Introduction: The power of bittersweet -- Part I. Sorrow and longing: how can we transform pain into creativity, transcendence, and love?. What is sadness good for? ; Why do we long for "perfect" and unconditional love? (And what does this have to do with our love of sad songs, rainy days, and even the divine?) ; Is creativity associated with sorrow, longing--and transcendence? ; How should we cope with lost love? -- Part II. Winners and losers: how can we live and work authentically in a "tyranny of positivity"?. How did a nation founded on so much heartache turn into a culture of normative smiles? ; How can we transcend enforced positivity in the workplace, and beyond? -- Part III. Mortality, impermanence, and grief: how should we live, knowing that we and everyone we love will die?. Should we try to live forever? ; Should we try to "get over" grief and impermanence? ; Do we inherit the pain of our parents and ancestors? And, if so, can we transform it generations later? -- Coda: How to go home.