Anna Novogratz ’14 Inspired to Teach Special Education

This article originally appeared in The Compass Spring/Summer 2019 issue. 

If Anna Novogratz could give one thing to every student, what would she give to them? An education at The Windward School. Why? After three years at Windward, the trajectory of Anna’s life was radically altered. She received endless support from her teachers, which instilled a desire for her to help others with disabilities, and she curated a toolbox of useful lifelong skills, which helped her reach her full potential. Anna’s experience at Windward had a profound impact on her, and her journey as a dyslexic lead her to where she is today. 

Following her graduation from Princeton University last June, Anna joined Teach for America as a special education teacher at a public elementary and middle school in the South Side of Chicago. The main reason she chose to work in her specific position was because of her time at Windward. 

“From my teachers at Windward, I learned how much change one person can effect,” asserts Anna. “After experiencing that level of support myself, I decided that I wanted to be a special education teacher, so I could teach kids with disabilities how to read because the ability to read is the key to life. Being a teacher is a real privilege; you can really make an impact on someone’s life.” 

She teaches a range of grades and subjects, including third- and fourth-grade math, seventh- and eighth-grade English, and seventh- and eighth-grade social studies. All of Anna’s students have special needs, from moderate to severe cases. Her school’s neighborhood, though vibrant and full of Latinx culture, has been plagued with poverty and gun violence over the years, and the district lacks sufficient resources. Although Anna admits that every day presents a different kind of battle, she loves her students and believes strongly in her work as an educator. 

I decided that I wanted to be a special education teacher, so I could teach kids with disabilities how to read because the ability to read is the key to life. 

Anna tells her students every day that each of them can achieve their goals if they truly work hard. She shares with them stories of her journey from feeling isolated and angry as a young child to gaining confidence from Windward’s specialized program to earning a degree from her dream school of Princeton.  

Anna was diagnosed with dyslexia when she was in second grade. She recounts the moment when her family knew it was time for her to get tested. Her younger brother was learning to rhyme, so the family was naming words that rhymed with ‘cat.’ Anna remembers feeling certain that her answer was right when she screamed ‘beaver.’ Her mother then suspected dyslexia. Her own father was a dyslexic and she thought the rhyme misunderstanding could be an indicator.  

Meanwhile, going to school was a draining experience for Anna. She desperately wanted to be able to read, to be like her peers, and grasp what was happening in the classroom. Despite her best efforts to be an engaged student, she had no success. With no explanation as to why, this led to extreme frustration. Anna constantly experienced moments where she felt like a failure—being unable to open a locker or tell time in front of the class—so she frequently lashed out at home. Finally, after her official diagnosis and much research seeking a place that could best help Anna, the Novogratz family found The Windward School. 

“My grandfather had dyslexia, and he was an extremely successful man who spoke multiple languages and had a PhD,” shares Anna. “So my mom knew Windward was worth the investment to give me the best possibility to reach my potential. But my dad was hesitant at first. And, now being on the other side of the table as an educator who deals with parents of recently diagnosed children, I understand his reaction. Parents hate to see their kid struggling, and they think it’s a reflection of themselves. I always reiterate that a diagnosis for a disability has nothing to do with the parents and not intervening will hurt the child. Some parents just need a little time to understand. That being said, I remember that once we visited Windward, my dad became ‘Mr. Windward’ and never looked back. We all thank Windward every single day, and we are very grateful.” 

Anna attended Windward from third to fifth grade. In her first year, she recalls how she finally grasped what dyslexia was. That clarity gave her confidence that she could be successful academically. Anna credits the Windward teachers, in particular, with helping her feel comfortable in the classroom.  

“At Windward, I was the priority for the first time in a long time,” emphasizes Anna. “Before I would feel like I was drowning because I was lost and no one would realize. But Windward was different. Windward didn’t give me a chance to be lost because my teachers were always there for me and invested in my success.” 

At Windward, I was the priority for the first time in a long time. 

Anna then outplaced to Columbia Grammar & Preparatory School for the rest of middle school before attending Poly Prep Country Day School for high school. She focused on excelling academically, but still managed to be a peer tutor, president of the Aids Awareness Club, and the student government president of her class.  

Years of perseverance resulted in Anna’s acceptance to Princeton University, where she studied African-American history. She was alarmed to learn how whitewashed history lessons were taught in most primary schools and the many notable stories left out of textbooks. Her thesis explored the untold story of a young girl named Barbara Johns who began a grassroots student strike in 1951 that contributed to the landmark Brown v. Board of Education Supreme Court case.  

In anticipation of her thesis, Anna admits she fretted over whether she could actually read through the dense informational texts required for her research or write a 120-page paper. She relied on the skills that she learned at Windward, however, to complete the work and earn her degree. “I’ve never changed the way I’ve written,” states Anna. “My language has become more sophisticated, but the way I look at how to write and how to structure a paper is completely based on what I learned at Windward.” 

Apart from her academics, Anna started teaching a GED course at a medium security youth facility through the Petey Green Program. She became passionate about the power of education to rehabilitate the incarcerated youth she taught. Anna joined the Students for Prison Education and Reform (SPEAR) club to advocate for education being treated as a right, not a privilege, for the incarcerated. Additionally, she worked as an English and language arts teacher with The Steppingstone Foundation, a Boston-based non-profit organization that prepares low-income students of color for educational opportunities that lead to college success.  

These experiences demonstrated to Anna the rewards of a teaching career that suited her well. Following her two-year commitment with Teach for America, she plans to transition out of the classroom to enroll in law school. Anna will study education policy in order to further pursue her belief that education can play a major part in dismantling the poverty to prison pipeline.  

The Windward School community will be able to hear more of Anna’s journey, and advice for graduating students, when she returns to the Westchester Middle School campus on June 13 to deliver the 2019 Commencement Address.