How Does Stoicism Help You Overcome Guilt and Shame?

Summary

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The Daily Stoic Podcast — April 18, 2026

Episode: How Does Stoicism Help You Overcome Guilt and Shame?

Host: Ryan Holiday
Location: Sydney Town Hall (Audience Q&A after a live talk)

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Episode Overview

In this engaging Q&A episode, Ryan Holiday discusses how the timeless teachings of Stoicism can help us address guilt, shame, and loss, as well as navigate ego, parenting, career transitions, and even psychedelic use. Recorded as a live audience session in Sydney, Ryan fields questions that prompt him to reflect on practical Stoic wisdom for modern life, drawing on personal anecdotes and historical Stoic texts from Marcus Aurelius and Seneca.

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Key Discussion Points & Insights

Rolling with Life’s Surprises: Stoic Flexibility

[02:36-04:00]

• Ryan recounts a recent incident where a fire alarm went off five minutes before he was due on stage in Sydney.
• He uses the story to illustrate the vital Stoic principle of “rolling with the punches”:
  • “You got to roll with the punches. You can’t let it shake you. You just got to deal with it.” (Ryan Holiday, 02:58)
• Stoicism isn’t just theoretical: it’s about responding skillfully to unpredictable events.

Ego Management and Staying Grounded

[04:15-07:52]

• Audience member asks how to stay honest about ego, especially during success.
• Ryan emphasizes the importance of honest feedback and tells how success stories inflate ego:
  • “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.” (04:34)
• He mentions Marcus Aurelius’s warning against being “Caesarified” or “dyed purple”—changed by power and adulation.
  • “You have to be careful not to be Caesarified or dyed purple...We can all be Caesarified, we can all be changed. They say power corrupts.” (05:40)
• Surround yourself with people who will tell the truth, not just what you want to hear.

Stoicism and Parenting (The Daily Dad)

[07:54-09:28]

• Question about Stoic values in parenting and public examples of good fatherhood.
• Ryan shares that the Daily Dad project forces him to internalize Stoic lessons as a parent:
  • “I lose my temper every single day...Wonder if you’re any good at this. Wonder if you’re doing this well. I think these are all important questions to be asking.” (08:56)
• Admits most public figures are imperfect parents and suggests learning from both positive and negative parental examples.

Guilt, Shame, and Accepting the Past

[09:32-12:16]

• Audience member asks about dealing with guilt/shame from past actions (often rooted in ego).
• Ryan invokes Seneca:
  • “Seneca said, when I think of all the things I have said, I envy the mute.” (10:12)
• He reflects on personal cringe/regret from past writing—a sign of growth and learning.
  • “If you look back on things you have done and said and...you never think, wow, I was an enormous idiot, you are probably in the sway of ego. You’re either a saint...or you’re delusional.” (10:42)
• Emphasizes making amends, owning mistakes, and self-forgiveness as Stoic virtues.
  • “The ability to make amends, to own mistakes, to be responsible for things, this is...key.” (11:13)

Letting Go of Career and Succession Planning

[14:34-16:54]

• Asked about the “succession plan” for his Stoic work, Ryan reflects on impermanence:
  • “I go into used bookstores and I’m always struck by the large piles they have of books that were once popular...no one cares anymore and no one’s moment in the spotlight is forever.” (14:57)
• Stresses focusing on the value of the work itself, not external recognition.
  • “The irony has been the less I’ve cared about the external results...the better I seem to have done.” (15:46)

Stoicism & Psychedelics

[17:18-19:31]

• Audience challenges a passage in Discipline Is Destiny on psychedelics.
• Ryan responds with skepticism toward any “magical solution”:
  • “If psychedelics help someone get that [insight], again, I’ve got no problem with it. What I dislike is a lot of people...telling people to fuck with their brain chemistry...because it’s the key to enlightenment and insight. I find that to be very alarming.” (18:13)
• Warns about non-expert advice and trendy thinking but supports personal, responsible experimentation for those in need.

Coping with Loss: Stoic Compassion

[19:42-22:16]

• Question about dealing with profound loss through Stoicism.
• Ryan highlights Seneca and Marcus Aurelius as models for feeling, not denying, grief:
  • “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.” (19:58)
• Story from Seneca’s consolations:
  • “If you told him...that after he died, that his memory...brought you crippling sadness and despair, he’d be like, what? That’s not how I want this to go at all.” (21:01)
• Stoics experienced tears and loss, but also sought perspective and healing through reflection.

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Notable Quotes & Memorable Moments

• “You have to be careful not to be Caesarified or dyed purple...We can all be Caesarified, we can all be changed. They say power corrupts.” — Ryan Holiday, 05:40
• “Seneca said, when I think of all the things I have said, I envy the mute.” — Ryan Holiday, 10:12
• “If you look back on things you have done and said and...you never think, wow, I was an enormous idiot, you are probably in the sway of ego.” — Ryan Holiday, 10:42
• “The idea that the Stoics were unfeeling...is to me totally belied by these beautiful, moving essays.” — Ryan Holiday, 19:58
• “What would this person want me to think when I think of them?” — Ryan Holiday, 21:12

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Key Timestamps

| Timestamp | Segment | |-----------|-------------------------------------------------------------------| | 02:36 | Story: Fire alarm interruption in Sydney; handling life’s setbacks| | 04:15 | Q&A begins – Ego and success | | 09:32 | Reflecting on past, guilt and shame | | 14:34 | Career, legacy, and letting go | | 17:18 | Psychedelics and philosophical caution | | 19:42 | Stoicism and coping with loss |

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Summary Flow & Tone

Ryan’s presentations mix humor, humility, and candid self-assessment, embodying the practical, compassionate aspects of Stoic philosophy. Though rooted in ancient wisdom, the advice feels direct, modern, and personal—embracing vulnerability (parenting, regret, loss), encouraging self-reflection, and championing the quiet virtues of honesty, responsibility, and perseverance through hardship.

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For New Listeners

This episode offers an accessible and heartfelt introduction to how Stoicism can inform real-world questions around failure, regret, ego, parenting, and grief. Through relatable anecdotes and thoughtful answers, Ryan shows that the Stoic path is not about emotional suppression, but about honest growth, connection, and compassion.

Transcript

[Ryan Holiday]

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[Ryan 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. 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 where are you doing your talks? And I was like, well, I'm going to be in Sydney. And they're 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, 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, 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 here I am two years later on my way back and. 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 16, 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 [e-mail] and in the meantime, here are some questions from some folks in Sydney that they asked me right after the fire alarm went off.

[Audience Member]

How you going on?

[Ryan Holiday]

Hi. 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

[Audience Member]

winning streak, how do you keep yourself

[Ryan Holiday]

honest and not be slave to your own ego? 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. 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 Mark Swiss, 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. 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 your Marx, Aurelius, and, and there is a hundred plus meter tall 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, 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 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. G'. Day. Ryan. Hi. Good to have you back. It's 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 the 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 of a company or a country? 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 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 at it quite a while and I think this made me better. I'm by no means perfect. I'm struggling with it every day. I lose my temper every single day. Lose my shit. Every single day is probably a better way to say it. Wonder if you're any good at this. Wonder if you're doing this. Well, I think these are all important questions to be asking. But 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. I'm a dad. It's one piece of parenting advice every day. But 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. And I'll leave it to their, their kids to decide whether they're good or not. But I do try to learn little things here or there. Oh, this is an interesting way to think about it. Or conversely, here's a colossal, tragic mistake that this person made that we can learn from. What do the parents who've lost children have to tell us? What are parents who lost touch with their children? What do they have to tell us? What do parents who little further along wish they'd done differently? That's what I've tried to build it around, and it's my favorite thing to do. So thank you for subscribing. Hi. Hi.

[Audience Member]

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.

[Ryan 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 you're delusional. 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, apologizing today for something I said when I was frustrated. 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 got to 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, is to learn things and be better and not be who we used to be.

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[Audience Member]

Such a big fan of yours.

[Ryan Holiday]

Oh, thank you.

[Audience Member]

I have your books here. Oh, 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?

[Ryan Holiday]

Well, what are you trying to say? Am I past my prime? No, look I have a thing I do. I go into 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 minute 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, 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 going to keep doing my best, I'm going to 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 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 water mark and if so, so be it. I'll gladly take that as a high watermark. And in the meantime, I just want to 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.

[Audience Member]

Ryan, sitting next to my boss definitely offered a few of the 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.

[Ryan Holiday]

Oh, I appreciate that.

[Audience Member]

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 U.S. granted, a lot of people do misuse psychedelics, but considering the abundant Research showing the positive impacts into things like anxiety, depression, PTSD and addiction. Tens of thousands of years of humanity using these things, if not longer, compared to the havoc which is wrecked by things like opioids, benzodiazepines, alcohol and so forth. Could you please expand upon that passage?

[Ryan Holiday]

Sure, yeah. Look, 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, should find the things that help them improve, that change the human mind is a wonderful thing, and it's also a terrible thing. And if yours is torturing yours, I fault no one for finding solutions. What I was just trying to say is two things. Number one, I am always very skeptical when people have a thing that they say is the magical solution to all of their problems. And then two, 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 key to enlightenment and insight. 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 unnerves me.

[Audience Member]

Just remind me of what the Stalwicks

[Ryan Holiday]

had to say about navigating profound loss

[Audience Member]

in terms of losing loved ones.

[Ryan Holiday]

Sure, yeah. This is a timeless part of the human experience, unfortunately. I talked about Marc Sorilius. 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. 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 reread when I lose someone, that I pass to people, when they ask me this question. 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, look, your father loved you a great deal. 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 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 Aurelius from other historical sources involve him crying over the loss of people that he loved. A tutor. 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 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?

[Audience Member]

Thank you.

[Ryan Holiday]

Yes,

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 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.

Foreign.

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[Ryan Holiday]

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