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

How To Achieve Human Leadership

Human Leadership: The Courage To Face Ourselves And Each Other is Kristen Hadeed ’s newest book. It’s a raw, personal account of losing herself in service to others and the challenging work of finding her way back.   It’s a story of burnout, ambition, resentment, grief, reinvention, profound self-examination, and the courage it takes to share what you discover with the people around you. By learning to face herself, tell the truth, and take ownership of her choices, Hadeed became a more courageous, compassionate leader and built a life and business that would take care of her, too.   Hadeed’s journey shows that leadership doesn’t have to mean endless sacrifice or self-abandonment. Human Leadership offers a different path―one where courage, honesty, and humanity become the foundation of meaningful leadership and a meaningful life.   Part memoir, part invitation, Hadeed’s story will empower you to:   Recognize the values, fears, and limiting beliefs driving your lead...

The Playbook For CEOs To Lead Under Pressure

“Most CEOs spend years mastering strategy, finance, operations, and execution,” says author Andrea Petrone , “Far fewer spend time defining who they are as leaders.” He adds that all too often the leadership style that got a CEO to the top becomes the very thing holding them back.   More specifically, after more than two decades coaching CEOs and senior executives at Shell, Unilever, Takeda, EssilorLuxottica, and PwC, Petrone noticed a pattern: sustained pressure was pulling leaders away from who they were. Fortunately, in his latest book, Reinvention at the Top: The Playbook for CEOs to Lead Under Pressure , Petrone introduces the Throughline, an architecture that helps leaders align their identity, message, and presence so they can lead powerfully under pressure. Whether stepping into a new role, navigating a crisis, or reinventing an organization, Throughline offers CEOs a practical roadmap for leading without losing themselves.   As you read the book you will discover: ...

How To Build A High Performing Sales Team

  Based on Stephanie Friedman 's 20 years of sales experience, her new book, Built to Grow: A Handbook For High-Performance Sales Teams , is the perfect step-by-step, go-to-market field guide for startup founders.   Friedman offers readers a structured and repeatable methodology for building a high-performing sales function from a company’s earliest days. The book is divided into three phases of startup growth— Experiment, Build, and Scale.   Within each of the three phases, Friedman covers: Sales Playbook Hiring Revenue Management Customer Success Compensations Culture Internal Collaboration   Some of my favorite takeaway tips from the book include:   No matter how experienced your salespeople are, any high-performing sales organization should follow one simple but important rule: No call without an agenda. This helps reinforce the necessary discipline around call preparation and ensures your customers have the best possible experience when talking to your...

3 Things To Avoid When You Give Your Next Speech

If you don't want to get your speech off to a bad start, the communications experts at Speechworks suggest you: Don't apologize (particularly about your anxiety or lack of preparation. Apologies put your audience on the defensive. Don't start by telling a joke (which may not be all that funny, or is irrelevant, or that may even be offensive to someone in your audience). Don't beat around the bush (including, don't list off a lot of people you want to thank. Don't waste your audience's valuable time) Instead: If you need to deal with your anxiety, practice like crazy . Rehearse particularly your first line over and over. Start your presentation by laying out for your audience a key issue that they are facing in their business . If you must thank someone, do it at the end, or thank your introducer briefly, pause, and then start right into the meat of your message .

How To Make One Bold Move A Day

  Shanna A. Hocking ’s new book, One Bold Move A Day , is all about meaningful actions women can take to fulfill their leadership and career potential.   Specially, Hocking reveals the transformative mindsets needed to make one Bold Move a day. Those are: Gratitude Mindset And Mindset Happiness Mindset Progress Mindset   “Each of these four mindsets individually plays a special role in the process of continuously showing up for yourself and others,” explains Hocking. “Each mindset contributes in a different way to your success, but they all complement each other and together they will become the foundation to your Bold Move Mindset.”   Hocking explains in her book that a Bold Move is one that challenges you to grow . “Sometimes it’s about capitalizing on an opportunity, and sometimes it’s about creating that opportunity for yourself,” explains Hocking.   Keep in mind, too, that a Bold Move for you might not be the same as someone else’s.   ...

How To Be A Tough Enough Leader

    Tomorrow brings a compelling and timely book about how tough enough you need to be as a leader to lead your team to greatness without being a jerk. The book is Tough Enough , by leadership coaches John Baird and Matt Hunter .   The authors explain that building a high-performing team requires a new form of toughness―not based on bullying and bravado, but rather pushing for exceptional results in a way that is firm, fair, and respectful.   Drawing on decades of coaching top CEOs, elite founders, and ambitious leaders, Baird and Hunter break down seven specific habits that define the strongest, most effective leaders, from being clear about the company culture to strategically unleashing emotional thunder. They set the record straight on when to prioritize understanding and empathy, when it’s time to be direct―and, most importantly, how to do both at the same time. Their no-nonsense approach gives readers the tools to calibrate their toughness and compassion in a ...

Six-pillar Roadmap For How To Move From Merely Surviving To Truly Mattering

  In the new book, The Mattering Effect: Creating A Life Of Meaning And Worth , podcaster and author John R. Miles reframes today’s most common struggles and empowers individuals and institutions alike to break bad habits and reclaim a sense of worth and belonging. “Organizations have spent the last decade chasing 'engagement' and 'psychological safety,' yet global productivity is stalling and 60% of employees report they do not feel valued in the places where they spend their days,” shares Miles.   He calls this “The Great Erasure”—a condition where high-achievers become highly visible to the organization while becoming invisible to themselves.   In addition, Miles argues that many of today’s most common struggles—burnout, anxiety, loneliness, and disengagement—are not personal failures or mindset problems. They are the result of unmattering: the gradual erosion of felt significance within modern systems that reward performance while overlooking presence.   Fortu...

Coherence: The Secret Science Of Brilliant Leadership

Coherence:  The Secret Science of Brilliant Leadership is the new book by author Dr. Alan Watkins . Trained as a medical doctor, Watkins is now  an honorary senior lecturer in neuroscience and psychological medicine at Imperial College, London and an affiliate professor of leadership at the European School of Management, London. According to Watkins, coherence is the biological state achieved when elite performers experience maximum efficiency and super effectiveness, where body and mind are one . Coherence provides one of the most unique approaches to showing leaders how to be younger, smarter, healthier and happier -- which gives them the power to make decisions under pressure and achieve sustainable success. Prepare to spend quality time reading Coherence . It's not light reading.  Kind of feels like a medical text book in parts.  But, it's worth your commitment to it. I particularly found useful Watkin's discussion on culture , where he w...

How To Improve The Way Teams Think, Collaborate And Make Decisions Under Pressure

  “Great decisions don’t happen by accident—they happen by design,” shares Dr. Ricardo Valerdi , author of the new book, The Five-Tool Team: Bringing Out The Best In People To Make Better Decisions .  This book is not about finding perfect answers. It is about building a framework that allows you to make good decisions repeatedly, even when conditions are imperfect, information is incomplete, and outcomes are uncertain.  More specifically, Valerdi reveals a practical framework for improving the way individuals and teams think, collaborate, and make decisions under pressure.   Drawing on lessons from sports, business, engineering, and real-world experience, Valerdi shows how the most effective leaders build teams that question assumptions, analyze consequences, and make choices grounded in clarity rather than instinct or urgency.  “Writing this book has been a phenomenal journey that started in 2018 when I was a visiting professor at the United States Military Ac...

Searching For The World's 2012 Fittest CEO

The CEO Endurance World Championship is a made-for-TV event covering six grueling stages of competition from September 13 - 16, 2012 , and featuring 25 top CEOs that combine success in business with a healthy and fit lifestyle. Each of the six stages is designed to test the CEOs - mixing strategy with endurance - and at the same time be very entertaining to watch. The goal of the competition is to identify the World’s Fittest CEO . The CEOs that have been chosen to take part in the event were hand-picked for their athletic ability and, more importantly, for the charity for which they will be racing. The overall winner will earn the coveted title of Fittest CEO® plus the opportunity to donate $50,000 to the charity of their choice. The entire competition will be filmed and packaged into a TV show (“The Fittest CEO®”) that will: illustrate the breath-taking beauty of the Great Smoky Mountains profile a number of charities that the CEOs will be racing for applaud CEOs who c...