is going to experience significantly lower return on investment than an involved A-student at Colorado State University who is building a strong support network, excelling in class, and connecting with mentors to find meaningful experiences. One of the best indicators of a student’s ability to succeed in college is being able to adopt a mindset of buying into an experience and making the most of it.

Framework #3: At a Crossroads

Lastly, I would argue there is a beneficial third framework that students can use to analyze this poem to help brainstorm college essay topics. Let’s take a step away from the intention of Frost’s poem and instead analyze the scenario in which he finds himself. Frost is at a crossroads, and with no ability to see the future, he has to make a decision. How would you make the same decision? Put aside the philosophical musings of reflecting on decisions made and instead reflect on a crossroads you might have encountered in your life. How do you analyze these choices? What weighs more heavily for you in your decision process, a logical approach or an emotional approach (or another approach)? Why might you ultimately choose one path over another? These are the questions that students can ask themselves to better understand how their values, personality, and characteristics interact with real crossroad scenarios they might encounter on life’s journey.


Now that we understand the three basic frameworks, let’s talk about how a student can use these ideas to help generate topics and insight to be used in their college essays:

  1. Framework #1: The Road Less Traveled

    1. Summary: With framework #1, I want you to embrace the common misinterpretation of Frost's poem. Create a list of times in the past when you had to make a decision and chose “the road less traveled”. In this context, your choice might have been to explore the unexplored, challenge yourself in a unique way, or diverge from a safe routine to try something new or ambitious.

    2. Prompt: Recall a time that you took "the road less traveled" and it resulted in a meaningful experience that contributed to your personal, academic, or professional growth.

    3. Examples:

      1. Personal: While visiting your favorite restaurant, you notice that they have added new items to the menu. You could order something familiar that you know you like, but instead you choose to order something new.

      2. Academic: You have always been on the standard math track at your high school, but you’ve recently been given the option to join the accelerated math track and you agree to do so.

      3. Professional: You have worked at the same part-time job every summer, but this summer you’ve decided to start your own business/side hustle.

    4. Questions:

      1. Why did you choose “the road less traveled”?

      2. Was forging your own path worth the extra effort?

      3. What did you discover about yourself by taking “the road less traveled”?

      4. Was your choice actually “the road less traveled,” or did you discover that you knew others who made a similar choice? If so, how did your experience change your perspective or connection with them?

  2. Framework #2: The Road Not Taken

    1. Summary: With framework #2, I want you to consider the original intent of Frost's poem. Create a list of times in the past when you had to make a decision and there was no “correct” choice. In this context, your choice might have little immediate impact, but upon revisiting your decision, you can assign value and worth to the choice.

    2. Prompt: Recall a time when you had to make a decision and, while there was no "correct" path, you had to choose nonetheless.

    3. Examples:

      1. Personal: You have a free Saturday with no responsibilities and you have to decide between two movies that you are equally excited to watch.

      2. Academic: When registering for your next year of high school classes, you are required to take an elective, but none of them interest you.

      3. Professional: While applying for part-time jobs, you receive two offers of employment from equally appealing employers.

    4. Questions:

      1. How has taking “the road less traveled” affected your long-term growth?

      2. Having made a decision, how do you cope with the lost opportunity of another potential path?

      3. After making a decision, how do you embrace your choice and buy into your new path?

      4. How do you frame decisions that resulted in difficult or challenging outcomes in a more positive light?

  3. Framework #3: At a Crossroads

    1. Summary: With framework #3, I want you to forget about the intent, misinterpreted or not, of Frost's poem. Create a list of decisions that you have made or still need to make. These decisions can be important or routine in nature, but in this context, your choice is not the main focus. Instead, I want you to think about how you make decisions and what that says about you as an academic, a professional, and a person.

    2. Prompt: Recall a time when you found yourself stuck at a crossroads and had to make a decision.

    3. Examples:

      1. Personal: Two of your closest friends have invited you to hang out at the same time, but both of them are currently fighting. How do you respond?

      2. Academic: Both of your most difficult classes have exams on the same day, but you only have time to effectively study for one. Which do you choose?

      3. Professional: You finish your shift at work, but your co-worker hasn’t arrived to replace you yet. With your manager gone today, how do you proceed?

    4. Questions:

      1. When faced with a decision, do you make the decision alone or seek counsel?

      2. Before making a decision, how do you work through the decision-making process?

      3. What weighs more heavily for you in your decision process, a logical approach or an emotional approach (or another approach)?

      4. Looking back at how you’ve made decisions throughout your life, how has your decision-making process changed over time as a result of what you’ve learned and your personal growth?

With all my support,

Sawyer Earwood

Independent College Counselor

Co-Founder of Virtual College Counselors

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