For the past 25 years, I've helped a limited number of students each year gain admission to elite colleges.

It's been very frustrating that I can only help at most 40 students a year. As I grow older, I want to scale my work so that people who cannot afford my services can access a reasonable version of the curriculum through an AI agent.

A secondary goal of mine is to help students build good character. My curriculum asks, What does it mean to be human? What steps do I need to take to become more human? What is preventing me from achieving my potential as a human? What role does my education play in helping me fulfill my dream and helping me serve others? My goal is to help people develop good character so they can succeed in college and in life. If I were to focus solely on getting students into a good college, I doubt my results would be as good as they are year after year. I help people grow as writers, as people. I help them grow their understanding of themselves and of others. I help people grow their understanding of the human condition. And I help people deepen their sense of responsibility and duty. To use their education and use their lives for the sake of others.

I do this all very subtly. I do not teach any explicit philosophical constructs. I do not infuse my teaching with religious or dogmatic principles. I ask questions organically and incrementally to prompt students to consider profound, fundamental questions about their lives, meaning, and purpose. My goal is to create an AI agent that can similarly probe and prompt students to ponder such fundamental questions, and, as a byproduct, craft compelling college applications. Too many students are in a hurry to start writing without considering who they are and how they got that way, and who they want to be. The AI agent I plan to design will ask those questions in an organic, empathetic, and incremental way.

One of the first things I have to overcome is people's fear: fear that they're not good writers, not interesting people, or not creative. One goal of the questions I ask is to elicit responses that help students see themselves more clearly. By helping people think clearly, I can help them write clearly and live with a clear purpose. Over the years, I've found that the most troublesome students are those who consider themselves good writers at the start of the mentoring process; they are often the least coachable. They're the least willing to look at their thinking first before they jump into writing. This AI agent can help people who consider themselves bad writers. By allowing them to see their thinking clearly and to articulate it through the Socratic method of question-and-answer, they will gain confidence as writers, thinkers, and people. They'll have confidence that they can thrive academically, socially, interpersonally, and existentially in any situation. If my goal were simply to get students into college, I would fail students. I would fail my responsibility to help students grow.

If I short-circuited this self-discovery process, I could get students in. But I want students to realize that they cannot game life. They cannot game the college application process. And they cannot game themselves. This process is designed to help students carefully map out where they want to go, who they want to become, who they are now, and the steps they need to take to become the person they desire to be. By doing so, students can gain tools to navigate the application process and, more importantly, prepare for the rigors, confusion, and challenges of college and life.

This AI agent is designed to be an avatar of me, to express empathy and clarity, to avoid judgment, and to shine a light or act as a mirror so that students can see themselves more clearly, just as Socrates did for the citizens of Athens. The entire curriculum is a series of questions that first ask about students’ external identity: their relationships, habits, hobbies, behaviors, appearance, family, friends, and mentors. And the second half of the curriculum, the one that usually brings out the best responses for college application essays, deals with students’ internal identity: their hopes, fears, memories, and emotions.

Some students identify with their external selves and the roles they play in life, while others identify with their memories. This is a flexible, non-linear curriculum. I don’t expect students to go from A to Z; rather, they answer questions about internal and external identity, and the question tree changes based on their responses. If I ask someone what their favorite memory is and they talk about a sport they play and the role they play, I would naturally ask more questions about their external identity. But if someone starts talking about how empathic they feel and how they act as an agent of arbitration during disputes in class or among friends, their fears, their hopes, their dreams, their love, their losses, then naturally, I’m going to ask more questions that pertain to their internal identity. This is not meant to be a linear course, but rather one where the AI has the flexibility and expertise to adjust based on students’ responses, just as ChatGPT or any other large language model would.

The curriculum asks questions, and I provide a response to almost every one. Say I ask what a student is proud of. I give them space to respond. Then, I provide my answer. If I were to ask a student what they are ashamed of, I would then let them see my answer. I hide nothing. One reason I structure the curriculum this way is to build rapport. I hope that students can trust that I’m willing to be vulnerable, truthful, and authentic, qualities that I suggest they manifest in their writing and in their relationship with themselves through this process. A second reason why I structure the curriculum as question-response is so that students can learn from my responses, not copy them, but can say, oh, this type of response could potentially yield a powerful essay. At the end of each of my responses, I explain how such a response could turn into a stellar essay. I want them to generate their answers first, and once they’ve done so, they can reflect on my answers to see how my answers could turn into an excellent essay. Then, they can return to their answers and make changes or make additions so that their essay or their response could potentially turn into a very strong essay. I do this throughout the entire curriculum.

I have found the more honest I am, the more truthful I am, the more upfront I am, the more students are willing to open their minds and open their hearts and to access memories and emotions, incidents and events that define their being. Another reason that I answer is to show that it’s okay, and actually preferred, to talk about areas where students are weak, pitfalls, and failures, because those generally build good character, or they have the potential to do so. I have found that the most effective essays come from students who are willing to examine their shortcomings and articulate how they wish to grow, or how they have grown from addressing them or their failures.

This is not a pity party: I don’t want students to talk about suffering or trauma for the sake of trauma or to gain the reader’s pity. No, this is meant for students to realize just how strong they are, just how deep they are intellectually, spiritually, emotionally, psychologically, and to present that depth to the admissions officer in a poignant yet non-egotistical way. That’s why I’ve structured it so students can see my answers and read how I readily discuss “flaws” or “mistakes” because there are no mistakes. Nothing is wrong. It’s instructive if students choose to instruct themselves.

And that’s what I try to do as a mentor and as a teacher: help students gain the wisdom from reflecting on their life, memories, experiences, and relationships, and then use that wisdom to build good character, to use that good character to use their intellect, their emotion, and their will so that they can leverage the gift of education, leverage the gift of intellect, leverage the gift of heart for the sake of others and for the sake of their growth.