Ryan Holiday's Crash-Out Proves Stoicism Was Never Going to Be Enough

Machine transcribed from the episode audio, lightly cleaned. Timestamps are approximate.

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The man who made Stoicism famous just showed us why Stoicism isn't enough. Check this out. Stoicism, I think like Marcus Aurelius' meditations is so informative on so many levels. I mean, here you have somebody who was literally an emperor, and he's writing this journal in a tent in a battlefield. So his perspective is amazing. And he once wrote that the soul becomes dyed the color of its thoughts. And I think about that all the time. The cost to me of living in a way that's inconsistent and not aligned with what feels right, what models the right thing for my children, what feels inherently true to me, it's too expensive. I mean, look, here's the thing. She's totally right.

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That's exactly what Marcus Aurelius said. That's exactly what Stoicism is about. She's just not living or acting in accordance with it in any way. If you did, you'd have an intervention with your dad. That's Ryan Holiday. He is the most well-read and probably the most well-known modern-day Stoic today. And he just publicly did the most un-Stoic-like thing that you could ever do. Look, before I jump too deep into this, I do want to address the fact that this is not a hit piece. His books, The Obstacle is the Way, The Ego is the Enemy, and Stillness is the Key,

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they radically changed my life. So again, this is not a hit piece. This is a diagnosis. And I think it's something that's so important for us to address. So I want to take you back to 2019. So I was back full-time coaching and consulting. I was pastoring the church. I was about seven years into pastoring the church that I was. I was husband, father. I was working so hard. My business was on an incredible trajectory at that point. And I mean, I was all in. The problem was, is I started to feel a little bit overwhelmed.

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It was really hard for me to keep up, to continue to push forward. And I knew that in that season, the Word of God's encouragement, at times command to rest, was something that I needed to listen to. Every version of Christian rest, though, around me looked like something that I just didn't really feel like I was. Most versions of Christian rest that I had seen from other Christians that were really faithful,

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that were doing really, really good. As I looked to the Word of God, all I saw was go lock yourself in a closet for quiet time. Go off on a three-day spiritual retreat with nothing but you, a Bible, and a journal. And I'm going to tell you right now, those ideas freak the living crap out of me. If you know me, you know that I'm just not wired that way. And I know that that could very well be an excuse. But in that season of my life, the idea that I was going to go lock myself in a closet or go away for a couple of days was just crazy to me. So as relatable as the Bible was to me, as deeply entrenched I was in my Christian faith,

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as much as I loved Jesus, I was really struggling with this idea of rest. And so what did I do? Nothing, right? I mean, that's what I was doing. And so the tension was building. By the way, you may recall if you've read my book that it was April 2019 that I totally lost it. Ended up in a fetal position in the corner of my office, not this office, another one, crying. I had to call my wife to be prayed for because I just experienced this debilitating anxiety attack for the first time in my life. And so it wasn't too long after that, that again, I was feeling this tension. I was feeling this need, this desire to do something a little bit different. But my own rhythms, performance, just pushing through, they had worked to that point.

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So I'm like, you know what? I'm just, I'm going to keep doing it. So 2019, Ian Holiday, who again had already inspired me by Ego is the Enemy and the Obstacle is the Way, releases this book called Stillness is the Key. And you can go check it out. You can read it for yourself. But there's a specific story in there that really captivated me. And it was this story about John F. Kennedy Jr. And in it, JFK, he, during the Cuban Missile Crisis, obviously this insanely tense time in our country, this insanely tense time for him as president of the United States,

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he found stillness by going and walking the White House Garden. He would just do laps around the White House Garden. He didn't go hide. He didn't go lock himself in a closet. He didn't go retreat away for a couple of days. I don't know what the country would have done if that would have happened. He just went for a walk. And man, that hit me. It hit me because for the first time, maybe in my life, I resonated with a version of stillness that I felt like would work for me. And so shortly thereafter, I started to build some discipline around that. I started going out and taking walks.

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And just during those walks, I would pray, talk to God, nothing crazy formal, just having conversations with God. Sometimes I would just put my AirPods in, turn them on, noise canceling, but not listen to anything. And I started to find rhythms of rest. And I really owe a lot of that to Ryan Holiday. I got what I needed. I got the right result. The reality of the matter, though, is, was I got the right result from the wrong source. Or maybe I should say I got the right result from an incomplete source. But I didn't know that at that time because it was working.

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I mean, if it isn't broke, don't fix it, right? I was stressed out. I was super anxious. I had a meltdown. And I read the story of JFK. And all of a sudden, I'm like, that feels pretty good. Look at this pattern, though. This goes way back. This is so much deeper than Ryan Holiday's crashing out recently, which if you Google Ryan Holiday crashing out, you'll find it. There's a lot of stories around just kind of these meltdowns. Not just the one I showed you at the beginning of this where he's attacking Ivanka Trump, rolling his eyes, acting like a child, imposing his opinions of Donald Trump on Ivanka,

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discounting her care, her concern for her family. He is judging her, reciting Marcus Aurelius. That was, by the way, a clip from the Diary of the CEO podcast. Her clip, not his. His was from his own channel. Anyway, so he's crashing out over the last name Trump. And as I see that, it just becomes more and more evident to me that this pattern, it just goes way deeper. I mean, like, think about this. You may not know. I'm not a stoic expert by any means. I've done a little bit of research over the years because I do appreciate some of their practices

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around mindset, around discipline, around how you treat people. You don't, you don't, you only focus on what you can control. So there's a lot of great things there. But go way back to Marcus Aurelius himself, who is, like, regarded as the stoic of all stoics. He was the most powerful man alive during his day. He wrote meditations as a private journal of his own failures. Failures, it would later be taken, published, and that's what a lot of people read today. But what's fascinating about a guy that is supposed to be the father of stoicism, the stable mind, he wrestled with his temper his entire life.

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And I'm not saying you have to be perfect to preach something, but it just seems kind of counter. Like, he couldn't even take his own medicine. The man teaching self-mastery could not master himself. How is Marcus Aurelius? Fast forward to Seneca, another very well-known stoic. He preached poverty and simplicity. So he really believed, and again, this is somewhat ignorant, a little bit of research, but he preached this idea that we needed to limit all that we had, so it did not own us, basically, the idea that he was after. And yet, he died one of the wealthiest men in Rome.

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He was tangled in politics. And it's just crazy for me to think that he was writing about freedom while accumulating insane amounts of money and power. He seemingly knew it all, but he couldn't limit. Fast forward a little bit farther to Chrysippus. Here's a guy that is regarded as one of the most important stoic thinkers in all of history. By many accounts, this kind of sounds crazy, but I've done a lot of research, and this seems to be true. He died of uncontrollable laughter, and you may be thinking, gosh, at least that's a fun way to go. He died because he could not control his emotions.

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Are we finding irony here? Every man who has tried to build self-mastery on human wisdom alone eventually proves, either to themselves or to the world around them, that it isn't enough. It's not because we're not smart enough. It's not because they weren't disciplined enough. Clearly, they were plenty disciplined. But then what was it? Well, it's because they built their entire being, who they were, what they believed, what they pursued, on the wrong foundation. Let's go back to Ryan Holiday.

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Ryan Holiday didn't lose the plot. And I've seen a lot of people say that. It's kind of a phrase that people use today. But like, Ryan Holiday didn't lose the plot. He never had the plot to begin with. That Ivanka clip, it wasn't a bad day. It was a crack that was always going to form. Look it. That's not his only clip. You can go search more. I could share more with you. He's had a few of them. They're typically politically driven. He's targeting Trump and anybody that he thinks could have any kind of association with him whatsoever. When your identity is fused with being the authority on a philosophy and someone outside your tribe quotes it and that threatens you, you have a problem.

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When the guy that is preaching to not focus on anything outside of your control, to only focus on the things that you can control, and he all of a sudden loses himself and overreacts. I mean, look back at that clip. He was rolling his eyes as she was quoting Aurelius. I mean, he would later in the clip act far more childish. I'll put the whole clip below so you can see it if you would like, if you're watching this via video, or hopefully you're doing it that way. Or if you're listening to the podcast, it'll be down in the show notes. But you are doing the very things that you preach against. You are doing the very things that you claim to have mastered.

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But that's not a Stoicism failure. Stoicism didn't fail Holiday. It didn't fail Chrysippus. It didn't fail Seneca. It didn't fail Marcus Aurelius. You see, they were all failed by something so much greater. And that's identity. Stoicism can train behavior, which is why I do have a lot of respect and appreciation for the ideas that surround it. But behavior training does nothing without identity transformation. Training and transformation are not the same thing. You see, the Apostle Paul, who would be regarded as one of the wisest people to ever walk the face of this earth, though he did not start out that way,

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he's quoted in Romans 12 as saying, Be transformed by the renewing of your mind. He doesn't say to be trained. He says to be transformed. And he says that because his foundation is built on God and the fact that only God can do the transformation. God can be the only one to truly renew your mind. Ryan Holiday has spent his entire career, sold insane numbers of books, been on incredible stages, huge podcasts, and probably made a whole bunch of money. He's done all of that, teaching people to manage what comes out of the heart.

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But he never addressed what the heart was anchored to. So what I want to do is I want to not just rant. And again, this is not an attack on Ryan Holiday. The guy's way smarter than me. He's far more successful than I am. But what I want to do is I want to show you, I want to help you to see that just because your mind is trained, just because your body is trained doesn't mean you've figured it out. I have experienced the most, interacted with the most successful human beings, some of the most fit human beings. And so many of them are missing this key component, which is identity.

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And so I just, I want to walk you through very briefly. I don't want to take a lot of time doing this. We've got a masterclass workshop that we're going to be releasing. We're going to be incorporating this into our weekend retreats. We're going to do some one-day intensives. So there's going to be a lot of stuff coming up on this. But I just want to offer you, I wish I could offer Ryan Holiday, a framework that I think would be really helpful. So I spent years of my life, definitely every single one of them before I became a Christian in 2006. But even for many years after, as I kind of ebbed and flowed with my Christianity, not that I was ever turning my back on God, which I, when I became a Christian,

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but it's really easy to get caught up in the world's knowledge and ideas because they seem to be working. You know, people are successful, people are healthy, people are fit. And so I just, sometimes I would get caught up. And so I kept reaching for the best tools from the most influential minds, like Ryan Holiday. And some of them, they worked. They were genuinely useful. I still, still practice. A couple of days, every single week, I go on a walk a couple of times a day. I walk a mile. And as I do, I talk to the Lord. I pray. Sometimes I'm just in utter silence. Because stillness is the key.

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I often recount Ryan Holiday quoting over and over again that the obstacle is the way. And that I don't need to avoid the obstacle because oftentimes the obstacle is a gift from God. And that the way to greatness is through it. I will never forget reading Ego is the Enemy and recognizing how often my ego destroyed my life, nearly ruined my marriage, caused financial ruin, broke relationships. My ego is my enemy. So they were all so helpful, so useful, so impactful.

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But good tools on a broken foundation, they're still going to crack. And so I've learned something that I want to share with you. And I hope that it's helpful for you. And it's these three things. The first one, and you've probably heard me talk about these in some variation. But the first one is, it's called The Gap. And the first one is grounded in identity. Your worth is settled before any performance. You see, you and I, I got into a debate with somebody on YouTube about this recently.

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You and I have been made eternally worthy, eternally valuable in Christ if we have put our faith in Jesus. We didn't do that. We weren't worthy and valuable. We were made to be that way when the righteousness, the perfection, the glory, and the goodness of Jesus was imputed on us. Literally, it was put into us as Christ died on the cross for us. And we receive that, accept that, and choose to follow. So when I'm grounded in that, I live from a place of sonship. I am a son of the living God.

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I am adopted into his family. You see, grounded in identity, you could say grounded in faith. But this is a man who knows who God says he is, and he doesn't need to defend that territory. As simply as I can put this, when you are grounded in identity, your worth, it's never on the table. You can continue to strive. I believe there is a healthy form of godly ambition. Ruslan is a guy, you can look him up. He recently wrote a book called Godly Ambition. Fantastic book. And it talks about all the healthy ways in which we continue to pursue greatness.

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I recently wrote an article talking about striving for the 1%, this idea that I can have an incredible marriage, an incredible relationship with my kids, that I can have a fully sold out and committed to relationship with Jesus, and I can achieve incredible financial success. But that's going to take striving. That's going to take a lot of pushing and a lot of growth. But whether I achieve the 1% or not doesn't change my worth. Because my worth and my value is grounded in Jesus Christ. That's my identity. My identity is I am a child of God. And you are too, if you put your faith in Jesus.

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If not, then you are a whole bunch of other things, but you are not the one sure and certain thing. That's grounded in identity. The second component to the gap framework is authentic in action. Integrity is about congruence. It's not about perfection. You see, Seneca, he knew the philosophy, but for some reason he couldn't live it. But what we need to understand is that is not a knowledge problem because he had all the knowledge the world had to offer. I mean, we live in an information age like nobody before us. With Google, with YouTube, with artificial intelligence.

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I mean, we can look up and receive and learn and understand anything and everything. There is nothing that we should be absent from understanding because of the information that we have access to. So we don't have a knowledge problem. And yet, it seems like we have a greater gap in a foundation problem. We seem to be, in many instances, so much farther away from truly grasping and understanding who we are. And so, my actions, my words, my actions, the things I do, the way I treat people, the way I respond to people,

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they don't look like Ryan Holiday rolling his eyes as Ivanka Trump was bragging on her appreciation for Marcus Aurelius. I mean, that was, it actually showed me that it is authentically who he is, but he is just not who he says he is. Because remember, he should master his mind. He should not allow other people to control his emotions and his circumstances. And yet, that's exactly what happened. He turned into a little baby throwing a fit. And I know we're all susceptible to these things from time to time. I mean, even for those of us that have an identity in Christ, as we try to live that out in action, it doesn't always look pretty. I'm not saying this is about being perfect.

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But if we're consistently misaligned, there seems to be a problem. And Ryan Holiday continues to crash out. Like, he continues to, like, be getting worse and worse when it comes to this. And I guess he's just fed up with Trump being in office. I guess he's just fed up with people supporting the idea. And let me tell you, Trump is no peach. Holiday is right. There are a lot of things that Trump says and does that are unkind. That are ungracious. That are not kind. Have a problem with that. Fine. But for that to cause you, the master of your mind, the king of stoicism, to throw a fit and roll your eyes like a baby?

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Come on now. Again, the saint of knowledge problem. It's a foundation problem. To be authentic in action is to live out who you say you are. As a child of God, I want to ensure that my words and my deeds reflect who I am in Christ. To provide for and protect for my family. To do business with integrity. To love my neighbor. To stand firm in my convictions. To live from the truth and the truth alone. To not let my mind be mastered by the things of this world. And finally, in the gap framework is this idea of being purposeful in pursuit.

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You see, when you are living on purpose, when your purpose is rooted in God's call, not in your own applause, not in your own tribe, not in your own whatever you have built or created, then you don't need to gatekeep. And you also don't need to attack. I mean, we all have problems with people that we disagree with. And I don't think that we need to reserve our ideas or our convictions. Speak them. That's fine. But when you do that and it happens in a very uncharacteristic, inauthentic manner, there's a problem there.

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You see, my purpose is to glorify God. That's what I've been called to do. My purpose is to share the good news of the gospel of Jesus Christ with as many people as I possibly can. For better or for worse. And try not to do that as a jerk. My purpose is to, as the husband to one wife, is to honor my wife with my lips, with my eyes, with my hands, with every part of my being. My purpose as a father is to do everything I can to raise my children up in the way of the Lord. But it is also to do my best to provide for and protect them. My purpose as a business owner is to use the gifts and talents that God has given me.

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To steward them in such a way that I can lift other people up. To help them generate more revenue for their businesses. Which is why I won't work with an unethical business. Because I can't, that's not a good steward of my gifts to help somebody else do bad things. It's to help men particularly, but men and women, to see themselves in the way that God sees them. As eternally worthy and valuable. To never prioritize the things of this world for the things that God has created you for. To honor God above all else. Purpose. And so if I start acting in such a way that is counterproductive to that purpose. Then I am no longer living on purpose. Look it. The whole purpose of this framework.

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Is to help us see that our life is not about being impressive. It's about becoming trustworthy. Like I, from this point forward, and I've seen this for quite a few years. I just, I can no longer trust what Ryan Holiday says or does. Because I've seen his true colors come out. Let me take you back. When I read Stillness is a Key, it wrote. When I read Stillness is a Key in 2019, it had great impact on my life. It changed my habit and discipline. It caused me to rest in a whole new way, which I absolutely loved. But the difference between me understanding Stillness is a Key in 2019 and me understanding Stillness is a Key in 2026 is this.

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Is my ultimate form of rest is found in Jesus, who says to me, All who are weary and heavy-lilled, I will give you. You see, walking the block, it's a helpful way to separate myself. But ultimately, if I'm not walking the block to cast my cares on Christ, then it's going to crack. My walks will only last so long. I can go away for a two- or three-day retreat, which sounds miserable to me. But it's not going to help me get any closer to Jesus, who is my rock, my firm foundation, if I don't put Christ at the center of that.

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It's not about the way. It's about the foundation. And that's the thing that Stoicism misses. That's the reason that anybody who attempts on their own to master their mind will eventually crumble. Stoicism was never going to be enough. Because it is, at best, a feeble replacement for who Christ calls us to be and what Christ calls us to do. To be grounded in Him. To be authentic in how we live that out.

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And to be purposeful in the pursuit of the things that He calls us to. And so my question for you is this. You may not have kept up on the Ryan Holiday saga. And that's okay. You may not even know what Stoicism is. And that's okay. But I just want to help you see this. And this is where we'll land. If your foundation is not in Christ. And the lens by which you see the whole world. By which you build your whole life. By which you speak and act. Is not through the lens of who God is. And who He calls you to be.

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Then you are on a path to destruction. You may feel like you're in a good spot right now. But it's not going to last long. And you say, Ryan, I've been doing this for 15 years. And I've been great. There's a day coming. And I want to warn you. That you don't have to face that day. Because today you can make a decision to turn to Christ. Maybe for the first time. Or if not, for the next time. Repent. Give yourself over to this idea that you've tried everything that the world has to offer. And realize. That you're done with those things. That they're good things. But they're never the best thing. Because the best thing is Jesus.

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And by the way. If Christ is your foundation. Then all those things. That you do read. That are not Christian. That are not godly. But maybe you're good. You will see them in a whole new way. And you can still use those things for your good. And even for God's glory. But you're just going to understand them for what they really are. A gap. Between who you are now and ultimately. Who God calls you to be. If you'd love to check out the Grounded Alignment Framework. If you want to see that laid out a little bit more. Go ahead and click the link below. And I'll be more than happy to share that with you. You can check that out.

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You can look through it. If you have any questions. Find me on any of the social platforms. You can DM me. Shoot me a note. I'd love to hear from you. I'd love to hear whether or not. This is something that resonates with you. Peace. You are out of here.