Break Through While You Still Can | Ask Ryan Holiday

Just as seedlings must break through soil, we must break through our comfortable patterns. Nature doesn’t stay dormant forever—and neither should we.1 DAY LEFT 👉 Go to dailystoic.com/spring and enter code DSPOD20 at checkout to get 20% off the Spring Forward Challenge! Challenge yourself to spring forward and become the person you aspire to be. The Spring Forward Challenge starts March 20, 2026.🎙️ AD-FREE | Go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 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.

• 0:15Ryan Holiday?

  Winter has a way of lulling us into bad habits and old vices. Like bears and hibernation, we're burrowed deep in our comfortable routines. We found our favorite spot on the couch, our go-to delivery meals, our perfectly temperature-controlled environments. We've mastered the art of avoiding the cold, the wind, the discomfort. They call this the velvet rut, and it's soft and pleasant, but it's still a rut. And yeah, after months of dark mornings and early sunsets, after trudging through slush and scraping ice off windshields, it's natural to grow comfortable.

• 0:56Ryan Holiday?

  It's reasonable to seek shelter in these comfortable patterns. But the Stoics remind us that true growth requires resistance. Just as seedlings must break through the soil, we must break through and out these patterns. Nature doesn't stay dormant forever. Neither should we. The idea is that we move with the seasons, and we must face the brisk winds of change head on. And that's what the Spring Forward Challenge that we do each spring with Daily Stoic is about. Not quick fixes, but it is about getting set for spring. And with 10 days of Stoic-inspired challenges, one per morning,

• 1:39Ryan Holiday?

  the idea is that you'll clear away some of winter's accumulated habits, just as you would clear dead leaves from the garden. You can plant new patterns that will grow and flourish throughout the year. Yeah, the world is crazy right now, but as Marcus Aurelius reminds us, these external circumstances don't define us. It's our response to them that does. And we have the power to transform challenges into opportunities for growth. "Stop wandering about," Marcus says to himself in meditations. Perhaps on the eve of a seasonal change like this one, he says, "Get busy with life's purpose. Toss aside your empty hopes.

• 2:22Ryan Holiday?

  Get active in your own rescue. If you care for yourself at all," he says, "do it while you can. This is the time. Do it now." We'd love to have you join us and thousands of Stoics all over the world in the Daily Stoic Spring Forward Challenge. The idea is it's going to help you with anxiety and stress, how to be present, how to get after it, how to get active in your own rescue, as Marcus Aurelius said. So we'd love to have you join us and we'd love to have you stop procrastinating. Break out, break free, get cleaning, challenge yourself. You can sign up right now at dailystoic.com/spring. We start in less than 24 hours. I will see you in there. I'm going to be doing it myself. We've got a special offer for podcast listeners.

• 3:06Ryan Holiday?

  20% off when you use code DSPOD20 at checkout. You can join me and thousands of other Stoics in the Daily Stoic Spring Forward Challenge. Just head over to dailystoic.com/spring and enter code DSPOD20 to get 20% off.

• 3:30Ryan Holiday?

  Hello there, Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. As you know, I love answering your questions, whether I get to see you in person, doing a bunch of talks. As I said, you can come see me in a bunch of American and Australian cities if you go to dailystoiclab.com. But if you don't want to travel all the way to Australia, maybe we just sit down and talk about how to have a good spring. That's what we're going to be doing in the Daily Stoic Spring Forward Challenge. It starts on March 20th. So if you want to get in there and do that together, you should join at dailystoic.com/spring. But in the meantime, here are some questions that I answered last year during the Spring Forward Challenge.

• 4:11Ryan Holiday?

  Maybe it'll help you think about what you ought to be doing going into the spring.

• 4:21Speaker 01

  This question is about today's challenge, uh, which spoke to me the most focus only on what we control, but past wounds can really, uh, kind of bleed into the present and feel ever-present. You know, for myself, it's really personal. I have a very, um, toxic mother. I don't really have a great relationship with and an uninvolved father. So like, how can I apply stoic wisdom to like truly actually move forward instead of just, I guess, suppressing the pain because so often I, I really feel that I've moved past it, but then I, I come to find that I've not.

• 5:03Ryan Holiday?

  Yeah. Well, that's rough. I'm sorry. I, I would say, yeah, we don't control that it happened. We don't control who we got assigned on this go around on the planet, but we control how we respond to it. We control whether we get help with it. We control whether we try to process it. We control whether we try to do better. You know, we control all the things that we do after. So like, I don't think Stoicism is just stuffing it down and pretending it didn't happen, but it's doing the work, you know, uh, whether that's with a therapist, whether that's with philosophy texts, whether that's just with, you know, a lot of long walks where you think and process and talk about things. To me, that's what Stoicism is. There is a great line from, from Seneca where

• 5:47Ryan Holiday?

  he says, "We don't get to choose our parents, but we do get to choose whose children we're going to be." And the idea of, of saying, "Hey, this is who I biologically come from, but, uh, I'm going to have a clean break and find myself the descendant of someone or something else. I'm going to choose a different trajectory for my life." That's a, that's a big part of it. I, I, I don't think I would describe my childhood as anything quite like yours, but, uh, but I think we all have issues from ours. And as I've tried to process and deal with mine, I'm trying to say, okay, for my own sake and for the sake of my kids, whose child am I going to be? What am I going to hail from? Who am I going to work with and talk to to sort of re-parent myself so that,

• 6:32Ryan Holiday?

  uh, that I can go forward and, and have a better sort of healthier? More well-adjusted life. So, so good luck and, and I think you're asking the right questions.

• 6:42Speaker 02

  Thank you so much. Like everyone has said, this has been really helpful. And you talked about serendipity earlier in this chat, and I can't remember which day it was, but Andrew said the quote, but one of the Stoic thought leaders said something to the effect of how if you like follow all of your curiosity streams, you'll end up not really doing anything. I'm super paraphrasing and changing terms. And that has always been a huge pain point for me because I think my broad curiosity is probably like at the core of my personality. And I'm a writer and it goes very slowly because I go down all these

• 7:24Speaker 02

  rabbit holes and I'm interested in everything and I want to do everything all at once. And I guess I'm embracing discipline and staying focused this year and it's, it's borne fruit. But I'm still curious about Stoic-informed advice for actually finding that balance and not letting your life become rigid.

• 7:45Ryan Holiday?

  Yeah.

• 7:46Speaker 02

  While still being productive and disciplined. So.

• 7:49Ryan Holiday?

  No, it's a, it's a great question. One of the things I try to remind myself when I'm working on a book because there's all these things that I want to include or all these things that I'm interested in, all these things that connect to it. I try to remind myself that this isn't the only book that I'm going to get to do. Right? And that, that the book that I'm doing here is about this. And I have to, for, for the sake of, of clarity of argument, but also for the sake of it reaching and resonating with an audience, I have to be disciplined about what that is for this brief period of time that I'm working on it. And then I'll go to the next one and the next one and the next one. And so, so sometimes it's, if we feel like, well, I'm just not going to be able to get to it, or if we feel like I'm going to try to get it all in, we're going to be constrained.

• 8:34Ryan Holiday?

  But if we say, hey, for now, I'm focused on this and then later I'm going to focus on that, it allows us to kind of go, okay, I'm not actually closing any doors. I'm just putting this stuff over here for a minute. And so there's so many things that I want to read about. There's so many things that I'm fascinated by. I, I would definitely default on the side of being more curious than less curious. I think curiosity is great, but I just have to remind myself right now, my focus is this. And then as soon as I finish, my reward for finishing is I get to go over here and get fascinated by this other thing. And so to kind of just have, hey, this is my deep dive into this, then I'm going to do a deep dive into this, and then I'm going to do a deep dive into that. But great question.

• 9:15Speaker 03

  Hi, Ryan.

• 9:16Ryan Holiday?

  Hi.

• 9:17Speaker 03

  The timing of your course was quite gratuitous for me. My divorce papers came in on Wednesday and I started the course on Friday.

• 9:24Ryan Holiday?

  Oh, sorry.

• 9:25Speaker 03

  No, it was a great opportunity to, you know, look inwards and to make much more the challenges about my emotional state or what I'm going through. I'm very, you know, familiar with the works and familiar with the books and familiar with the resources, but I'm still feeling lost. I'm still feeling that the next few steps that I take are the, the most important ones I'm going to take. I'm still not sure if I have a direction and, you know, I want to thank everybody here on the call who have been so kind and so forward when I send messages on the, on the platform. I've found all your comments and messages to be very helpful.

• 10:02Ryan Holiday?

  Well, that's one of my favorite part about these challenges, watching the sort of community come together and, and people sort of help each other. And I know I learn, I learn stuff from, from the chats also. So wait, why, walk me through why you feel like you're, you're struggling directionally?

• 10:17Speaker 03

  I feel like I'm at a fork. I feel like the next path which I choose will be the one that defines me for the rest of my life. I feel like I have so many options in front of me that I'm paralyzed by the choice.

• 10:28Ryan Holiday?

  Well, that might be something you're inflicting on yourself a little bit in the sense that you're making this kind of an all or nothing choice, when in fact it's one choice of thousands, millions of choices that you will have to make in the future. So I, I might think about what's the best choice I can make here now? And understanding not only do I have many subsequent choices to make, but I can also choose to remake this choice, right? To come back to this crossroads again. I think sometimes we paralyze ourselves with needing to get everything perfectly right. We raise the stakes on things. We act like this is a matter of life and death, and usually it is not. Usually our decisions are much less permanent than they feel in the moment.

• 11:12Ryan Holiday?

  So I probably, I try to lower the stakes here. That's one of the things I think about. Albert, you want to go?

• 11:18Speaker 04

  Oh, thank you, Ryan. Things that I really enjoyed in this challenge went well, and a special thank you. I was very depressed after the election with the turnout. Well, not very depressed, but I let the external thing, it wasn't a good stoic affect me. So I bought the Daily Dad and I bought it for my son-in-law. And I got adult kids and I'm trying to be like Xeno and use two ears and one mouth in general of everybody I meet, you know?

• 11:41Ryan Holiday?

  Yeah.

• 11:41Speaker 04

  But how can I talk to my kids? Because I have a son who I think is in pain, you know? How do you talk to your adult children without putting on airs? Is something that I need to work on?

• 11:52Ryan Holiday?

  No, no, look, I don't have any experience talking to adult children yet, but I guess I am an adult child. And I think your instinct about listening more than you talk is great. And so you know what I would do? I would ask more questions. The more questions you can ask, probably the more you'll get.

• 12:14Ryan 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.