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One of Reynolds’s earliest poems dealt with his grandmother’s death in 1994 when he was 10. He wrote a few lines in an effort to console his mother, who printed the poem on the program for the funeral, and after that Reynolds wrote poems as each of his grandmother’s siblings passed. Moved by these experiences of “the power of language”, he continued to pursue poetry through high school, graduating from Bishop McNamara High School in 2000, and college, even as he received poor grades and discouragement from professors in his English courses at the University of Maryland (he ultimately graduated with a BA in English.)
Eventually Reynolds returned to New York, again working in retail while he applied to graduate school, unsuccessfully because of his college grades. Nevertheless he began writing a young adult novel—”often while standing at the cash register when business was slow” at the Rag & Bone store he managed—spurred by his friend Chris Myers, son of Walter Dean Myers and himself an author and illustrator. Reynolds had told Chris he had basically stopped writing, but Chris pointed out that with his father aging (the elder Myers died in 2014), there would soon be a shortage of new works written about young black children, particularly black boys. He suggested Reynolds look at some of his father’s old works, and The Young Landlords particularly connected with Reynolds; the work gave Reynolds the confidence to “write in my voice, use my tongue, my language, my style, and write a story. Before that I always felt like I wasn’t good enough because I wasn’t Baldwin, or Toni Morrison, or Richard Wright,” but after reading Myers’s work, “the floodgates were opened.”