In her mid-forties, Gwendolyn Bounds attended a dinner party where someone asked a little girl: "What do you want to be when you grow up?" It struck Bounds: In middle age, no one asks you that anymore. So, she put the question to herself. The answer set her on an unexpected five-year path of transformation from an unathletic office executive glued to her screens into an age group medalist and world championship competitor in obstacle course racing. In this book, Bounds explores how tackling something new and hard upended her expectations for middle age-while also helping the author reconcile regrets of her youth. Her story takes us from playgrounds and gyms where Bounds relearns childhood movements (swinging from monkey bars, climbing a rope) to far-flung Spartan Race courses where she strives to master running in difficult terrain and conquering challenges.