David Rakoff, amid positive-pyschology titles.(Photoillustration: Tablet Magazine; Rakoff photo: Paul Roosin)

In his new essay collection, Half Empty, author and actor David Rakoff dissects a variety of cultural phenomena—from the musical Rent, to the patient-therapist relationship—with insight, sharp wit, and deep wariness. His is a deeply pessimistic perspective, as he’s the first to acknowledge. But, as he argues explicitly in the first essay and implicitly elsewhere, pessimism is not the same as a bad attitude, and it may, in fact, be an effective survival strategy.

On Vox Tablet this week, host Sara Ivry presents Rakoff, a Tablet Magazine contributing editor, with three scenarios generally deemed to be good fun and asks him to present his more cautious take on them. (Sound designer Jonathan Mitchell helped her in the project.) Rakoff also discusses the origins of his pessimism and how he copes with a life-threatening illness—while writing the book, he learned he had cancer and is now undergoing chemotherapy—without the armor of positive thinking.