Essay Coaching

Essay Coaching

Students who have worked with me have been admitted to a wide variety of colleges and universities.

See a complete list of acceptances here.

For more than a decade, I have specialized in essay coaching for students applying to college, transferring between colleges, and applying to graduate school. I have also coached younger students applying to independent middle schools and high schools.

I can provide the full range of help, from the start of a student’s search, or jump in at any point along the way.

  • Evaluate and discuss prospective college list
  • Strategize main essay and supplemental essay responses
  • Brainstorm outlines
  • Organize drafts
  • Revise drafts
  • Refine and line edit final essays
  • Build, write, edit, and redesign student resumes
  • Prepare for interviews
  • Oversee email correspondence
  • Assist with Common Application activity form

“We give Caroline our highest recommendation for interview coaching and essay preparation after having two children work with her on college applications. Her connection with students is positive and genuine – my sons truly enjoyed working with her. ”

— Westchester, New York parent

Reviews from parents and students

My son came home in such a good mood and said, ‘Thanks, Mom!  She is the best!  She rejuvenated my writing and reinvigorated my spirits!’  I am so happy and relieved!

–Mother of a Scarsdale High School senior

“My daughter had been through several revisions of her college application essay but was struggling with how it was turning out.  Her teachers tried to help but were either too busy or too disorganized themselves to offer good constructive help and actually rewrote parts of her essay.  This was not her voice and not the help she needed.  With Early Decision just around the corner, Caroline Gilpin came to help just in the nick of time.  She helped my daughter focus in on her unique story, removed the parts that were not about her, organized her ideas and asked her thought-provoking questions to accurately assess who she was and how to communicate it.  After just one meeting, my daughter was so relieved and confident that she would have the best essay that she could have written.  Caroline worked with my daughter diligently and efficiently spending only the necessary amount of time needed to get to an essay she would be proud to submit to college.”

Mother of a Scarsdale student.

“Caroline was the extra push I needed to complete my college applications. She gives constructive feedback without being discouraging. We were able to creatively brainstorm, and she kept me on task as well.”

—Bronxville student, grade 12

“When my mother first introduced the concept of meeting with a writing coach to get back in the groove, and finish my applications essays strongly, I was worried. Worried that even with help, I would not be able to complete the essays in time and, also, that by the time I was done, the writing would no longer be my own. Just thirty minutes into my first meeting with Ms. Gilpin, I felt my legs slowly stop shaking, as I began to subconsciously regain my confidence. To my surprise, she began not with any specific, detail-oriented work, but instead focused on what my goals were. She guided me through each decision I made, helping me to pivot towards a new approach, one that offered unparalleled flexibility while allowing me to stay true to myself. Once I was comfortable with the direction we had settled on, we got to work. I was amazed at the dedication that Ms. Gilpin displayed, even cross-referencing the style guides from each school, suggesting slight alterations to better suit the university in question. She modeled for me how to best shift focus from the macroscopic to the microscopic, all within the context of the situation, ensuring my success. In addition to the concrete lessons she taught me about effective writing, Ms Gilpin encouraged me to relax and focus on my strengths. Her easy-going nature and evident dedication to my success, facilitated a bond between the two of us during the short amount of time we worked together. I know, with the utmost certainty, that Ms. Gilpin will continue to aide those around her, revealing their strengths and fostering their confidence, allowing them to reach unprecedented levels of success.”   

— Scarsdale senior boy.

Caroline’s professional expertise is detailed and comprehensive, and her methods are successful.

–Father of a Rye Country Day School senior

“When I worked with Caroline at the beginning of my senior year, I was stuck on a VERY rough draft and no idea what to do to improve it. After a one hour and a half session, she helped me redirect my essay in very concrete ways, and helped me tighten the language and add new thoughts. She patiently helped me improve the essay in such a way that it was still my writing and my words, but we had moved it in a direction I felt good about. After another hour and a half session, I actually felt like I had a REAL college essay that I could continue to work on. It was comfortable working with her, and it much easier than dealing with either of my parents. Without her, I really have no idea what my essay would look like today, but I am 100% sure it would not be nearly as good.”   

— A Rye Country Day School senior.

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