Candid, hilarious essays from the star of The Book of Mormon and Girls on anxiety, ambition, and the uncertain path to adulthood, which ask, How will we know when we get there?

In Uncle of the Year, Andrew Rannells wonders: If he, now in his forties, has everything he’s supposed to need to be an adult—a career, property, a well-tailored suit—why does he still feel like an anxious twenty-year-old climbing his way toward solid ground? Is it because he hasn’t won a Tony, or found a husband, or had a child? And what if he doesn’t want those things? (A husband and a child, that is. He wants a Tony.)

In deeply personal essays drawn from his life, as well as his career on Broadway and in Hollywood, Rannells argues that we all pretend we are constantly succeeding—for friends, partners, parents, and others—in the process known as “adulting.” But if this acting is leaving us unfulfilled, then we need new markers of time, new milestones, new expectations of what adulthood is and can be.

Along the way, Rannells navigates dating, aging, mental health, bad jobs, and much more. In his essay “Uncle of the Year,” he explores the role that children play in his life, as a man who never thought having kids was necessary or even possible—until his siblings have kids and he falls in love with a man with two of his own. In “Always Sit Next to Mark Ruffalo,” he reveals the thrills and absurdities of the awards circuit, and the desire to be recognized for one’s work. And in “Horses, Not Zebras,” he shares the piece of wisdom that helped him finally come to terms with his anxiety and perfectionism.

Filled with honest insights and a sharp wit, Uncle of the Year challenges us to take a long look at who we’re pretending to be, who we know we are, and who we want to become.