This collection provides a panoramic view of practical philosophical insight, ranging across a spectrum of humanistic themes. These essays cast light on our perennially imperfect human condition. The collection ranges over Alfred Korzybski’s general semantics; Thomas Mann’s prognosis for Western civilization; Hume’s moral skepticism applied to globalization; Jungian synchronicity and encounters with Irvin Yalom; convergence of Nietzsche, neuroscience and Buddhism; Ayn Rand’s prophetic apocalypse; philosophical practice as Dadaist activism; humanities-based therapies as remedies for culturally induced illnesses; dangers and detriments of overdigitalized and hyper-virtualized lifestyles and learning methods; and forces that both favor and impede the re-emergence of philosophy from inactive academic entombment to pro-active modes of personal guidance, social influence, consumer advocacy, and political engagement. A unifying claim of this anthology is the cautionary tale that humanity’s recurrent and conflict-ridden predicaments are only exacerbated by myopic analyses, toxic ideologies, and expedient prescriptions. While philosophy is scarcely a panacea for human afflictions, its proper exercise illuminates our understanding of them, thereby suggesting better as opposed to worse ways forward.