5 Questions Every Counselor Must Be Able To Answer (With College Essay Guy)

How would you answer UChicago’s essay supplement: “How did you get caught? (Or not caught, as the case may be)”?

If anybody knows how to answer this question, it’s Ethan Sawyer, known (and loved) as the College Essay Guy. You might know him from his popular website where he gives out free essay resources, from his bestselling book College Essay Essentials, or from his workshops at NACAC, HECA, or IECA.  

But Ethan didn’t always plan on being known as the essay guy. After growing up as a missionary kid, he first studied to become a screenwriter (BS Speech, Northwestern), then an actor (MFA, UC Irvine), and then a counselor (UC Irvine). College essays only came after.

To paraphrase Joseph Campbell, I followed my bliss. I kept doing what I loved until I found myself in this place. To answer the question more specifically: it was probably after I noticed that teaching college essay writing is basically just teaching writing. Which was basically after working with my first few students over a decade ago.

So what would Ethan’s response to the UChicago prompt be?

My answer would begin, “I turned myself in.”

And it would have something to do with (my) Presbyterian guilt.

But first, what not to do

The worst essay Ethan’s seen? Former POTUS John F. Kennedy’s Harvard application essay.

The reasons that I have for wishing to go to Harvard are several. I feel that Harvard can give me a better background and a better liberal education than any other university. I have always wanted to go there, as I have felt that it is not just another college, but is a university with something definite to offer. Then too, I would like to go to the same college as my father. To be a “Harvard man” is an enviable distinction, and one that I sincerely hope I shall attain.

April 23, 1935

John F. Kennedy

Not only is JFK’s admissions essay wholly generic, it’s identical to his application for Princeton:

My desire to come to Princeton is prompted by a number of reasons. I feel that it can give me a better background and training than any other university, and can give me a true liberal education. Ever since I entered school, I have had the ambition to enter Princeton, and I sincerely hope I can reach my goal. I feel the environment of Princeton is second to none, and cannot but help having a good effect on me. To be a “Princeton Man” is indeed an enviable distinction.

The five questions all counselors should be able to answer

JFK was admitted to both Harvard and Princeton, but most of us aren’t JFK. For the rest of us, we need to go further.

In this video, Ethan describes the five questions counselors should be able to help their students with:

  1. How do I figure out what to write about?
  2. How do I structure my essay?
  3. How do I outline my essay?
  4. How do I revise my essay?
  5. How do I bring my essay to life?

These five questions are recognisable as questions most, if not all, students will ask at some point in their essay journey. Ethan then describes four types of student storytellers:

Type A: Student has faced significant challenges and knows what s/he wants to do in the future.
Type B: Student has not faced significant challenges and knows what s/he wants to do in the future.
Type C: Student has faced significant challenges and does not know what s/he wants to do in the future.
Type D: Student has not faced significant challenges and does not know what s/he wants to do in the future.

Each of these students needs to be treated differently and should write different type of essays. For the Type A and Type C (challenge) essays, Ethan recommends Narrative Structure, which connects story events in a causal way: I faced X challenge, so I did Y and the impact was Z.

Answering the Challenge Essay

The narrative structure is the foundation of most films. You might know it as the monomyth, or the Hero’s Journey popularised by American mythologist Joseph Campbell.

Ethan refers to this as the narrative structure, and its basic elements are:

  1. Status Quo
  2. The Inciting Incident
  3. Raise The Stakes
  4. Moment Of Truth
  5. New Status Quo

The narrative structure is so appealing because it appeals to our psyche. Human existence finds meaning in a hero’s journey and significance in his victory.

“The journey of the hero is about the courage to seek the depths; the image of creative rebirth; the eternal cycle of change within us; the uncanny discovery that the seeker is the mystery which the seeker seeks to know. The hero journey is a symbol that binds, in the original sense of the word, two distant ideas, the spiritual quest of the ancients with the modern search for identity, always the one, shape-shifting yet marvelously constant story that we find.” – Phil Cousineau

But what about the No Challenge essay?

For Type B and D (no challenge) essays, Ethan recommends Montage Structure, which connects story events thematically. The theme could be anything from “This essay represents the scrapbook of my life“ to “Endodontics.”

You’ve probably seen a montage before in a film. A montage is a collection of several very short scenes — sometimes only a single shot each — designed to show a series of action over time.


Montages are a part of a whole, condensing time and space for the sake of the abstract. They paint a picture to tell the whole story, and according to Ethan, this technique can be applied to essays as well.

Plus, montage essays need to revolve around a focusing lens. Just as Pixar focused on Carl and Ellie’s relationship, students writing montages (and their helpers) need to identify a focusing lens to connect the elements of their story.  

Teaching Counselors vs Teaching Students

When Ethan works with students, he provides tools to help write their essays. When he works with counselors, he helps them help their students.

“It’s a totally different experience and set of challenges guiding students through their own essay writing journeys vs. guiding counselors who are guiding students through essay writing. Though there is of course overlap, the challenges students face are different than those that counselors face.”

When Ethan works with counselors, he focuses on sessions that help answer counselor-specific questions.

  • How do I get my student to open up and be vulnerable in workshops and one-on-one sessions?
  • How can I manage essay guidance for 25-30 students x 15-20 essays each?
  • My students won’t write at all in between essay sessions — what do I do?

These are questions that don’t come up in student-focused sessions. Lesson learnt: what works for a single student cannot necessarily be applied to counselors who work with dozens of students at once.

How not to drown in essay management

The bright side of essays is that many topics overlap, from the “describe yourself” and “why us” to the “discuss an issue”.  While you should never repurpose an essay wholesale, you won’t get a strike for adapting an existing essay for a new application.

Ethan calls these the Super Essays. These are essays that can be reused for many essay topics, so that students can spend more time having a few well-written essays rather than 20 “just OK” essays. For students applying to highly selective schools where there are upwards of 20 essays to write, this is a godsend.

But that’s still a lot of essays for a single counselor to manage.

To ease your workload, organize. Through his online courses, Ethan teaches counselors how to help students map out an approach across the application and save time on the supplemental essays. “It takes about an hour to organize,” Ethan notes, “But it’s fun to do and actually produces better supplemental essays.”  

Cialfo’s automated task lists

And decide on an internal organizational system — whether that’s on a college guidance platform like Cialfo or Google Drive, knowing how you and your staff are going to name and structure student files and folders will save yourself a lot of confusion.

How to improve your essay counseling skills

The personal statement can make or break your students’ applications. College Essay Guy’s Personal Statement Boot Camp for counselors includes 7 video lessons and a 32 page workbook of exercises and instructions. Click here to sign up for the course.  

Struggling to manage all the essays you’re helping students with? Cialfo’s college guidance platform can help you. Sign up for a free trial here and learn why leading IECs use Cialfo for peace of mind.

Further Reading

Ethan’s Picks
Story by Robert McKee
Save the Cat! The Last Book on Screenwriting You’ll Ever Need by Blake Snyder
Art of Dramatic Writing by Lajos Egri

Cialfo’s Picks
The Hero with a Thousand Faces by Joseph Campbell
The Writer’s Journey: Mythic Structure for Writers by Christopher Vogler
On Writing: A Memoir of The Craft by Stephen King


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