Holiday builds a book around a line from Marcus Aurelius, that what stands in the way becomes the way, and organises it into three parts corresponding to the Stoic division of perception, action and will. Perception covers how a person interprets a situation, action covers what they do about it, and will covers what they endure when nothing can be done.
The perception section argues for controlling the emotional response before assessing the facts, for recognising that the label placed on an event determines the response to it, and for practising objectivity by describing situations without evaluative language. The action section argues for persistence, for starting with what is immediately in front of you, for iteration over planning, and for using an opponent's strength against them where direct confrontation would fail. The will section covers acceptance of what cannot be changed, preparation for setbacks through negative visualisation, and the argument that a person can always choose to persist.
The historical cases include John D Rockefeller during the 1857 panic, Ulysses Grant, Amelia Earhart, Rubin Carter, Thomas Edison and Theodore Roosevelt, each used briefly to illustrate a principle.
The book contains no research and the cases are simplified to fit. Holiday moves quickly and repeats himself across his books. The argument that obstacles are opportunities can encourage a reading in which genuine harm is reframed as benefit, and Holiday does not distinguish carefully between situations where the framing helps and situations where it obscures a real problem. As a compressed and readable statement of applied Stoicism for a working audience, it does its job.
Operators facing a specific setback who want a compressed and readable application of Stoic practice rather than the primary texts.
Author and media strategist; former director of marketing at American Apparel and owner of the Painted Porch bookshop in Texas.
The Obstacle Is the Way and Ego Is the Enemy convert Stoic practice - separating what is controllable from what is not, treating recognition as a threat to judgment - into working habits for people running companies, which is why the books circulate so widely among founders. Trust Me, I'm Lying and Growth Hacker Marketing document how online media incentives can be manipulated, written by someone who did it professionally.
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