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

12 Data-Driven Steps To Finding A Job You Love

In 2024, I named  Be The Unicorn: Data-driven Habits That Separate The Best Leaders From The Rest ,  by  William Vanderbloemen , as the  best new leadership book  of that year.   The book is timely, incredibly practical, and immediately usable for any leader wherever they are on their leadership journey.   Through extensive research of more than 30,000 top leaders and proprietary data, Vanderbloemen identified in the book the twelve habits that the best of the best leaders have in common. These superstar leaders are the unicorns – highly desirable but that are difficult to find or obtain.   And recently, Vanderbloemen followed up that gem of a book with another terrific book called,  Work   How You Are Wired: 12 Data-Driven Steps To Finding A Job You Love . It’s a great companion book to  Be The Unicorn .   Those 12 steps align with these 12 personality traits/interpersonal habits: Fast Authentic Agile Solver Anticipator Prepar...

Seven Ways To Be A Collaborative Leader

Edward M. Marshall 's book,  Transforming The Way We Work -- The Power Of The Collaborative Workplace , remains relevant today, more than a decade after Marshall wrote it. Particularly useful is the book's section that teaches readers how to be a collaborative leader. Marshall says that there are  seven different, important roles and responsibilities of collaborative leaders when leading teams , and those leaders should select the appropriate style to meet the team's needs. The seven roles are : The leader as sponsor  -- You provide strategic direction, boundaries and coaching for the team. You also monitor progress and ensure integrity in the team's operating processes. The leader as facilitator  -- You ensure that meetings, team dynamics, and interpersonal relationships function effectively. You also ensure internal coordination of activities among team members. The leader as coach  -- You provide support and guidance and you serve as a sounding board. The lea...

Discover How Ken Blanchard Changed The Way The World Leads

I would be hard pressed to find a leader, someone who studies leadership, or an aspiring leader who during the past 43 years hasn’t read the iconic and business classic The One Minute Manager (1982) or the updated new addition, The New One Minute Manager (2015).   For decades, these two books, both co-authored by Ken Blanchard and Spencer Johnson , have helped millions achieve more successful professional and personal lives.   Now, in Chapter 9 of the new biography of Ken Blanchard, you’ll discover the story behind the idea and ultimate launch of the original The One Minute Manager .   Chapter 9 is in the insightful and intimate biography, Catch People Doing Things Right , authored by Martha C. Lawrence . In it and through extensive access to personal papers, letters, and interviews spanning six decades, she reveals how Blanchard became a leadership guru and bestselling author of more than 70 books.   Lawrence shares insights and intimate details about Blanchar...

How To Uncover Your Blindspots To Become A Better Leader

What you don't see about yourself can hold you back as a leader. That's typical for many leaders. What we don't see is what we  can't  see: we have  blindspots . Your blindspots prevent you from achieving your greatest success.  “It turns out that we're often not great judges of ourselves, even when we think we are. Sometimes we're simply unaware of a behavior or trait that's causing problems,” explains  Martin Dubin , author of the new book,  Blindspotting: How To See What’s Holding You Back As A Leader . “Bottom line: until we uncover these blindspots, we can't move forward. The good news is that you can learn to do your own  blindspotting .”   “Most of us understand the idea of blindspots in a general sense—areas we can’t see, to take the term most literally, or places we have gaps that we may not even realize, to be a little more abstract,” says Dubin.  “But in the context of this book, I’m defining blindspots quite specifically: They are...

How To Be More Playful To Build Resilience, Navigate Challenges And Find More Joy

  “Research reveals that playful adults excel at problem-solving and stress management and consistently report higher life satisfaction,” explains Piera Gelardi , author of the new book, The Playful Way .   The Playful Way is a mindset that transforms how you experience everything from airport security lines to career transitions to navigating grief.   More specifically, Gelardi says playfulness is:   Finding humor and lightness even in tense moments. Staying open to possibilities rather than fixating on one “right” way. Experimenting rather than seeking perfection. Bringing an ethos of curious exploration to difficulties. Finding wisdom in the body when the mind’s tied up in knots. Tuning your attention to notice details and find wonder. Reimagining dull tasks through reframes and games. Improvising when things go sideways.   Gelardi guides readers in uncovering the mental barriers and inner critics that restrict playfulness, offering practical techniqu...

How To Reclaim Your Time And Be Time Smart

“Four out of five adults report feeling that they have too much to do and not enough time to do it,” reports  Ashley Whillans , author of the book,  Time Smart: How to Reclaim Your Time and Live a Happier Life . “These time-poor people experience less joy each day. They laugh less. They are less healthy and less productive.” And, in one study, time stress produced a stronger negative effect on happiness than unemployment.   Drawing on the latest science, Whillans teaches us how to escape the time traps that make us feel this way and keep us from living our best lives.   She explains that the  six most common time traps  are: Constant connection to technology. Obsession with work and making money. Limited value placed on time. Busyness as a status symbol. Aversion to idleness. The Yes…and then regret it effect.   Her playbook shows you how to :   take back the time you lose to mindless tasks and unfulfilling chores. improve your "time affluence.” f...

Let's Meet At The Intersection Of Marketing, Leadership And Blogging! A Q&A With Debbie Laskey

  Credit: iStock Photo For the past 16 years, I have relied on Debbie Laskey's Blog for expert leadership guidance and always interesting insights into marketing best practices and recaps of marketing trends.  Fortunately, through the years, Debbie has also shared her expertise through a variety of postings on my blog, and I'm honored again today to feature Debbie with the following Q&A's:  QUESTION: You've featured many leadership experts on your blog through the years. What is a common theme from all the Q&A's? DEBBIE LASKEY : Back in 2011, I met Mark Herbert, a leadership expert and author based in Oregon, as a result of our interactions on Twitter/X. I interviewed him several times, and he provided a quote that I will always remember and share often: "Leadership doesn't require you to be the smartest person in the room. It requires you to block and tackle for others." That quote has appeared on my blog countless times over the years because...

How To Unleash The Most Powerful Force In Business

In Marcus Buckingham ’s latest book, Design Love In: How To Unleash The Most Powerful Force In Business , he details the one hidden skill at the heart of all the best leaders today—and what you can do in your own working life to cultivate it. The skill is leading lovingly —what Buckingham calls Design Love In (DLI). Being a leader, whom people say they love working for and for whom they’d walk through walls. A leader who gets the absolute best out of their employees and who builds the kind of team employees desperately want to be on.  “Love fuels our resilience, sparks our creativity, and bonds us together as collaborators,” shares Buckingham. “Love means a passionate commitment to something or someone. Love means deep loyalty. Love is advocacy. And, of course, love can also be hard-edged, hence ‘tough love.’” Buckingham recommends leaders create experiences that: Make employees feel bigger. Allow employees to feel safe enough to open up. Help employees flourish. Further, Buckingh...

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

How to Be a Leader – 9 Principles from Dale Carnegie

Today, I welcome thought-leader Nathan Magnuson as guest blogger... Nathan writes : This is it, your first day in a formal leadership role.   You’ve worked hard as an individual contributor at one or possibly several organizations.   Now management has finally seen fit to promote you into a position as one of their own: a supervisor.   You don’t care if your new team is only one person or ten, you’re just excited that now – finally – you will be in charge! Unfortunately the euphoria is short-lived.   Almost immediately, you are not only overwhelmed with the responsibilities of a team, but you quickly find that your team members are not as experienced or adroit as you.   Some aren’t even as committed.   You find yourself having to repeat yourself, send their work back for corrections, and staying late to fill the gap.   If something doesn’t change soon, you might just run yourself into the ground.   How did something that looked so easy ...