Supplemental Essays: A Matchmaking Process

Answer: Essays can be the tie-breaker in your favor at competitive colleges. The Personal Essay You will be competing against thousands of others with a great GPA, an excellent SAT score, and meaningful extra-curricular pursuits - research, community service, entrepreneurship. An engaging, insightful personal essay that demonstrates personal growth can be the deciding factor that leads to your acceptance. Admissions officers at selective colleges are increasingly looking beyond traditional metrics to evaluate if a student has the maturity to master the pressures of college life, make sound decisions, and contribute to a vibrant campus life . Mike Sexton, vice president for enrollment management at Santa Clara University, says that when admission officers read student essays, they ask themselves, "Would you like this person to be your roommate? Would you like to work on a group project with this person?" If you look on Harvard’s website, they seek students who are determined to make an impact on critical global issues. The essay can reveal, better than any test score, whether you meet the profile they are looking for. This can feel like a daunting task as it’s likely the first time you’ve had to identify the expectations of your audience and then write an essay that meets those expectations - especially when the essay has a very significant impact on your future. Most others parts of the application are meant to show academic and extracurricular achievements. The personal essay compels you to divulge who you are as a person, focusing on your inner strengths. This can be stressful. So first and foremost, it’s important to choose a life experience that demonstrates personal strength: initiative, willingness to take a risk, resilience, curiosity, concern for others, and self reflection. This may seem impossible at first. So that’s when I point out that the experience need not be dramatic. In fact, it’s not a good idea to write about an ongoing crisis that is unresolved. Focusing only on pain without showing growth might make a school feel worried about you and decide you’re not ready for the demands of college life. Colleges mainly want to know how you handle everyday obstacles. How do you face the disappointment when you don’t reach a goal you set for yourself? How do you deal with a person with whom you totally disagree? How do you overcome the fear of learning a new skill? How do you react in a room of strangers? Are you able to ask for help? These are the sorts of issues that are sure to arise in college and counselors want to see evidence of how you handle these challenges. They want to know if you reflect on difficult experiences and learn important insights about yourself. Finding the right experience is often the most challenging part of the essay process. Here’s great way way to get the ball rolling. Think about activities outside of class: jobs, internships, volunteer work, summer school, clubs, musical or theatrical performances, art or poetry exhibitions, research opportunities, entrepreneurial ventures. Activities like these show right away that you have initiative, and if you managed to stick with the activity, you likely have had to overcome challenges. I encourage students to summarize three meaningful events that happened in the past two or three years, even if they seem ordinary. Then they evaluate to see which one best meets their needs. For this type of essay, it’s more important to dig deep into one event rather than skim over several events. And, it’s important convey the information in a compelling narrative. We’ll go over a whole range of literary techniques that grab a reader’s attention: start in the middle of action, include dialogue, use vivid verbs and colorful descriptions, show don’t tell, introduce a conflict. As you write the narrative, your strengths will naturally emerge … and if you don’t see them, I will definitely point them out. By incorporating these insights into the story, you will show counselors a person ready to learn from others, contribute to campus life, and thrive in a college setting. Of course, you may need a few, or several, rewrites. But that’s a normal part of the process. As the essay unfolds, students are often surprised to realize how much they have grown and what they are capable of. Writing the personal essay can actually help you feel more confident as you take the enormous step away from home and into an exciting future.

For most students, the college application personal essay is a dreaded task. They struggle not only with what to say, but also with the pressure of competing against millions of other applicants. In 2023–24 alone, more than 9.4 million first-year college applications were submitted. It’s the perfect breeding ground for stress. Feeling overwhelmed, it’s understandable that students consider turning to artificial intelligence for help. Even colleges send mixed signals. Brown University states that AI use is “not permitted under any circumstances,” while the University of California allows limited use, emphasizing that “content and final written text must be their own.” Meanwhile, AI detection software continues to improve, and many schools warn that if an essay is flagged as AI-generated, the application may be rejected outright. The stakes are high. At Sage Hill, our goal is to provide the kind of thoughtful, personalized support that helps students feel confident in their own abilities—so they don’t feel drawn to rely on AI. Colleges encourage students to seek help with brainstorming and editing from parents, counselors, and tutors because these adults are invested in nurturing a student’s unique voice. Still, striking the right balance between supporting a student and taking over can be tricky—and it’s certainly not something to hand off to a machine. Under pressure and lacking confidence, students may begin to doubt their own ideas. This past year, several students confided in me that they allowed AI to expand on their thoughts because, as they put it, “AI can do it so much better than me.” These comments reveal a troubling sense of disempowerment. But the college application process should be an opportunity for students to recognize their strengths, develop their voice, and gain confidence. One student sat quietly after reading the essay prompts, eyes downcast. When I gently asked what was wrong, she said she felt that “nothing worthy of writing about” had happened in her life. This was the perfect moment to pause and look inward. I invited her to describe three recent experiences that felt meaningful—without judging their importance through a college admissions lens. As she spoke, her confidence began to grow. She realized she did, in fact, have meaningful stories to tell. One experience stood out, but soon her worried expression returned. When I encouraged her to explain, she admitted, “It might make me look weak. I was afraid to sign up for that summer program. I thought no one would like me, and I’d feel left out.” Another perfect teaching moment. I reminded her that colleges aren’t searching for superheroes. They want real students—students who face fear, take risks, and grow. “The important part of your story,” I told her, “is that you did sign up. You did participate. And you found your way to connect.” While AI can respond to words, it cannot perceive body language, tone, hesitation, or emotion—often the true language of teenagers. Those subtle cues guide us toward deeper insight, encouragement, and connection. At Sage Hill, we help students uncover their strengths rather than dwell on their fears. Many are surprised when they realize how much courage, resilience, empathy, and determination their experiences reveal—even in moments of challenge or failure. The right balance of guidance preserves each student’s authentic voice while bringing emerging abilities to light. And perhaps most importantly in this modern age, the process nurtures something AI never can: a genuine connection between two living, breathing people.

A reflection after the 2025 application season As the 2025 application season comes to a close, seeing learning across a wide age range makes one thing very clear. AI changes how students learn, but it does not change what students need to become. AI is a tool. Like any powerful tool, it amplifies what already exists. Used well, it accelerates growth. Used poorly, it weakens independence and creates quiet dependence. For younger children, especially in elementary school, AI has no role. Learning at this stage is physical and sensory. Cutting paper, drawing by hand, building with blocks, telling stories out loud. These are not simple activities. They are the foundation of thinking itself. Before children use tools made by others, they must first master the tools they were born with: hands, attention, and imagination. In middle school, structure begins to form. This is when students should learn logic, mathematics, and basic programming, not by relying on AI, but by struggling through problems on their own. Reading and writing should remain entirely human and handwritten. At this stage, both AI and smartphones are distractions from the deeper work of learning how to think. High school is where AI can begin to play a constructive role. Once students understand how to ask real questions, they can use AI to explore ideas, organize research, and test assumptions. But AI should never replace original thinking or core academic work. Colleges are not looking for polished outputs. They are looking for ownership, judgment, and intellectual honesty. By college and adulthood, AI can become a powerful partner in building larger systems: research projects, platforms, services, or ventures. Even then, AI should not be used to make life decisions or serve as emotional support. It is a technology, not a mentor. This is where a critical distinction must be made. AI can provide information, structure, and speed. What it cannot provide is discernment. It cannot understand a student’s values, fears, contradictions, or long-term potential. It cannot challenge a student when they are choosing the easy path over the meaningful one. A real counselor does exactly that. Good counselors see patterns across years, not prompts. They notice when a student’s interests are genuine versus performative. They help students connect learning to identity, effort to purpose, and ambition to responsibility. Most importantly, they hold students accountable in ways no algorithm ever will. In every strong application I saw this year, the same truth appeared. The student did the thinking. The student made the choices. AI may have helped along the way, but a human mentor helped them grow. The future belongs to students who know how to use powerful tools without surrendering their agency. AI will continue to evolve. Human judgment, character, and guidance will remain irreplaceable. If there is one lesson from this application season, it is this. Use AI to move faster, but rely on people to move wisely.

After the 2023 SCOTUS decision to ban race-conscious admission was released, I noticed a recurrent theme pop up in college application essay prompts: diversity. These prompts require students to reflect on ways in which they have experienced diversity be it about race, religion, ethnicity, income, ideology, or interests. The prompt also encourages students to explain how these experiences have impacted their beliefs and values. Many of my students are first or second generation immigrants, and this prompt has triggered heartfelt responses about how they deal with the blending of cultures. Some have felt torn between the values and expectations of their immigrant parents and those of their American born friends and teachers. I worked with one Chinese American student who struggled to find her authentic self among what she considered two strong yet conflicting ideologies. A media savvy friend, who knew of her struggles, invited her to participate in a blog he created that addressed issues raised by multiculturalism. By sharing her personal journey publicly, she was attempting to, as she put it, “help others in a similar circumstance feel less alone in their confusion.” Afterwards, the student felt empowered by how her story could lend support to a vulnerable and often invisible group. This process of finding her voice transformed into a compelling essay. Another student, a boy who grew up in a bi-racial household, found a unique way to act as a bridge between cultures. Although his parents were of European and Chinese ancestry, he confided that for a long time he had felt more in touch with the European side of his family. Then during the previous year, his school had offered a perfect opportunity for him to help those in need while exploring his Chinese identity. The teacher of his Chinese Language and Culture class worked out a plan with a local food pantry that needed help communicating with a group of Chinese elders. The whole class then volunteered their services, tasked with finding out how the pantry might better serve their needs. At first, the student was concerned about whether he could communicate effectively with seniors, especially as he had a limited Chinese vocabulary. But he took on the challenge, spending a week doing activities with them: visiting Chinatown, taking a museum tour, eating lunch, and riding public transportation. He also video-interviewed one of the women to understand what it was like for her to grow up in China. He included an especially touching moment in his essay. One morning a “Shen Nai Nai,” as he called her, walked in with a basket of oranges. She peeled each orange and passed them out to everyone. The teens insisted that she eat as well, but she refused until they all received an orange, saying “You must eat first.” The student wrote, “This small instance of kindness encapsulated how loving and compassionate all of the Asian elders were toward us. As my friend put it best, ‘I feel like we are their grandchildren.’” It’s been inspiring to see how both of these teenagers mastered the challenges that arise from living in a diverse society with compassion, understanding, and service for the larger community. College application prompts often ask students to reflect on complex issues, but with support, students describe life experiences that address the prompt and reveal incredible strengths in their personalities. 

Parents and students alike may wonder why it's so hard to sit down and write college application essays. After helping scores of students accomplish this task, I have gained some important insights into this matter. Typically, the first application essay that students write is the personal essay for the Common App. This is likely the first time students have written about personal issues for absolute strangers, and to make matters more stressful, these are not just any strangers: these are admission counselors who stand between each student and his or her dream college. Faced with a task that makes them feel vulnerable, many students freeze. Suddenly, they can't imagine anything has happened in their lives that would be important enough to send to a college. So first and foremost, I reassure students that everyday experiences are actually great material for this type of essay. Last year, I worked with a teenage boy who had dreams of becoming an engineer. He had interned the past summer at a medical design company, and when I asked him if anything had happened there that was worth writing about, he shrugged and told me “not much.” He added that he had worked on a design that the engineers had rejected as being impractical to build because of its expense. So I gently probed a bit more, reassuring him that it was an impressive feat for a high school student to actually create a design that worked. This positive feedback helped him reveal more details. It turned out that he had been promised the opportunity to work with a team of engineers and participate in designing a product. Upon his arrival, the boss wanted him to read articles about product design and do online market research about the medical industry, but didn’t set him up to participate in any real design work. After a week of sitting in a room by himself, the student had a feeling he’d been forgotten and might need to remind the boss of his existence! In telling me the story the first time, he remembered only his uncertainty and anxiety about how to handle the situation and felt embarrassed about it. But as we chatted, he realized that this situation had challenged him in a new and important way. This wasn’t like high school with teachers keeping an eye on you; this was a professional work situation and he needed to take initiative himself if he wanted change. Although it took a few days of working up his nerve, he approached his boss and asked if it might be time for him to join a design team. His boss immediately apologized and assigned him to a group of engineers. The student finally realized he had great material for a personal essay that highlighted his ability to problem solve, determination to succeed, and courage to take on a challenge - all qualities colleges want to see in their incoming students. This student ended up attending Cornell. Writing this personal essay often becomes a transformative experience. Students not only see that they have the inner power to write a compelling narrative, they also gain confidence as they discover hidden strengths they didn't even know they had!

The supplemental essay that students struggle with the most is, "Why do you want to attend our college?" Left to their own devices, students tend to offer reasons that could apply to any school, basically writing a generic form letter. I help them understand that colleges are seeking students that have done background research on their particular school and resonate with its unique attributes. I show students how to search the school website looking for courses, programs, professors, research and internship opportunities that capture their interest. This type of essay lets colleges know that the student is truly invested in attending. Supplemental essay prompts also elicit answers to why a student has chosen a particular major. Schools want to know what drives the student’s interests and what kind of success they’ve already had in those fields. A common question might look like this: “Why are you interested in the major you indicated as your first-choice major?” This type of question can be challenging if the student has only recently chosen this area of interest, but even those with a background in the field can fail to recognize the value of their actions. In one case, I worked with a student who felt ashamed of experiences that actually demonstrated her strengths! She wanted to major in business and was struggling to find a “good” topic when I learned that she was an international fashion model. Eventually, she confided her concern that colleges might adversely judge her for participating in a “superficial” endeavor. As I listened to her story, I helped her understand the treasure trove of topics embedded in her modeling career that would underscore her strengths. Because of her three years spent modeling, she had already successfully held down a job in a highly competitive adult world. She had acted in a highly responsible way, always being on time for job interviews and modeling shoots, and always acting in a professional manner. No one ever knew she was a teenager unless she told them. Considering she planned to pursue a business major, her ability to not only survive but thrive in this environment would likely work in her favor. Once she understood how her modeling career highlighted her communication skills and her maturity, she wrote an amazing essay. This student ended up attending NYU. Accurately understanding each supplemental essay prompt and addressing it with relevant information is probably the biggest hurdle for students to overcome. Then comes the next hurdle: putting it all into words. For this step, I offer tips for creating a narrative that is narrowly focused with no extraneous details. Then I explain how to insert insights that help admissions counselors gain a better understanding of why this individual would be a great addition to their particular university.

Since immigrating to the United States, our journey through the American education system has been unfamiliar and challenging. With limited knowledge of adolescent psychology and the intricacies of the education system, we sought a counselor who could bridge the cultural gap and provide comprehensive guidance for our children's higher education. It is with great appreciation and respect that we have entrusted this crucial role to the exceptional and proficient Mrs. Jenny Wan. Under Jenny's professional guidance, our youngest son successfully gained admission to a prestigious private middle school in Boston in 2022. More recently, our eldest daughter received an acceptance letter from her top-choice university through Early Decision. The impact of Jenny's dedication and support has been transformative. Jenny has been tutoring our eldest daughter since the tenth grade, especially during the challenging period of online learning due to the pandemic. With regular communication, she supervised our daughter's daily studies, assisted in planning extracurricular activities, and provided gradual guidance for university applications. Throughout this process, we observed a remarkable transformation in our daughter. She developed a deeper appreciation for learning and further education, cultivating a strong sense of self-motivation and determination. Overcoming challenges became second nature to her, resulting in increased confidence and resilience. Jenny's positive energy, compassionate listening, and persuasive guidance contributed to our daughter's growing sense of optimism, fostering open and peaceful discussions between our family members about planning and college selection. In the tenth grade, as our eldest daughter began planning her college applications, Jenny identified her interests in education and economics. Jenny meticulously crafted a two-year plan, outlining course selection, extracurricular activities, and summer engagements. Under Jenny's guidance, our daughter participated in educational psychology courses offered by Brown University, completed online microeconomics AP courses, organized a children's summer camp, engaged in chess training, volunteered with the Best Buddy organization, completed early education and practical courses with assistant teacher certification, and participated in Cornell University's economics summer program. Through Jenny's systematic and targeted planning, our daughter not only acquired knowledge and practical experience in education and economics but also developed unique personal qualities and life experiences that enriched her university application. For our youngest son, who was applying to private middle school upon completion of the sixth grade, Jenny's guidance began early in his academic journey. The application process, including paperwork and interviews, was entirely new territory for our 12-year-old son and us as parents. However, Jenny provided unwavering support, coaching us step-by-step, word by word, throughout the entire process. She helped our son recognize his strengths and directed his efforts toward effective interview preparation. Thanks to Jenny's guidance, our son's self-confidence and interview skills have flourished. A crucial aspect of our youngest son's application process has been the interviews with school admissions officers. For a 12-year-old, this presented a significant challenge. To alleviate tension and ensure preparedness, Jenny conducted rehearsals with our son, emulating the characteristics of each school he would interview with. These sessions improved his familiarity with the schools and his interview experience. As a result of Jenny's effective guidance, our son successfully completed interviews with seven schools, receiving positive feedback and high praise for his performance. Jenny's deep understanding of both Chinese and American cultures, coupled with her insight into the psychological development and value systems of American students, has proven invaluable. Throughout our three-year relationship, we as parents have gained a new perspective on our children's development, relinquishing unrealistic expectations and gaining a better understanding of their growth needs. With Jenny's guidance, constructive exchanges, and mutual respect, we have achieved smooth consensuses on significant issues. In addition to her vast knowledge, information, and impartial decision-making abilities, Jenny possesses exceptional communication skills. She adeptly analyzes problems and provides guidance and solutions while considering the perspectives and opinions of others. When diverging views arise, Jenny demonstrates remarkable wisdom and emotional intelligence by proposing alternative approaches that honor the principles involved. As a result, decisions made collectively by students, parents, and Jenny resonate and are seamlessly implemented, yielding highly satisfactory outcomes. With sincere gratitude, we acknowledge Jenny's instrumental role in our children's success. The profound impact of her expertise, meticulous guidance, and compassionate support has empowered our children to reach new heights. We are forever grateful for her unwavering commitment to their long-term happiness and development. With warm regards, Wang Family, Massachusetts

Dear Jenny, Today marks an important milestone as Ravenna reveals that most schools have received all the application materials. With great joy, we can say that our son's high school application journey has come to a successful close. We extend our heartfelt gratitude for your unwavering support, step-by-step guidance, and meticulous editorial assistance over the past three months. Without your expertise and patient cooperation, this achievement would not have been possible. We would like to express our sincerest thanks and utmost respect for your professional guidance throughout this process. Your dedication and commitment to our son's success have been truly remarkable. The countless hours you devoted to providing individualized guidance and ensuring the quality of each application document have made a significant impact. The entire school application journey has profoundly enlightened Evan about the path he wishes to pursue in the future. Your guidance has instilled in him the importance of perseverance and the value of taking steady steps towards his goals. As we move forward, we anticipate the need for your continued support and guidance to help Evan further excel and grow. With heartfelt appreciation and warm regards, Evan's parents, Massachusetts