I met Jason at the same time I met his siblings, Sam and Dylan. Yes, this was my chance to work with triplets and I was all in. But not before I met Bailey, the prettiest girl with a boopable snoot, floofy ears, and curly pantaloons. Despite her legs, measuring no more than 8″ in length, she successfully made it atop the dining room table as I made my way into the family area. She serves as the official greeter and I was a new human that needed sniffing. Plus, she had pink bows perfectly affixed to her ears from a recent trip to the groomer. The fact that her humans didn’t want her on the table mattered not; she also smelled like Lillian Ruff blueberry puppy shampoo. Bailey was getting on that table if it was the last thing she did.
I fell for my new client family at that precise moment and I’d not met one college-bound student. I felt, in a word, like I had arrived home. There were animals, mail to be opened on the table, shoes at the door, sibling bickering, and the smell of something wafting from the kitchen. Well, and the family matriarch is a badass. This family was never getting rid of me.
Jason sauntered in, and to say he made an immediate impact would be an understatement. His sense of urgency could best be described as liquid cat. He was going nowhere fast and when he did go, it would be entirely under his own volition. I’ve been working with students like Jason for decades and I have come to see their peculiarities as age and developmentally appropriate. If you find a group of motivated, timely, and self-aware teens, call the CDC or something because they are rare and deserve to be studied.
Jason wore the typical teen boy uniform, which is to say athletic shorts, a tee shirt bearing a respectable percentage of wrinkles, socks, and sneakers. His thick, dark mane of hair was perfectly tousled and effortlessly cool. Messy but not too messy, in a fabulous and head-turning sorta way. As a mom of a 17-YO teenage boy myself, I know that Jason’s locks took time, but nobody else could know that. His mahogany curls met his eyebrows with precision and drew my attention to his single most important asset: his smile. Pearly whites no doubt obtained by several thousand dollars and hours in an orthodontist chair. His big toothy grin was only partially obstructed by the mouthful of Buc-ee’s sours he had shoveled in moments earlier. Jason carried the opened bag in one hand and his cell phone in the other. I suppose, in my GenX nomenclature, he would be considered, “cool.”
We sat at the table: all three siblings, two parents, the dog, and the bag of sour candies. As the triplets looked at me with skepticism, their mom asked, “who’s going first?” To my surprise, Jason chimed in, “I will.” His sister booked it out of the room as if running a marathon and announced from the next zip code over that she’d go last. So my meetings were set for the day: boy, boy, girl. I had no idea what I was in for. Triplets. How different can they be from one another?
My job largely consists of helping students navigate the ever-changing landscape of the admissions process and avoid pitfalls so they shine as individual candidates.
I answer questions at any hour, call them out on their crap, keep them on task, serve as a huge cheerleader, spend weeks proofreading PiQs, am their behind-the-scenes worrier, debater of topics and whether or not a LoR is worthy, a confidante listening to their tears and fears, sit by them during denials, a makeshift editor from my car, pseudo teacher, and mentor. I am an entirely different secret keeper for their parents, support mechanism, and source of sanity, I hope. Incidentally, I’m tasked with telling students that, while renting jet skis in Malibu might sound like a fun job, their parents likely wouldn’t approve of the career path, especially after they paid for my services.
Jason sits down, jams more candy in his mouth, and says, “hey.” And with that one word, I’d like to introduce you to the teenager that changed my perspective on the graduating class of 2026 and fixed my years-long existential crisis in 3 minutes.
My first meeting with every client is never the same, but they share one goal: get inside a student’s head and find out what makes them tick. Why? Because I have to help them arrive at a writable topic that will differentiate them from thousands of other applicants. In a short 90 minutes, I have to disambiguate the nascent brain sitting opposite me and get them to grasp the concept of a hook for the Common App essay and apply it to some real-world situation in their lives. Given the state of high-school English and literature education from the east to west coast, this is no easy undertaking. I do not care the ranking or cost of your private school, writing for the college essay is not taught anywhere.
I usually begin with some disarming question, like “why are you wearing purple socks with sandals?” There are myriad tactics to get new writing students to open up. My challenges became vapor with Jason. He not only wanted to write about something unique – and he was quite realistic about what constitutes a distinct topic – he was predisposed to thinking this way. He led me down the path less taken. Suddenly, my next 90 minutes went from a teeth-pulling task to lobbing Socratic jabs at each other. It was fantastic. And we shared sour candy. His favorite flavors are wrong and gross, but I’ll give him a pass for that.
With every question I had for Jason, he returned a more turgid one back at me, with a boyish grin, messy hair, while tapping his fingers on the table. And while I spent 12 years in graduate school learning how to construct airtight methods and formulate sound arguments, he was the best I’d ever seen from someone his age. I found myself backed in a theoretical corner by Jason on more than a handful of occasions. This was fun. Game on, buddy.
The topic we ended up with was sticky and had a sharp hook. Jason penned a catchy story of the delectable, ubiquitous, and perfectly crumbly black and white cookie and how it’s illegal to throw bricks from highway overpasses in Iowa. I kid you not. It was about as far-fetched as I’d ever gone with a student before. Risky. Slippery. Hard to articulate. The end result? A perfect metaphor for Jason’s views on how Jewish life in society has become a task of minimizing exposure to the lowest common human denominator. We had lost the self-determinism that are hallmarks of American culture. His prose was fluid and on point and it reflected his particularities and peculiarities. They came to life, his words, dancing on paper. It was the single hardest essay I have ever mentored anyone through and he probably wanted to hate me at revision 15,001.
In our time together, Jason proved that he will be a kick ass lawyer one day, and he will be on the right side of history. Fighting for the underdog, whomever that may be. Or he will be a scathing food critic, and a damn good one. For every question I had, he returned 32 more, each deeper and more profound than the previous. I realized through Jason that I’m not meant for teaching in the college classroom; I have always felt like I was missing out on something. Come to find out, I’m not. I’m meant for heady 1:1 interactions with young minds that cannot ask enough questions and will back me into a theoretical corner and not think twice. Jason gave me that priceless gift.
I would be remiss if I didn’t admit that he added to my grey hair or that I didn’t feel somewhat guilty having to call his mom when he’d fallen asleep eating ice cream on a midnight facetime call. Teens today are busy, and working around them nets the best work product. It also earns me cool points that I’m as old as their moms, “but stay up way later.”
Jason is on par with the top 20% of my clients in terms of raw intellect. Like many teen boys, there existed a gap between his goals and the depths to which he thought necessary to go in order to achieve those goals. It was a short-lived experiment in laxidasicality; you see, the dream – effort gap never started with Jason. It originates in American educational pedagogy. Jason was another unwitting benefactor of a system that seems to reward mediocrity of mind. A few good debates revved him right up and set him up for one hell of a race. Like most, Jason had a large swath of schools on his radar. For him it was about finding the right one. He ended up with acceptances at places most only dream of, but none captured his altruistic heart. Except Tulane. He lives in the service of others. And the waiting was torture…for me.
Jason and I worked together for nearly 12 months. We spent hours debating synonyms, talking sentence structure, literary devices, and more. In the end, Jason wrote one Common App essay and approximately 22 supplemental essays. I also had the thrill of working with him on his AP Government capstone project and about 10 LOCI. His world became part of mine; I amassed his goals as my own. I found myself pacing the floors on the days his ACT/SAT results were returned. School decision days were pure hell for me because I saw raw, unbridled potential in him and I believed everyone should see it. I wanted Jason to earn his ride on the Green Wave.
I cried like a toddler sitting at LensCrafters the day he called to tell me about his acceptance.
After so much time together, I can say Jason will be the secret weapon in any professor’s arsenal of tools, in whichever class that might be. He sees the world differently than 99% of the other students I’ve worked alongside, many of which were actually in the college classroom. A complex architectural structure serves as the perfect metaphor for Jason, his approach to learning, and his thought processes. Most students obtain entry to nuanced cerebral concepts via a front or back door; some via side windows. Pretty direct, little thought. Some with brute force. Some give up even trying to get in because it is all too confusing. Jason has already familiarized himself with the interior and eaten all the snacks by the time his peers arrive. How? He accessed the structure via an obscure and previously unthought of entry method. Quite simply, Jason’s worldview opens him up to turgid concepts in ways I have rarely seen from a high school senior. He’s sorta a mashup if there was YouTube video on how to clean your AirPods that was narrated by John Locke or Marcus Aurelius.
Jason is lightening fast on his feet. You could practically see a huge if – then equation running in his noodle when I’d ask him off-the-wall questions to get him out of writer’s block. The thing is, he loves push back. It gets his motor running like a Ferrari circling Vatican City. Most short-sighted people would see Jason as flippant, arrogant, or maybe disrespectful, and that would be an error of significant consequence. Students like Jason need a place to flex their brains, fall flat on their face, and feel safe enough to get up and try again. As teachers and mentors, it’s our responsibility to provide a safe space for students to exercise their intellect.
Oftentimes, the most effective teacher isn’t the one leading the classroom, the tutoring lesson, or writing session; indeed, it can be a student who is uniquely conversant, gifted with an ability to make large and abstruse concepts granular, therefore much easier to understand, and who is as articulate in his oratory as he is nimble in its delivery. The most effective teacher in our sessions was evenly split, half him and half me, and it’s an honor to admit that. Remember, his Common App topic was extraordinarily nuanced. I needed his help connecting the dots in his head. Jason’s subject framing is enlightening to those around him not only because of his words, but because of their delivery. He is convivial and approachable without being aloof; likewise, he is logical and deeply cerebral without being an insufferable and pompous ass.
Heck, I might book a weekend in NOLA just for the spectacle and sneak in the back of a Friday seminar class. There is a part of me that remembers my first graduate teaching gig, when I got shredded by a brilliant undergrad student I was wholly unprepared for. I get all angsty thinking about the first instructor he stumps in front of an entire class. But the other part of me wants to watch it all go down as I giggle because I had the honor of working alongside, and in support of, him as he busted his tail to get into Tulane.
My parting wish for Jason is this: take a moment for introspection. Slow down, look in the mirror, and realize that you have more potential in your pinky finger than most can conjure in their imaginations, and it all comes from your huge heart and love of humanity. The world has much to learn from you and there are a lot of kids out there waiting for your help; when school and life get hard, remember that. Also, at the rate you eat ice cream, I’d suggest a larger freezer for your dorm room.
Listen to Sooner or Later by Michael Tolcher. Whenever it pops up on my Spotify list, I am reminded of all I learned from you and how enormously grateful I am.
