You’ve Been Given a Fresh Chance | 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.

• 0:05Ryan Holiday?

  Welcome to the Daily Stoic Podcast, where each day we bring you a Stoic-inspired meditation, designed to help you find strength and insight and wisdom into everyday life. Each one of these episodes is based on the 2,000-year-old philosophy that has guided some of history's greatest men and women, help you learn from them, to follow in their example, and to start your day off with a little dose of courage and discipline and justice and wisdom. For more, visit DailyStoic.com.

• 0:56Ryan Holiday?

  It's kind of a funny tradition when you think about it, isn't it? How we stay up late each year and count down the final seconds of the year together. "Five, four, three, two, one, Happy New Year!" We cheer, we celebrate. It's a big show to mark the end of the year. But how many of us, in a rush for a kiss or as the glasses clink together, really feel what's just happened? Those seconds we were counting down were seconds we'll never get back. Our time here, tick, tick, ticking away. A year of our lives is gone forever. "Tempest Fugit, Memento Mori." The Stoics did not take note of how fast time flies

• 1:40Ryan Holiday?

  and the shortness of life to be morbid. No, they sought invigoration, they sought perspective, they sought clarity. Seneca said that if you went to bed thinking that you would live your whole life, the morning would feel like a bonus. We can apply the same thinking annually. Who we were in 2025 is dead and gone. Here we are, lucky enough to rise again in 2026, a year that perhaps many of us did not ever expect to see. We have beaten death. We have been given a fresh chance at life. Who will we be? How will we spend it?

• 2:23Ryan Holiday?

  This is an incredible gift you have been given, a wonderful opportunity. Forget business as usual. Live. Have something to show for the next 365 days. Have something to show for today, for this very moment.

• 2:52Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I am in Hollywood, Florida at the moment, doing my last gig of the year. I'm in that big hard rock guitar hotel. It's pretty cool. I'm gonna go downstairs, what, in two hours, to do this little talk. You're listening to this on New Year's Day, probably, or somewhere around New Year's, not when I'm recording this. This is mid-December. But I'm gonna go down and give a talk here in a couple hours, and then I'm gonna answer some questions, which is my favorite part of what I get to do. I've met people all over the world doing this, and it's my favorite thing, answering your questions. Then usually, you have to come to one of my talks in person to ask me a question,

• 3:37Ryan Holiday?

  except we also answer questions as part of the Daily Stoic New Year, New You Challenge, which kicked off today. You are listening to this on the first day 2026. I hope it's off to a good start. If you want to jump in to the Daily Stoic New Year, New You Challenge, you can still do that. It's at dailystoic.com/challenge. And we have our first Q and A, I think, coming up in a few days. So you can ask me questions about Stoicism. You can ask me questions about resolutions. You can ask me questions about anything you want. In today's Q and A episode, I'm gonna bring you some questions that we got asked in previous year's challenges, and we'll get into it. But as I said, if you want to pop into the Q and A in a couple days, I'd love to have you join us.

• 4:22Ryan Holiday?

  It's not too late to sign up for the Daily Stoic New Year, New You Challenge. It's dailystoic.com/challenge. And we're gonna kick the year off with 21 days of Stoic-inspired challenges. But as for me, I'm gonna go get ready for this talk and meet some folks here in person. I hope you are well. Happy New Year. I'll see you in the challenge.

• 4:45Speaker 01

  I wanted to ask you a question, not specifically to the challenge, but like it is to about the community. And I want to know how essential it is to be a part of a community that shares my Stoic values on a daily basis.

• 5:00Ryan Holiday?

  That's a good question. I mean, is it helpful and is it nice to have people that share your values, that challenge you, that make you better, that embody what you want to embody? I think so. There's something called the Socratic circle, which I write a little bit in Lives of the Stoics, and I write about more in the Wisdom book. There was this group of Stoics in ancient Rome who'd get together and they would have these sort of meetings and they would talk about these philosophical questions. And I think anyone who's ever been part of a scene of like-minded thinkers or, you know, whatever it is that you do, it's wonderful. I think you do have to have a community like that. That being said, should you only be in a community with people who are like you? Should you only be around people who believe and think the same things as you? No, that's probably not good either.

• 5:45Ryan Holiday?

  So I think you want to cultivate a support system or a network. I don't know what you do, but I am positive there are clubs and scenes and groups and conferences of people who are doing precisely that. I'll give you, here's how I know this. I gave a talk a couple of months ago in Houston, and it was the most specific group of people that I have probably ever spoken to and would not have thought existed. This was a conference and there was like several hundred people there. And it was, the premise of the conference was advice to doctors who own the buildings that their practices are in.

• 6:29Ryan Holiday?

  And so I was like, oh, that like, I would have thought that was like 10 people, but clearly it was like a large group of people. And then I was like, oh, this would be interesting, right? Because these are all doctors and surgeons and, you know, people went to medical school and have this very specific set of medical skills, but then by nature of their, their business and the success they've had, they've come to also be landlords and real estate investors.

• 6:52Speaker 01

  Right.

• 6:53Ryan Holiday?

  Some of them are better at one thing and some of them are better at other thing, or some of them are further along in this journey than others. And they've all kind of learned these different lessons along the way. And they want to get together and share and communicate with each other. And so I guess what I'm saying is you should find what that scene is for you. And you should be a part of it, whether it's exactly stoic or not. To me is less important than than finding people who are do what you do and make you better at it.

• 7:25Speaker 01

  Sounds great. Thank you so much.

• 7:27Ryan Holiday?

  Yeah, love it.

• 7:28Speaker 02

  Hi, Ryan. Can you hear me?

• 7:30Ryan Holiday?

  I can.

• 7:31Speaker 02

  It's my second time joining the New Year, New Year challenge.

• 7:36Ryan Holiday?

  What brought you back?

• 7:37Speaker 02

  For me, it was very, very uplifting. I think all the, the comments and the chats are, um, yeah, very insightful, not only. And it gives you more depth, thinking about things that are not obvious to your, to yourself. But I had experience from other people over the world makes you think more deeply about things. So this, yeah, for me, this is very nice.

• 8:01Ryan Holiday?

  That's great to hear. Well, so glad to have you back.

• 8:03Speaker 02

  And my question is, if I, if I look at stoicism, I always get the impression that it is focused on getting structure in your life and a purpose in your life. If I look at items like creativity and, and coming up with new ideas, I often think, and I'm looking purely at my life, that I need chaos and I need unstructured think, things to come up with creativity. So for me, it's, it's always a little bit a kind of idea. Is there a kind of combination I can make with creativity and stoicism? Or are they really opposite things? So what's your, what's your take on this?

• 8:48Ryan Holiday?

  Well, look, many of the Stoics were artists and artistic. I mean, even Marx's Trilis's meditations, I would say, is for such an ordered and disciplined person, you know, sort of a beautiful, chaotic work of art. Seneca writes these plays. There have been Stoics who have been painters, Stoics who have been playwrights, Stoics who have been musicians, and there are people doing all those things today also. So I certainly don't think Stoicism is at odds with creativity. But I go to what I was saying earlier, which is, I agree that the work needs inspiration, and it needs freedom, and play, and a little bit of chaos.

• 9:33Ryan Holiday?

  At the same time, if your life is absorbed by those things, I think it saps your energy. I think it saps your focus. It actually takes away from the freedom you need to do and be those things. So like, when you're saying you need unstructured time, I would agree. But if all of your time is unstructured, then you don't have unstructured time to do that stuff. I think you need to structure in having that. Because also, as much as we like to think of great works of art being the result of sort of stream of consciousness, they stayed up all night and did... No, most work is actually much more methodical.

• 10:13Ryan Holiday?

  And certainly, the polishing and the refining and the finalizing of work is very different than the kind of raw, creative place of work also. So I do think it's a tension. I think it's both. But I certainly don't think Stoicism is at odds with that in any way.

• 10:33Speaker 02

  Okay, thank you very much.

• 10:35Ryan Holiday?

  Yeah, great.

• 10:36Speaker 03

  Hello, Ryan. How are you?

• 10:37Ryan Holiday?

  Hello, I'm doing great.

• 10:38Speaker 03

  So I always wanted to ask you a question around social media, because

• 10:42Ryan Holiday?

  Okay.

• 10:43Speaker 03

  I'm like 22 years old, and I'm an entrepreneur, and I'm trying to create. But then, it's like always this question of, should I create content or not? Because honestly, I've been there, creating content for a year or two, and it's amazing, and it goes well. But I feel super distracted, and all of the virtues I cannot practice. It's so much harder when you're out there. And on the other side, through 2024, I was basically without social media for the whole year.

• 11:13Speaker 03

  I'm feeling so good, courage, wisdom, justice. Everything's going right. I've made more money ever before. So I'm like, okay, for 2025, should I create in social media?

• 11:25Speaker 03

  So it's a hard question. I haven't found really wisdom on that answer. And that's why I'm bringing it up here.

• 11:31Ryan Holiday?

  No, it's a great question. I think about this a lot because obviously my work has spread through social media. I've had friendships I've developed from social media. Maybe many of you get value out of what we do in Daily Stoic on social media, or that might even be how you discovered our stuff. These algorithms are extremely popular and it's also extremely powerful. And it's also how people discover things today. It would be wonderful if you could just go off in a cave and write a book or start to have a business idea and then it would just magically find its people. It's not. That being said, I do think spending a lot of time on these platforms fights for the resources needed to make great stuff. And it's also toxic and it breaks your brain.

• 12:15Ryan Holiday?

  I think Elon Musk is a great example of someone who's just showing us in real time what social media algorithms can do to a really smart person's brain, which is to say they can break it. It can become a massive distraction and have enormous consequences, not just for you, but for the world. So I spend a lot of time making stuff for social media and I spend very little time on social media. So I see them as communication. I see them as broadcast platforms as opposed to back and forth. If I want to have a back and forth, if I want to engage, if I want to get feedback or information, I want to do that with people I actually know or people I actually care about and I want to do it in a contained way.

• 12:59Ryan Holiday?

  I don't want to get feedback from millions of people who I don't know, who might not even be real. So I spend a lot of time making stuff. I was just down at the beach making some Daily Stoic reels. Those will go to someone to get edited and be posted. Now, obviously I'm in a position where I can do that at this point in my career. At the beginning of my career, I would have been doing all this stuff myself, but I would still be. Uploading and scheduling as opposed to pulling up Twitter and reacting to stuff. All the dumb things that I've ever said on social media have been in real time, like on an app,

• 13:39Ryan Holiday?

  which is why I don't really have the apps on my devices anymore. So I think using the stuff is great, but having the discipline and the boundaries to not be controlled by them is really important.

• 13:54Speaker 03

  Thank you, Ryan. That's really helpful. I appreciate it. Quick follow up just on that.

• 13:59Ryan Holiday?

  Yes.

• 14:00Speaker 03

  Do you think in 2025, it's different what we're seeing in social media? And the presence needs to be there or is it just like your ego trying to get there?

• 14:11Ryan Holiday?

  I think it's both. I mean, I do think you have to have a presence. I think this is how you engage and connect with people. It's also, you know, one of the ways that I connect with people, like my DMs or my messages is like texts. You know, it's like how you connect with people. So I do think it's important. I just, you've got to make sure that you're using it as opposed to it using you.

• 14:34Speaker 04

  Okay, Ryan, this is my first goal at this challenge. It seems like you're very, very well organized in your day. Like, you know, for the first hour, you don't even touch your phone and whatnot. And then you do your walk with kids and then you do your two hours of your concentrated work. And it seemed very organized. Now, do you just naturally know, okay, now it's time to move on to the next? Or do you physically time it somehow?

• 14:59Ryan Holiday?

  Oh, that's a good question. I do have kind of a rhythm, a sense of when to move on from the next project. I'm a big believer in noticing diminishing returns. So like, I don't write exactly for this amount of time, but I write until it's kind of stopped.

• 15:19Ryan Holiday?

  Working and then I move to the next thing. So that's kind of how I think about it. I just kind of have these periods where this is what I'm supposed to be doing for this, for this amount of time. And if it's really still working and I'm getting a lot of traction, it's going, I might extend it. And if I'm just pounding my head against the wall, I might, I might wind it down early. So that's kind of how I think about that. And, and I would say also, even with the routine itself, it changes and evolves. You know, my kids are older, they go to different schools. Some parts of it have changed. Other times, you know, like I think about it as seasons, you know, how I structure my day is a little bit different when there's a lot more daylight than there is when there's

• 16:04Ryan Holiday?

  very little daylight, you know? I kind of move it through seasonally as well. So I, I, I think, again, when we're talking about ranges, having a routine, having structure is great, but you also have to have the flexibility to be able to, you know, make that work for the moment of time that you're in.

• 16:23Ryan 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.