We Are Free…and Not Free | Ask Daily Stoic

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Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:03Ryan Holiday?

  Welcome to the Daily Stoic Podcast, where each day we read a passage of ancient wisdom designed to help you in your everyday life. But on Fridays, we not only read this daily meditation, but I try to answer some questions from listeners and fellow Stoics who are trying to apply this philosophy, whatever it is they happen to do. Sometimes these are from talks. Sometimes these are people who come up to talk to me on the street. Sometimes these are written in or emailed from listeners. But I hope in answering their questions, I can answer your questions, give a little more guidance on this philosophy we're all trying to follow.

• 0:57Ryan Holiday?

  We are free and not free.

• 1:02Ryan Holiday?

  One of the most difficult concepts in Stoicism, indeed in many philosophical and religious traditions, is this idea that we're not in control, not in the little things, nor the big things. Whether you call that God's will or the logos, as the Stoics did, it's difficult to accept that free will is more circumscribed than we'd like to admit. The Stoics once compared human beings as a dog tied to a cart. And while we might have some slack in the line, for the most part, we have little say over where life is going. Does this mean that life is predetermined? That our thoughts and choices are totally chosen for us or are utterly meaningless? Far from it. As Brand Blanchard, one of Marcus Aurelius's most eloquent biographers, explained,

• 1:44Ryan Holiday?

  "Constraints do not deprive us of our agency. They merely direct it." "When a mathematician is making his deductions," he writes, "and his thought is caught up and carried along by the logical necessity to a valid conclusion, is he thinking freely?" "Yes, again, though he is under the constraint of the necessity he is following." The Stoics believed that we could resist this logical necessity, or we could go with it. The dog can lay down and be dragged if it likes, but what's the point? We can see our fate and chance in the direction of the universe as an oppressive force or as a guide. That is our call. That's our choice. But the constraint of necessity is

• 2:24Ryan Holiday?

  always there. The cart is always moving. And the world is much more powerful than we ever will be.

• 2:38Speaker 01

  Ryan, Micah.

• 2:39Ryan Holiday?

  Hi.

• 2:40Speaker 01

  I'm the product leader on Dave's team. Red obstacles away, fantastic, but I'm listening to Courage is Calling.

• 2:49Ryan Holiday?

  Oh, thank you.

• 2:50Speaker 01

  With my sons on the way home from soccer practice at night. And so we paused and discussed, but I heard you mention that you have children. So what I'm interested in is, are there any points that you leverage that you're teaching others through your books with your children that maybe I should be aware of and leverage as well?

• 3:09Ryan Holiday?

  How old are your kids?

• 3:11Speaker 01

  Three boys, 10, 9, and 6. So they're all clustered together.

• 3:16Ryan Holiday?

  So I have a five-year-old and a two-year-old. So they're a little younger. But one of the things I did do during the pandemic, because I wrote a kid's book about Marcus Aurelius, which is really supposed to be kind of a parable of leadership. Like, what I think is so fascinating about Marcus Aurelius is, you know, his father was an emperor. He was just chosen. It's one of the only times in history that just like a random person is just chosen to be emperor. And so he knows from a relatively young age that he will someday be king, but he doesn't know when. And he doesn't feel like that it's in his blood. He feels like it's this thing that he has to earn, which to me is such an interesting parallel to leadership. Like, we feel called to do something. We

• 4:01Ryan Holiday?

  have talent or acumen, but then we have to figure it out. Like, how do we do it? And, you know, there's this moment. In Marcus's life, so I think there's two interesting stories. We were told that he begins to cry when he's told that he's going to be a king, because he knows how many bad kings there have been, right? He's thinking about all the ones that have been corrupted by power. You know, he says Caesarified, like stained by the cloak that they wear. So he's aware that it's possible to do it bad, and that there's like a real responsibility in it. And he wonders if he can measure up to the task. And this is all of which is a story I've talked to my son about many times,

• 4:44Ryan Holiday?

  and did in the early days of the pandemic as I worked on this book. But he has this dream, the night before he's supposed to ascend to the throne, and he dreams that his shoulders are made of ivory. So to me, like the doubts, this is this imposter syndrome that we all have. Like, do I have what it takes? Am I capable? Am I going to measure up? Am I going to let people down? But this dream is that he has stronger shoulders than he knows, that he is capable of it, and that he can do it. And he obviously goes out and does his best ultimately. But I just think Marcus is this fascinating example. I was just writing about this recently.

• 5:25Ryan Holiday?

  There's this, the best presidents they've found have not wanted to be president, right? It's the people who sought the office, who very badly wanted power, tend to be in it for the wrong reasons. And there was this great expression I read. It said, "Happy to serve, reluctant to lead," right? But that that set of attributes actually makes really great leaders, because they're not in it for like, they're like, "I want to contribute. However I can contribute, let me know." And then it, but they're like, they're not like, "But the only way I'll contribute is if I get to boss everyone around," right? And so I think Marcus is this remarkable parable and story about what that kind of leadership looks like.

• 6:08Ryan Holiday?

  And it's something I'm working on, obviously, with my kids, that, you know, they are more capable than they think. But again, the world doesn't revolve around them. And this is something that you sort of have to earn and be worthy of, is something I've been thinking a lot about.

• 6:30Speaker 02

  Dear Ryan, I'm Tom Bing from Singapore.

• 6:33Ryan Holiday?

  Yes.

• 6:33Speaker 02

  Probably before. But anyway, when I was reading, now I started to read more Buddhist religions as well, meditations. I find that there are many parallels between Stoicism, Western philosophy, as well as Eastern,

• 6:48Ryan Holiday?

  Yes.

• 6:48Speaker 02

  more Buddhist kind of philosophy. What are some of the, when you used to talk about stillness, how different or similar is stillness versus mindfulness, you know, being in the moment?

• 7:01Ryan Holiday?

  I think they're very similar and to me, the idea that two independent schools of philosophy and thought and culture, which have almost no overlap until relatively late in history, that they independently come to some of the same conclusions is really exciting and edifying, in my view, it's like, it's like convergent evolution, that they, that they adapted similar features or traits, but from independent ancestors. I find that to be, to be really interesting. I think there's a lot of, a lot of similarities. Like I was saying, I think the, the Eastern thought, maybe mindfulness meditation, the

• 7:44Ryan Holiday?

  Western thought, you know, Marcus, meditations, he's not, he's not actually meditating, but he's meditating through writing, these are different ways of getting to the same place. So I think there's a lot of, a lot of overlap. To me, what I'm, the, the kind of Buddhism I'm most interested in, the kind of Stoicism I'm most interested, the kind of philosophy I'm most interested in, where I like, in the Western world, the distinction between the Stoics and the Epicureans are very similar, is that the Stoics were still actively engaged in life, right? So I think often, when we look at, at some of the Buddhist tradition, or there's a sort of monkish quality to it, a withdrawal from the world quality to it, which, which I certainly

• 8:29Ryan Holiday?

  appreciate and enjoy, but what I like about the Stoics is that, you know, Marcus is the emperor of Rome and Seneca is a playwright and a power broker and, and... And a political leader. What I like about the Stoics and where I think they work well, or certainly the sort of Western philosophy works well in the Western world, is that, you know, it is designed around this sort of active engagement or connection to the polis or the civic society. I think that's really, really important. There's a way you could become so philosophical that you disengage, which obviously I'm speaking to a for-profit company here. Like, that's not what, what obviously would make this continue to work.

• 9:13Ryan Holiday?

  So the idea of that it's possible to be philosophical, that it's possible to find stillness, that it's possible to, you know, get to a place of humility and that you can be resilient. But in the, in the context of like being good at your job, I think there's, that's what excites me about Stoicism at least.

• 9:35Speaker 03

  Hi.

• 9:36Ryan Holiday?

  Hi.

• 9:36Speaker 03

  Hi, Marla. Hi, nice to meet you. I was saying your comments talking about sort of the way that it reminded him of some of the Eastern philosophies when I read it. I'm not super religious, but it actually reminded me, some of the chapters reminded me a lot of Christianity in terms of accept what's happening to you. When you're saying, you know, this, it's almost felt like it's God's way. And I know Christianity is a lot about things are going to happen to you. It's God's bigger plan. So I was kind of struck and I thought of my own life. I have two grandmothers, one was very Christian, one was not. And the one that was very Christian, she just had a better attitude and actually lived longer because all these things would happen to her.

• 10:19Speaker 03

  And she would just be like, oh, it's God's way and I'm just going to go through. That's what he's testing me to do. So I thought that was very interesting.

• 10:26Ryan Holiday?

  So the Stoics talk about the logos, which is in...

• 10:33Ryan Holiday?

  For the Stoics, translates as "the way." In the Bible, the logos translates as "the word." But this idea that there is sort of an out-of-your-control-ness to everything that's happening, but that someone or something is determining how they go, I think the Stoics certainly overlap there. In the ancient world, the Stoics and the Christians, they don't get along exactly well, Marcus Aurelius. Before Marcus Aurelius and through Marcus Aurelius, there's a number of persecutions of the Christians by the Roman state, of course. But what is really interesting to me about the overlap is that the cardinal virtues of Stoicism

• 11:16Ryan Holiday?

  are the same as the cardinal virtues of Christianity: courage, temperance, justice, wisdom. And how much of that is them coming together? How much of them is, like with the Eastern tradition, just independently coming to the same ideas? But I like the idea that they're more or less in agreement about the bedrock principles of what the good life is, what we need to focus on, what we should live by. Again, one can base that ethic in a supernatural or in a metaphysical sense. The other can root it in just sort of pure logic and reason. But I think they're coming at it from... They're ultimately getting to a similar place from different reasoning. And again, to me, that lends an extra

• 12:00Ryan Holiday?

  layer of credibility to it, for sure.

• 12:03Speaker 03

  I agree. It's like, go without my faith or go without my logic.

• 12:07Ryan Holiday?

  Yes.

• 12:07Speaker 03

  It's still a good way to live, if you will.

• 12:10Ryan Holiday?

  Yeah, I was thinking about it. It's like, look, you can be a bad person and maybe you will go to hell. But also, bad people tend to live in hell while they are alive, right? No one's more miserable than the disordered, addicted, disconnected, self-absorbed person. And so the Stoics, I think, are making a pretty self-interested case, a logical case, against many of these same things. And yeah, so I like your distinction as well.

• 12:39Speaker 04

  One question, right? A lot of what you've talked about so far is really personal, right?

• 12:43Ryan Holiday?

  Yes.

• 12:44Speaker 04

  Holding a balance between stillness and action. How do you take those kind of personal traits and turn that into advice for leading, especially large teams, right, like the books of value?

• 12:55Ryan Holiday?

  Yeah. I mean, when we think about this culturally, right? We want a team that's calm. We want a team that's cool under pressure. We want a team that, you know, is connected and unified, not a team that's sort of, you know, a bunch of, you know, sort of egotistical, sort of planets in their own orbit. We want a team that's resilient, right? So I think what I like about Stoicism is that it is a somewhat individualistic philosophy in that it's like, what do you control? You don't really control the people. You control who you are. You control how you hold yourself. You control the standards that you try to live by. At the same time,

• 13:37Ryan Holiday?

  we can build those things organizationally by modeling them, right? By selecting for people who are in agreement with that. And by, you know, ideally also sort of articulating and speaking about those values. But I try to, I try to think of my role, like for instance, inside my organization, as first modeling those traits, but then also keeping the opposite of those traits out of the organization. So we could see, I was just watching the new Uber Showtime series. It's like, you can see where a culture that, you know, prizes just performance

• 14:21Ryan Holiday?

  over the opposite of, the opposite of those traits can be successful in the short term, but, you know, tends to fall apart in the medium to long term. So I kind of think about my role as the sort of cultural enforcer in the organization to go like, not only have to model this, but like, hey, I'm not going to tolerate ego or fragility or, you know, busyness. You know, I'm going to try to, I'm going to try to select for and support those traits in the people inside the organization because I find that's not only where the collaboration comes from, but also the sustainable long-term performance from individuals comes from also.

• 15:03Speaker 04

  And a quick follow up, I love giving this team homework. You talk about the universal being personal and personal being universal. You've mentioned a lot of folks in your book, it's clear you've read a lot of biographies. Any that stand out to you as useful in some outlook for leaders?

• 15:19Ryan Holiday?

  Yeah, for sure. You know, I just read this biography of Angela Merkel, which I really enjoyed. I just had her on the podcast. I don't think it's come out, but it's Catty Martin's The Chancellor. You know, we tend to, again, think of leaders as this sort of charismatic, bold, visionary,

• 15:41Ryan Holiday?

  you know, sheer force of personality. And what I thought was fascinating about Merkel was just that she's essentially the opposite of all those things in every way. And yet, you know, has this remarkable 16-year tenure. She still lives in the same rent-controlled apartment that she had before she was,

• 16:01Ryan Holiday?

  you know, before she was chancellor. You know, anyways, I thought that book was really great. And then one book I also read during the beginning of the pandemic was Doris Kearns Goodwin's Leadership in Turbulent Times, which is basically a biography of Lincoln, both Roosevelts, and then Lyndon Johnson. So not just leadership, you know, in all moments, but she really focuses on leaders during moments of adversity, which of course, the last two years have been defined by. But as we see this sort of trailing logistical, you know, nightmare that you guys are in especially, you know, that's not going away anytime soon. And certainly doesn't look like the world

• 16:45Ryan Holiday?

  is getting more stable. So I thought that was a really great book. And I've thought about it quite a, quite a bit since I finished it.

• 16:58Ryan Holiday?

  It's not that life is short, Seneca says. It's that we waste a lot of it. The practice of Memento Mori, the meditation on death, is one of the most powerful and eye-opening things that there is. You built this Memento Mori calendar for Daily Stoic to illustrate that exact idea, that your life, in the best-case scenario, is 4,000 weeks. Are you going to let those weeks slip by? Or are you going to seize them? The act of unrolling this calendar, putting it on your wall, and every single week, that bubble is filled in, that black mark is marking it off forever. Have something to show, not just for your years, but for every single dot that you filled in,

• 17:42Ryan Holiday?

  that you really lived that week, that you made something of it. You can check it out at dailystoic.com/mmcalendar.