Regulation First, Happiness Second | Ask DS

We talked recently about a piece of advice from the therapist and children expert Dr. Becky Kennedy (she has a great book called Good Inside and was an awesome recent guest on the Daily Stoic podcast). She was saying that the key to raising happy children is to focus on emotional regulation first. By helping them name and manage their emotions, she explains, we are creating room for happiness. “Regulation first,” she writes, “happiness second.”-And In today's Ask Daily Stoic, Ryan talks discipline is destiny, how businesses use the same form of stoicism, and creating work that is timeless to 150 Entrepreneurs from all over the world + diverse range of industries (Tech, Hospitality, Service, Ecommerce, NYT Best-Selling Authors, etc)✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, 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.

• 0:06Ryan 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. But thank you for listening, and we hope this is of use to you.

• 0:48Ryan Holiday?

  Regulation first, happiness second. Marcus Aurelius might not seem like he's a happy guy in the pages of Meditations. He dwells on some of the darker parts of life. He talks a lot about managing his temper, talks about all the sources of frustration and disappointment out there. The inevitability of death and what it means is ever-present in Meditations. Where is the happiness? Where is the joy? Where is the laughter and the fun? Well, actually, it's there in his life, not just in the book. And these two things are related. In fact, one is not possible without the other. We talked recently about a piece of advice from the therapist and child expert, Dr. Becky Kennedy. She has this great book called Good

• 1:29Ryan Holiday?

  Inside. She was on the podcast also. She was saying that the key to raising happy children is to focus on emotional regulation first. By helping them name and manage their emotions, she explains, we are creating room for happiness. Regulation first, she writes, happiness second. Effectively, this is what Marcus Aurelius is doing in Meditations. You have to remember, he was not writing this book for you. He was writing it for himself. Meditations is the journal where Marcus Aurelius was regulating his emotions, dealing with his fears and frustrations, so that they didn't overwhelm his life, so that they didn't quench happiness and joy in life.

• 2:10Ryan Holiday?

  By processing his temper, his envy, his tendency for despair, he was actually cultivating happiness. And that's what Stoicism is. That's why we journal. That's why we run through these exercises. That's why we read these books. It can be a little dark, but it also creates the opportunity for life. And actually, you know, January is a great time to start a journaling habit. I'm just starting the, I guess, eighth year of the one line a day journal I do. I'm on the sixth years on the Daily Stoic Journal. Got my, swapped out a new edition, I guess in November. I put it in the leather cover that we've got in the Daily Stoic store. And as soon as I finish this, as it's nighttime, I'm gonna go sit

• 2:55Ryan Holiday?

  in my bed and do my evening journaling in the Daily Stoic Journal and in my other journals because it's, it's just a wonderful habit. And maybe if you pick up the same habit, you can flip through your edition of the Daily Stoic and the Daily Stoic Journal. You can check all that out at stuart.dailystoic.com.

• 3:35Ryan Holiday?

  Hey, it's Ryan. Welcome to another Thursday episode of the Daily Stoic Podcast. If you listened to my Sunday episode back in the fall, I had this crazy couple of days where I flew down to LA, I interviewed Arnold Schwarzenegger, I drove up to Ojai, California. I had dinner with a former podcast guest and friend, the comedian Pete Holmes. Then I did a talk for this amazing group called Mastermind Talks, Jason Gainerd and his wife Candace. I have known them since they started Mastermind Talks. I went before my book Growth Hacker Marketing came out for the first time. I went the second time when Obstacle is Coming out. I've been many times over the years. He's been awesome to me. So I did a long

• 4:16Ryan Holiday?

  Q and A there, which is what I'm gonna bring you a chunk of today. Then I went back down, did an event with Robert Greene, flew home for the night. Then flew to Seattle to do another event with Robert Greene. So I told that whole story about how you sort of stay stoic and calm amidst a crazy, overwhelming travel schedule. So that was me talking about it. If you want to hear me in the middle of that craziness, that's where I am in today's episode. I did about an hour, hour and a half Q and A with a bunch of these interesting entrepreneurs from all over the world. Some are authors, some are in e-commerce, some are influencers, some are fitness people, some are, some run call centers.

• 4:58Ryan Holiday?

  They're just all sorts of interesting entrepreneurs, really nice folks. And if you haven't been to Mastermind Talks, you should. I think they're taking a break this year, but I'm sure you can get on the waitlist for next year if you're thinking about coming. Thanks to Jason for sending over the audio of this and thanks to everyone in the audience who asked some very interesting questions. I'll be bringing pieces of that over the next couple of months, but I'll give you a chunk of some stoic themed questions right now.

• 5:33Ryan Holiday?

  I'm about to start what will be the fourth book in the Virtue Series I'm doing. So I did Courage, Discipline, Justice, basically went into publisher last week. And then I'll have to start sometime in the next couple of months, actually really like really working on what will be the fourth one. So right now that's just a box, one of those boxes 100% filled with note cards in no particular order. So the first, the first thing, and I have like a standing desk, like I just have a big table in my office, like a conference table that goes up and down. I sort of raise that up to like chess level and I just start going through the cards and I am looking for like patterns or things that go together. And so

• 6:15Ryan Holiday?

  Eventually, some kind of order starts to emerge just organically. And then from that, then I go, you know, oh, actually, I'm gonna move this. And then, actually, I need more of this. Like, this is the germ of an idea, but I need more of this. So it just starts to kind of accumulate. So when I was writing that note to myself about just go through the cards, it was like, there is this period, it's usually like a month, where I'm taking all the stuff I've brainstormed, and I'm, I have the excitement of starting the book, and you immediately hit what Paul Graham calls the trough of despair, where you're like, there is nothing here, there's no. But I've done it enough times now that I know if I just keep, eventually, patterns start to emerge. And I go, oh, you know who would be perfect for this? This person. And, and the sort of characters start to come up.

• 7:00Ryan Holiday?

  And then that sends me to sort of a second round of research. And that's, that's kind of how that system goes.

• 7:06Speaker 01

  And thank you for everything you're writing. I just love it. What is your process in terms of writing to say every day, I'm gonna read between those hours and those hours? And what is also your process when you say 50 pieces of content a day? You say like, every first three days of the month, I'm gonna record and then have the team dealing with it?

• 7:23Ryan Holiday?

  Okay, so as far as my process, I try to write in the morning. So I drop my kids off at school, and then I usually have between one and three hours before I have anything scheduled. And that's my sort of writing time. And that, if I'm working on a book, the book is gonna take up the bulk of that writing time. If I'm not working on a book, then it's usually, the first things would be like, articles or the Daily Stoic emails, which is the biggest, the Daily Stoic and the Daily Data. So I do two emails every single day, 365 days a year. And I have now for eight years. So it's a lot, it's a lot, just that is a lot.

• 8:05Ryan Holiday?

  But like with Daily Stoic, my, I have like a managing editor who sort of takes all the stuff and puts it into where it goes. She told me last week that I don't have to write any Daily Stoic emails for the rest of the year. Like, that's how far ahead I am. So I'm, I'm, I'm just always making stuff. And then I have people on the team who help me take that stuff and find out where it goes, manage it, give me, hey, If you write another Daily Stoic email today, it's just gonna sit for three months. But by the way, you have seven days of Daily Dad emails till you run out. So I'm kind of thinking about it like that. And then I do, probably once or twice a week, I'll specifically sit down and make sort of like social media content, like videos.

• 8:50Ryan Holiday?

  And that's usually someone on my team taking stuff from the books or from articles, stuff I've written and sort of re-going like, "Hey, take this thing you were talking about here and give me 30 seconds or 60 seconds." So I'm not, when I'm doing all that content a day, it's not... The thing about it, so there's LinkedIn, TikTok, Instagram, Facebook, Twitter, YouTube. So like, if you're just doing one a day on each of those things, that's almost 10 right there, right? So I'm making stuff, knowing that it can be used on multiple different platforms. And I try to think about like, what is the base unit of... So if I sit down and I write a 6,000-word article,

• 9:34Ryan Holiday?

  that's good for places that take 6,000-word articles, which is not that many. If I sit down and I go, "What would be a really good way to take this Stoic idea and do it in 60 seconds?" I can do that on Instagram, TikTok, Facebook, LinkedIn. I can do a YouTube short. I can combine it into a, like, I can do that in multiple places. So my team kind of helps me take the ideas or the things I want to talk about and translate it into all these different mediums. The idea being that these algorithms are the most powerful, basically, in discovery engines in the world. And when you make stuff for them, they surface your things to people. So it's kind of created this flywheel where people are being, "I first heard about you here, I first heard about you here."

• 10:19Ryan Holiday?

  It's just generating all this stuff that is... Surfacing the work to different people who prefer different kinds of content, who have different lifestyles, you know, they're in different silos and I'm just making, I'm trying to take the core thing, which is what I care about, which is, you know, philosophy and books and make it accessible in all these different ways.

• 10:41Speaker 02

  When I was writing By Them Built, I read Perennial Seller twice. And it really gave me the approach that I needed and the right mindset to create what became the definitive work in the space in which I wrote. The book is okay, but Garrett Gunderson actually gave his name to it. So it launched feverishly. Awesome. Yeah, thank you. But my question is this, it was sort of like, when I write, it's frustratingly difficult. And I guess I'm just wondering, as someone who has, you know, written 10 books or whatever over the last 10 years, like, does it get easier? In other words, when you are trying to write something that is so deep and so good,

• 11:23Speaker 02

  that it can define a space, I find that I'll write a chapter, it takes me like a month, and then I have to rewrite that same chapter like seven times. And so now it takes me like four years to write a fucking book. And I'm just like, how do I, how do I like do this? How do I get deeper faster?

• 11:38Ryan Holiday?

  Well, one thing I try to tell myself is that if it was easy, everyone would do it. Right? And so it's good that it's hard, right? Like, that's what keeps the riffraff out. Can it get easier for you as you do it more? To a degree, but you're still trying to do an incredibly difficult thing, which is take something in your head that makes sense to you, and not only make it make sense to other people, but make it interesting to other people. And then, you know, ideally make it shareable or of value. Like, you're trying to do a really hard thing, right? And so, like, I'm more confident as I go because I know what to expect. Like, I know where the dips are and I know how long it's supposed to take.

• 12:20Ryan Holiday?

  And, you know, I have recall of certain things, you know, I have that. But it's still fundamentally, you're starting with a blank, like, I am dreading what I'm gonna have to start in the next couple of months because I know, like...

• 12:38Ryan Holiday?

  I know what to expect, which is why it's gonna be hard. You know what I mean?

• 12:42Speaker 02

  How many times do you rewrite a chapter? Like, are you so organized going in that you're like, nailed it?

• 12:47Ryan Holiday?

  I mean, you definitely want to, in all facets of your life, avoid moments where you're like, I'll figure it out on the fly. Right? Because sometimes you do, but a lot of times you don't. And so when I hear people, they're like, oh, you know, I cut 50,000 words out of this manuscript. Or, you know, I'm like, okay, that's a sign of poor planning. But I do, you do, editing is really important and refined. So like, the Justice Book, which I just finished, I spent the month of July in LA. When I, I remember, just because I was talking about it, is like, the book was 78,000 words when I, done, but going into doing a round of edits, 78,000 words.

• 13:31Ryan Holiday?

  And by the time I left, a month later, it was 72,000 words. But that's only counting words that no longer exist, not words that were done and redone and redone. So there is this process of going over and over and over again, and that's where it gets better. Sometimes you get it right the first time, and there's something special about it, and a lot of times you don't. So I don't think there's, there are very few people that spit out perfect first drafts of anything, you know? And the whole idea of like, the Stream of Consciousness album, idea, you know, movie, whatever. It's more a myth than a reality.

• 14:18Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us, and it would really help the show. We appreciate it, and I'll see you next episode.