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Ryan Holiday: Book Recommendations From a Modern Stoic

Ryan Holiday is a multi-talented man, excelling in marketing, entrepreneurship, writing, and stoicism. He creates buzz and sparks discussions with his provocative campaigns like the "Legalize Gay" T-shirts and the "Ask me to take it all off" ad, leveraging the power of publicity. His book recommendations are a treasure trove of wisdom, covering stoicism, marketing, and business.
by Chris Allmer | Jun 19 2023
Ryan Holiday Book Recommendations

Ryan Holiday is a man of many talents. He’s into marketing and entrepreneurship, he’s a writer, and he also has a vested interest in stoicism. From conceiving the infamous “Legalize Gay” T-shirts to the controversial “Ask me to take it all off” ad, this man always manages to set the media abuzz and get people talking about the brands he’s promoting. After all, they say that all publicity is good publicity. He also has a knack for dishing out epic nuggets of wisdom, so Ryan Holiday’s book recommendations are a go-to repository for anyone seeking literary wisdom.

From mind-blowing insights into stoicism and proven tips on marketing and business, reading Ryan Holiday’s book recommendations is a real eye-opener. If you want to expand your knowledge horizon and up your bookshelf game, the Ryan Holiday book list is the best place to find some real gems.

So, put on your reading glasses, let’s explore Ryan Holiday’s book recommendations and find out what’s outstanding about every one of them.

Top 10 Ryan Holiday Book Recommendations

1. Letters from a Stoic by Seneca

Letters from a Stoic is a collection of letters that the ancient Roman philosopher Seneca wrote to her friend Lucilius. In those letters, Seneca shared some of his wisdom on a range of topics, including ethics and virtues and dealing with adversities. He admonished his friend to embrace the principles of stoicism, especially self-control, self-awareness, and resilience.

2. The War of Art by Steven Pressfield

In The War of Art, Steven Pressfield shares some timeless gems on how creatives can overcome the forces blocking their creativity. The author explores the creative process and uses the metaphor of “resistance” as an enemy that stops creators from really getting their creative juices flowing. Pressfield identifies resistance as procrastination, self-doubt, and fear of failure. He emphasizes the need for discipline, professionalism, perseverance, and dedication to craft, as weapons for fighting these adversaries.

3. Bird by Bird—by Anne Lamott

Considering that he is an author himself, a list of Ryan Holiday’s book recommendations wouldn’t be complete without a special book for writers. Anne Lamott’s Bird by Bird is a witty, compassionate, and thought-provoking memoir designed to guide writers through the writing process.

Lamott proposes a bird-by-bird approach to writing, which entails taking it one step at a time. She opines that this approach proves more productive than wanting to write a whole book at once. She also emphasizes the need to find one’s own voice, seek perfection and shun self-doubt.

4. Deep Work by Cal Newport

In this inspiring book, Cal Newport proffers a solution for those who constantly fight to stay focused and to achieve a great deal of work in an increasingly distracting world. In today’s world where everything is connected to the internet, it is quite challenging to keep one’s focus on work for hours without picking up the phone or falling for any other kind of distraction. The author teaches us how to eliminate distractions, get into a state of deep workflow, and manage time and energy more efficiently.

5. Discipline Equals Freedom by Jocko Willink

Discipline Equals Freedom is a timeless, no-nonsense manual that emphasizes the role of discipline in achieving personal and professional success. Jocko Willink, a former Navy SEAL and leadership expert, argues that discipline doesn’t necessarily mean deprivation. Instead, it means being in complete control of your thoughts, actions, and habits. He emphasizes the need to eliminate excuses and assume full responsibility, and claims that these are the antidotes for pushing oneself towards success and freedom.

6. How to Decide by Annie Duke

Annie Duke’s masterpiece, How to Decide, explores the human decision-making process and provides an insight into how to make better decisions. Drawing on her experience as an ex-poker player, Annie demonstrates how to make decisions with confidence and clarity.

The author argues that instead of making decisions based solely on their perceived outcomes, it is best to adopt probabilistic thinking, consider multiple perspectives, and embrace uncertainty. She opines that this strategy is instrumental in managing biases and avoiding pitfalls.

7. Man’s Search for Meaning by Viktor Frankl

In Man’s Search for Meaning, Viktor Frankl recalls his harrowing experience as a prisoner in a Nazi concentration camp during the Holocaust. In the first part, Frankl describes the dehumanizing conditions, loss of loved ones, and the threat to his life that he faced during that horrific period. Despite all that, he still maintains that man can find meaning and purpose even in the darkest abyss. In the second part, he proposes the theory of logo therapy, which professes that the search for meaning is the strongest motivation for living.

8. Mastery by Robert Greene

Bestselling author Robert Greene demystifies some beliefs about geniuses in Mastery. The book explores the process of achieving greatness in any field and asserts that anyone can achieve mastery in any skill if they embody the virtues of patience, humility, and a growth mindset. The author presents his facts based on interviews with people who achieved greatness in different fields. He emphasizes the need for constant experimentation, creativity, and perseverance to develop one’s own unique style in any skill set.

9. How to Think Like a Roman Emperor by Donald Robertson

In this book, Donald Robertson introduces readers to the principles of stoicism, following the model set by the Roman emperor Marcus Aurelius. Using the story of the emperor’s life, the author expounds upon the need to embrace meditation and other Stoic principles, including an application of virtue, wisdom, and resilience in the face of adversity.

10. That One Should Disdain Hardships by Musonius Rufus

This book is a compilation of a series of lectures delivered by first-century Stoic philosopher Musonius Rufus. The central theme of those lecturers is that hardship and difficulties should be embraced and not feared or disdained, as embracing them provides us with an opportunity for growth.

Ryan Holiday Books: Trust Him, He’s Lying

If you’re inspired by Ryan Holiday’s book recommendations, then you should also consider reading his books, especially Trust Me, I’m Lying. In this thought-provoking book, Ryan takes us on a journey into the world of online media. He explores the ways bloggers and other media outlets manipulate the media for their personal gain and that of their clients.

It’s also worthwhile reading other Ryan Holiday books like The Obstacle Is the Way, Courage Is Calling, Ego Is the Enemy, and Lives of the Stoics.

The Perfect Blinkist Reading List on Philosophy

ryan holiday books

Don’t just stop at Ryan Holiday’s book recommendations. You can extend your understanding of stoicism and philosophy by creating a perfect reading list using the vast number of books in the Philosophy category on Blinkist. Create an account now to enjoy your 7-day free trial with unlimited knowledge up for grabs.

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