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What to read next

Books like The Obstacle Is the Way

If you liked The Obstacle Is the Way by Ryan Holiday, here are 8 non-fiction books to read next — hand-matched on shared themes and authors, not an algorithm. Each links to where to get it.

  1. Ego Is the Enemy by Ryan Holiday — book cover
    #1 · same author

    Ego Is the Enemy

    by Ryan Holiday

    The companion to Obstacle. Most failures aren't incompetence — they're ego refusing to do the boring foundational work.

    Shared theme: Stoicism + Stoic philosophy

    Read the key ideas
    Buy Ego Is the Enemy on Amazon·🎧 Free 30-day Audible trial
    Affiliate links — as an Amazon Associate, Read Stacks earns from qualifying purchases and Audible trials at no extra cost to you.
  2. Man’s Search for Meaning by Viktor E. Frankl — book cover
    #2

    Man’s Search for Meaning

    by Viktor E. Frankl

    Stoic without being labeled. Frankl's logotherapy arrived at Aurelius's insight independently — reading both makes both clearer.

    Shared theme: Stoicism + Stoic philosophy

    Read the key ideas
    Buy Man’s Search for Meaning on Amazon·🎧 Free 30-day Audible trial
    Affiliate links — as an Amazon Associate, Read Stacks earns from qualifying purchases and Audible trials at no extra cost to you.
  3. Meditations by Marcus Aurelius — book cover
    #3

    Meditations

    by Marcus Aurelius

    The foundation. Marcus Aurelius wrote it for himself; the recurring theme is control what you can, accept what you can't, do right now.

    Shared theme: Stoicism + Stoic philosophy

    Read the key ideas
    Buy Meditations on Amazon·🎧 Free 30-day Audible trial
    Affiliate links — as an Amazon Associate, Read Stacks earns from qualifying purchases and Audible trials at no extra cost to you.
  4. The Courage to Be Disliked by Ichiro Kishimi & Fumitake Koga — book cover
    #4

    The Courage to Be Disliked

    by Ichiro Kishimi & Fumitake Koga

    Adlerian psychology in dialogue form. Heavy overlap with Stoic ethics — separation of tasks, choice of meaning, focus on control.

    Shared theme: Stoicism + Stoic philosophy

    Read the key ideas
    Buy The Courage to Be Disliked on Amazon·🎧 Free 30-day Audible trial
    Affiliate links — as an Amazon Associate, Read Stacks earns from qualifying purchases and Audible trials at no extra cost to you.
  5. #5 · same author

    The Daily Stoic

    by Ryan Holiday

    Another Stoic philosophy pick — same territory as The Obstacle Is the Way.

    Buy The Daily Stoic on Amazon·🎧 Free 30-day Audible trial
    Affiliate links — as an Amazon Associate, Read Stacks earns from qualifying purchases and Audible trials at no extra cost to you.
  6. #6

    A Guide to the Good Life

    by William Irvine

    Another Stoic philosophy pick — same territory as The Obstacle Is the Way.

    Buy A Guide to the Good Life on Amazon·🎧 Free 30-day Audible trial
    Affiliate links — as an Amazon Associate, Read Stacks earns from qualifying purchases and Audible trials at no extra cost to you.
  7. #7

    How to Think Like a Roman Emperor

    by Donald Robertson

    Another Stoic philosophy pick — same territory as The Obstacle Is the Way.

    Buy How to Think Like a Roman Emperor on Amazon·🎧 Free 30-day Audible trial
    Affiliate links — as an Amazon Associate, Read Stacks earns from qualifying purchases and Audible trials at no extra cost to you.
  8. #8

    Letters from a Stoic

    by Seneca

    Another Stoic philosophy pick — same territory as The Obstacle Is the Way.

    Buy Letters from a Stoic on Amazon·🎧 Free 30-day Audible trial
    Affiliate links — as an Amazon Associate, Read Stacks earns from qualifying purchases and Audible trials at no extra cost to you.