Applied Stoicism and Vain Hero-Worship

Ryan Holiday, The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

I wanted to like media innovator Ryan Holiday’s brief introduction to Stoic philosophy. He eschews Philosophy 101 jargon, focusing instead on lived experiences by people who embody Stoic principles. By apprenticing ourselves to life’s rolling hardships, Holiday promises, we overcome momentary setbacks and make apparent obstacles into lasting triumphs. And Holiday promises to distinguish true capital-S Stoicism from pop images of stone-faced impassivity.

Then I got past the introduction and read the chapters. Holy schnikes.

Historian James Loewen writes that the process he calls “heroification” turns “flesh-and-blood individuals into pious, perfect creatures without conflicts, pain, credibility, or human interest.” Holiday uses object lessons from people who willfully or coincidentally lived Stoic lives. But he engages in rank heroification, not only contrasting our tumultuous lives to immobile hagiographies, but turning his exemplars’ lives into the exact opposite of what their actions really accomplished.

Yes, John D. Rockefeller pulled fortunes from extreme economic turmoil. He also dumped so much industrial filth, including gasoline, into the Cuyahoga River that the water itself caught fire. Holiday praises Rockefeller’s refusal to crack for federal prosecutors. But Rockefeller got prosecuted because he ignored laws, using his monopoly to manipulate markets. Adjusted for inflation, Rockefeller was probably the richest man ever; but he was also a criminal and profiteer.

Yes, Rubin “Hurricane” Carter emerged from prison triumphant. But he was never exonerated; prosecutors simply declined a third trial, because after twenty-two years, too many witnesses had died or moved away. During his second trial, Carter beat bail bondswoman Carolyn Kelly so severely, she required hospitalization, and he’s never explained why. Despite intermittent celebrity endorsements, Carter’s case remains far more ambiguous than Norman Jewison’s starry-eyed 1999 biopic would admit.

One could continue. Holiday’s blatant heroification tactics freeze complex humans in moments so abstract, it’s downright dehumanizing. Sure, Ulysses S. Grant fought admirably in war, but war’s rigors shaped his goals. In civilian life, his business ventures folded, he was a chronic drunk, and historians consider his Presidency a failure. Holiday repeatedly discusses entire groups of people, like astronauts, Allied soldiers in Europe, and “the Greeks,” like great faceless masses.

Marcus Aurelius

Nobody requires deeper explication in Holiday’s telling. But this isn’t just about Holiday’s narration. His human examples, basically mere anecdotes, exemplify his entire technique. Where Stoic pioneers like Seneca, Cicero, and Marcus Aurelius slowly unpacked principles as modes of lifelong training, Holiday gallops quickly through strings of bromides (“you’re probably not going to die from any of this,” “outward appearances are deceptive”) that never much occupy his time.

But Holiday hides the solution to his problems in his text. It’s hidden so deeply, he perhaps misses it himself. But quoting Epictetus, Holiday tells readers to imagine supposed sages having sex: “See them in your mind, grunting, groaning, and awkward in their private life—just like the rest of us.” Bloody good advice. Holiday could apply it to the heroes he unthinkingly extols throughout this frustratingly underexamined book.

Marcus Aurelius spent decades discovering and refining the thoughts comprising his Meditations. Life, for him, was an ongoing philosophical boot camp. He never stopped asking himself important questions: what opportunity does this challenge present? Does this worry really merit my time? What did this defeat teach me? Hardly some proverbial to-do list, Stoicism was, for Marcus Aurelius, a never-ending process of discovery and re-invention.

One could apply this same tactic to Holiday’s various heroes. Pericles became an accomplished general, in part, to overcome embarrassment for his father’s ostracism and his own weirdly misshapen head. Gandhi arrived at his nonviolent philosophy only after struggling with the morality of two world wars. No wonder Catholic activist Dorothy Day’s dying wish was to never be canonized: sanctification freezes humans in amber.

Admittedly, while he cherry-picks his facts, Holiday never says anything philosophically wrong. He adroitly encapsulates Stoic principles in memorable sayings and concise (if self-serving) contexts. But nothing, evidently, merits much of Holiday’s time. He takes Stoicism, a complex and multifaceted approach to the well-lived life, and reduces it to a checklist of platitudes. That sells books, but probably doesn’t change lives.

And that’s a damn shame. If any philosophy’s time has come ‘round again, surely it’s Stoicism. Its steely-eyed, objective approach to life contrasts with today’s highly emotive “culture of psychotherapy.” (I know, that totally misrepresents psychotherapy. Bear with me.) As frustrated as Holiday’s bullet-point approach leaves me, his energetic but ultimately unrealized thesis inspires me to reread the source materials:

Epictetus, Discourses and Selected Writings
Seneca, Letters from a Stoic
Marcus Aurelius, Meditations




CODA: After posting the commercial version of this review to Amazon.com, I began getting negative votes and very harsh ad hominem attacks, generally coming in clusters—I got nearly twenty negative votes in under two hours. This reaction seemed extreme for a book which, then, wouldn't be released for over a month. Only afterward did I learn that Ryan Holiday has confessed, in the past, to using Asian "click farms" to distort online feedback for his work, and work by his paying clients.

This tells me that, besides doing a lackluster job selling his philosophical standpoint, he also doesn't live by it. I've read Marcus Aurelius' Meditations, in which the author extols the virtues of a mild temper and a refusal to let others' emotions cloud one's judgment. I have a hard time imagining Marcus, or any other true Stoic, trying to manipulate public perception through covert tactics. I refer you, again, to the original source texts; Ryan Holiday is a poor salesman for his philosophy.