Taking stoicism seriously: lessons from Stockdale and a live Q&A

Executive overview

Admiral James Stockdale credited stoicism with helping him survive seven years as a prisoner of war — and still wanted to go deeper afterward. The question he faced is the same one serious students of philosophy face: what does the next step actually look like?

The philosophy only works if you treat it as a living practice, not a subject you've already studied.

Stockdale, Durant, and the case for lifelong study

• After returning from Vietnam, Stockdale met philosopher Will Durant and asked about deepening his stoic practice
• Durant pointed him to a passage in Life of Greece: stoicism "produced the strongest characters of its time" — Marcus Aurelius, Epictetus, Cato
• Marcus Aurelius himself kept attending philosophy lectures as an old man — remaining a student is the practice
• Seneca's principle: "How much progress shall I make? Just as much as you try to make"

Passing stoicism to children

• Kids are rarely interested in what parents find educational — forcing it backfires
• Look for small, natural sparks of interest and put energy behind those
• One example: a child uninterested in Rome became obsessed with Greek history via a podcast, leading to trips to Greece
• The adjacent interest (Greek history) is close enough — take the opening when it appears
• Trying to meet kids where they are (Mr. Beast, dinosaurs) is part of the work

Stoicism and governance

• The stoics were deeply interested in governance; Zeno wrote a Republic — now lost
• Marcus Aurelius in Meditations credits his brother Severus with introducing him to figures like Cato and Brutus
• Marcus describes the ideal as "a society of equal laws governed by equality of status and of speech and of rulers who respect the liberty of their subjects above all else"
• The gap between the ideal and reality (an emperor articulating liberty) mirrors Jefferson — the idea matters even when imperfectly lived

On writing, teaching, and reaching people

• Ryan Holiday's primary medium is books — talks and public appearances are the opposite of what drew him to writing
• Content in multiple mediums (podcast, video, etc.) is an attempt to meet people where they are
• No formal workshops or clubs planned — but the idea holds appeal for smaller groups
• Teaching his own children stoicism, however resistant they are, remains the most direct version of this work

Running the Marathon to Athens

• Holiday ran the original Marathon-to-Athens route — and got heat stroke, arriving sick at the Olympic Stadium
• Lessons: don't run it alone in July; plan nutrition and caloric intake, not just willpower
• Came out too fast (low-six-minute miles for the first miles) — not sustainable over 26 miles on a concrete, hilly, industrial course
• Discipline includes restraint — holding back is as important as pushing through
• Practical note: a shirt is required to enter the Olympic Stadium