The summer after fifth grade, Charles Guerrero almost failed out of Prep for Prep, a competitive non-profit program that readies exceptional students of color for life at independent schools. “I wanted to get kicked out,” Guerrero says. He tried not turning in homework, but the program instructors set up meetings with him to help him get organized. He moved on to faking sickness on the bus. No dice — his mom kept sending him anyway.
That summer, Guerrero was required to attend eight weeks of full school days with three hours of homework per night. In sixth grade, he spent his Wednesdays after school in Prep for Prep classes and attended all-day classes on Saturdays. The summer before seventh grade, he had another eight weeks of full school days.
“Rigorous is probably an understatement,” Guerrero says.
Guerrero always knew education was critical. His grandmother grew up in South Carolina, and “as an African American woman, her options in education were very limited.” Still, she managed to get her associate degree in education and imparted to Guerrero’s mother and him the importance of learning. Like his grandmother and mother, he was a voracious reader and an excellent student. At his small New York City public elementary school, Guerrero took classes grade levels ahead and eventually skipped a grade. But nothing could prepare him for the academic demands of Prep for Prep.
The motivation did trickle in, slowly. That Prep for Prep summer program was the first time he’d attended school with kids as smart as — or even smarter than — he was, and the students looked like him, “which was even more amazing,” he says. Guerrero started forming connections with the other kids in his cohort, and the prospect of a more exciting future — a better high school, college, or career — kicked in.
Perhaps the best way to sum up Guerrero’s lifelong attitude is the phrase “I can figure it out.”
Prep for Prep took students on tours of elite independent schools, opening up entirely new possibilities. “What loomed ahead for middle school and high school in my area of the Bronx was pretty bad,” Guerrero says. Prep for Prep offered an alternate path. Invigorated by a chance at a different future, Guerrero turned things around, doing his homework diligently, participating actively in classes, and even giving up on the fake stomachaches.
“It was the hardest thing I’ve ever done. This is not hyperbole,” he says. But, he also adds, “it was an incredible gift.”
Seeing ECFS for the first time on a Prep for Prep tour impressed Guerrero. “Especially for someone who grew up in a New York City housing project, I’d never seen a school like this before. I didn’t know that schools like this existed in New York City. But when you came on campus, the interactions with the people on this campus, with students, with faculty, with the administrators at the time — it just made us feel at ease. We were people who had no business feeling at ease in a school like this. But we came here and we felt really at ease and that’s something that’s remarkable.” With Prep for Prep’s guidance, he applied to ECFS and was accepted, joining the class of 1989 as a seventh grader.
Seventh grade got off to a rocky start. Guerrero was late every day his first week, trying to figure out the commute from the Soundview neighborhood in the South Bronx. The journey was one-and-a-half hours each way on multiple buses, including one route on which he got on at the first stop and off at the end of the line. Guerrero would fall asleep and wait for the bus driver to wake him.
But he remembers the moment things changed and he began to feel like he belonged. It was his first gym class, and he made his way down to the lower field in his orange and white gym clothes. For some reason, he was the first one there. As he sat down, he thought to himself, “What’s going to happen next?” A classmate approached and introduced himself. “We talked, and just that moment of treating me like a normal kid, like, ‘hey, this kid’s my classmate now’ — it was one of those small things. I finally felt myself exhale.”
Perhaps the best way to sum up Guerrero’s lifelong attitude is the phrase “I can figure it out.” Look no further than his first project after getting a Bachelor's degree in English at Harvard: forming and running a theatre company. With no experience of any kind.
Guerrero wasn’t worried. At a Senior Week party, a friend suggested the venture, and Guerrero went all in. “My Fieldston and Harvard educations really made me feel like there's nothing you can't learn how to do. If you don't know it, you can figure it out. That's how it works. And so I was like, ‘Okay, that sounds great. How hard could that be?’” Guerrero and his friend went back and forth on potential cities: Chicago? Too saturated with theatre and too cold. New York? Too expensive. New Orleans? Too hot in the summer.
San Francisco? Why not?
Guerrero and some friends who came on board for the project moved into an apartment in the Mission district, where each paid less than $300 a month for rent. (Unlike today, “mere mortals could live” in San Francisco, Guerrero says). First, they bought books on how to incorporate as a 501(c)(3) non-profit organization, which they did almost entirely as a DIY venture. Then, they rented an old shoe store, turning it into a 40-person black box theater. They started producing original plays, charging a sliding scale of $3–6 per ticket.
The company ran for seven years, producing over 20 plays. Guerrero wrote two full-length musicals and numerous short pieces. “It was really one of the greatest experiences I've ever had in my life,” he says. However, the theater never really made enough to support its staff, and Guerrero and his friends all worked day jobs.
In 1999, the theatre company came to a crossroads. Did the group want to level up the business and really make this their career, or did they want to try something else? Charles was torn. “Even though I think art is incredibly powerful and incredibly important, it wasn't the kind of impact that I wanted to have,” he says. The group decided to disband: one went into television writing, one moved back to New York to continue acting and directing theatre, and a set of twins moved to LA and opened a restaurant and bowling alley. And Guerrero got a call from the executive director at Prep for Prep.
He had worked for Prep for Prep in high school. Now, the executive director wanted him as the next director of college counseling. Guerrero’s response? “I can learn how to do that.” He moved back to New York and stayed at Prep for Prep for 19 years.
“Nineteen years is a long time in any one place,” Guerrero says. “It goes by pretty quickly, but the prospect of another 20” was daunting. And it was time for a new challenge. Guerrero wasn’t actively looking to leave Prep for Prep, but when an opportunity to try something new presented itself at ECFS in 2018, he jumped at the chance.
In his current role as director of admissions, financial aid, and institutional research, Guerrero aims to bring an increased level of transparency to admissions processes and to recognize that different students thrive in different environments. “If ethics aren’t important to you, if service isn’t important to you, and if diversity isn’t important to you, this is not a place for you,” he says. He also hopes to provide more families with financial aid to ensure that ECFS can be as accessible as possible.
It was at ECFS that Guerrero learned how to take on new challenges with confidence and poise. “This place instills in you a curiosity, a desire, an almost fearlessness to take risks and confidence and a love of learning,” he says. “As I'm here in the school now and in this role, I feel all of those things coming back.”
“I never stop and worry: Can I do this? That's not a thing that I think typically. My thought process is: How can I figure out how to do this?”