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

Three Essential Parts Of A Mission Statement

A lot of companies struggle when creating their mission statement. Author  Peter F. Drucker  provides the following good advice in one of my favorite book's of his,  The Five Most Important Questions You Will Ever Ask About Your Organization : Every mission statement has to reflect three things : Opportunities Competence Commitment In other words, he explains: What is our purpose? Why do we do what we do? What, in the end, do we want to be remembered for? How well does your mission statement meet Drucker's recommended three requirements?

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

6 Ways To Seek Feedback To Improve Your Performance In The Workplace

Getting feedback is an important way to improve performance at work. But sometimes, it can be hard to seek out, and even harder to hear.  “Feedback is all around you. Your job is to find it, both through asking directly and observing it,” says David L. Van Rooy, author of the new book,  Trajectory: 7 Career Strategies to Take You From Where You Are to Where You Want to Be . As today's guest post, Van Rooy offers these  six tips for how to get the feedback you need to improve performance at work . Guest Post By David L. Van Rooy 1.       Don’t forget to as k :  One of the biggest mistakes people make is assuming things are going perfectly (until they make a catastrophic mistake). By not asking, you’re missing out on opportunities for deep feedback: the difficult, critical feedback that gives you constructive ways to improve. 2.       Make sure you listen :  Remember, getting feedback is about improving your performance, not turning it into a “you versus the

10 Quotes From The 5 Levels Of Leadership -- John C. Maxwell

Soon I'll post my full review of John C. Maxwell's latest book, The 5 Levels of Leadership .  In the meantime, here are some of my favorites quotes from the book that I believe should become a must-read book by any workplace/organizational leader: Good leadership isn't about advancing yourself.  It's about advancing your team. Leaders become great, not because of their power, but because of their ability to empower others. Leadership is action, not position. When people feel liked, cared for, included, valued, and trusted, they begin to work together with their leader and each other. If you have integrity with people, you develop trust.  The more trust you develop, the stronger the relationship becomes.  In times of difficulty, relationships are a shelter.  In times of opportunity, they are a launching pad. Good leaders must embrace both care and candor. People buy into the leader, then the vision. Bringing out the best in a person is often a catalyst for

5 Tips For Generating Ideas From Employees

Your employees have lots of ideas.  So, be sure you provide the forums and mechanisms for your employees to share their ideas with you.  Hold at least a few brainstorming sessions each year, as well. And, when you are brainstorming with your employees, try these five tips: Encourage ALL ideas.  Don't evaluate or criticize ideas when they are first suggested. Ask for wild ideas.  Often, the craziest ideas end up being the most useful. Shoot for quantity not quality during brainstorming. Encourage everyone to offer new combinations and improvements of old ideas.

3 Things Your Mission Statement Must Have

A lot of companies struggle when creating their mission statement. Author Peter F. Drucker provides the following good advice in one of my favorite book's of his, The Five Most Important Questions You Will Ever Ask About Your Organization :" Every mission statement has to reflect three things : Opportunities Competence Commitment In other words, he explains: What is our purpose? Why do we do what we do? What, in the end, do we want to be remembered for? How well does your mission statement meet Drucker's recommended three requirements?

How To Survive And Then Reset To Ultimately Thrive

“Uncertainty is here to stay. Rather than seeing it as an obstacle to overcome, integrate it into your strategic approach to invigorate your high-growth potential and outperform competition under any market condition,” explains Rebecca Homkes , author of the new book, Survive, Reset, Thrive .   “Most books aren’t honest enough about how hard it is to reset ,” adds Homkes. Yet, resetting and leaning into change is essential. “If you are ready to embrace change as a central element of your growth strategy, this book is for you.” Homkes’ book is a timely, comprehensive, and essential read for business leaders looking to take the next step toward ensuring high growth for their companies. The book brings together more than 15 years of Homkes working directly with high-growth companies of all sizes and across a wide variety of industries.   Survive, Reset, Thrive (SRT) is a practical and innovative interconnected three-mode approach :   Survive : Stabilizing your business when

3 Coaching And Mentoring Tips

Here are three great tips from the book, The Everything Coaching and Mentoring Book : Coaches do not motivate their employees; they inspire them to motivate themselves.  This is best accomplished by allowing employees to see clearly where they stand in the organization versus where they want to be in their careers.  That is, what are their self-interests versus what the company can offer them. A mentor always exercises the power of suggestion. That is, wise mentors offer up plenty of suggestions to their mentees. They pose alternatives.  But they refrain, as much as possible, from telling their mentees what to do. Mentoring is all about sharing experiences.  It is about mentors imparting the multiple lessons that they've learned to their mentees and helping them better navigate through their own careers.  By absorbing these lessons--of mentors' mistakes and successes--mentees are better prepared to move forward with knowledge and confidence.

Use A Board Of Advisors

David Burkus often provides valuable comments to my various Blog postings, and he's a person who effectively uses a board of advisors, instead of mentors, to help him achieve success. "I've found that in my life, it was easier and more effective to set up a board of advisors," said Burkus, the editor of LeaderLab . "This is a group of people, three to five, that have rotated into my life at various times and that speak into it and help me grow. I benefit from the variety of experience these people have." LeaderLab is an online community of resources dedicated to promoting the practice of leadership theory. Its contributors include consultants and professors who present leadership theory in a practitioner-friendly format that provides easy-to-follow explanations on how to apply the best of leadership theory. Community users can download a variety of research reports and presentations about leadership and leadership versus management. For example, a pr

How To Avoid 8 Common Performance Evaluation Pitfalls

As the year comes to a close it's likely time for many business leaders to tackle the annual performance appraisal process. So, here is a good reminder from author Sharon Armstrong about how to avoid eight performance evaluation pitfalls .  These are in what I consider is the best chapter of the book The Essential HR Handbook , that she co-authored with Barbara Mitchell. 1.  Clustering everyone in the middle performance-rating categories 2.  Overlooking flaws or exaggerating the achievements of favored employees 3.  Excusing substandard performance or behavior because it is widespread 4.  Letting one characteristic - positive or negative - affect your overall assessment 5.  Rating someone based on the company he or she keeps 6.  Rating someone based on a grudge you are holding 7.  Rating someone based on a short time period instead of the entire evaluation period 8.  Rating everyone high, to make you look good There's other great information in this 250-page book th