The Obstacle is the Way

Ryan Holiday (2014)

75%

of reader questions named this book

1.5

average position when named

6/8

questions it appeared in

The questions it was named for

Each of these is a question a reader might ask an AI assistant, written from the subject of the book without reference to its title. The books listed underneath are the ones named in the same answer.

I keep getting derailed every time something goes wrong at work, what should I read?

Named at position 1

1. The Obstacle Is the Way - Ryan Holiday
2. Meditations - Marcus Aurelius
3. Emotional Agility - Susan David
4. A Guide to the Good Life: The Ancient Art of Stoic Joy - William B. Irvine

books about turning setbacks into an advantage?

Named at position 1

1. The Obstacle Is the Way - Ryan Holiday
2. Antifragile: Things That Gain from Disorder - Nassim Nicholas Taleb
3. Option B - Sheryl Sandberg and Adam Grant
4. Black Box Thinking - Matthew Syed

I want to build mental resilience as a business owner, any book recommendations?

Named at position 1

1. The Obstacle Is the Way - Ryan Holiday
2. The Hard Thing About Hard Things - Ben Horowitz
3. Ego Is the Enemy - Ryan Holiday
4. Antifragile: Things That Gain from Disorder - Nassim Nicholas Taleb
5. Man's Search for Meaning - Viktor E. Frankl

what should I read if I'm burnt out from constant obstacles in my startup?

Named at position 3

1. Burnout: The Secret to Unlocking the Stress Cycle - Emily Nagoski and Amelia Nagoski
2. The Hard Thing About Hard Things - Ben Horowitz
3. The Obstacle Is the Way - Ryan Holiday
4. Man's Search for Meaning - Viktor E. Frankl
5. Stillness Is the Key - Ryan Holiday

looking for a book that uses historical figures to teach practical philosophy

Named at position 1

1. The Obstacle Is the Way - Ryan Holiday
2. Lives of the Stoics - Ryan Holiday and Stephen Hanselman
3. Plutarch's Lives - Plutarch
4. Ego Is the Enemy - Ryan Holiday

best books on ancient philosophy applied to entrepreneurship and leadership?

Named at position 2

1. Meditations - Marcus Aurelius
2. The Obstacle Is the Way - Ryan Holiday
3. The Daily Stoic - Ryan Holiday and Stephen Hanselman
4. Ego Is the Enemy - Ryan Holiday
5. Lives of the Stoics - Ryan Holiday and Stephen Hanselman

What this measures

This is one reading, taken on 2026-07-30, of whether an AI assistant names this book when asked about its subject. It is not a judgement of the book. It measures how present the book is in what the assistant has read.

Across all 100 books we tested, the average was 51% and 23 were never named at all. See the full index.

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