Lessons in Tutoring by Caitlin

Lessons in Tutoring by Caitlin - June 2025 Scholarship Essay

Each Tuesday, as I trekked to tutor at my local middle school’s test-prep program, I dreaded hearing my students state three familiar words: “I don’t know.”
“Well, what don’t you know?”
“Umm… I just– I don’t know.”
On and on, we would circle, until I was finally able to pick up on a specific aspect of a math problem or a tricky vocab word that had stumped my student. As I kept coming back to tutor, week after week, I began to notice that not only was I able to more quickly identify what students did not understand, but also that the sometimes confusing dynamic I had with my students was one that I mirrored in my own relationships with my teachers.
“I don’t know,” and “Can you just re-teach this whole part?” were often questions I said to my teachers, not realizing that their vagueness would impede me from zeroing in on the key elements of whatever it is that I did not understand. Tutoring taught me that I needed to reflect on my confusion before expressing it, as simply saying that I was “confused” by Plato’s Allegory of the Cave or “didn’t get” derivatives only stood to waste a few minutes of my teacher’s time and energy that they would need to spend prodding me for specifics. Quite simply, I learned the importance of asking quality questions.
Additionally, the ability to teach someone a complicated topic is a skill that tutoring breeds, and one that everyone should learn. Turning a complicated subject into a fun analogy, or distilling a sprawling concept into a few words demonstrates a quick-thinking mastery of a subject, and allows people to forge bonds with those in their broader community. Tutoring allowed me to meet with so many younger kids, kids who I was able to give advice on topics ranging from the Pythagorean Theorem, to how to make friends your freshman year of high school. Not only does tutoring improve interpersonal skills and encourage you to approach topics from new angles, but it provides you with a key experience, one that allows you to bloom into a better learner: you learn what it means to struggle both as a teacher, and a learner. Occupying both roles in your daily life causes you to approach education in a different way.
Every student would benefit from being a tutor, as they will not only learn a wide variety of hard skills but will also be able to dissect how their own student-teacher dynamics may be hindering their own performance in the classroom. Tutoring taught me new ways to learn and connect with others, and I believe each and every young person would benefit from having an experience similar to mine.