“The name Ryan Holiday is now almost synonymous with the modern resurrection of Stoicism, the 2,000-year-old philosophy that somehow remains spookily applicable to life today.” Holiday’s influence extends beyond his popular books; lessons he teaches about perspective, discipline, and perseverance have transformed how so many people approach adversities in both their personal and professional lives. Ryan Holiday has become on of the most qualified experts on golf and self-help alike, distilled into this practical advice.”
A Brief Overview of Ryan Holiday
Ryan Holiday has taken a somewhat unconventional route into the realms of philosophy and literature. Greene, 36, was raised and trained for a marketing career (she interned for The 48 Laws of Power author Robert Greene) at a young age. Holiday’s work also quietly echoes Greene’s, from the way he brings historical details and philosophical precepts to life to give texture to his gripping narratives.
By the time Holiday burst on the waves the marketing director at American Apparel, he had already earned notoriety for some of his unorthodox, at times inflammatory, methods. Instead, he quickly became a writer, realizing that he wanted to spread Stoic ideas to the world. Through his work, Ryan Holiday revived stoicism and brought its teachings back into the popular conversation, providing millions of readers with a playbook to address the complexities of daily life.
Ryan Holiday’s Thoughts and Impact
Ryan Holiday’s philosophy is based on the ancient school of Stoicism, a school prioritizing values like knowledge, courage, justice and self-control. Stoicism teaches that we are not responsible for external events, only responsible for our response to those events. This “rule,” Holiday said, is something that’s important to follow if one wishes to live a happy and vigorous life. Popularizing Stoic ideas, his work reframes Stoicism to give modern advice on contemporary problems.
Holiday offers a practical, hopefully inspirational contemporary reading of stoicism. Challenge, he argues, should be welcomed, not dreaded. Obstacles in his world make stepping stones forge barriers and hurdles. His advice on perseverance and the toughness of the mind, both directly taken from Stoic ideals, has spoken to all readers, from business men and women to sports men and women to artists to even military leaders.
The thesis behind all of Holiday’s writing is that adversity and struggle are not something we should cringe from, but rather something that are good, and necessary. Alternatively, Holiday provides a new perspective on success and motivates people to view challenges as paths to perseverance. His ideas about cutting the bullshit, only doing what is necessary while putting yourself through minimal pain has established him as a leader in self-help and business literature.
Important Pieces by Ryan Holiday
Ryan Holiday’s book is footnoted with an extensive bibliography of insightful quotes both in history as well as first-hand accounts. And all together his major works are engaging in their own way with extraordinary problems — ego, silence, resilience — yet they are using the values of the Stoics.
1. The Way Is the Obstacle (2014)
One of Ryan Holiday’s most popular books, “The Obstacle Is the Way” does a brilliant job teaching you how to turn obstacles into opportunity. That the stoic truism — success is generally on the other side of the trials we most want to dodge — might so nearly be contained in the headline. Invoking Marcus Aurelius, Holiday approaches the question based on how we respond when things get tough. The book outlines three critical building blocks for overcoming any adversity: “
- Perception: The way in which we perceive and identify our challenge. If we examine any challenges we may face in a different light, we can use them as accelerants for our growth.
- Take action: You know what needs to be done, now simply do it. Once in a while you drop a name and they regard your guide like stone. This is the value Holiday articulates of versatility and ingenuity.
- Will: Building courage and accepting what we can’t change and recognizing what we can.
The Obstacle Is the Way resonated widely with readers around the world and has become something of an owner’s manual for readers looking to tame the obstacles in their personal and professional lives. Everyone, from NFL teams to corporate leaders, latched on to its principles, nixing any question of its place as a mainstay of the self-help universe.
2. Ego is the Enemy (2016)
In Ego Is the Enemy, Ryan Holiday takes on one of success’s worst enemies: with us. The case they make in this book is that without challenge, ego, vanity, and self-importance can mislead even the best of us. Holiday illustrates how some of history’s greatest minds — people akin to General William T. Sherman and media giant Katharine Graham — succeed by controlling their egos with the help of literature, philosophy and history.”
There are three parts to the book:
- Aspirations: the perils of allowing ego to get in the way of our goals.
- Succeed: How, if we do succeed, could we possibly fail, because we are blinded by ego?
- Failing: Ego is perhaps, in many ways, the leading cause of failure — and learning how to be humble could bring us back.
The Ego Is the Enemy is an excellent reminder that self-awareness, humility, and lifelong learning engender lasting success. The ego-control cultivation of Ryan Holiday’s is as classic and applicable a road map to leadership and personal development as you’ll find.
3. The Daily Stoic Journal (2017) and The Daily Stoic (2016)
“The Daily Stoic is an invaluable tool for anyone looking to apply stoicism to everyday living. This book, co-written by Ryan Holiday and Stephen Hanselman, has 366 reflections on life lessons, resilience and the craft of living. Every post starts with a quotation from a Stoic philosopher like Epictetus, Seneca or Marcus Aurelius, and ends with a brief explanation of how the lesson could be put to use in everyday life.”
Holiday’s also released The Daily Stoic Journal, a supplementary work intended to help readers contemplate the meditations as well as use the principles of stoicism in their lives. These tools have helped thousands of people develop a stoic mindset, one day-at-a-time, through daily reflection and focused writing.
4. In 2019: Stillness Is the Key
In Stillness Is the Key, Ryan Holiday muses on the idea that calmness and tranquility are prerequisites for living a happy life. And by applying the tenets of Buddhism, stoicism and other philosophical traditions, Holiday argues that calmness is more important than ever within a distraction- and noise-filled society. The book espouses finding inner peace, slowing down and focusing on what matters.”
There are three sections to the book:
- Mind: Cultivating Clear Heads, Control, and Focus
- Spirit: Expanding in wisdom, humility, and gentleness.
- And body: Prioritising the physical | Rest, wellness
Using historical figures like Anne Frank, Winston Churchill and Tiger Woods as case studies, Holiday illustrates how greatness can emerge from quiet. Many readers have reported the practical advice in Stillness Is the Key helpful in achieving balance and peace of mind in an ever more frantic world.
5. The Call of Courage (2021)
“Bravery Is Calling” explores the nature of bravery itself, “The Obstacle Is the Way” focuses on continuing to craft through the hard moments. This book is the first in a series of four books that Ryan Holiday is publishing that each cover one of the four Stoic virtues: courage, discipline, justice, and wisdom. In “Courage Is Calling,” Holiday argues that courage is more than a series of monumental acts: It’s about the little choices we make, daily.”
Holiday categorizes bravery into three categories:
- Moral Courage: Championing the right thing, against all odds.
- Bodily Courage: Trucidating with bodied risk or hardship.
- Psychological Courage: Overcoming uncertainty and fear.
Including examples from historical and modern figures, Holiday shows that courage is a choice that we have to make continually. Whatever else, the book Courage Is Calling calls on readers to face their fears, live fearlessly.
6. Discipline Is Destiny (2022)
Discipline Is Destiny, the second book in Ryan Holiday’s centennially named series on the Stoic virtues, emphasizes the importance of discipline and self-control in our going to the top. Using examples like Queen Elizabeth II, Lou Gehrig, George Washington and more, Holiday makes the argument that discipline is the ingredient behind greats. It is your discipline which creates the separation of a successful person and an unsuccessful person be it by hunger pain, scheduling yourself or abstaining from temptation.’
Holiday’s insight into the way human beings tick and his practical advice on building self-discipline are what turn Discipline Is Destiny into a holy grail for all who seek to control their basal impulses and fulfill their dreams.
Putting Ryan Holiday’s Teachings into Practice
In part, Ryan Holiday’s work has resonated so deeply because it is prescriptive, and can be integrated into everyday life. Along with being theoretical reflections, his works also give practical advice on how to overcome obstacles, control ego, and become a stoic.
Application in Private Life
Many have done Ryan Holiday Lessons and later on applied them in there own life. The stoic principles offer a way to approach challenges — from fighting with family and failing at work to living a more purposeful, sturdy life. Second, the idea that “the obstacle is the way” has allowed people to view their difficulties as a chance for self-improvement, a few of the lessons that have helped promote a more constructive attitude toward the trials that life can bring.
Holiday’s focus on what’s within our control can be a powerful remedy for the worry and stress many people experience. You cannot control everything, and by releasing what you can’t control and directing your energies to what you can, people can reduce unnecessary stress and enjoy greater peace.
Use in Leadership and Business
Ryan Holiday is a popular author among business executives, business leaders, and business owners. The issues that come with running a company are highly applicable to the principles of stoicism — staying calm under pressure, making unemotional decisions, keeping the bigger picture in mind. And organizational leadership that understands these ideas are more insulated and able to response and contend with the inevitable highs and lows that businesses face.
Holiday’s caution against hubris, extended in Ego Is the Enemy, is all the more relevant in the corporate world, where unchecked ego can leave fertile ground for bad decisions and toxic workplaces. In this space, Holiday’s admonition rings particularly true. Holiday’s work has inspired a generation of leaders who value self-improvement over self-promotion. Toward that end, she urged humility and curiosity and a commitment to education.
Use in Athletics and Performance
These lessons have also been learned by athletes and entertainers, said Ryan Holiday. The three Stoic characteristics that strongly correlate with the mental toughness necessary to succeed in athletics are resilience, discipline, and focus. Both team and individual professionals alike have adopted the philosophies of The Obstacle Is the Way, pushing through adversity, bouncing back from failure, and finding their way towards attaining their goals.
Work such as Holiday’s has long been commended by coaches and individual athletes as an essential component of that mental toughness needed to compete successfully at the highest levels. Most athletes can perform in moments of pressure by being stoical and only focusing on what is within their control.
His influence is enormous and, importantly, cuts across all educational and professional backgrounds. In the midst of the revival and mainstreaming around Stoicism, Holiday has created an instructive framework for coming to terms with the challenge that is part of the human experience of life in the present day. His writings are evergreen direction and easy to read, interesting and useful.
Big Picture: Through “obstacle theory”, learning to control the ego, and creating an inner meditative state, Ryan Holiday has shaped how we view a successful and fulfilling life. His work is highly motivational to understand first that challenges are part of the journey, and before trying to find how to overcome them, the solution is the awareness and acceptance that they are part of the journey, and that there is no escaping from them
“Thanks to the work of Ryan Holiday, I feel confident that his influence will be felt for generations to come as more people adopt the value of stoicism and teach their children how to deal with adversity with resilience and fortitude and wisdom.” Through applying contemporary examples to timeless wisdom, Ryan Holiday has changed our relationship to struggle and sparked a guide to a life driven by virtue and meaning.