The Time Is Now | Ask Daily Stoic

Marcus Aurelius didn’t always make the right choices. Neither will we. The important thing is what we do after we come to this realization, after we realize we’ve put something off for too long. Since we received such great feedback from the launch of 2025's New Year New You Challenge, we decided to RE-OPEN the challenge for February. Head over to dailystoic.com/challenge today to sign up.🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:02Ryan 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. Well, on Thursdays, we not only read the daily meditation, but we answer some questions from listeners and fellow Stoics who are trying to apply this philosophy, just as you are. Some of these come from my talks, some of these come from Zoom sessions that we do with Daily Stoic Life members, or as part of the challenges. Some of them are from interactions I have on the street when there happened to be someone there recording. Thank you for listening, and we hope this is of use to you.

• 0:43Ryan Holiday?

  The time is now. Obviously, the best time to plant a tree was 20 years ago, because the earlier you get started on something that takes time, the bigger and better the results will be. It would have been better if you made the changes you needed to make in your life two years ago, or in 2023, or in 2024. Look, it would have been better if you did it at the first of the year, but, you know, January 1st, 2025 has come and gone. That would have been a great time to start new habits. A new year, a new you, right? Fresh moment, fresh calendar. And these missed opportunities can haunt the best of us. In meditations, though, Marcus really reminds himself not to feel exasperated,

• 1:27Ryan Holiday?

  or defeated, or despondent, because your days aren't packed with wise and moral actions. He says, "You've got to get back up when you fail, to celebrate behaving like a human, however imperfectly, and embrace the pursuit you've embarked on." So, we're all going to fall short. We all procrastinate. We all avoid making necessary changes. But so what? What matters is the choice you make after you come to that realization. So, yeah, it would have been better to plant the tree a while ago. But the second best time is now, because it's not too late. It's never too late. You can still do that here now in 2025. You can break old habits. You can forge new ones. You can build a framework, a system that allows you to be more resilient, more focused,

• 2:10Ryan Holiday?

  tougher, braver, more virtuous, whatever it is. If you want some help with that, we are relaunching the Daily Stoic New Year, New You Challenge. Thousands of Stoics all over the world just spent the last 21 days, the first 21 days of the year, tackling one Stoic challenge after another. We all did it as a team. We checked in with each other throughout the three weeks. We shared what we were dealing with. I got a bunch out of doing the challenges with other people. It's too late for that, but it is not too late for you to do the challenges by yourself, because as I said, we've relaunched the challenge. It's going to be open from now until February 1st. You can start it right now. You don't have to put it off. You don't have to wait for some start date. You can start it right now,

• 2:48Ryan Holiday?

  and I would love to see you in there. DailyStoic.com/challenge, because today is the day. Stop waiting. Stop putting it off. You could be good today, as Marx really said, but instead you choose tomorrow. Doesn't matter if January didn't go as planned. The whole year is not lost. What matters is that you make the right choice now, and I would love to see you in there. DailyStoic.com/challenge. It's your last chance to do the Daily Stoic New Year, New You Challenge with us. I'll see you in there.

• 3:20Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I feel pretty good. I'm actually remarkably well rested, even though my son woke up at like 4:30 this morning. Part of the reason is because we've been going to bed earlier. That was one of the challenges that we did in the Daily Stoic New Year, New You Challenge, which is to set a bedtime, right? The Stoics talk a lot about waking up early, which is important and requires willpower, but I find what time I go to bed, I have less discipline about. And I was just, just doing a talk in San Diego, and I was, someone was asking me this beforehand, and I was like, have you heard of this thing called revenge bedtime? Like revenge bedtime is when you stay up late just to get extra time to yourself. It's something that parents

• 4:01Ryan Holiday?

  sort of inflict on ourselves. You're just scrolling on social media, watching TV, or whatever. You're just like, I just need this me time. But it's actually punishing you and your kids the next day. Anyways, that's like one of the things that I took out of the challenge. It's been, it's been awesome. I haven't Absolutely perfect about it, but I have been more focused on what time I go to bed. So that whatever time I wake up, even though I have a time I have to wake up by, I'm not so fried, although as I said in something else, maybe I don't know what order these are coming out. I do look like I have bags under my eyes. I went out and I swam this morning and the goggles keep pressing on my face. So I gotta figure out when I'm going to be on camera. But anyways, where does that leave us today on Thursday?

• 4:44Ryan Holiday?

  A little Q and A. So we are relaunching the New Year, New You Challenge. We got a bunch of emails from people who are like, hey, I missed it. I wasn't ready the first week of January to start the year off with 21 consecutive Stoic challenges, but I still want to do it. Well, it is not too late. You can join us. We're just running the challenge now. And my favorite part of the challenge is the Q and As that we do together. So I'm going to bring you some of those Q and As from the challenge we all just did. And you can get the Q and A and all 21 Stoic challenges. It's not too late this year or for the challenge. You can sign up now at dailystoic.com/challenge. And then remember, of course, if you sign up for Daily Stoic Life, you get the challenge and all the challenges. We got a bunch more planned this year for free.

• 5:28Ryan Holiday?

  So check that out, dailystoic.com/challenge. And here's me doing the Stoic office hours as part of that challenge. Listen in.

• 5:41Speaker 01

  Over the last year, I've gotten really into all your stuff. So just really

• 5:44Ryan Holiday?

  Wonderful. So this is your second time?

• 5:47Speaker 01

  No, first challenge, I've just like read, been reading all your books and read all the, just really, really into it. And particularly in like a work context, where I run a small business or growing business, like 400 people.

• 6:00Ryan Holiday?

  That's not a small business. Congratulations.

• 6:02Speaker 01

  We're startup mode, but yeah, a lot of people. And my question relates sort of the business context. So I know there's a lot about like, focusing on what you can control, especially like not controlling other people. And I feel like I've really Grasp that concept, but the thing I struggle with or would love your take on is like in my job, particularly, I feel like there's a lot of needing to influence people or

• 6:26Ryan Holiday?

  Yes.

• 6:27Speaker 01

  Trying to motivate people, lead people. And obviously like Marcus, how that's his whole life. But I'm trying to make sense of this like balance between, I know that I can't control like my employees or other people, but am accountable to the business that's performing and I need to influence them. So like, I don't know if you have any tips on like how to make sense of the pressure I put on myself to like have people do certain things, but knowing at the end of the day, like

• 6:51Ryan Holiday?

  Control them. This is a great question, and I think it's really important. And sometimes this is why I think taking Stoicism out of the academic domain and thinking about it in the real world with real people is so important. I wrote a book called Lives of the Stoics, where obviously I was looking at the biographies of the Stoics. And when you just look at what the Stoics talk about, it can be very easy to render the words very differently than they were, they were obviously meant. So when the Stoics talk about focusing on what you control and reminding yourselves that you don't control other people, it could be mistaken to think that they're just like, yeah, just focus on you,

• 7:32Ryan Holiday?

  write everything else off. But obviously Marcus Aurelius at the head of the Roman army was not like, well, I can't tell people what to do. I mean, literally his job was to tell people what to do. And there were Stoics who, who served in all different assets and facets of leadership. So I think your word influence there is important. One of the things I think is so fascinating about Marcus Aurelius is that he didn't seem to be intent on changing anyone. He seemed to find a way to get things out of people, even when he disagreed with them or disliked them, or found that they had, in some cases, cross purposes to him. So what I think we're talking about there is leadership and leadership is influence, it's persuasion,

• 8:14Ryan Holiday?

  it's obviously leading by example also. And then I think it's a lot about selection, you know? If we, if we could take for granted that We can lead a horse to water, but we can't make them drink. We do want to make sure that we're only, now this metaphor is getting pretty tortured. We're only hiring horses that like to drink, you know? And so, so that's one of the ways I, I'm thinking about this in my own practice is like, okay, if I can't change anyone, I can't force anyone to do or be a certain way. What I can do is get much better at who I select and who I de-select. Right? And so I'm thinking a lot about that. But you know, it's funny, um, in the leadership challenge, we interviewed this guy named,

• 8:59Ryan Holiday?

  um, General Dan Kane is a two-star general in the air force. And, um, he was saying that in his like 20, 30-year career, he can remember giving two direct orders in his whole, like we think, we go, okay, sure, we can't really control people, but generals can. Marcus Aurelius is an all-powerful general, obviously could. And I thought that was so interesting because sometimes people in business are sort of jealous of people like, say, in the military or in like the president, like, oh, they can really make someone do stuff. And he was saying, even then, the same limitations on our power are there. And understanding that it really is about persuasion and it's about influence. It's about modeling. It's about setting up incentives.

• 9:43Ryan Holiday?

  I, I think about this tension a lot. It's not that the Stoics go, hey, I don't control other people, so I don't even try. It's understanding that we have certain limitations. And then it's understanding how within those limitations, we do have opportunities to influence and direct. And that's where we got to put our energy. Cool. Appreciate it. Awesome. Yeah. Great question.

• 10:03Speaker 02

  So my question for you is through my practice, I've learned my personality traits that have harmed myself and have harmed others.

• 10:15Ryan Holiday?

  Yeah.

• 10:16Speaker 02

  I've also learned my personality traits that have helped myself and helped others. And through and because it's an ongoing thing until I die, I have more to learn. So my question is, what personality, are you prepared to be vulnerable?

• 10:34Ryan Holiday?

  Yeah.

• 10:35Speaker 02

  And share the personality traits that you've discovered?

• 10:37Ryan Holiday?

  I I'm glad you said traits, plural, because I have many that cause problems for myself and others. But I I would say a big one is, you know, I'm sort of driven and intense. And I like to do things the way I I like to do them or the way I think they they should be done. And that sort of should or that ought to, although it feels good for me, can be oppressive to other people. Right? Because they didn't sign up necessarily for my assumptions. They don't necessarily agree. I have a tendency to stress people out. That intensity can, you know, sort of crash against other people. So I I find that I have to sort of keep that in check or I have to be understanding that,

• 11:20Ryan Holiday?

  you know, sort of not everyone has the same constitution as me. Not everyone reaps the same rewards from the stuff as me. And sort of trying to figure out a balance between me sort of maximizing what I'm trying to do or achieve what I'm trying to do and coexisting and having positive relationships with other people. That that is definitely a struggle for me. But great question. I appreciate that.

• 11:50Speaker 02

  And then the other side of that is, what are your strengths? What have you found that have been helpful for you and also with the world around you?

• 12:00Ryan Holiday?

  I mean, I'd like to think I'm a good communicator, that I'm good at taking, you know, the these ideas or these sort of ways of thinking about things and making them applicable and accessible to people, not just in my my writing, but in my actual life. So, you know, I I'd like to think I'm I'm good at that and it has a positive impact on people.

• 12:21Speaker 03

  My question, I wanted to go back to the word of the year.

• 12:25Ryan Holiday?

  Yes. What's yours?

• 12:27Speaker 03

  Oh, my word of the year, it's initiative.

• 12:29Ryan Holiday?

  Oh.

• 12:30Speaker 03

  I was trying to figure out, I was like, oh, you know, I'm trying to deal with procrastination. And I also play D and D. So I was like, oh, just roll for initiative every day. So I have my D20 and I'll roll it as like a symbolic.

• 12:41Ryan Holiday?

  That's awesome.

• 12:42Speaker 03

  So I think my question and what I'm kind of struggling with is, do you have any recommendations to account for like nuance in the word? Because I know I have a tendency to like always go in and like take action, but like maybe, you know, the opposite side of that is like you're chasing, right? And like

• 12:59Ryan Holiday?

  Sure.

• 13:00Speaker 03

  kind of fall into that trap. So I think what kind of recommendation would you have just to like either temper it or find the balance of the word rather than go all in?

• 13:09Ryan Holiday?

  Well, I think temper is a great word, right? When we think of temperance, particularly in America, if people are familiar with that word at all, they think the temperance movement, which was about not drinking alcohol, right? But temperance in the ancient world was about like the right amount, right? That's what Aristotle's definition of virtue was. And to him, virtue sat in the midpoint between two vices, right? So like the, his famous example is about courage, that too much courage is recklessness and not enough courage is cowardice. And, and courage was right in the middle. And you could probably say the same thing about initiative, right? So too much initiative, if you're always making the first move, if you're always diving in,

• 13:52Ryan Holiday?

  if you're always chasing, you're probably going to get yourself in trouble, just as if you never have any initiative, you're, you're going to get yourself in trouble. And so I think the word as a virtue that you're aspiring towards is, is as Aristotle says, the right amount in the right way, at the right time, to the right, you know, it's that dialing in that's essential. I think having the word there as kind of a default is, is really helpful. But knowing that, hey, doing it all the time to the nth degree is also not right. That you've got to find the right amount in the right way. That's, that's really important.

• 14:31Speaker 03

  Yeah, totally. That, that definitely makes sense.

• 14:33Ryan Holiday?

  All right. Great word, though.

• 14:39Ryan 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.