8 books like The Obstacle Is the Way
Holiday turns Stoic philosophy into three moves: see the problem clearly, act on it, and accept what you cannot change. If that worked for you, these go further: to the original Stoic notebook, to Holiday's companion books, and to writers who reached the same idea through prison camps, war or psychology.
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#1Meditations
by Marcus Aurelius
The source. The title comes from a line in Meditations: what stands in the way becomes the way. Reading it shows the private notebook the whole method grew out of.
Shared theme: Stoicism + Stoic philosophy
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Affiliate links — as an Amazon Associate, Read Stacks earns from qualifying purchases and Audible trials at no extra cost to you.- The Daily StoicRyan Holiday#2 · same author
The Daily Stoic
by Ryan Holiday
One short Stoic passage a day with a few lines of commentary. The easiest way to keep the practice going once you have finished the book.
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#3 · same authorEgo Is the Enemy
by Ryan Holiday
Holiday's next book in the same vein. This time the obstacle is your own ego, followed through three stages: aspiring, succeeding and failing.
Shared theme: Stoicism + Stoic philosophy
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#4Man’s Search for Meaning
by Viktor E. Frankl
The hardest test of the book's third discipline, the will. Frankl found in the camps that the one freedom left was the attitude a person takes to what happens.
Shared theme: Stoicism + Stoic philosophy, resilience
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#5The Courage to Be Disliked
by Ichiro Kishimi & Fumitake Koga
Adler's psychology as a dialogue. His idea of separating your tasks from other people's is a close cousin of the Stoic split between what is and is not up to you.
Shared theme: Stoicism + Stoic philosophy
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#6Antifragile: Things That Gain from Disorder
by Nassim Nicholas Taleb
Holiday says an obstacle can be used. Taleb goes one step further: some people and systems get stronger because of stress, and you can set yourself up to be one of them.
Shared theme: resilience
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#7Grit: The Power of Passion and Perseverance
by Angela Duckworth
The research version of persistence. Duckworth shows why sustained effort toward one goal predicts achievement better than talent does.
Shared theme: resilience
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#8Tribe: On Homecoming and Belonging
by Sebastian Junger
The part Stoicism mostly leaves out: people bear hardship better together, and often miss that closeness when the hard time is over.
Shared theme: resilience
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Appears in these topics
The Obstacle Is the Way is part of 2 curated reading lists — each a “best books on X” cluster with a synthesis on how the books fit together.