Headley is a 2020 World Fantasy Award winner, a 2012 Nebula Award Finalist, a 2013 Shirley Jackson Award Finalist, a MacDowell Colony Fellow, and has attended The Bread Loaf Writers' Conference, The Sundance Playwright's Lab, The Kennedy Center's New Visions/New Voices workshop, Brave New Works, and the WordBridge Playwright's Lab. She has been a featured author at ABA Winter Institute, Bumbershoot, Wordstock, and the Texas Book Festival. In 2017, she was nominated for a World Fantasy Award in Short Fiction for "Little Widow."
Headley is a 2020 World Fantasy Award winner, a 2012 Nebula Award finalist, and a 2013 Shirley Jackson Award nominee. She has also received fellowships and attended notable writing conferences like The Bread Loaf Writers' Conference and the Sundance Playwright's Lab.