In this deeply smart and sneakily poignant collection of essays, the bestselling author of Fraud and Don’t Get Too Comfortable makes an inspired case for always assuming the worst—because then you’ll never be disappointed.

Whether he’s taking on pop culture phenomena with Oscar Wilde-worthy wit or dealing with personal tragedy, Rakoff’s sharp observations and humorist’s flair for the absurd will have you positively reveling in the untapped power of negativity.