A Modern Look at Stoicism, “An Art We Need to Bring to Our Own Lives”

Book Review: The Obstacle Is the Way by Ryan Holiday

(This is a book review of The Obstacle Is the Way by Ryan Holiday.)

Part of the trouble with philosophy is that it’s not easy to put into practice. For systems that were originally designed to teach people how to live, philosophy has become, in many cases, too abstract for people to apply the lessons to their lives.

Philosophy can even seem absurd. Why spend your time debating the existence of God if you can’t prove your answer? And who cares what the definition of “is” is? No one less charismatic than Bill Clinton caught in a lie could find that argument useful in their lives:

Transforming philosophy into action

To get something useful out of philosophy, this is the typical path you must take:

  1. Spend hours digesting a dense philosophy text
  2. Distill concrete principles
  3. Finally, put those principles into action

I’ve been reading and studying philosophy for many years and still I find this process extremely challenging. I can’t even point to a moment where I was able to successfully complete the cycle on my own. I get more out of self-help books, and they require far less effort.

That’s why a book like The Obstacle Is the Way has a place on your book shelf. If you are interested in Stoicism but can’t get through the source texts, or if you have read Seneca’s or Marcus Aurelius’ writing and wondered what to do next, Holiday’s book will help you skip ahead.

In the introduction to the book, Holiday explains:

“This is also not an academic study or history of Stoicism. There is plenty written about Stoicism out there, much of it by some of the wisest and greatest thinkers who ever lived. There is no need to rewrite what they have written— go read the originals. No philosophic writing is more accessible. It feels like it was written last year, not last millennium.”

Instead, The Obstacle Is the Way is a book of actionable advice and simple instructions (“simple, not easy”). Holiday read the source texts and extracted the core principles so you don’t have to. Read his book to jump right to the good part: taking action.

Examples of Stoicism in recent history

Instead of quoting source material, Holiday uses examples of recent historical figures and events—Steve Jobs pushing crazy deadlines against the odds, Amelia Earhart accepting a crappy offer for the chance to fly—to illuminate and explain the philosophical approach of Stoicism:

“Great individuals, like great companies, find a way to transform weakness into strength. It’s a rather amazing and even touching feat. They took what should have held them back— what in fact might be holding you back right this very second—and used it to move forward.

As it turns out, this is one thing all great men and women of history have in common. Like oxygen to a fire, obstacles became fuel for the blaze that was their ambition. Nothing could stop them, they were (and continue to be) impossible to discourage or contain. Every impediment only served to make the inferno within them burn with greater ferocity.”

The examples work well because they’re relatable. I know their names. I’m familiar with their legacies. Their struggles are my struggles, and I root for them in a way that I never can when reading the journals of a Roman emperor.

The book read by the NFL

The Obstacle Is the Way by Ryan Holiday (cover)I heard about The Obstacle is the Way for the first time about a year ago. Like most books I’m interested in, I added it to my Amazon wishlist. There it stagnated for many months—until a Sport Illustrated article reporting on the popularity of Holiday’s book in the NFL brought the book back onto my radar:

“Soon after that encounter, Holiday heard from Michael Lombardi, a voracious reader who works as an assistant with the Patriots. Lombardi recommended the book throughout the league. He had Holiday send copies to his favorite team, the Saints.

The book does contain some sports examples. Holiday wrote about Nick Saban, the Alabama football coach, for instance, and his famous process, how he refused to be distracted by what might happen in the future, or what had happened in the past. He focused on the next game, the next day, the next hour. He didn’t get emotional, except in press conferences, when yelling at reporters. He focused on what mattered, what he could control.

That’s stoicism.”

This passage convinced me. I bought the book before I finished reading the article.

It’s amazing how something can come back onto your radar so many months later and influence a book buying decision so profoundly. (The book marketer in me is certainly taking notes.)

The three legs of the Stoicism tripod

After the introduction, The Obstacle is the Way is divided into three parts: Perception, Action, and Will. According to Holiday, these are the three essential practices of the Stoic way of life.

At this point, the book becomes a sort of quasi-self-help book, with the famous examples peppered throughout. The chapters are titled things like “Steady Your Nerves,” “Practice Persistence,” “Iterate” (at this point the tech entrepreneur is nodding enthusiastically), and “Build Your Inner Citadel.”

Now that I’ve read the book, I have a greater appreciation for the structure. The chapters are titled in a way that if I come home from work after a difficult day, I can reflect on what I did poorly and thumb through the book until I find a useful section. If I got nervous during a phone call, I could go back to “Steady Your Nerves” for a short refresher course. If I lost a big client, I might be interested in rereading “Love Everything that Happens: Amor Fati,” in search of a path to acceptance.

The Obstacle is the Way is both an introduction to Stoicism and a reference book for life when it gets hard. I urge anyone who dislikes self-help books to look past your resistance and give the book a try. It’s not your typical self-help book, and will surely help you.

My highlights from The Obstacle Is the Way

Here are a few more passages I highlighted during my reading.

I was raised Jewish and have sat through many a Seder, so this passage about Passover and the inner strength of Jews throughout the ages sparked a memory in me:

“During Passover Seder, the menu is bitter herbs and unleavened bread—the “bread of affliction.” Why? In some ways, this taps into the fortitude that sustained the community for generations. The ritual not only celebrates and honors Jewish traditions, but it prompts those partaking in the feast to visualize and possess the strength that has kept them going.”

I also like the short lists of suggestions that Holiday includes. It’s an interesting stylistic approach, and eminently practical. Consider this mind-set list from the chapter titled “Practice Persistence:”

“Once you start attacking an obstacle, quitting is not an option. It cannot enter your head. Abandoning one path for another that might be more promising? Sure, but that’s a far cry from giving up. Once you can envision yourself quitting altogether, you might as well ring the bell. It’s done. Consider this mind-set.

never in a hurry
never worried
never desperate
never stopping short”

I can see how this chapter might succor my wounded pride after a difficult day of battering my head against an obstacle.

Here’s a paragraph about focusing on what’s in front of you and not getting distracted:

“Whether it’s pursuing the pinnacle of success in your field or simply surviving some awful or trying ordeal, the same approach works. Don’t think about the end—think about surviving. Making it from meal to meal, break to break, checkpoint to checkpoint, paycheck to paycheck, one day at a time.”

It’s a well-documented human phenomena that those closest to death feel the most alive. Here’s a lovely passage about how you don’t need to wait for a terminal diagnosis to live your life to its fullest, and how you should let go of what’s outside of your control:

“It’s a cliché question to ask, What would I change about my life if the doctor told me I had cancer? After our answer, we inevitably comfort ourselves with the same insidious lie: Well, thank God I don’t have cancer. But we do. The diagnosis is terminal for all of us. A death sentence has been decreed. Each second, probability is eating away at the chances that we’ll be alive tomorrow; something is coming and you’ll never be able to stop it. Be ready for when that day comes. Remember the serenity prayer: If something is in our control, it’s worth every ounce of our efforts and energy. Death is not one of those things—it is not in our control how long we will live or what will come and take us from life.”

Ryan Holiday, author of The Obstacle Is the Way
Ryan Holiday, author of The Obstacle Is the Way

I got a lot out of this book that I never got from reading the Stoic texts themselves. I’m familiar with Marcus Aurelius’ Meditations and Seneca’s letters, but were it not for The Obstacle Is the Way, it would have been difficult to put Stoicism into action in my life. Holiday makes Stoicism accessible and actionable in a short, enjoyable read.

My only real complaint was that the profiles weren’t longer. I would have liked to learn more about Edison and Steve Jobs and Ulysses S. Grant and how they embodied Stoicism. I’ll have to turn to the biographies and history books for more. Now, at least, I’ll know what to look for.

Holiday concludes with one of my favorite quotes from the whole book. He rephrases Marcus Aurelius:

“What stood in the way became the way. What impeded action in some way advanced it. It’s inspiring. It’s moving. It’s an art we need to bring to our own lives.”

Do these passages from The Obstacle Is the Way intrigue you? Have you ever read any of the Stoics, like Marcus Aurelius or Seneca? Share your thoughts in the comments.

Buy The Obstacle Is the Way on Amazon (links to Amazon are affiliate links).


  1. Jim Finley says:

    Interesting! And an excellent review, articulate and organized. I want to read this book.
    Some of the points sound quite a bit like 12-step philosophy (even leaving aside the Serenity Prayer): “Simple but not easy” is something heard over and over in meetings, and the focus on acceptance in general. In one of the key chapters in the Big Book (and one that people quarrel about the most), the person telling his story argues that any time he finds something unacceptable, the problem is in himself, not the thing he’s refusing to accept. Also, a key idea is that the experiences and circumstances that are our greatest afflictions can become things we use to empathize and communicate with others going through similar trials, and help them by showing them that they aren’t alone and that people do get through those trials and out the other side.

    It also reminds me of one of my wife’s favorite poems, a Rumi piece titled “The Guest House” (too long to include here, but only a minute or two to read.) She just had it made into a poster and framed it.

    It’s helped me to frame acceptance as simply acknowledging reality as it is in the present moment. Doesn’t mean I like it, certainly doesn’t mean I won’t do all I can to improve it. Since the definition of psychosis includes believing in or perceiving unrealities, acceptance is just practicing sanity.

    One of the all-time lows of my life was a period when my anger was out of control. It nearly cost me my family and career, but it also motivated me to get into recovery and counseling. Many years later in a job interview, a panel member asked about the worst mistake I’d ever made on the job and what I’d done about it. I figured, “Okay, I can kiss this one off,” but went ahead and told the story (I’d been a Marine DI and gotten busted for assaulting a recruit.) They hired me. Months later that guy (now my supervisor) asked whether I remembered that question from the interview. I told him I’d figured they’d summarily reject me once I answered it. He laughed and said, “We hired you because you were the only applicant who answered that one honestly.”

    I had a great philosophy professor a long time ago. He presented each philosophy so persuasively that it seemed obviously the one we should all live by; then he shredded it just as persuasively. Whenever anyone asked about his own personal philosophy, he just said, “You aren’t here to study me.” Of all the schools of thought, though, stoicism made the most sense to me and does so even more now.

    • Matt says:

      Sounds like you have some great stories, Jim.

      I’ve always wanted to have an excellent philosophy professor like you had. Unfortunately, the one I had in college was rather dry and dull. I wanted to talk about Stoicism, or Nietzsche, but we spent that entire class arguing the existence of God—yawn.

      I just searched and found that Rumi poem you mentioned—at least, I think this is it. It’s not too long at all. Here’s a link if anyone else is interested in checking it out: http://allpoetry.com/poem/8534703-The-Guest-House-by-Mewlana-Jalaluddin-Rumi

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