Susan Cain’s Bittersweet: How Sorrow and Longing Make Us Whole is about the value of a “bittersweet” outlook on life. Notably, Cain speaks to the workplace, and how “[i]t’s the chronic suffering, and the everyday suffering—triggered by relationship challenges, financial struggles, non-life-threatening afflictions, work stress, office politics, poor management, etc.—that is largely suppressed and/or undiscussable at work.” The ultimate question—how do we, as business owners, leaders, and supervisors, create an atmosphere in which such suffering is not “undiscussable” without breaching boundaries?