How Does Stoicism Help You Overcome Guilt and Shame?

In today's episode, Ryan answers questions from a live audience in Sydney, Australia. Some of these questions include: How do we keep our ego in check when things are going well? How does a Stoic handle guilt and shame? What do the Stoics say about navigating profound loss? + more! Ryan Holiday is coming to a city near you! Grab tickets here | https://www.dailystoiclive.com/🇺🇸 USA dates: Portland, Oregon - June 8 San Francisco, California - June 11 Minneapolis, Minnesota - August 18 Chicago, Illinois - August 19 Detroit, Michigan - August 20 🇳🇿 NEW ZEALAND:Auckland, New Zealand - October 13 🇦🇺 AUSTRALIA dates: Sydney, Australia - October 16 Melbourne, Australia - October 18 Brisbane, Australia - October 20 Perth, Australia - October 21 🎥 VIDEO EPISODES | Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail 📢 Share | ⚙️ Manage Subscription

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

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:14Ryan Holiday?

  Hey, it's Ryan. Welcome back to another episode of the Daily Stoic Podcast. The dates for Australia are all booked. I'm going to be there in October. Our travel is all booked. And I was talking to my kids. I was like, hey, are you guys ready? I'm going to be doing talks. And they're like, where are you doing your talks? And I was like, well, I'm going to be in Sydney. And they were like, is Sydney the place where the fire alarm went off right before you went on stage? I was performing at Sydney Town Hall two Julys ago. And yeah, right before I was supposed to go on, they just loaded everyone in. The fire alarm went off. And I just totally forgotten about it, which was hilarious. Actually, here's a clip from that. So I'm like, five minutes before going on stage to do my talk here in Sydney.

• 0:58Ryan Holiday?

  And then the fire alarm went off. And we've all had to evacuate. The whole place is empty. They just let me back in. It's never a dull moment, which is actually what I'm going to talk about a little bit in the talk, which is that you got to roll with the punches. You can't let it shake you. You just got to deal with it. It's funny, right? Like, you could talk about Stoicism. But if you do anything out in the world, if I was getting there talking about, I don't know, black and white movies, I'd still have to be Stoic in response to the fact that right before I'm about to go on stage, something goes totally sideways, and I'm not in control. And I just have to figure out how I'm going to respond. And how do I make sure that doesn't throw me that the fans are already a little off? They're a little frustrated. Things are late.

• 1:43Ryan Holiday?

  Actually, not only can I not let it ruin it, I have to figure out how to compensate for it and make things better as a result. And, you know, here I am, two years later, on my way back, and I get to tell that story and share for you. That's one of the perks of being a writer, or making YouTube videos or podcasts. You can always use this stuff as material. So I will be back in Sydney on October 16th, and then also Melbourne, Brisbane, Perth, and Auckland. Before that, I'm going to be in Portland, San Francisco, Minneapolis, Chicago, and Detroit. You can grab all those tickets at dailystoiclive.com.

• 2:22Ryan Holiday?

  And in the meantime, here are some questions from some folks in Sydney that they asked me right after the fire alarm went off.

• 2:32Speaker 01

  How are you doing, Ryan?

• 2:33Ryan Holiday?

  Hi.

• 2:34Speaker 01

  I just wanted, kind of off the back of that question, how do we keep ourselves more honest about our own ego? And especially in the times, it's pretty easy to stay humble if things aren't going well for you. But if things are starting to improve and you're on a bit of a winning streak, how do you keep yourself honest and not be slave to your own ego?

• 2:55Ryan Holiday?

  Yeah, I was talking about the stories that we tell ourselves, right? It's especially hard not to tell yourself a story about your success when that success is public and other people are telling a story about you. When you're seeing it in print or in video, right? When you're seeing other people tell you, oh, you're a genius. Oh, you're special. Look how great this thing you did was. So we do have to actively kind of go and remind ourselves of how things actually were, what we didn't know. We have to kind of repeatedly insist on the truth, maybe even a bit cynically, just to make sure we're not getting puffed up by things. I think that's, that's really, really important. People around you who can tell you the truth is so important. This is Elon Musk's big problem.

• 3:39Ryan Holiday?

  These companies all have all these handpicked board of directors who are all very indebted to him and nobody tells him, like, you're being crazy. This is insane. Don't do this. His, I think his second wife, the one he married twice, she said her job was to keep him from going king crazy, like the way that a king goes crazy. Well, they're obviously not together anymore. I think we've seen the results of that. But in meditations, Marcus, he explicitly talks about this. He says, you have to be careful not to be Caesarified or dyed purple. The emperor of Rome would have a purple cloak. And we can all be Caesarified. We can all be changed.

• 4:22Ryan Holiday?

  They say power corrupts. Having people tell you what you want to hear, not getting feedback, not having people who can deliver truth to you, hearing the stories of your greatness and success. Imagine you're Marcus Aurelius and there is a hundred plus meter tall.

• 4:43Ryan Holiday?

  Marble monument, you know, detailing your genius and accomplishments. Right. There's a triumphal arch of your greatness that you go under every day. Caesar, Caesarification was a real thing. People are worshiping you as a god. And what he does in meditations, what he, he repeats to himself how worthless clapping is, how worthless compliments are, how worthless it is to be remembered. He's trying to overcorrect to, to deal with all the stuff and the unnaturalness of that success. And we all have our own versions of that that we need to work on.

• 5:25Speaker 02

  G'day, Ryan.

• 5:26Ryan Holiday?

  Hi.

• 5:27Speaker 02

  Good to have you back. So lovely to hear you describe your time here in our beautiful country with your family, which leads me to ask, you didn't mention Daily Dad, which as a father and a stepfather, I find enormously valuable. You've given us a few examples of people who aren't doing this work in the public eye. Who in your mind is doing this work so well as a father and perhaps even a leader, either of a company or a country?

• 5:52Ryan Holiday?

  That's a great question. You know, I got so much out of writing The Daily Stoic that every day thinking about these things, being forced to think about them from these different angles, to repeat these kind of timeless principles over and over again, has been so valuable to me personally. The reason I started Daily Dad was to force myself through that process as a parent. What's important, what actually matters, what's easy to miss, what are the values that I want to parent by? So, so I started Daily Dad around that idea. It's, I think I started it when my youngest was maybe two or three. So I've been, I've been at it quite a while. And I, I think this may be better. I'm by no means perfect. I'm struggling with it every day. I lose my temper every single day.

• 6:36Ryan Holiday?

  Lose my shit every single day is probably a better way to say it. Wonder if you're any good at this. Uh, wonder, you know, if you're doing this well. I, I think these are all important questions to be asking, but I, I've been doing Daily Dad for that reason. And I've gotten a lot out of it. And you can sign up if anyone wants to, to get it. It's just dailydad.com. It's not for dads. It's, I'm a dad. It's one piece of parenting advice every day. But, um, I, I wish I could say, hey, these people are great parents. Unfortunately, most people in the public eye are not. We find that out in retrospect.

• 7:13Ryan Holiday?

  And I'll leave it to their their kids to decide whether they're good or not. But I I do try to learn little things here and there. Oh, this is an interesting way to think about it. Or or conversely, here's a colossal tragic mistake that this person made that we can learn from. What what do the parents who've lost children have to tell us? What are parents who, you know, lost touch with their children? What do they have to tell us? You know, what what what do parents who are a little further along wish they'd done differently? That's what I've tried to build it around. And it's just my it's my favorite thing to do. So thank you for subscribing.

• 7:46Speaker 03

  Hi.

• 7:47Ryan Holiday?

  Hi.

• 7:49Speaker 03

  I think a lot of people in this room would be in a similar boat where you may have invested time to become more self-aware or conscious of your ego, which also catalyzes you to reflect on your own life and things you may have done in your life. And I've personally experienced moments of reflection or maybe guilt or shame of previous actions which may have been as a result of your ego. And they are no longer within your control. So wondering how you navigate those experiences where you feel like you're not in control anymore and moving forward with those feelings of guilt or shame.

• 8:29Ryan Holiday?

  Seneca said, when I think of all the things I have said, I envy the mute. As someone who has had the deeply unpleasant experience of editing my own books that have come out, I can relate to that. Nothing makes you cringe more than having to see things that you put out in print for millions of people. And now you go, what was I talking about? Or how did I possibly feel qualified to say that? So, yeah, I think if you look back on things you have done and said in ways you've treated people and you never think, wow, I was an enormous idiot. You are probably in the sway of ego. You're either a saint, which you are almost certainly not, or or you're delusional.

• 9:15Ryan Holiday?

  This sort of cringe and pain that we feel, I mean, a positive way to think about it is, we feel that because we've changed and evolved. And it would be strange if we look back at who we were when we were younger, when we knew less, when we experienced less. And we're just like, yeah, I got it totally right. And everything that's happened subsequently has added zero new information or perspective. Right? So it's good that we have this. But the ability to make amends, to own mistakes, to be responsible for things. This is a key, a key thing. This is certainly key as a parent. I know I don't remember my parents ever apologizing for much. I try to apologize. So apologizing today for something I said when I was frustrated.

• 10:00Ryan Holiday?

  I try to own what I've done. I try to look honestly in the mirror. Sometimes that's really painful. Sometimes you can't look at it straight on. You gotta see it from an angle and you're working on it. But to me, that's a sign of progress. And I'm trying to get better at making amends. And I see that as part of that self-improvement process. That's why we're doing the work. It's to learn things and be better and not be who we're, we used to be.

• 10:36Speaker 04

  Such a big fan of yours.

• 10:38Ryan Holiday?

  Oh, thank you.

• 10:38Speaker 04

  I have your books here.

• 10:40Ryan Holiday?

  Oh.

• 10:40Speaker 04

  I wanted to ask you about the daily stoic of today. Today's one is about not letting your career, you know, be your life sentence and eventually letting it go. Since your career and way of life is stoicism, what is your succession plan? How do you plan to let it go?

• 11:00Ryan Holiday?

  What are you trying to say? Am I a pastime friend?

• 11:04Ryan Holiday?

  No, look, I, I. I have a thing I do. I go into like used bookstores and I'm always struck by the large piles they have of books that were once popular and then people got rid of them. They don't want them anymore and no one cares anymore. And we can see, we know no one's moment in the spotlight is forever. We say that everyone has their 15 minutes of fame. You know, no one's career goes on indefinitely. So I try to remind myself, look, there's, at some point you reach the peak and it's all downhill from there. It might be slow,

• 11:44Ryan Holiday?

  it might be steady, but at some point you have done your best work and everything else is an echo or a shadow of that. And I try to be honest about the fact that that will happen to me. Maybe it's already happened to me. But in the meantime, I'm gonna keep doing my best. I'm gonna keep showing up. And I generally though, try not to think that much about how things are selling or how they're doing. You know, early on in my career, I was, as I said, I was like, how did this do? What did they say about it? I would say I was probably 90% focused on that and 10% satisfied with the work that I did. I've tried to flip that. The irony has been the less I've cared about the external

• 12:24Ryan Holiday?

  results and the status or the recognition of it, the better I seem to have done. Right Thing Right Now debuted at number one in the US in June, which was actually a surprise. It was very cool, but it wasn't what I was thinking about. Now, maybe that's the high watermark. And if so, so be it. I'll gladly take that as a high watermark. And in the meantime, I just wanna keep doing what I love doing. And I'd keep doing it if the audience was half as big, or 10% as big, or 5% as big. Maybe if it got... To a certain level, I'd stop publishing it and just do it for me. But I'd still be doing the thing because I get the value out of doing it.

• 13:07Speaker 05

  Uh, Ryan, um, sitting next to my boss definitely offered a few of the, um, negative feedback compliment sandwiches in my time. Mate, Discipline is Destiny, definitely one of your best books to date. Thank you so much for that.

• 13:19Ryan Holiday?

  Oh, I appreciate that.

• 13:20Speaker 05

  One thing which really surprised me was the passage on psychedelics. And it seemed to have, you conflated it in a way with the opioid epidemic over in the US. Granted, a lot of people do misuse psychedelics, but considering the abundant research showing, uh, the, the positive impacts into things like anxiety, depression, PTSD, uh, and addiction, tens of thousands of years of, uh, humanity using these things, if not longer, compared to the havoc which is wreaked by things like opioids, benzodiazepines, alcohol and so forth. Could you please expand upon that passage?

• 14:05Ryan Holiday?

  Sure. Yeah, look, uh, first off, if you're suffering from severe trauma, you have treatment-resistant depression, if you are really going through it, you've tried everything, I have no interest in judging you or what you're working on or whatever works, right? Like, everyone should go on their own journey, uh, should find the things that help them improve, that change. I, it, the, the, the human mind is a wonderful thing and it's also a terrible thing. And, uh, if yours is torturing yours, I, I fault no one for finding solutions. I, what I was just trying to say is two things. Number one, uh, I am always very skeptical when people have a thing that they say is the magical solution to all of their problems.

• 14:50Ryan Holiday?

  And then two, uh, I've talked to a lot of people that have done psychedelics. And I would just say, I haven't heard a single thing from one of them that is not in every philosophy or religious text. These are basic assumptions or insights that humans have unleashed over thousands of years, also of tried and true experience. And so. Is there obviously some difference between knowing them and knowing them? Yes. And if psychedelics help someone get that? Again, I've got no problem with it. What I dislike is a lot of people who are definitely not doctors telling people to fuck with their brain chemistry, you know, at dinner parties because it's the it's the key to enlightenment and insight.

• 15:35Ryan Holiday?

  I find that to be very alarming. I just happen to know a lot of those people who have built big platforms around it and that that unnerves me.

• 15:45Speaker 06

  Just remind me of what the Stoics had to say about navigating profound loss in terms of losing loved ones.

• 15:53Ryan Holiday?

  Sure. Yeah, this is a timeless part of the human experience, unfortunately. I talked about Marx's realist, he buries half of his children. Seneca buries his only child. He writes a series of very beautiful essays. They're a series called Consolations. He writes one to his mother when Seneca is exiled. He writes another to the daughter of a friend who had died.

• 16:23Ryan Holiday?

  The idea that the Stoics were unfeeling, that they were unaffected by loss or pain or grief is to me totally belied by these beautiful, moving essays that I I reread when I lose someone, that I pass to people when they ask me this question. I there's some of the most beautiful, profound writings that the Stoics have ever produced. My favorite one, in one of the essays, Seneca is writing to this woman who lost her father. And she's talking about how the memory of him, you know, every time she thinks of him, she just breaks down crying. She's so upset, she can't function. And he says, but your father loved you a great deal.

• 17:05Ryan Holiday?

  Obviously, he wants to be remembered by you. But if you told him, he says, if he's up there somewhere, you could tell him that after he died, that his memory, whenever you thought of him, it brought you crippling sadness and despair. He'd be like, what? That's not how I want this to go at all. We don't want people to be glad that we're gone. But our our memory should be something positive, right? And I think if you can, I just think about that all the time. What would this person want me to think when I think of them? And so. The Stoics are not saying you feel sadness and loss, stuff it down, don't be a weakling. Some of the only stories we have about Marcus Rilis from other historical sources involve him crying over the loss of people that he loved.

• 17:50Ryan Holiday?

  At Tudor, he weeps over the victims of this plague, this devastating pandemic that he experiences. So the Stoics were not unfeeling, they were not brutes. But they did try to, when they were overcome by those feelings and when they were crippled by them, tried to go, okay, let me think through this. Let me question some of these assumptions. And how can that help me move on and process these feelings instead of denying them? Thank you. Yes.

• 18:24Ryan Holiday?

  Hey, it's Ryan. Thank you for listening to the Daily Stoic Podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple of years we've been doing it. It's an honor. Please, spread the word, tell people about it. And this isn't to sell anything. I just wanted to say thank you.