Finalist for the Thurber Prize for American Humor "In this surprisingly upbeat memoir, Annabelle Gurwitch writes about the financial curveballs that can hit you in midlife . . . Somehow, Ms. Gurwitch manages to find humor in these setbacks. Ultimately, this is a story about harnessing resilience and learning how life’s disappointments can teach you about the things that matter most." —Tara Parker-Pope, The New York Times From the New York Times bestselling author of I See You Made an Effort comes a timely and hilarious chronicle of downward mobility, financial and emotional. With signature "sharp wit" (NPR), Annabelle Gurwitch gives irreverent and empathetic voice to a generation hurtling into their next chapter with no safety net and proves that our no-frills new normal doesn't mean a deficit of humor. In these essays, Gurwitch embraces homesharing, welcoming a housing-insecure young couple and a bunny rabbit into her home. The mother of a college student in recovery who sheds the gender binary, she relearns to parent, one pronoun at a time. She wades into the dating pool in a Miss Havisham-inspired line of lingerie and flunks the magic of tidying up. You're Leaving When? is for anybody who thought they had a semblance of security but wound up with a fragile economy and a blankie. Gurwitch offers stories of resilience, adaptability, low-rent redemption, and the kindness of strangers. Even in a muted Zoom.