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Welcome to the Daily Stoic Podcast designed to help bring those four key stoic virtues, courage, discipline, justice and wisdom into the real world. Hey, it's Ryan. Hope you are well. I am just working on my talk. I'm going to be giving a talk in San Francisco and Portland in mid June. I'd love to see you there. You can grab tickets@dailystoiclive.com if you're not on the west coast. You want to see me in the Midwest or on the east coast to Tickets are up Chicago, Minneapolis, Detroit, Boston, D.C. i'm forgetting another one. And then I'm going to be in Australia in October as well. All Those tickets@dailystoiclive.com. No. This is the mission. You thought you were supposed to be doing this. You thought your job was to do that. You were on a mission to do something very specific. But then what happened? Life happened. Stuff happened. Other people happened. And now, now that is the mission. When Marcus Aurelius wrote his famous passage about how the obstacle is the way, this is what he was referring to. There can be no impeding our intentions or dispositions, he said, because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting. Nothing can prevent our mission, he was saying, because the mission adapts. We thought our assignment was one thing, but now we realize it's might be less fun, it might require more patience than we planned, more forgiveness than we possessed, demand more creativity than anticipated. But that's the point. We are growing and changing and expanding to meet this new mission. The obstacle isn't a detour, it is the path. It's crazy to me. Last year was the 10 year anniversary of the obstacle is away and now it's the 11th year anniversary of it. I just, it's not anything I could have imagined without that book. I don't know, my life would be very different. Certainly we wouldn't be here talking. If you haven't read the Obstacle Is the Way yet, you can check it out. We have a 10 year anniversary edition. I'll sign your copy. We've got leather bound editions in the Daily Stoics tour as well. I'll link to all that in today's show. Notes. Being an effective leader is difficult, right? You gotta keep your ego in check. You gotta know how your business works, how the team operates for peak effectiveness. But most leaders are making decisions about their teams based on assumptions and not reality. And that's exactly the problem that today's sponsor, Scribe, was built to fix. Scribe Optimize passively captures how your team works across approved business apps and it uses AI to automatically surface workflows, inefficiencies and improvement opportunities. No interviews, no manual discovery, no extra work for your team. Scribe is trusted by 80,000 plus enterprises, including nearly half of the Fortune 500. Scribe Optimize follows work across every tool involved. If someone starts something in Salesforce and finishes it in a completely different tool, it tracks it the whole way. And Optymyze shows you where your biggest inefficiencies are with AI powered recommendations on how to fix them so you're not just identifying problems, you're getting clear directions on how to improve the kind of visibility that used to take months now is always on. And Optimize only works on applications. Your admin improves so no personal activity is captured and no one's privacy is at risk. If you want to see what Optimize could look like for your organization, visit Scribe How Stoic S C R I B E How Stoic I just heard this stat that shocked me given that I hear from the sales staff at my publisher quite a bit. The stat is Sales teams spend about 50% of their time on admin work instead of selling relationship building closing deals, which means they're not selling right? And that's where today's sponsor comes in. Pipedrive. It's a simple, intelligent CRM tool for small and medium businesses. Pipedrive was built from the ground up to strip away that manual work, that stuff that's wasting your time taking your sales team away from doing the thing you pay them to do, which is sell stuff. They've got smart automations to handle repetitive tasks and you can even customize these automations to fit your unique sales process. Plus they've got AI features that will analyze your pipeline, flag stall deals, surface what needs attention and tell your team what to do next without them having to go look for it. Switch to a CRM built by Salespeople for salespeople and join over the 100,000 companies already using Pipedrive. And right now when you use our link, you'll get a 30 day free trial. No credit card or payment needed. Just head over to pipedrive.com stoic to get started. That's pipedrive.com stoic to be up and running in minutes. Kindness is always the right response. This is the May 12 entry from the Daily Stoic. Kindness is invincible only when it's sincere, with no hypocrisy or faking for. What even can the most malicious person do if you keep showing kindness and if given the chance, you gently point out where they went wrong, right as they were trying to harm you. This is Marcus Aurelius, Meditations 11:18. What if the next time you were treated poorly, you didn't just restrain yourself from fighting back? What if you responded with unmitigated, sincere kindness? What if you could, as the Bible says, love your enemies and do good to those who hate you? What kind of effect do you think that would have? The Bible says that when you can do something nice and caring to a hateful enemy, it is like heaping burning coals on their head. The expected reaction to hatred is more hatred. When someone says something pointed or mean. Today, they're expecting you to respond in kind, not with kindness. And when that doesn't happen, they're embarrassed. It's a shock to their system. It makes them and you better. Rudeness, meanness, cruelty, these are a mask for deep seated weakness. And kindness in these situations is only possible for people of great strength. You have that strength. Use it. I read a book by James Peck, who was one of the freedom writers. In fact, the book is called Freedom Rides, but it's his memoir. James Peck was one of the few white freedom writers, one of the early white participants in passive resistance to the horrendous injustice that was segregation and Jim Crow in the American South. And in the book, he talks a handful of times about when he's being. He's attacked, all these different occasions, and how in the middle of being beaten or bullied or attacked or whatever, he would often say something to the person attacking him. Like he'd ask them a question or he wouldn't respond to an insult. He'd say something nice and how often. This was like a record scratch moment. In some cases, it would shake the person out of their sort of spiral of rage and hatred because they just expected to get nastiness back. And when they didn't, it didn't always work, of course, but it was like, whoa, what am I doing? Who is it? It kind of reminded them, oh, this is a human being I'm about to do this to. Not this abstraction that I've projected all this stuff to. Nonviolence, of course, is the highest expression of this sort of biblical wisdom. The Christlike suggestion of turning the other cheek. It's extraordinarily difficult to do. The people in the civil rights movement, they didn't just hear about this once and then magically become these saints. There was real training. One of the amazing stories, Martin Luther King is attacked on stage as he's speaking to a large leadership conference in the civil rights movement. And he's being beaten by this Nazi, a literal member of the American Nazi party. And the crowd watches, like, is he going to fight back? Is he going to lift his hands to protect themselves? And they note the incredible discipline in which Martin Luther King drops his hands actually makes himself less defended. Again, that was a lifetime of training and meditation and planning and experience that gets him. They're not unlike the training that a Special Forces operator would have under fire. And then when the person is apprehended, Martin Luther King insists that he not be hurt. He takes him to a back room. Not to beat the crap out of him, not to neutralize this threat, which, you know, Malcolm X would say he ought to have done. But he has, like, a pleasant conversation with him. And again, that's a record scratch. Like, the amount of discipline that that takes. I'm not asking that of you because I'm not sure I could give it myself. But Seneca's point, that, look, everyone we meet is an opportunity for kindness. But to see these moments when we're provoked, when we're attacked, when we are treated unfairly, when we are abused, that makes the kindness all the greater, all the more impressive. And I want you to see that not as a weakness, but as a part of those disciplines of courage and discipline and justice and wisdom. Martin Luther King realizes that, you know, blacks and believers in racial equality in the United States were hopelessly outnumbered, that the forces of segregation, in many cases had control of the police and the military, and that it was insane to try to fight that violence with violence. So we decided to treat it instead with kindness, with grace, with forgiveness, with discipline. And in the end, it was the only thing that made a difference. I'm not perfect at this. I respond to provocations and insults and attacks. It's never really to my benefit. I almost always regret it. It's not the kind thing to do. It's easy to have a comeback. It's easy to dunk on the idiot who's attacking you. It's therapeutic and cathartic, even. But it doesn't help us move forward. It's not a great look. It certainly doesn't change their mind. So let's focus today on meeting everyone and everything with kindness, especially particularly unkindness. Let's meet that kindness with unkindness. See what kind of difference it makes. Let's see who it stops short and whose attention it catches.
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Host: Ryan Holiday
Date: May 12, 2026
In this episode, Ryan Holiday explores two core Stoic ideas: adapting to life's unexpected missions and responding to adversity with sincere kindness. Drawing from the teachings of Marcus Aurelius, biblical wisdom, and real-life examples from the civil rights movement, Ryan reflects on how to embody Stoic virtues—particularly in moments of challenge or provocation—and the transformative power of kindness as a personal discipline.
On adapting to change:
“The obstacle isn't a detour, it is the path.” —Ryan (01:18)
On kindness:
“Rudeness, meanness, cruelty, these are a mask for deep seated weakness. And kindness in these situations is only possible for people of great strength. You have that strength. Use it.” —Ryan (07:02)
On nonviolent courage:
“Martin Luther King drops his hands, actually makes himself less defended...And then when the person is apprehended, Martin Luther King insists that he not be hurt...But he has, like, a pleasant conversation with him.” —Ryan (08:54)
On personal imperfection:
“I'm not perfect at this. I respond to provocations and insults and attacks. It's never really to my benefit. I almost always regret it.” —Ryan (10:09)
Ryan maintains a thoughtful, candid, and motivational style—rooted in classical references but grounded in relatable, modern self-reflection. He openly shares his own struggles with defensive reactions and encourages listeners to experiment with Stoic principles in real, everyday situations. The tone is both aspirational and pragmatic, inviting the audience into the continued practice rather than promising perfection.
This episode is a powerful reminder that our real mission is to rise to the occasions life presents—with adaptability, sincerity, and, above all, kindness, especially when it's most difficult.