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Yale University

I stood on the stage looking out at dozens of expectant stares, waiting for my formal introduction. “And now, Caleb is going to stand up and recite the 50 states in alphabetical order!” Scattered applause and continued stares. I felt a deep unease in my gut; my hands were trembling, and my mouth was parched. I wanted so badly to crawl into a corner and hide, but I couldn’t move. And I tried, I mean really, really tried, to recite those 50 states, but after an uncomfortably long silent pause, I caved under the pressure of those unforgiving eyes and ran off of the stage, sobbing, embarrassed and utterly destroyed. That was kindergarten.

My life has been typified by self-criticism and anxiety, and for no good reason. My family constantly showered me with love, affection and encouragement. I was put through a top-tier preschool program, attended an elementary school for gifted students and graduated from Michelle Obama’s high school alma mater. Whenever I met someone new, they would always tell me something along the lines of “don’t forget me when you get rich and famous.” It became an implicit belief that I would be the one to usher my family to their place among the dynastic American elite. Alongside the Kennedys and Bushes in history textbooks and museums would soon be the Dunsons.

But when I stepped into the world, my confidence fell short of those expectations. I never felt like I fit in, nor that my ideas were worth sharing. I was just some random kid from the West Side of Chicago that didn’t belong in the same classrooms as the kids who came from big money on the North Side. I didn’t deserve to walk the same halls Michelle Obama once walked.

To escape those feelings, I participated in a dizzying amount of extracurricular activities, hoping to convince myself that I was destined for greatness, as other people thought. But my persistent lack of confidence led me to cast doubt on every accomplishment I obtained. So as I set my sights on college at the end of my junior year, I made sure to temper my expectations.

Counselors, friends, family members and even a few strangers advised me to “shoot for the moon” in the college application process, citing my activities and grades as reasons for my guaranteed success. But after perusing U.S. News & World Report to check the acceptance rates of some of the schools they recommended, I knew there was no way any of them were thinking straight.

I indulged them anyway and let my mom, bubbling with excitement, plan a tour of the Ivy League during spring break. One place stood out in particular: Princeton University.

Sprawling, ivy-covered, gothic-designed buildings hidden behind glistening magnolia and cherry trees, a bustling college street with all the food you could ever want, bronze tiger statues almost everywhere you looked, several secret student hangout spots hidden in the campuses nooks and crannies, and hundreds of prominent professors milling about, dedicated to producing the next generation of America’s leaders. I was in paradise.

But my joy quickly turned sour as I noticed the prospective students that screamed privilege, all of them eager to earn admission to the university. As the campus tour started, I did my best to ignore them, but being a single black face in a sea of white made that quite difficult. It was clear that I didn’t belong, that I was the odd man out … again.

Yet despite my deep doubt in my ability to earn admission to Princeton, it still intrigued me. What would it be like to go to the best university in the country? What would it be like to have something everyone wants? What would it be like to call myself a Princeton man?

Maybe this would finally be the achievement I needed to believe in myself. Maybe, once I was gifted with the opportunity to don the orange and black for four years, I would finally be able to justify my place at my storied high school and prove that I was supposed to lead my family to their place among the elite.

So the summer before my senior year, I did everything I could to give myself the best shot at getting in.

I committed myself to a self-improvement regiment that rivaled the ambition of a professional athlete: 6:00 a.m. wakeup, work out, midmorning ACT prep, work to launch my nonprofit, more ACT prep, more nonprofit work, summer homework, evening business program, researching colleges and getting a blink of sleep to keep from passing out.

In three months, I had earned a top score on the ACT, drafted a business plan from scratch, done my summer homework and gotten ahead on extra assignments, and made a list of the colleges I planned to apply to (Princeton was at the top, of course).

I ended my summer with a new sense of confidence, ready to conquer my applications.

The letter from Princeton came in December, the same evening as a Christmas party I had been planning to go to. I knew the date and time of the electronic letter’s release with pinpoint precision: Dec. 12, 2019, at 6 p.m. CST.

In the months leading up to that day, I managed to distract myself with yet another set of extracurricular activities. I stumbled into writing for a business magazine, threw myself into my senior year project and, once done with those, occasionally found myself listlessly wandering around downtown Chicago.

But as the days inched closer to Dec. 12, my stress increased exponentially. I downloaded a PDF of my application and reviewed it, pretending to be an admissions officer deciding whether or not to admit myself. After finding two typos in my application, I decided my world was effectively over. There was no way real Princeton students had mistakes in their applications.

So as I rode the train to the Christmas party with my mom at my side that night, I sat in dismay, the two typos swirling around in my head, teasing me sardonically.

With the clock on my phone approaching 6:00 p.m., my mom and I hopped off of the train, dipped into the nearest store and sat on the indoor benches waiting around extravagant Christmas decorations in nervous anticipation for what the storied institution thought of my pedestrian prose, unimpressive extracurriculars and average grade point average.

At 5:56 p.m. we prayed together, and my thoughts went back to those damned typos. At 5:58 I prepared myself for rejection. At 5:59, I began thinking of what other schools I could go to. At 6:00 p.m. my mind and body filled with desperate hope. I took one last deep breath and opened the e-letter.

“Congratulations! I am thrilled to offer you admission to Princeton’s Class of 2024!”

Release. Every pent-up emotion. Every negative thought. Every feeling of inferiority. Release.

And as the months went by, the acceptances kept rolling in. Michigan. Vanderbilt. UChicago. Congratulations! Congratulations! Congratulations! I even got a call from Yale University’s admissions office letting me know early that I would get an admission letter come March.

But negative thoughts would not stay down for long. Why me? Did they make a mistake? How’d you manage to trick them all, Caleb?

By mid-February, there was one university I had yet to hear from: Harvard. It was then I realized that maybe Harvard was what I was missing. Maybe if I could just get into the university everyone in the world knows about, the place that is synonymous with success, I’ll have done enough to prove to myself that I’m destined to be among the best of the best.

Harvard’s admissions letters were to be released on March 26, 2020, at 6:00 p.m. CST, and as that date inched closer, I once again worked tirelessly to keep my mind off of the looming decision.

Then COVID hit, and I was stuck at home with thoughts of Harvard consuming my every waking moment. The days crawled along, and my stress grew exponentially. Soon I found myself lurking on online college forums, the place where all stressed and slightly obsessive kids go when waiting for decisions to release, and watching YouTube videos of students reacting to receiving their acceptance letters, hoping I could be like the kids that jumped and yelled and cried and celebrated after getting into their dream colleges.

Finally, at 6:00 p.m. on March 26, my mother called up as many of my family members as humanly possible to watch me open my decision letter. Once everyone congregated virtually on our tablet, desktop and two phones, all angled so that they could see me and my computer screen, I gave everyone the rundown.

Four point five percent acceptance rate. Best economics program in the country. Richest college in the world. I opened the letter quickly, trying to rip the bandage off and start the grieving process:

“Dear Caleb, Congratulations! I am delighted to inform you that the Committee on Admissions has admitted you to the Harvard College Class of 2024. A transformative college experience awaits you.”

I had everything I wanted. I had been accepted to every college I applied to. I was in a position most kids only dream of … and yet I felt no different. There was no jumping and screaming and crying. I sat in my chair with a sheepish, forced smile and didn’t say much more than “wow, that’s cool.”

In the weeks that followed, I struggled to decide which college to choose. Almost fatefully, it came down to Harvard, Princeton and Yale.

Harvard was the most famous university on the planet, and as I imagined myself enrolling there, I dreamed of the surprised and impressed reactions people would have when I said, “I go to Harvard.” I loved it. There would be no question of whether I was meant to be among the best and brightest.

Princeton was my dream college. Being at the top-ranked university in the country was something I had coveted for over a year, and I finally had that chance. I would no longer fear that I didn’t belong because of my skin color -- I had an admissions letter and could soon have a class schedule that said differently.

Yale had never really been on my radar. Simply put: it didn’t provide the validation I was looking for. It wasn’t the top-ranked university in the country (even though it was close), and its name recognition was incredible, but nowhere near the gravity of Harvard’s. Yet for some reason, I just could not take it off of my list. It was something about the way students spoke about their experience with such joy and passion, about the way the admissions officers and professors treated me like family, about the way the other prospective students showed kindness and compassion as we all struggled to make our college decision before the May 1 deadline.

Each day I nearly committed to one of the three colleges. I bookmarked website links with college merch, scouted classes for my first semester and began planning my move-in day strategy, just to throw it all away and start over with a new school the next day. But without fail, at the end of each day, I felt empty. I still felt like nothing had changed for me, like I still couldn’t prove my intelligence or my worth.

On an unusually cold evening in early April, after going another day having not yet decided on which college to attend, I couldn’t fall asleep. I lay in my bed, gazing through dim orange lamplight, looking at the messages I wrote in black Sharpie on printer paper and taped to my bedroom wall years ago to encourage myself. “Confidence is a habit,” one of the messages said. “Don’t worry what others think of you,” read another. Looking at my old handwriting, I realized I had overlooked something profoundly important about myself and the admissions process.

No matter what great thing I did, I was bound to focus on my failures. Even if everything went perfectly, I would somehow find a way to justify self-criticism. It was never about the accomplishments I obtained or the status I achieved, it was always about the way I thought and acted. For so long, I had focused my energy on my mistakes as I strove to fit an unrealistic mold of what I thought others expected me to be, and it took a tremendous toll.

I missed my last homecoming game and dance, I missed my last pep rally, I missed skipping class to hang out, I missed my last wild adventure exploring the streets of Chicago with my friends, all to get into schools I never liked for the right reasons. I can’t get those experiences back.

So after mulling over my college options, I chose Yale. Not because of the name, or the reputation, or the promise of helping my family climb the social ladder.

I chose Yale because it made me happy.

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