Ten years revisiting The Obstacle Is the Way: lessons on growth and revision

Executive overview

Fear of starting is the trap Seneca identified: fools delay, letting fear and laziness win. The antidote is courage, discipline, and recognising that what you're putting off may matter to others.

Revisiting work a decade later is humbling and instructive. What doesn't age well is certainty, simplification, and harsh judgment. The real lesson isn't the embarrassment — it's using that discomfort to do the next thing better.

Every time you go back to old work, you're measuring how much you've grown.

Fear of starting and the stoic virtues

• Seneca: "That's the one thing all fools do — they delay to start."
• Courage pushes past fear; discipline wills you to act regardless.
• Justice adds weight: if the work could help people, inaction has a cost to others, not just yourself.
• Seneca: "No man is more unhappy than he who never faces adversity, for he is never permitted to prove himself."

The 10th anniversary revision process

• The book sold millions of copies across 40 languages — far beyond the original prediction of 5,000 copies.
• Revision method: physical notecards accumulated over a decade, printed manuscript, handwritten edits.
• Holiday worked in fragments — not long sessions but small daily contributions to the manuscript.
• Re-recording the audiobook forced a slow, word-by-word pass; it surfaced problems a read-through misses.
• The river metaphor applies: "We never step in the same river twice" — the reader and writer are both different.

What gets cut, added, and softened

• Added: a fuller portrait of Marcus Aurelius — the plagues, floods, lost children, years at war — not just the aphorism.
• Added: Chris Hadfield's line from space: "There's no problem so bad that you cannot make it worse also."
• Cut: the section on Rommel.
• Qualified: the Rockefeller chapter — at 24, Holiday focused only on the heroic arc; a decade of reading on ego, stillness, and justice forced a more nuanced portrait.
• The stories themselves don't change; what jumps out at you does, and the meaning shifts with it.

What a decade of growth actually looks like

• Certainty, simplification, and judgment are the things that age worst in writing.
• Going back and finding nothing to fix is a warning sign, not a compliment — it implies no growth since the work was done.
• Stoicism's popularity has transformed: when the book was written, the subreddit had 9,000 subscribers; now it has half a million.
• The original task was to popularise an unknown philosophy; now the obligation is to give a fuller, more nuanced picture of it.
• Subsequent books — on ego, stillness, discipline, justice — changed what Holiday sees in the same source material.

Discipline and process

• Holiday's rule during revision: you don't need to make enormous contributions — just one or two good things to the manuscript each day.
• He writes with physical notecards, reads physical books, and works from a printed, bound manuscript.
• Even on Thanksgiving, on vacation, in green rooms before TV appearances — the work continued in whatever time was available.
• Gratitude, not pride, is the dominant feeling: the book, the platform, and Stoicism's reach exist because of reader feedback and collective engagement.