50 Timeless Philosophical Takeaways from Ryan Holiday’s The Obstacle is the Way

The Obstacle is the Way

The impediment to action advances action. What stands in the way becomes the way. – Marcus Aurelius

I read Ryan’s book, “The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph,” during a relatively tough period in my life. I’d been working 60-80 hour work weeks and felt like I was missing out on my life. I was always irritable and I could barely find the time, or energy, to hang out with my new wife (in our first year of marriage no less). Not to mention, I had virtually zero time for all the other hobbies I’m passionate about, things like like reading books, writing, thinking and perhaps most importantly, trying to help people by sharing interesting things I learn here on this blog.

During this time, my wife and I talked a lot about re-framing; a powerful concept that we try to employ often.

“The Obstacle is the Way” is the ultimate re-frame.

Here are 50 of my favorite timeless philosophical takeaways from Ryan’s book:


1. Every obstacle is an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice and creativity.

2. The essence of philosophy is action — in making good on the ability to turn the obstacle upside down with our minds.

3. We blame our bosses, the economy, our politicians, other people, or we write ourselves off as failures or our goals as impossible. When really only one thing is at fault: our attitude and approach.

4. “The things which hurt, instruct”. — Benjamin Franklin (Click to Tweet)

5. “Objective judgment, now at this very moment. Unselfish action, now at this very moment. Willing acceptance–now at this very moment–of all external events. That’s all you need.”  — Marcus Aurelius


On the Discipline of Perception:

6. Where one person sees a crisis, another can see opportunity. Where one is blinded by success, another sees reality with ruthless objectivity. Where one loses control of emotions, another can remain calm. Desperation, despair, fear, powerlessness–these reactions are functions of our perceptions. You must realize: Nothing makes us feel this way; we choose to give in to such feelings.

7. There are a few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try:

  • To be objective
  • To control emotions and keep an even keel
  • To choose to see the good in a situation
  • To steady our nerves
  • To ignore what disturbs or limits others
  • To place things in perspective
  • To revert to the present moment
  • To focus on what can be controlled.

On Recognizing Your Power:

8. Rubin “Hurricane” Carter, after being sentenced to prison, maintained that he still had choices. Instead of breaking down, and many would, he declined to surrender the freedoms that were innately his: his attitude, his beliefs, his choices.

9. 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.

On Steadying Your Nerves:

10. When we aim high, pressure and stress obligingly come along for the ride.

On Controlling Your Emotions:

11. Do I need to freak out about this? No, because I practiced for this situation and I can control myself. Or, No, because I caught myself and I’m able to realize that that doesn’t add anything constructive.

On Altering Your Perspective:

12. Perspective is everything.

13. Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.

On Is it Up To You?

14. Focus on what you can control:

  • Your emotions
  • Your judgments
  • Your creativity
  • Your attitude
  • Your perspective
  • Your desires
  • Your decisions
  • Your determination

On Living in the Present Moment:

15. We get ourselves so worked up and intimidated because of the over thinking, that if we’d just gotten to work we’d probably be done already.

On Thinking Differently:

Lessons from Steve Jobs:

16.To aim low meant to accept mediocre accomplishment. But a high aim could, if things went right, create something extraordinary.

17. Learn to reject the first judgments and the objections that spring out of them because those objections are almost always rooted in fear.

On Finding the Opportunity:

1. It’s one thing to be overwhelmed by obstacles, or discouraged or upset by them. This is something that few are able to do. But after you have controlled your emotions, and you can see objectively and stand steadily, the next step becomes possible: a mental flip, so you’re looking not at the obstacle but at the opportunity within it.

19. With this new attitude and fearlessness, who knows, you might be able to extract concessions and find that you like the job again. One day, the boss will make a mistake, and then you’ll make your move and outmaneuver them. It will feel so much better than the alternative — whining, bad-mouthing, duplicity, spinelessness.


On Practicing Persistence:

20. We will not be stopped by failure, we will not be rushed or distracted by external noise. We will chisel and peg away at the obstacle until it is gone. Resistance is futile.

21. Genius is often really is just persistence in disguise. (Click to Tweet)

22. Action mindset:

  • Never in a hurry
  • Never worried
  • Never desperate
  • Never stopping short

23. Energy is an asset we can always find more of. It’s a renewable resource.

On Iterating (i.e. Learning from Failure):

24. Failure is a feature. It’s the preceding feature of nearly all successes. (Click to Tweet)

On Following the Process:

25. Follow the process and not the prize.

On Doing Your Job and Doing It Right:

26. When action is a priority, vanity falls away.

What’s Right is What Works:

27. Pragmatism is not so much realism as flexibility. There are a lot of ways to get from point A to point B. It doesn’t have to be a straight line. It’s just got to get you where you need to go. But so many of us spend so much time looking for the perfect solution that we pass up what’s right in front of us.

28. Thing progress, not perfection. (Click to Tweet)

In Praise of the Flank Attack:

29. Great masters exert only calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics.

30. You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there. Or you look for leverage to make them listen. Or you create an alternative with so much support from other people that opposition voluntarily abandons its views and joins your camp.

On Channeling Your Energy:

31. Physical looseness combined with mental restraint? That’s powerful.

On Preparing for None Of It To Work:

32. The world could use fewer martyrs. We have it within us to be the type of people who try to get things done, try with everything we’ve got and, whatever verdict comes in, are ready to accept it instantly and move on to whatever is next.


33. Too often people think that will is how bad we want something. In actuality, the will has a lot more to do with surrender than with strength. Try “God willing” over “the will to win” or “willing it into existence,” for even those attributes can be broken. True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition. See which lasts longer under the hardest of obstacles.

On The Discipline of the Will:

34. Clearheadedness and action are not always enough.

35. If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul.

36. Certain things in life will cut you open like a knife. When that happens — at that exposing moment — the world gets a glimpse of what’s truly inside you. So what will be revealed when you’re sliced open by tension and pressure? Iron? Or air? Or bullshit?

On Building Your Inner Citadel:

37. You’ll have far better luck toughening yourself up than you ever will trying to take the teeth out of the world that is –at best — indifferent to your existence.

On Anticipation (i.e. Thinking Negatively):

38. “If You’re not humble, life will visit humbleness upon you.” — Mike Tyson

39. It’s far better to seem like a downer than to be blindsided or caught off guard. (See also: The Upside of Pessimism)

On the Art of Acquiescing:

40. We instinctively think about how much better we’d like any given situation to be. We start thinking about what we’d rather have. Rarely do we consider how much worse things could have been. And thing can always be worse.

On Loving Everything that Happens:

41. To do great things, we need to be able to endure tragedy and setbacks.

42. The next step after we discard our expectations and accept what happens to us, after understanding that certain things –particularly bad things– are outside our control, is this: loving whatever happens to us and facing it with unfailing cheerfulness. It is the act of turning what we must do into what we get to do.

On Perseverance:

43. Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.

44. No one else is to blame when you throw in the towel.

On Something Bigger Than Yourself:

45. When we focus on others, on helping them or simply providing a good example, our own personal fears and troubles will diminish.

46.This kind of myopia is what convinces us, to our detriment, that we’re the center of the universe. When really, there is a world beyond our own personal experience filled with people who have dealt with worse.

On Meditating on Your Mortality:

47. Death doesn’t make life pointless, but rather purposeful.

48. Thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because it’s invigorating.

49. They figure out what they need to do and do it, fitting in as much as possible before the clock expires. They figure out how, when that moments strikes, to say, Of course, I would have liked to last a little longer, but I made a lot out of what I was already given so this works too.

On Preparing to Start Again:

50. Passing one obstacle simply says you’re worthy of more.

Photo Credit: odolphie