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EPISODE 53 — Ryan Holiday — The Obstacle is the Way

Ryan Holiday is the best-selling author of books such as The Obstacle Is the Way, Ego Is the Enemy, Stillness Is the Key, and many more. His writings on Stoicism bring the philosophy out of 300 BC Athens into the modern world and help people overcome contemporary problems with the same philosophies founded and honed by thinkers like Zeno of Citium and Marcus Aurelius.

In this episode, Ryan gives us a crash course in Stoicism and details how ourselves and our businesses can benefit from adopting some Stoic teachings, applying the philosophy to our everyday lives.

EPISODE 53 — Ryan Holiday — The Obstacle is the Way
Show Notes:

2:08 – What is Stoicism? “We tend to think of philosophy as this sort of abstract, theoretical thing — and it can be that. But it’s also meant to be applied. It’s meant to meet the rubber of the road of real life. It’s probably not a coincidence that a big chunk of the Stoics in ancient Rome were lawyers in some capacity or another. But the idea of Stoicism as a philosophy is basically routed around this idea that we don’t control what happens. We control how we respond. What I love about the Stoics and why I think they remain relevant today is that the Stoics weren’t necessarily known for their brilliant writing or their beautiful writing. They were known for what they actually did in real life.”

4:31 – Life is the stories you tell yourself about it. “You look at the last year. Did you get screwed? Was it horrible? Was it the worst thing that could have happened? That’s one story you could tell yourself about it. The other story you could tell yourself about it is that it was a giant forced lifestyle experiment, that it was a test or a challenge, that it was an opportunity to do things differently, that it was a time to spend more time with your family. You decide what you’re going to do with it. We don’t control what it is, largely. We do control what we’re going to do about it, and that starts with how we’re going to see it.”

9:02 – Stoicism is not about removing all emotions — it’s about removing destructive emotions. “People think that Stoicism is the absence of emotions, because that’s sort of what the word means in the English language. I think what the Stoics are really focused on is destructive emotions. Does this emotion make it better or worse? Does holding on to this emotion longer than I ought to make it better or worse? That’s really what we’re thinking about. ‘This is unfair. I’ve been screwed over. This is not my fault. Why me? I’m never going to recover.’ you know, those sorts of things. They may well be true, but are they moving the ball forward in any way?”

13:09 – ‘When things go back to normal’ is a preposterous phrase. “We see people do this thing, particularly with the pandemic. You hear people saying ‘when things go back to normal,’ which is a preposterous phrase, first and foremost because normal is what caused this. Second, the idea that this is not normal is also just historically untrue. I would defy a person to find me a single ‘normal’ decade in American history. Things like this happen. This exact thing happened exactly 100 years ago. In 1968, there was not only a flu epidemic. There were also the worst racial riots in American history. History repeats. We know this. Things happen. This is a preposterous idea, that because things are not the way that I want them to be they’re ‘not normal.’ And in fact, just even this expression ‘normal’ is implying a certain judgment.”

16:05 – Post-traumatic growth is possible. “We talk a lot about post traumatic stress, which does exist. But there’s also such a thing as post traumatic growth. There are athletes that come back better for the experience of having been injured. As you get older, as you get more experienced, as you go through what you’ve gone through, you learn other skills. You learn how to compensate. You learn how to redirect your energy and your efforts. That’s what you want to think about it. It’s not that you can magically find that it’s not negative and it’s positive. It’s that you can find some positive thing to do because of what happened.”

19:11 – After controlling your perspective, take action. “Mindset is key. Perception is key. But we’re not talking about The Secret key or manifestation. You have to take action. Perception teess up action, because by focusing on what’s in your control, by focusing on what’s positive, by focusing on your response, you now have a direction to go in. But if you don’t go in that direction, all you’re doing is playing around in your mind. You’re not changing anything. So yes, for the Stoics it’s about action.”

29:08 – Accept what is outside your control. “Life will kick your a**. You don’t win every time. If you are so determined and so persistent that you never have the ability to just accept, ‘Okay, this didn’t go how I wanted it to go. This didn’t work out.’ You’re going to end up enduring something longer than you actually should endure it. I talked about preparing for nothing to work. That leads into that third discipline of Stoicism: the willing acceptance of external events or things that are outside of your control.”

31:15 – Willpower is about endurance. “Will is harder because it’s just about putting up with stuff. it’s just about enduring. It’s just about hanging on. It’s about that really difficult thing of acceptance. I define will as that sort of inner soul power that we have that allows us to say, ‘This thing was supposed to take two weeks and here we are 12 months later.’ I think, you know willpower is the swing vote there.”

37:15 – Which leader do you want to be? “Let’s compare two hypotheticals. There’s the company that when things are starting to look bleak, the CEO announces everyone’s taking a 20% pay cut. ‘We’re laying off this many people. You can no longer expense the following things.’ And then the other firm who announces that the CEO and president are temporarily not going to draw a salary. ‘We don’t want people to come into the office. We want people to stay home and be safe. What tools or software or things do you need to be successful? What adjustments do we need to make?’ Not only are those I think morally the correct thing to do, but now, once we do come out of this in some way, which company is going to have undying loyalty and a close-knit team, and which company is going to have a bunch of people looking for new jobs?”

47:43 – Being a game changer means making a positive difference. “My friend George Raveling says, ‘Are you going to choose to be a positive difference-maker today?’ I would assume that the implications of the word ‘game changer’ means a positive difference. You can change the game for the worse, and that’s almost easier than not. Do you wake up every day and move the ball forward? Do you improve the people that are around you? Do you do work that makes you better? To me it’s all about getting a little bit better every day.”

Ego is the Enemy by Ryan Holiday
The Daily Stoic by Ryan Holiday
The Obstacle is the Way by Ryan Holiday
Ancient Rome
Marcus Aurelius
Antonine Plague
COVID-19 pandemic
William Shakespeare
Rubin “Hurricane” Carter (boxer)
Ernest Hemingway
Tommy John
New York Yankees
1968 flu pandemic
Simon & Schuster
Meditations by Marcus Aurelius
Nick Saban
University of Alabama
Bill Belichick
Go for No by Andrea Waltz and Richard Fenton
James Stockdale
Good to Great by Jim Collins
Man’s Search for Meaning by Victor Frankl
Jocko Willink
Tony Robbins
George Raveling

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