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Ancient Wisdom for Modern Life: Ryan Holiday’s Recommended Reads

Want to learn from the lessons of history and mistakes of others in order to live your best life? Check out marketing whiz Ryan Holiday’s favorite books.
by Natallia Darozhkina | Nov 23 2021

Ryan Holiday, bestselling author and media strategist, is known for his love of Stoic philosophy and ancient history. He developed his own efficient method of reading philosophical and historical books, extracting their key lessons, and connecting ancient ideas to modern life.

In this book list, Holiday suggests some great reads on personal development, writing mastery, and general advice on life and love.

Ryan Holiday’s Book Recommendations

One of the world’s most famous and influential books, Meditations, by the Roman emperor Marcus Aurelius (A.D. 121–180), incorporates the stoic concepts he used to cope with his life as a warrior and administrator of an empire. In the wake of war and natural disasters occurring during his reign, Aurelius set down a series of private reflections, outlining a philosophy of commitment to virtue above pleasure, and tranquility above happiness.

Ryan says:

“The idea that the most powerful man in the world was also jotting down admonishments to himself for how to be better, more philosophical…and that these notes survive for us to read is almost unbelievable.”


2. What Makes Sammy Run by Budd Schulberg

This classic book shaped how two generations viewed the film industry and introduced Hollywood archetype, Sammy Glick. As Budd Schulberg follows Sammy’s rise and fall, he creates a virtuoso study in character that manages to be hilariously appalling yet deeply compassionate.

Ryan says:

“A novel of ambition and what it does to the people that have it, the importance of hustle and gumption but the price we pay if these traits aren’t balanced out by ethics and purpose.”


3. What I Talk About When I Talk About Running by Haruki Murakami

While simply training for the New York City marathon would be enough for most people, Haruki Murakami decided to write a book about it as well. The result is a beautiful memoir about his intertwined obsessions with running and writing, full of vivid memories and insights, including the eureka moment when he decided to become a writer.

Ryan says:

“The link between writing and running is under-explored. Indeed I think every creative person should balance out their cerebral career with a form of intense physical exercise.”


4. Tiny Beautiful Things: Advice on Love and Life from Dear Sugar by Cheryl Strayed

Sugar—the once-anonymous online columnist at The Rumpus, now known as Cheryl Strayed—is the person thousands turn to for advice. Tiny Beautiful Things brings the best of Dear Sugar to one place and includes never-before-published columns. Rich with humor, insight, compassion and absolute honesty, this book is a balm for everything life throws our way.

Ryan says:

“Wonderful advice here for any young person, anyone trying to follow their dreams, from a thoughtful, articulate and wise woman.”


Simplify Extra Credit Reading

Based on the latest episode of Simplify with Ryan Holiday, we created a book list that you can read (or listen to!) on Blinkist in 15 minutes or even less.

Told from the personal perspective of author Anne Lamott, Bird by Bird is a guide toward becoming a better writer and improving your life along the way. Lamott’s distinctive approach, honesty, and personal anecdotes make this book a must for writers or anyone who wants to become one.

The 48 Laws of Power takes an irreverent look at the fundamental characteristics of power, and how to understand it, defend against it, and use it to your advantage. It offers compelling insights, backed by historical examples, into the dynamics of competition and control.

In The Obstacle is the Way, Ryan Holiday brings the age-old wisdom of Stoic philosophy up to date. By examining the struggles of historical figures of inspiring resilience, Holiday shows not only how obstacles couldn’t stop them, but more importantly, how these people thrived precisely because of the obstacles. Holiday shows how we can turn obstacles to our advantage, and how we can transform apparent roadblocks into success, both in our businesses and our personal lives.

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