Skip to main content

Interview With Ryan Holiday, Author Of, The Obstacle Is The Way




Ryan Holiday's newest book is, The Obstacle is the Way: The Timeless Art of Turning Adversity to Advantage.

Deeply influenced by the Roman emperor, Marcus Aurelius, and ancient Stoic principles, Holiday shows leaders how to turn setbacks or problems into a platform for achieving goals by controlling perceptions through swift and energetic action and true force of will.


  • "Great individuals, like great companies, find a way to transform weakness into strength," explains Holiday.


Recently, Holiday shared insights into his book with me.  But first some background. Holiday is a prominent writer on strategy and business, and author of, Trust Me, I'm Lying.

After dropping out of college at 19, he apprenticed under Robert Greene, author of, The 48 Laws of Power.

In The Obstacle is the Way, Holiday pulls from stories throughout history, illustrating how icons such as John D. Rockefeller, Amelia Earhart, Abraham Lincoln and Steve Jobs took what appeared to be nearly impossible situations and made some truly astounding lemonade.





1.  Why this book now?

Holiday:  I believe that you write the book that you have to write. And this is a book I’ve really wanted to write for a while. I first discovered this Stoic exercise, of turning obstacles upside down, when I was 20 years old. Since then it’s been seared into my brain regardless of what I’ve done and I’ve always tried to think about my problems and opportunities in life through that frame.

I left college right as the financial crisis hit, which was scary. And as I worked through the dip I saw how unprepared everyone was because we all operated on assumptions or promises that didn’t exist anymore. I wanted to go back in history and ancient philosophy, to find people who overcame difficult situations. Everyone faces difficult and sometimes terrible circumstances, but clearly there’s been much worse things in history that people have overcome and I used ancient philosophy to find the strategies that those people used to come to terms with adversity and thrive despite it.

So it’s also directed toward to my peers who I saw struggling to adjust to the hand we’ve been dealt with the financial crisis and unemployment. I saw a lot of people acting entitled or defeated regarding their prospects and I wanted to give them the approach I learned to get through it.

2.  What is the single most important concept you want readers to take away from the book?

Holiday:  I think the most important idea of the book is the Stoic maxim that the book is based on:

“The impediment to action advances action. What stands in the way becomes the way.”

The first section of the book is about the discipline of perception, which is essential to overcoming adversity. Instead of giving into panic, fear, and anxiety when we are faced with an obstacle, we can flip it on its head and instead look for an advantage or positive to pull from it.

Marcus Aurelius has another great quote about this, “Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been.” It’s so important not to given into our basest emotions and instincts when we are hit in the mouth in life. Because there is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means.

The people I write about in the book, like John D. Rockefeller, Thomas Edison and Amelia Earhart, were all able to adjust their perceptions and separate themselves from the events in their lives. But it wasn’t natural for them, it was learned behavior. They learned to not give in to their immediate, emotional reactions to the obstacles that inevitably came their way. This is what allowed them to act boldly and succeed in the face of tremendous adversity.

3.  How do you think your career would be different had you finished college?

Holiday:  I was actually thinking about this recently for a column I wrote. I think I probably would have ended up more or less in the same place, but would have taken a much different path to get there.

Ambitious people who want to do great things aren't held back by the decision to finish school or not. They don’t see these types of obstacles as road blocks, but as opportunities to prove themselves. So I think it’s important to bet on yourself when it comes to the “big” decisions in your life, because then you’re able to develop a self-confidence and self-sufficiency that can be very valuable down the road.

4.  Do you expect this book to be as controversial as Greene's The 48 Laws of Power and Mastery?

Holiday:  I didn't necessarily set out to write a controversial book like I did with Trust Me, I'm Lying, so I don't think so. But unlike other books, The Obstacle Way isn’t written to puff you up or fill your head with meaningless platitudes. It was written for people who want to accomplish things in the real world, not just put the book back on the shelf and forget about it when you’re done with it. So its been interesting so far to see the reactions from readers so far.

Robert's books are controversial because he brought to light a lot of the darker behaviors and motivations that he saw other people exhibit in his life. But if The Obstacle Is The Way could have half the success that The 48 Laws of Power has had I'd be thrilled.

5.  If you could have been an apprentice to someone featured in the book (The Obstacle is the Way)  in a prior life, who would that person have been?

Holiday:  I’ve been lucky enough to have apprenticed under two great people already in my short career. Robert Greene, who taught me how to be a great researcher and write well. Then Dov Charney at American Apparel, who taught me everything I know about business today. If I had to choose someone else, I might pick a great philosopher like Marcus Aurelius or Epictetus. Or perhaps a great general like William T. Sherman.


 Learn more about the books Holiday recommends.



Comments

Popular posts from this blog

The Benefits Of When Everyone Leads

It’s only January and the new book, When Everyone Leads , could likely be my pick for the best new leadership book of 2023. It’s that good. There’s still nearly a whole year ahead of us so we’ll see what other books debut. In the meantime, add this book to your must-read list.   You’ll learn that: Leadership is an activity, not a position. Leadership is mobilizing others to make progress on the most important challenges. Leadership is interactive, risky and experimental. Leadership comes in moments. Leadership is always about change.   When Everyone Leads , by Ed O’Malley and Julia Fabris McBride , presents a revolutionary approach to leadership; not based on position or authority, but an activity that anybody can undertake by learning to spot opportunities for improvement and taking the initiative to engage others.   “It can be unfamiliar and uncomfortable, but in a culture where everyone leads, organizations start to make progress on their most difficult problems,” explain t

Effective Listening: Do's And Don'ts

Here are some great tips from Michelle Tillis Lederman's book, The 11 Laws of Likability .  They are all about: what to do and what not to do to be a leader who's an effective listener : Do : Maintain eye contact Limit your talking Focus on the speaker Ask questions Manage your emotions Listen with your eyes and ears Listen for ideas and opportunities Remain open to the conversation Confirm understanding, paraphrase Give nonverbal messages that you are listening (nod, smile) Ignore distractions Don't : Interrupt Show signs of impatience Judge or argue mentally Multitask during a conversation Project your ideas Think about what to say next Have expectations or preconceived ideas Become defensive or assume you are being attacked Use condescending, aggressive, or closed body language Listen with biases or closed to new ideas Jump to conclusions or finish someone's sentences

Five Must-Read Business Books To Read This Summer

  Stumped for what business books to add to your summer reading list? Here are  five must-read books for leaders  well worth adding to your list: Lead With A Story  -- A Guide To Crafting Business Narratives That Captivate, Convince, and Inspire . Author Paul Smith explains why storytelling has emerged as a vital skill for every leader and manager. In the book, you'll find over 100 ready-made stories you can use as templates to tell your stories. Stories are so powerful because they are simple, timeless, demographic-proof, contagious, easy to remember and inspiring. Most important, they put the listener in a mental learning mode. What's The Future Of Business? (WTF?)  -- Changing The Way Businesses Create Experiences . This book, by Brain Solis, details the incredible transformation happening in business today, driven by new social and mobile technologies. And, he explains how experience design helps your business and how you can harness its power for business growth. This book

How To Make The Leap To Becoming A Leader

Here’s another must-read book to add to your list as you transition from manager to leader. It’s The Leap to Leader , by Adam Bryant . As the creator of the iconic “Corner Office” column in the New York Times , Bryant has spoken with more than a thousand leaders over the years about the challenges and nuances of leadership. Many of his discussions are included in his interview series on LinkedIn.  “The goal of this book is to provide an intensely practical guide to making that transition by sharing insights, stories, and approaches from hundreds of leaders to build the skills you will need to make the leap to leader,” explains Bryant.   He adds that the book is useful to everyone who is interested in leadership, regardless of where they are in their career.   The book covers:   The central paradox of leaders: selfless vs. self-centered. How to perfect the do-to-say ratio. Ways to navigate office politics. Tactics to making better decisions. The crucial art of compartmentalizati

Seven Tough Questions To Ask Your Team

High-functioning teams can disagree and still produce excellent products and results. Team members can also disagree and still care about each other. And, they can challenge each other to think differently. Best-selling leadership book authors  Scott J. Allen  and  Mitchell Kusy  recommend that leaders ask seven tough questions of their teams to help maximize their results. Here are those questions to ask each team member: What are some obstacles  affecting this team? What are opportunities  we could take advantage of that we have been largely ignoring? Where can you take greater ownership  on this team? Where have you let this team down ? Compared to other teams with which you are familiar,  how are we doing ? When was the last time you complimented the team  or one of its members? How open are you to giving direct feedback  to team members?

How To Listen Effectively

Here are some great tips from  Michelle Tillis Lederman 's book,  The 11 Laws of Likability . They are all about: what to do and what not to do to be a leader who's an effective listener : Do : Maintain eye contact Limit your talking Focus on the speaker Ask questions Manage your emotions Listen with your eyes and ears Listen for ideas and opportunities Remain open to the conversation Confirm understanding, paraphrase Give nonverbal messages that you are listening (nod, smile) Ignore distractions Don't : Interrupt Show signs of impatience Judge or argue mentally Multitask during a conversation Project your ideas Think about what to say next Have expectations or preconceived ideas Become defensive or assume you are being attacked Use condescending, aggressive, or closed body language Listen with biases or closed to new ideas Jump to conclusions or finish someone's sentences

How Leaders Can Move Teams From Isolated To All In

Here is a book that provides workplace leaders an urgently needed methodology for helping companies to reduce worker loneliness, and it delivers a blueprint for building strong, high-performing workplace teams. The book is,  Connectable: How Leaders Can Move Teams From Isolated To All In , by  Ryan Jenkins  and  Steven Van Cohen .   “72% of workers suffer from loneliness. And, what was once a simmering problem shifted to a crisis when COVID-19 and the sudden transition to remove work isolated workers from each other as never before,” report the authors.   “Loneliness is the absence of connection,” explain the authors. “Loneliness is not defined by the lack of people, because someone can be lonely even while surrounded by others. We require more than the presence of others. We require the presence of others to dream, strategize, and work toward commons goals.”   Furthermore, “workplace loneliness is defined by the distress caused by the perceived inadequacy of quality connection to team

The Benefits Of When Everyone Leads

Today's FLASHBACK to earlier in the year: It’s only January and the new book,  When Everyone Leads , could likely be my pick for the best new leadership book of 2023. It’s that good. There’s still nearly a whole year ahead of us so we’ll see what other books debut. In the meantime, add this book to your must-read list.   You’ll learn that: Leadership is an activity, not a position. Leadership is mobilizing others to make progress on the most important challenges. Leadership is interactive, risky and experimental. Leadership comes in moments. Leadership is always about change.   When Everyone Leads , by  Ed O’Malley  and  Julia Fabris McBride , presents a revolutionary approach to leadership; not based on position or authority, but an activity that anybody can undertake by learning to spot opportunities for improvement and taking the initiative to engage others.   “It can be unfamiliar and uncomfortable, but in a culture where everyone leads, organizations start to make progress on

A Playbook For How Women Advance Within Business

Describing the new book, In Her Own Voice , by Jennifer McCollum , Anne Chow (former CEO of AT&T Business) says that “for women, the book does a beautiful job of explaining not just what to do to advance in your career, but also what to expect. For leaders, it helps you recognize the gap between what you think women seeking advancement want and what they really need.”  Chow adds, “the book is based on the experiences of tens of thousands of women, with guidance that is applicable to every one of us, no matter where we are on our own unique journey.”  McCollum divides her book into three parts:  Understanding the hurdles to women’s advancement Overcoming the hurdles Eliminating the hurdles  She professes that women have unique gifts and abilities. “Businesses need talented women, now more than ever. We need to do everything possible to engage, develop, and inspire them—and to advance them into leadership roles, all the way to the C-suite and board positions, if they so c

How To Be An Inclusive Leader

“No matter your title, or how advanced you already consider yourself to be as an inclusive leader, I believe this book will help you evolve and motivate you to take action,” says  Jennifer Brown  about her book,  How To be An Inclusive Leader: Your Role In Creating Cultures Of Belonging Where Everyone Can Thrive .  The book is the second edition of the bestselling title from 2021. This newest installment includes a new introduction and addresses challenges posed by the pandemic—including remote work, flexibility, and mental health.  “It also gives increased attention to embedding equity, empathy, and anti-racism in the inclusive leader framework,” shares Brown. “I’m proud that this second edition will help leaders and organizations respond to the changes unfolding around us in relevant, culturally competent ways and take action to address systemic inequities that persist in the workplace.”  In her book, Brown explores how power and authority are changing fundamentally. She explains tha