Look Both Ways Study Guide

Reynolds grew up in Oxon Hill, Maryland, an unincorporated suburb of Washington, D.C. While a young student, Reynolds grew frustrated by what his teachers assigned him to read—he found that he couldn’t identify with the characters or get interested in books about subjects that seemed to have little to do with his lived experience. Because of this, he didn’t read a novel until he was 17. Two things began to turn Reynolds onto literature and poetry: rap music in the form of Queen Latifah’s album Black Rain as a young kid, and reading Richard Wright’s novel Black Boy as an older teen. Inspired by Queen Latifah, he wrote poetry all through his teen years and through college, even as he failed English classes. His first novel, co-written with Jason Griffin, was a critical and financial failure, so Reynolds took a job managing a Rag and Bone clothing store and contemplated giving up on writing. A friend, however, encouraged Reynolds to write in his own voice. The result was When I Was the Greatest. Since then, Reynolds has written several other young adult novels, mostly about young Black characters living in neighborhoods that resemble the one where he grew up. His goal is to help improve literacy rates and, specifically, to try to convert “book-haters” by writing books that he would’ve been interested in as a young person. Since 2020, Reynolds has been the Library of Congress’s national ambassador for young people’s literature. His books have won the Coretta Scott King award, the Carnegie Medal (which Look Both Ways won in 2021), and have been named finalists for the National Book Awards.

In interviews, Jason Reynolds has said that he wanted to write Look Both Ways about the only time of day when young kids often don’t have adult supervision: their walk home from school. While in decades past it was normal for kids to have lots of unsupervised time, this began to change in the 1980s as fears of kidnapping and childhood sexual abuse climbed in the U.S. However, later analyses have found that advocacy organizations and the media overstated how many children were abducted yearly, and it wasn’t made clear that the vast majority of children reported missing actually ran away or were kidnapped by one of their own parents. While some parents have been charged with child abuse or neglect for allowing their children to walk to school or play at parks unsupervised, a 2016 federal law protects parents’ right to allow their children to walk to school alone. Many states and municipalities also have their own rules regarding at what age, and under what circumstances, children can be unsupervised in public. Beyond this, Reynolds situates Look Both Ways firmly in the late 2010s; his stories mention social media sites, cell phones, and the video game Call of Duty. It’s also possible to situate Look Both Ways within the broader movement to portray and celebrate Black people’s joy, and to tell stories about Black people that aren’t simply about racism or other struggles. On social media, this takes the form of hashtags like #BlackGirlMagic and #BlackJoy, the latter coined by The Black Joy Project.

Reynolds has been upfront about the purpose of his books: to speak to young readers who don’t often see characters that look like them in books. Because of this, most of his books, including When I Was the Greatest, The Boy in the Black Suit, and Miles Morales: Spider-Man, follow young Black characters going through events and experiencing things that Reynolds experienced as a young person, and that kids of color still experience today. Look Both Ways is often considered a part of the cultural movement to highlight stories about Black characters that aren’t just about the characters struggling with racism. Other young adult and children’s books that share this distinction include Ibi Zoboi’s My Life As an Ice Cream Sandwich, Shuri: a Black Panther Novel by Nic Stone, and Rebound by Kwame Alexander. The humorous aspects of the collection, as well as the stories’ focus on bullying, also recall Diary of a Wimpy Kid by Jeff Kinney. As inspirations for his writing more generally, Reynolds has listed Black Boy by Richard Wright as the novel that sparked his love of literature and spurred him to discover other African American authors, such as Zora Neale Hurston (Their Eyes Were Watching God), Toni Morrison (Beloved; Song of Solomon), and James Baldwin (Go Tell it On the Mountain; If Beale Street Could Talk).