When I dropped out at 20, my sister told everyone: “She’s the family failure.” Twelve years later, I’m Yale’s dean of admissions. One essay read: “My family overcame my aunt’s failure.” The name? Amanda Chen.
My niece. I picked up my red pen and…
The Thanksgiving dinner table went silent when I made the announcement. November 23rd, 2012, 6:47 p.m.
“Dropping out of college,” I said, setting down my fork. My mother’s hand froze halfway to her mouth. My father put down his wine glass with a sharp clink.
My sister Jennifer stared at me like I had just announced I was joining a cult. “You’re what?” my father said. “Dropping out.
I’m leaving Northwestern at the end of the semester.”
“Rachel,” my mother said carefully. “Is this a joke?”
“No joke. I’ve already submitted the paperwork.”
“But you’re a sophomore,” Jennifer said.
“You’re halfway through. Why would you?”
“Because I hate it.” The words came out more forcefully than I’d intended. “I hate my major.
I hate my classes. I’m miserable, and I’m wasting your money.”
“What you’re wasting,” my father said, his voice rising, “is your future. Do you have any idea how competitive it is to get into Northwestern?
How many people would kill for your opportunity?”
“Then they can have it.”
“Rachel, be reasonable,” my mother pleaded. “Every college student feels overwhelmed sometimes. That doesn’t mean you quit.”
“I’m not quitting.
I’m choosing a different path.”
“What path?” Jennifer demanded. “Dropping out to do what? Work at Starbucks?
Live in our basement?”
“I’m moving to New York. I have a job lined up as an editorial assistant at a publishing house.”
“An editorial assistant?” My father laughed, but there was no humor in it. “That’s a glorified secretary position.
Rachel, you’re throwing away a Northwestern degree for an entry-level job that pays maybe $30,000 a year.”
“It’s a start.”
“It’s a disaster,” he interrupted. “Your sister graduated from Yale, went to law school, and is now working at a top firm in Chicago. That’s what success looks like.
Not this.”
Jennifer leaned back in her chair, arms crossed. “I worked my ass off to build a career. I did everything right.
And you’re just going to throw away your education because you’re miserable? That’s pathetic.”
“Jennifer,” my mother said weakly. “No, Mom.
Someone needs to say it. Rachel has always taken the easy way out. High school was too hard, so she went to community college first.
Now university is too hard, so she’s dropping out. When are you going to grow up and finish something?”
“I did finish community college with a 3.2 GPA,” she said. “Barely.
And you only got into Northwestern because you wrote some sob story essay about being a late bloomer.”
That stung because it was partially true. My path hadn’t been traditional. I’d struggled in high school, gone to community college, then transferred to Northwestern.
I’d been proud of that journey. My family had been tolerant of it. “This is a mistake,” my father said firmly.
“A huge mistake, and I won’t support it financially.”
“I’m not asking you to.”
“Good, because you’ll get nothing from us. No money for rent, no money for food, nothing. You want to make adult decisions?
Fine. Face adult consequences.”
“Harold,” my mother said, “that seems harsh.”
“She needs to learn, Patricia. She can’t just drift through life expecting us to catch her every time she fails.”
“I’m not failing,” I said, my voice shaking.
“I’m making a choice.”
“A bad choice,” Jennifer said. “You’re 20 years old with no degree, no real skills, moving to one of the most expensive cities in the world for a job that probably pays minimum wage. You know what we call that?
Failure.”
I stood up from the table. “I should go.”
“Rachel, wait,” my mother started. I didn’t wait.
I grabbed my coat and walked out into the cold Chicago night. I moved to New York three weeks later with $1,800 in savings and a suitcase full of clothes. The publishing job was exactly as bad as my father had predicted.
Editorial assistant at Hartley and Sons Publishing, a small, prestigious house specializing in literary fiction. I made $28,000 a year, worked 60-hour weeks, and my primary responsibilities were filing, coffee runs, and reading slush pile manuscripts that would never get published. My apartment in Brooklyn was 280 square feet.
The shower was in the kitchen. I could hear my neighbors’ every conversation through the paper-thin walls. I ate ramen noodles for dinner four nights a week.
My family barely spoke to me. My mother called once a month with updates I didn’t ask for. Jennifer got engaged.
Jennifer made partner track. Jennifer bought a condo. “Your sister’s doing so well,” my mother would say.
“We’re so proud of her.”
The implication was clear. Unlike you. Jennifer called exactly once in those first six months.
“I heard you’re living in some shoebox in Brooklyn,” she said. “Mom’s worried about you.”
“I’m fine.”
“Are you? Because from where I’m sitting, it looks like you made a huge mistake and you’re too proud to admit it.”
“I’m happy, Jennifer.”
“You’re 20 years old, making less than minimum wage when you calculate your hours.
That’s not happiness. That’s delusion.” She paused. “Look, it’s not too late.
You could reenroll. Go back to school. Get your degree.
Stop embarrassing the family.”
“Embarrassing the family?”
“Yes, Rachel. Embarrassing us. Do you know what I tell people when they ask about you?
I have to say, my sister dropped out of college to work in publishing. Do you know how that sounds?”
“Like I’m following my passion?”
“Like you’re a failure. Like our family couldn’t produce two successful children.”
She hung up before I could respond.
That was the last real conversation we had for 12 years. But I wasn’t failing. Not really.
The publishing job was brutal, but I was learning. How books were acquired, edited, marketed, how the industry worked. I read manuscripts until my eyes hurt, learning what made good writing, what made compelling stories.
After two years, I was promoted to assistant editor. After four years, associate editor. After six years, senior editor.
I developed a reputation for discovering new talent. Three of my authors won major literary awards. Two hit the New York Times bestseller list.
But more importantly, I’d found my real passion: helping young writers develop their craft. I started teaching a writing workshop at NYU. Just one adjunct class for extra money, but I loved it.
Loved working with students, helping them find their voices, watching them improve. One of my students, a professor in the English department, noticed. “You’re a natural teacher,” she said.
“Have you ever thought about higher education as a career?”
“I don’t have a degree.”
“You should get one. Not for the paper, but for the opportunities. With your experience and your talent, you could do real things in academia.”
That conversation planted a seed.
At 26, I enrolled in Columbia’s MFA program in creative writing. I worked full-time, attended classes at night, wrote my thesis in stolen hours on the subway. It was the hardest two years of my life.
I graduated at 28 with my MFA and a job offer from Columbia to teach undergraduate creative writing courses. At 30, I was promoted to assistant professor. At 31, I published my first book, a collection of essays about the publishing industry that became a surprise bestseller in academic circles.
At 32, I became associate professor and was asked to join Columbia’s undergraduate admissions committee. That’s where everything changed. Reading college applications, I realized I had a gift for seeing potential.
Not just in grades and test scores, but in the stories students told, in the struggles they’d overcome, in the unique perspectives they brought. I could see the students who would thrive at Columbia. The ones who’d contribute something meaningful.
The ones who just needed someone to believe in them like me all those years ago. When Yale reached out about their dean of admissions position, I almost didn’t apply. “You should do it,” my department chair said.
“You’re made for this. And Yale is, well, it’s Yale.”
I applied. Six interviews later, they offered me the position.
Dean of undergraduate admissions at Yale University. At 32 years old, I was one of the youngest deans in the Ivy League. The irony wasn’t lost on me.
The college dropout was now deciding who got into one of the world’s most prestigious universities. I moved to New Haven in August 2024. My mother called to congratulate me, the first time she had called in three years.
“Dean at Yale,” she said. “That’s wonderful, Rachel. Your father will be so proud.”
“Will he?”
Silence.
“He’s trying. He asks about you.”
“Does Jennifer?”
More silence. “Your sister’s very busy.
She has Amanda now, you know. She’s 16. Such a bright girl.”
My niece.
I’d seen her exactly three times. Once as a baby, once at age five, once at age 10. Jennifer had made it clear I wasn’t welcome in her daughter’s life.
“I’m sure she is,” I said. “Maybe now that you’re doing well, you could reconnect with Jennifer. With all of us.”
“Maybe,” I said, knowing I wouldn’t.
The application reading season started in November. We received 52,000 applications for 1,550 spots. Every application got read by at least two admissions officers.
As dean, I personally reviewed thousands of them, including all the borderline cases and special circumstances. It was grueling work, reading applications from brilliant students who’d overcome incredible odds. Students who’d started nonprofits, conducted research, won international competitions, students who’d survived poverty, violence, loss.
Most of them we’d have to reject. That was the hardest part. I was in my office on a Friday evening in January 2025, reviewing a stack of applications from the Chicago area.
My eyes were tired. I was on my fourth coffee of the day. Then I saw the name Amanda Chen.
My sister’s married name was Chen. Her husband, David Chen, the corporate lawyer she’d married 11 years ago. My hands started shaking.
I opened the application. Amanda Chen, age 17. Northbrook High School, Northbrook, Illinois.
GPA 4.0 unweighted. SAT 1570. Valedictorian.
National Merit finalist. Captain of debate team. Volunteer at local literacy nonprofit.
Impressive. Very impressive. She’d applied as a prospective English major.
Wanted to be a writer. I scrolled to her personal essay. The prompt: reflect on a time when you faced a challenge or obstacle.
What did you learn from the experience? I started reading. My family doesn’t talk about my aunt Rachel.
I grew up hearing whispers. How she dropped out of college. How she threw away her opportunities.
How she became the family embarrassment. My mother would shake her head whenever someone asked about her sister. “Rachel made her choices,” she’d say.
“Bad choices.”
For years, I thought my aunt was a cautionary tale, a warning about what happens when you quit, when you don’t follow through, when you disappoint your family. My mother used her as an example whenever I complained about school. “Do you want to end up like Rachel?” she’d ask.
“Working some dead-end job because you couldn’t finish what you started.”
The lesson was clear. Rachel was a failure. Our family’s black sheep.
The one we’d overcome. Then when I was 16, I Googled her. I stopped reading, closed my eyes.
This was my niece’s college essay about me, about how I was the family failure. I should recuse myself. Pass this application to another admissions officer.
That would be the ethical thing to do. Then I kept reading. I expected to find nothing, or worse, confirmation of the family narrative.
Some sad Facebook profile, maybe a LinkedIn
What happened next changed everything…
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