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COLLEGE ESSAY COACHING FOR HIGH SCHOOL STUDENTS

Transform College Essays from Burden to Breakthrough

The college essay doesn't have to be another source of family stress or student paralysis. What if this pivotal piece of writing could become something more meaningful—a kaleidoscopic moment where your experiences interlock to create new insights about who you are and where you're headed?

I believe the college essay is far more than an admissions hurdle. It's a profound opportunity for reflection at one of life's major turning points, a chance to define your values and articulate how you've lived up to them—or what you've learned from falling short.

Working together, we'll transform what feels overwhelming into something clarifying. You'll discover your authentic voice rather than producing something that sounds mass-produced. By the end of our collaboration, you'll possess not only stronger writing skills but a clearer sense of your own identity and values—tools that will serve you well beyond college applications, in job interviews and every other moment when defining yourself becomes essential.

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My Background

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I’ve always possessed a talent for writing and a joy in teaching, going back to the days when, as an eleven-year-old, I would gather all my younger cousins and instruct them from Grandma’s 1958 encyclopedia set (don’t worry, my pedagogy is more progressive now). However, I struggled mightily with procrastination as a student. I felt I couldn’t write without the pressure of a looming deadline and spent many sleepless nights typing out assignments that were due the next morning. It wasn’t until my time as an English major at Yale and a graduate student in Medieval Studies at Notre Dame that I fully grasped the value - and necessity - of breaking down the task into smaller steps. I find my students often have similar difficulties. Conventional wisdom around college essays is filled with vague maxims like “find your voice,” but with little advice on how to achieve that goal, which leaves young writers discouraged and overwhelmed.

I have worked for over two decades in the high school setting as a college counselor and an English teacher. I have counseled applicants through every step of the application process, with many students accepted to highly selective private institutions across the country, every University of California campus, out-of-state public flagships, universities in Canada and the UK, and more. I was also responsible for revamping our college essay workshops for hundreds of students at a time, which taught me to work efficiently. As an English teacher working with juniors, I’ve helped students distill their life experiences into clear, concise, and enjoyable non-fiction pieces using core principles of storytelling. I love working with young people, and I’m proud of the energy, enthusiasm, and encouragement I bring to the process. 

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My Approach

The college application process creates stress for students and parents alike. Not only can it feel incredibly high-stakes, but because colleges ask for such personal stories through the essay, acceptances and rejections can also feel like moral judgments rather than dispassionate evaluations. Even deciding what to share with a school can feel paralyzing, and students can find themselves obsessing over every detail or else avoiding it entirely. Working with me through the essay process creates a sense of direction and momentum, while also making it one less task for parents to nag about. 

My belief is that the essay is not a mere hurdle to cross during the college application process, but also allows a tremendous opportunity for reflection at a major turning point. It’s a chance to look back at everything they’ve accomplished while also looking to future goals. It lets the writer define what’s important to them and assert how they have lived up to those standards, or what they’ve learned from falling short of them. At its best,  it is a kaleidoscopic moment in which seemingly disparate experiences interlock to create new meaning and insights.

My goal for the students I work with is that, by the end of our work together, they will have a stronger sense of their own values and identity, as well as the ability to articulate those clearly. They will be more confident in their writing skills, and their writing will reflect their personality rather than feeling mass-produced. These skills will serve them in good stead not only in the application process, but in many other circumstances in which defining oneself is essential, including job interviews down the road.

My work as an English teacher has taught me the importance of giving students models to be inspired by and strive for. Therefore, part of my approach involves sharing and discussing excellent pieces of contemporary creative non-fiction with my students so they can learn by example how successful authors achieve a unique voice, create meaningful structure, and convey their purpose successfully.

The Right Story, The Right Way

(Including a story about being a two-time “Jeopardy!” champion.)

Students often think they must tell the story of the most important or unusual thing that’s ever happened to them. Extremely common topics I have encountered include practicing hard and winning a sports championship, rehabbing a serious injury, participating in a service trip abroad, and grieving the death of a relative. This isn’t to say these stories can’t be told well, but it’s easy to tell them in a cliched way that will glaze an overworked reader’s eyes over and miss the opportunity to shine.

For example, one of the most interesting and important accomplishments of my own life is becoming a champion on “Jeopardy!” It’s the high point of a career in trivia competitions going back to my middle school days. One way of recounting that story would be to go through each stage in that journey - competing at national tournaments in high school, becoming a coach and leading a team to nationals, placing above Ken Jennings in a trivia contest, and so forth - but, honestly, this would turn out fairly tedious and not a little braggadocious. 

Another way of telling the story, which a high-level soccer coach friend and hardcore J! fans have found interesting, details exactly how I spent four months training and studying to be on the show by identifying my knowledge gaps and mastering wagering strategy. To a more general audience, though, that too would quickly grow dull. 

My favorite version of the story focuses on the fact that I was terribly anxious about embarrassing myself on television by not knowing something. And, in fact, I totally biffed a Daily Double on the beloved children’s book Bambi. Couldn’t even come up with a guess. Made a silly flummoxed face and everything. As excited as I was to have won, I was sure that when the episodes aired, my students would tease me relentlessly. Lo and behold, it turned out they were far more excited for me than interested in hassling me (except for one, and he only cared that I didn’t know a Led Zeppelin song)! That Christmas, when my mom gifted me old battered copy of Bambi, I was able to laugh about it. It still has a place of pride on my shelf reminding me not to take myself quite so seriously. 

Depending on the context, any of these could be the right approach. But personally, I think the third is the best at capturing my personality and what I want others to understand about me and the value of that experience.

MY SERVICES

Tailored Coaching to Your Child.

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Full Essay Coaching

(My Full Process: The Six- Hourlong Sessions)

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Essay Feedback Only

(A Smaller Service: The Written Feedback)

Kind Words

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    "Chris Fleitas’ approach to working with students on college application essays is transformative. His support allows students to think more deeply about themselves and to more accurately share their perspectives. Chris encourages students to explore their different writing styles and opinions allowing the finished product to be an authentic glimpse into the life of the writer."

    Joseph, college counselor and long-time colleague

  • Working with Chris transformed my overwhelming college essay process into an empowering experience. He has a remarkable gift for asking exactly the right questions that helped me turn scattered thoughts into a compelling, authentic essay. Chris introduced structured writing methods that enhanced rather than limited my creativity, and encouraged me to draw thoughtful inspiration from other sources. Throughout the process, I felt both supported and challenged in the best way. I ended with a result I was genuinely proud of—an essay that felt authentically mine while standing out among thousands of applications.

    —Annika H.