A Journey from Steppingstone’s Classrooms to Judicial Courtrooms

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Esteban Gutierrez-Alvarez ’12 joined Steppingstone fifteen years ago because his mother had a vision for his future. “She wanted me to have what she called a life-changing opportunity: a network of teachers and advisors who could push me to aim higher.” 

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Today, Esteban affirms: “Steppingstone delivered.” The graduate of Milton Academy and Harvard University—and soon, Columbia Law School—has accepted an opportunity to serve as a judicial law clerk to the Hon. Elizabeth N. Dewar of the Massachusetts Supreme Judicial Court.

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“Law always made sense to me.” 

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Looking back on his application to Steppingstone, Esteban found a younger version of himself “wanting to help others and make sure my peers and community would benefit from my work. That instinct stuck.” 

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As a J.D. candidate at Columbia, Esteban has learned much about United States legal institutions “and how to use them to advance the common good.” He keeps coming back to the core lessons he learned at Steppingstone: ”about persistence, about community, about using whatever position you hold to help others. Those lessons shape the kind of lawyer I want to be.”

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Esteban’s First Teachers

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Esteban learned these core lessons from the community supporting him through Steppingstone. In addition to his mother and father, his “teachers” included friends and staff.

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He smiles: “I look back fondly on those semesters when my classmates and I studied math and then sprinted outside for recess to play as much four-square as humanly possible. At a young age, I found a community of brilliant, kind peers who would support me through the years ahead. We have all taken different paths since those four-square games, but we remain connected by what this place built in us.”

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Mary Sullivan, who serves Steppingstone today as Vice President of The Academy, was Esteban’s English teacher in his early years. “She taught me the mechanics of writing, but more than that, she helped me find my voice.” 

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He recalls Mary sitting by his side, showing him ways to make his arguments stronger and his points clearer. “The close reading skills she taught me still guide my work through law school casebooks. The basic writing principles she introduced still hold as I draft amicus briefs bound for appellate courts across the country as part of my work for the Appellate Litigation Clinic at Columbia.”

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Finding His Place at School

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Before Mary’s English class helped him to succeed at Columbia, it first prepared Esteban to gain admission to Milton Academy. Steppingstone’s evidenced-based programming for college access and career readiness relies on this key step: helping families to identify and apply to right-fit schools that will lead to college.

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“The adjustment was hard at first,” Esteban remembers. “I felt like an outsider, and I leaned on my Steppingstone Advisors to help me find solid ground. Eventually, I did. I fell in love with my classes, performed in many plays and musicals—a highlight includes the role of Lord Farquaad in Shrek the Musical—and captained the Speech and Debate team.” 

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Esteban’s time at Milton prepared him for admission to Harvard. While settling into his first semester, he noticed feelings of imposter syndrome creeping back. “I found myself surrounded by enormous resources and opportunities, but I struggled to figure out how to access them and how to take full advantage of what Harvard had to offer.” 

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Steppingstone was there to guide him. “Conversations with Annie Wu and other Advisors helped me understand that I belonged at Harvard and showed me how to navigate the institution. They helped me see that the skills Steppingstone had built in me—the confidence to ask questions, the willingness to seek help, the determination to push through uncertainty—were exactly what I needed.” 

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This led to a transformative four years, studying under leading scholars in law, classics, political science, and music. In his senior year, Esteban served as the 165th president of the Harvard Glee Club: the oldest collegiate chorus in the United States.

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Impacting the Courts, and the Next Generation of Scholars

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As Esteban celebrates the milestone of earning his J.D. this spring, he looks forward to launching his career—building on previous opportunities as a summer associate at Ropes & Gray LLP, and judicial extern to the Honorable Kiyo A. Matsumoto of the U.S. District Court for the Eastern District of New York.

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After Esteban’s clerkship at the Massachusetts Supreme Judicial Court, he will return to Ropes & Gray: “a firm that has shaped the legal landscape in Boston and nationally for more than a century and continues to handle some of the most consequential legal matters of our time.” 

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Even as he fulfills many of the goals he set as a Scholar, Esteban remains committed and connected to Steppingstone as an Alumnus. He explains, “Steppingstone’s impact lasts through every stage of a career and a life. . . I look forward to giving back to the next generation. I want to hear from current and future Steppingstone Scholars who have questions about careers or need advice. That is how this network works: each generation lifts the next.”

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“When we invest in Steppingstone Scholars, we not only help them access opportunity. We create professionals who carry this community’s values into courtrooms, classrooms, hospitals, and boardrooms across the country.”

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