At the core of all PR is humanity, and David Rakoff understood humanity like no one else. His insights were naked and powerful, his life heartfelt and poignant. Boldly insecure and damned funny, Rakoff connected with people because he was honest about being sad. For Rakoff, being unhappy was OK, even normal. For many of us, this unwelcome truth was beaten out of us as children and replaced with Santa Claus.

As noted in this Gothamist post, Rakoff opened his most recent book, Half Empty, with the lines “We were so happy. It was miserable.” If that doesn’t make you laugh, then I’ve got some terrible news for you about Santa Claus. Rakoff wrote two other collections of essays, Fraud and Don’t Get Too Comfortable, in addition to publishing pieces in magazines from GQ to Spin. He was also a popular contributor to This American Life on NPR.

Rakoff’s death was especially notable because he treated his disease with humor, which is a form of courage we give to others to spare them our pain. Rakoff, born in Canada, was also a classic New Yorker—the kind of New Yorker who believed that art and its ability to bring together, and not money and its ability to separate, was at the core of the city’s soul. He will be missed. RIP David Rakoff. You can relax now.

Rakoff visited The Daily Show in 2010 to discuss cancer and pessimism: