Kayla Kirshenbaum
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36 Under 36 (2017)Education

Kayla Kirshenbaum

A Passion for Teaching, from Shul to Prison School

It’s a 90-minute weekly commute for Kirshenbaum from the Upper West Side, where she is assistant director of education at the Stephen Wise Free Synagogue, to the East River. Two subways, then a bus ride to make the under-10-mile-trip.

But the distance between her day job and her destination, Rikers Island, New York City’s main jail complex, where Kirshenbaum volunteers every Thursday evening, can’t be measured in minutes or miles. “It’s a different world,” said Kirshenbaum, who serves as a volunteer in educational programs for young men and women at the correctional facility.

In 2015 she founded the Daddy Reads Educational Initiative, a reading and writing program for male prisoners ages 18-21. Her interest in working in the prison system grew out of similar work she had done at the Westchester County Correctional Facility while studying at Sarah Lawrence College, where she earned an MFA in creative writing.

After graduation, Kirshenbaum, who grew up in Skokie, Ill., and lives on the Upper West Side, was no longer eligible to teach in the Westchester program. “I liked the work so much,” she said, “I was set to find a similar opportunity” here. She’s lost track of how many inmates have taken part in her classes at Rikers Island — “there’s so much turnover.”

Maintaining discipline among her students in prison is not a problem, Kirshenbaum said — sometimes a surprise to outsiders. Daddy Reads is an elective — all the participants want to be there. The students are attentive, well-behaved. And protective of her. If a new student whistles at her or uses inappropriate language, she said, the veteran students advise him, “Not with Miss Kayla.”

Music in her soul: Director of the all-girls choir at her Modern Orthodox day school in Chicago, Kirshenbaum joined Tizmoret, a Jewish a cappella group when she arrived at Queens College. She sang with the group for four years, including a performance at Lincoln Center. “I grew up singing,” said Kirshenbaum, who has taken voice lessons over the years. “I love music.”

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