Today’s guest, Ryan Holiday, has been on my dream list of interviews for a long time. He is the best-selling author of many books including Ego is the Enemy, The Obstacle is the Way, and his newest Stillness is the Key, along with the Daily Stoic, a book I read one page from each morning.
Ryan’s ideas have changed the way I parent, and I think you’ll see why after this episode!
Episode Highlights With Ryan Holiday
- Learn how Ryan and Katie both dropped out of college at 19 and why
- The core ideas of stoicism including that we don’t control what happens to us, we only control how we respond
- Core stoic virtues of wisdom, justice, courage, and temperance
- How ancient stoic ideas are applicable to modern life and parenting
- The importance of a mindset shift about obstacles
- Why to never waste a trigger
- How to go from obstacles being bad to seeing them as beneficial
- And more!
Resources We Mention
- Book: The Little Girl at the Window
- Book: Antifragile: Things That Gain from Disorder
- Book: The Second Mountain: The Quest for a Moral Life
- Book: Fishing for Fun: And to Wash Your Soul
Books by Ryan Holiday
- Stillness Is the Key
- The Obstacle Is the Way (With Tim Ferriss)
- Ego Is the Enemy
- The Daily Stoic Journal
More From Wellness Mama
- 657: Meditations of Parenting, Love, and Raising Great Kids With Ryan Holiday
- 281: Building Resiliency, Mindset and Doing the Impossible With Joel Runyon
- 230: Chalene Johnson on How to Protect Your Mindset & Live a Balanced Life
- 223: Mindset for Moms & Tips to Get More Done & Stress Less This Year
- 206: Your Parenting Mojo on Why We Need to Let Our Kids Take More Risks
- 8 Life Lessons to Learn From Children
Did you enjoy this episode? Please drop a comment below or leave a review on iTunes to let us know. We value knowing what you think and this helps other moms find the podcast as well.
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Katie: Hello and welcome to the Wellness Mama podcast. I’m Katie from wellnessmama.com. And today’s guest, Ryan Holiday, has been on my dream list of interviews for a long time. He is the bestselling author of many books, including “The Obstacle is the Way,” “Ego is the Enemy” and his newest “Stillness is the Key” that just released. He also wrote “The Daily Stoic” and its companion journal, which is a book I read every morning. I read one page corresponding to the day and it’s had a big impact on my life.
He’s a prolific writer. He’s also written for many publications and he’s written books on other topics besides just stoicism, although that’s what we go deep on today. And he has been accredited by “The New York Times” as kind of ushering in the modern popularity of stoicism. And in this episode, we really go deep on how this can apply in the modern world, especially to parents and as specifically to parents and with a lot of practical and tangible methods that we both employ in our daily lives to make that happen. This is one of my favorite interviews I have done. I know that you are going to enjoy it, too. And without further ado, let’s jump in. Ryan, welcome. Thanks for being here.
Ryan: Thanks for having me. I wish I could be where you are.
Katie: Well, you’re always welcome here. We love it when you come visit, but I can’t wait to interview you. You’ve actually been on my list of people I’ve wanted to interview for a really long time and you’re one of my favorite authors, so I can’t wait to get to spend this time with you and record it. And I think we actually share an interesting piece of past that I don’t think most people share, which is the, I also dropped out of college at 19. And if I remember correctly, you did as well. Is that right?
Ryan: I did. I did. Although this is why you should always be, you shouldn’t compare yourself to other people’s biographies because I’ll give you this. I moved to LA, left college on June 15th and I turned 20 on June 16th. So, I say that I dropped out at 19, but technically it was 20. So sometimes, you know, you always gotta realize that people are slightly exaggerating and inflating their biographies to make them as cool as they can be because that’s the point of a biography. So I’m curious did you actually drop out at 19, or is it more like 20 like me?
Katie: It was actually 19. I’m pretty young…
Ryan: So you’re better.
Katie: Well, but I was almost done with college. I had done everything pretty early and I had entered college essentially as a junior because of testing out of stock.
Ryan: Oh, nice. And you still dropped out?
Katie: I did. I was like really close to being finished and realized I was journalism, pre-law and international studies thinking I could, you know, change the world through that and realized once I got in there that you weren’t gonna change the system from the inside out. And I also realized I wanted a family and wanted to do things in my own way. So I walked in, I was actually the presidential scholarship, and I walked in and quit.
Ryan: Wow. So had you met Seth yet?
Katie: I had. I had met my husband that summer before walking. And we actually did a nonprofit walk from Los Angeles to DC, and we hit long distance dating since then. And I just knew like that was the direction I wanted to go with my life and that I definitely did not want a political career or journalism career in the traditional sense. And I just walked in and quit. And he’s like, “You can’t really do that. You’re on scholarship.” And I’m like, “Well, I am.” And I did. I’m curious what your story was. Why did you end up dropping out?
Ryan: So similar story in that I’d already met my wife, so like, you know, sort of number one goal of college crossed off. I’d met the mentor and the writer who I admired and wanted to be like in Robert Green and I had a job offer to go work at a management firm in Hollywood, which is sort of where I wanted to go career-wise. And I had a bunch of other awesome stuff going on. So I felt like I wasn’t leaving college, you know slinking off into the night. I’d accomplished a lot of what I wanted to do there. And like you, so I was set to graduate in three years and I left in two years. So I probably did like two and a half years of academic work in college. But it was primarily, I felt like I had accomplished everything that I would have used to say that my college career was successful.
So I wasn’t gonna turn my back on that to keep going to class. But the funny thing was, and I think people should bear this in mind when you’re thinking about making some of these life-changing decisions, is they can feel very drastic, but they are much less so. I also had a scholarship, it was not president’s, this was a chancellor scholarship. So I think it was 75% of my tuition. And I walked in and I said, “I’m here to drop out.” And they said, “You know, that’s not a thing like you don’t drop out of college.” And I was like, “What do you mean?” And they said, “Well, look, you just take a semester, you just don’t enroll in classes for a semester and you can come back whenever you want.” And I think I actually have a couple years left, maybe that I don’t know how long it is.
But the point is you don’t drop out, you just stop going and you can always go back, right? And so these things often feel much scarier than they are. Like people go, I don’t wanna quit my job and start a company. It could ruin my life. No, if the company doesn’t work, you would just go get another job. Like there’s millions of jobs out there. So we’re intimidated because we don’t wanna lose the status quo, but often you can very easily get right back to the status quo.
Katie: That’s a good point. I think any kind of life changes like that, they always seem so daunting until you get through them. I always try to remember that metric of in 10 years is this gonna seem as big and daunting as it seems right now and almost never does it. I’m curious, I wanna get deep on stoicism, but first, I’m curious, what do you think about college now that you have kids? Is it something you’re going to encourage and push them to do, or do you have a different view of it now?
Ryan: Yeah, I mean, I have a different view of it in that I know that it’s possible to succeed without college, but I also know that the fact that I was college-ready that I’d succeeded at college was partly why I was able to succeed as a college dropout, right? So when I hear from young kids, they write me and, you know, they’re like, I’m failing out of college, I wanna drop out like you. And it’s like, that’s a very different thing, right? Like if you can’t figure out how to make college work, that’s a sign that the real world is gonna be quite difficult for you as well. And in fact, I think college is easier than the real world. So I’m torn. I mean, we save for college, we have, you know, money taken out of our bank account each month to put our children in a position to be able to afford college if that’s what they choose to do. But I’m not gonna be like my parents, which, you know, sort of collectively lost their mind and, you know, did some very serious damage to our relationship by not supporting me in that decision that I decided to make. And so I think the idea is like, keep your options open. Colleges, neither the solution for every kid and it’s not, you know, to be avoided by every kid. It just depends on who you are and I think what you wanna do.
Katie: I think that’s a great point. And I had the same experience, not quite to that degree with family, but I come from on both sides of family of academics and PhDs and even now at family reunions, I’ll have relatives be like are you gonna go back to school and get a PhD?
Ryan: Right, right. Man, you’re like, I’m doing good. I’m probably doing better than you. But that college does occupy some degree of safety to people. That’s what I think it represents. And that’s great, you know, but I also, you know, going to college because you don’t know what you wanna do with your life and then racking up $200,000 in debt to find out that actually what you really wanted to be was a nurse or what you really wanted to be was a welder or you really wanted to open your own small restaurant, well that was actually a really dangerous decision for you to make then.
Katie: That’s a great point. Yeah. Especially with the amount of debt so many kids take on to get through college. Okay. So you are widely known for, in fact, I think “The New York Times” even said that you are largely responsible for the modern rise and the interest in stoicism. So I think that’s another place I’d love to start and to hear what brought you into that and how you discovered it yourself.
Ryan: Yeah, stoicism seems like this sort of stodgy old useless philosophy, right? When we hear the word stoic, we think has no emotions and it almost feels like it’s the opposite of where we should be going, especially as, you know, culturally we’ve come to understand the importance of vulnerability and the importance of empathy and the importance of processing your emotions. Well, I’m here to tell you that’s not what stoicism is. Stoicism is a way of living. It’s a guide to what the stoics would call the good life, human flourishing. And really at the core of stoicism I think is two assumptions. Number one, we don’t control what happens to us. We control how we respond, right? And I think this is something that intuitively mothers understand probably better than other people. You don’t control that your kid is throwing a temper tantrum, but you control whether you’re gonna make it worse, whether you’re gonna use this as an opportunity to teach them something, right? Mothers are constantly in the position of responding to the stresses and the difficulties of life. And I as a father, I am as well, right? Like how can I control how I respond to this situation? I can’t magically make it go away. I can’t make this hard thing easier. All I can do is focus on what I control, which is my emotions, my thoughts, and then the actions that I take. So that’s, I think point number one about stoicism.
The second is I would just give sort of four virtues that I think are essential to stoicism and I think they’re probably ironically or fittingly the same virtues most of us associate with our grandparents, with really wise or powerful people that we admire. So the first virtue of stoicism is courage, right? Courage under fire. Courage in painful situations, the ability to persevere, right? How do you stand up and do a really tough thing? The next is the discipline of justice, right? Doing the right thing. That’s good morals, that’s good values. That’s how do you have the courage to do the right thing when everyone is doing the wrong thing, right? So all these virtues are related. The next virtue is the virtue of temperance or moderation, right? This is something we have to teach our kids, right? You might think you want to eat this entire box of cookies, but you will feel awful after, right? Or drinking might be fun. It might be something your friends are doing, but it can get you in trouble if you don’t have self-control, right? The importance of resisting peer pressure or the importance of being too obsessed with what people think or being too dedicated to sports or this activity or that.
And then the final discipline of stoicism and the final virtue is a virtue of wisdom, right? How do you learn, how do you make education a priority? How do you better yourself? How do you expose yourself to things you disagree with or new perspectives or ways of thinking? And so those are the virtues, courage, justice, wisdom and temperance. And I think if we can teach those to our kids, if we can model them ourselves, we are gonna be happier, they’re gonna be happier and more importantly, I think the world will be a better place.
Katie: I love that. And I think you’re so right. I think those are things that moms are very on the ground day-to-day involve with kids. I mean, justice with working out and I know yours are still pretty little, but like sibling rivalry is a constant thing and temperance, teaching that to kids is a huge point. I think obviously wisdom for all of us is a lifelong journey. But I’m curious, what was your entry point into stoicism? Has it always been part of your life or did you discover it at some point?
Ryan: I mean, I wish that I could say that my parents had exposed me to this, right? I feel like it’s something I’m gonna do better with my kids is like, what are the great books, what are the great ideas, who are the great thinkers that I wanna make sure my kids are exposed to. A book recommendation for everyone, Senator Ben Sasse from Nebraska. He’s a Republican. You might not like him or maybe you’ll love him. But he wrote this book called “The Vanishing American Adult.” And it’s about how too many parents are basically raising infants, like sort of perpetual adolescents. This is kind of the things we’re seeing on college campuses these days. And he said every family should have a 5-foot bookshelf filled with the wisest best books that teach the values and the ideas and the insights required to be a successful adult. So that’s gonna be different for each family depending on what you do, what religion you are or what culture you’re from that everyone should have a book that they’d go, these are the books that we cherish as a family, that we read, that we talk about, that we reference.
So I wish I could say that’s how I found out about stoicism. But as it happens, I was a journalist in college. I was writing for the college newspaper and I was at a conference about sex that Dr. Drew, the television personality, was speaking at. And I went up to him afterwards and I just, I said, “Hey, like I’m young, I’m learning. You seem smart. What are some books you’re reading?” And he told me about Epictetus, one of the stoic philosophers. And from that, I went back to my hotel room. I bought the books and my life’s never been in the same since.
Katie: Wow, that’s awesome. And that I have not heard that book recommendation, but I’m definitely gonna check it out. I’m completely in agreement on that point. And that’s something that my husband and I have actively really thought about is how can we make sure that we’re raising competent adults and not perpetual children. And so we have some kind of principles in our house and things like we won’t do things for our kids once they’re capable of doing it themselves. So once they’re physically capable of doing their laundry, they do their laundry, they help in the kitchen, they help cook, and they are largely responsible for their relative existence. And also, we have like these things we say all the time explaining that life is not fair for instance, or that we were made to do hard things. So I’m curious, how does that, I know your guys are still young, but how does that roll over into your parenting?
Ryan: Yeah, I think there’s all sorts of great lessons from the stoics. One would be that thing we were talking about earlier that I think I wish I had learned earlier, right? We don’t control what happens. We control how we respond. So even the lesson you were just saying like about life’s not fair. Life’s not fair. Someone hurt you. Someone cheated and got away with it. You know, someone lied and didn’t get caught. Someone, you know, their parent lets them do this and I don’t let you do that. We don’t control that particularly as children, because so much of the world is outside of the control of young people, adults get to decide. Well, that’s true, but the child does retain the power and no one can take the power away from them that they decide how they’re gonna respond. They decide what they’re gonna do about it.
So are they gonna throw a temper tantrum about this? Are they gonna complain about it? Are they gonna whine about it or they’re gonna cry about it. They’re gonna blame other people for it. You know, you had this toy and you knocked it off the counter and it broke. Okay. So we can be sad about that. We can be mad about that. We can whine until we get an a, you know, to that we need a new one. Or we can decide we’re gonna figure out how to put it back together or we’re gonna decide to break, have fun breaking it apart even more. Or we’re gonna, you know, we’re gonna be more careful next time, right? Or we’re gonna wait, what are we gonna learn from this? How are we gonna benefit from it? And to me, that’s kind of the central lesson of stoicism.
But one of the things I’ve taken from stoicism and that I’m trying to think about now as a parent, I started this website on Father’s day this year called Daily Dad. And it’s just an email that goes out every day where I sort of write about the lessons that I learned from the sort of ancients that I think apply to parenting. And so I would say one of the things that, a mistake I see moms and dads make and I’ve seen my friends make is people are way too focused on like the trends of the moment as far as parenting, right? So people are like, do we do this or do we do that? What does the research say about X, Y, or Z when really like, clearly humans have been successfully raising children for, you know, hundreds of thousands of years, right? The broad strokes we’ve got.
And so one of the things I think people should do and what’s influencing my current parenting strategy is like going backwards. What are the best practices from history? And I think some of the ones you just touched on are exactly right. You know, teaching self-sufficiency, teaching that the world is relatively indifferent to you or your desires. So if you want something, you have to make it happen, right? We wanna look backwards to history to learn the best parenting strategies. We don’t wanna look at what the latest parenting magazine is telling us the fad of the moment is.
Katie: That’s such a great point. And it’s something I actually remember my grandmother saying when I had my first child is that our generation tries to make parenting so complicated and so much more difficult than it needs to be. And I think like the, I know this is something else that you’ve written about, but with parenting as well as with life, it’s almost like the less that we do and the less that we try to take on, the happier, calmer and more successful it is. Because I find kids are naturals at, you know, finding obstacles to overcome and climbing creativity. And so often we put all these things in place thinking we’re benefiting them when really we’re taking away opportunities where they could be exercising their own natural creativity or their own natural problem solving.
Ryan: That’s totally right. I actually wrote about this as one of the early emails for Daily Dad. I was thinking, why do kids like grandparents so much? It’s because grandparents are just way more chill than parents, right? The parents are thinking, no, you can’t do that. No, you’ll spoil your appetite. You know, parents are stressed so much more than they need to be, right? And they’re trying to, like, you never get a…look, there’s obviously bad grandparents out there, but grandparents are so much better at accepting kids for who they are and giving them the space to become whoever they’re gonna come, right? In a way, grandparents are better at, I think that unconditional part of parenting, right? Even if they struggled with it, with their own kids, the distance of that extra generation allows them to step back and give kids the space that they need.
I was just, I’ve read a bunch about Mr. Rogers. It was, I think it was grandpa McFeely was his grandfather. You know Mr. Rogers was his kind of sickly kid. He had allergies. He was chubby. His parents were a little clingy. They tried to keep them inside all the time. His grandfather was the one who encouraged him to go out and experiment and to get into trouble and to mess around. His grandfather was the one who told him, look, you make the world special just by being who you are. That was what empowered Fred Rogers to become the amazing human being that he did and influence and impact all these kids. And I think grandparents just because they’re less anxious, they’re less worked up maybe because they know they get to go home at the end of the day, do actually provide a great model for how parents should think more about their own parenting.
Katie: That’s such a good point. Yeah. I think grandparents are such a gift and that’s probably one of the very big reasons why. I’m also curious, so you’ve written, I’d love to go a little bit granular about some of the things you, because you have multiple bestselling books and I’ve really enjoyed all of them. But I’m curious what the thought process was of tackling each of those subjects in that order. So for instance, the first one, “Ego is the Enemy,” what was the impetus for tackling ego first? And I’d love for you to just walk us through some of the core principles of that.
Ryan: So I actually wrote “The Obstacle is the Way” a little bit before “Ego is the Enemy,” and it comes from a quote from Marcus Aurelius. He says, “The impediment to action advances action. What stands in the way becomes the way.” And what he meant is that every obstacle, every difficulty, every messed up thing that we didn’t want to happen, as undesirable as it may be presents also an opportunity, right? Someone is rude to you or mean to you, betrays you, that’s a chance. Yes. That’s not fun. But it’s also, if you think about it, a chance to practice forgiveness or a reminder of why you can’t trust so easily, right? The computer eats all your work, that’s really frustrating. Obviously, you don’t want that to happen, it’s a reminder of why you need better practices for saving your work. And it’s a chance if you think about it, to start over from scratch with no baggage, right? Every difficulty we face in life is, in a way, an opportunity to practice a different virtue.
And so the stoics thought of obstacles as fuel. Marcus Aurelius says, “You know, what you throw on top of a fire is fuel for the fire.” And so that book is really about that mindset. How do we decide that I’m gonna be better for all the adversity and difficulty that life throws at me? And I wanna expand people’s definition of what adversity is. Adversity is not just what happens to you because you’re a minority, you know, because you’re a woman, because you grew up poor, because you lost an arm in an accident. Adversity is waking up to two sick kids, right? Adversity is going out to the garage and finding the car tire is flat. You know, adversity is, you know, one of the parents is on a business trip and the other has to, you know, do double duty for the next 48 hours. How are you going to respond to this? What’s the mindset you need to bring? What are the tools and creativity you need to bring and how do you have the strength to persevere through that difficulty?
So that’s what “The Obstacle is the Way” is about. And then the next book was “Ego is the Enemy.” Because what I realized is that ego is something that gets in the way of doing what we were just talking about, right? Ego is this kind of force field between you and being a great parent, being a great employee, or being a great boss, being a great neighbor, being a great leader. I don’t think it’s a political point to say someone like Donald Trump has taken a difficult job being president, probably the hardest job in the world and made it much harder with his ego, right? He’s created unnecessary enemies. He’s passed up easy opportunities for compromise. He said things, you know, out of arrogance or anger that have come back to haunt him, right? And that’s what ego does. It just makes a hard thing harder. And I don’t think any parent, any business person has ever thought, you know, what would make this really tough situation that I’m in easier, like more ego. No, ego makes hard things harder. So that’s what egos about.
And then the third book in the trilogy is “Stillness is the Key.” And I think stillness is another thing that stillness makes overcoming obstacles easier. Stillness is what you get when you sweep ego away. We all benefit from slowing down, thinking more clearly, being intentional, having routines, getting rid of chaos or unnecessary obligations and burdens. And so that series that it’s all influenced by stoic philosophy, but it’s really about, you know, how can we improve important domains in our life through that philosophy.
Katie: Got it. And my apologies. I read he goes the enemy first and so they always reversed those two when I think about which one was written first.
Ryan: No, they’re not really meant to be in any order. That’s just sort of the journey I went on as a writer. But I think people should just pick up if they are willing to give the books a chance, I would just say pick up whichever one feels like it resonates more with where you are in your life. If you’re anything like me or probably you, I would imagine that just we’re all suffering from like information overload, over commitment, mental exhaustion. And so to me, I feel like stillness is this urgent sort of epi…stillness is a solution to an urgent epidemic that we have as a culture and as a society right now. But you know, maybe you’re going through a difficult obstacle in your business or your personal life or with one of your kids and that’s the best place to start. They’re all interchangeable.
Katie: Let’s talk a little bit more about stillness because I’m guessing there might be some moms listening who are thinking things like, that’s a great idea, but I have kids and that’s not possible. And it’s always chaos because I think an important point that I pulled when I read “Stillness is the Key” is that stillness doesn’t have to mean physical stillness, doing nothing. That was really important distinction. I loved that explanation of like that the stillness of being wrapped up or fully immersed in an activity. So like for me, paint more, or drawing or writing. But let’s talk more about stillness and practical applications when we are in such a busy world.
Ryan: Totally. Well, look, what I would say is that it’s the busy mom who needs stillness more than ever and needs to be able to…I’m not saying like move to an ashram in India or go on a 30-day silent meditation retreat. Most of us can’t do stuff like that financially or, you know, just time wise. So what I’m talking about is how does the mom or the dad or the CEO cultivate stillness inside the chaos? Right. I opened the book with the story of Seneca, who’s trying to write in Rome in, like, the year 100 AD. And he’s just distracted by all the ear-splitting noise outside of his window. And he talks about how you have to develop strategies for tuning all that out and focusing on what’s in front of you because you can’t control the noise, as you were saying you can only control how you respond to the noise.
So, you know, it’s funny that like, I feel like most of the times in my books I’m really writing about things that I learned from my wife and my wife has just this model of stillness. I think we bring different strengths and different traits to the relationship, but like and you helped us with this because you gave us advice on this that smart pillow that helps put kids to sleep. But our son, Clark, I would say for the first two and a half years of his life, never slept. Like, I’m not sure how he’s alive. He never slept more than two hours or three hours in a row. It was brutal. And so bedtime was a nightmare. Like putting him down, it was so hard. So much easier with our second. But I think we just, you know, that’s just sort of who he was.
But like my wife would go in to put him down to bed and I might not see her again for like two hours. Like it was a two-hour experience of nursing and holding and putting him down and just getting him like, you know, the transition from your arms to the cradle and then, oh, it didn’t work. And she would just, the stillness required to do anything that hard in the dark for two hours. I mean, I can’t even do anything for like seven minutes without getting impatient or frustrated. And so, you know, to me, the patience and the stillness that mothers bring to parenting, to me embodies all the things that I’m talking about in the book. I’m talking about cute Kennedy and the Cuban missile crisis and the brilliance and the patients and the perspective and the empathy that he brought to that difficult situation. How he was able to resist the advice that his generals had to rush into action. He’s like, no, we should think about why the Soviets did this and how we can give them a way out and what they’re gonna do in response. I feel like and this might seem a little sexist, but I bet Jacqueline Kennedy, if she had been invited into the room, intuitively would have known and suggested all of those things. And so stillness to me is something we can take a lot of inspiration from women for, but we all naturally possess stillness. And the key is how to cultivate it and develop it so it’s more at the forefront of our lives.
Katie: That’s such a great point. And you’re right. I think that was one of the lessons for me several years ago and actually when I was kind of delving into the idea of stoicism was that when it comes to cultivating these things, it can’t be left into the like little bits of time that we have left over or just added to a to-do-list. And I realized this in my own life when I almost, I think had a nervous breakdown trying to balance everything between the blog, the family and all of it. And came close to actually deleting “Wellness Mama” because I realized I couldn’t do everything at that level anymore and I wasn’t willing to sacrifice family. And in that moment, I realized there was a drastic difference in how I was managing the two things.
So in business, the most important things always happened first. And I had objectives and goals and I objectionably evaluated things. Whereas at home, I was trying to juggle everything in my head and just manage it myself and take on everything. And that wasn’t realistic. And so I sort of switched the entire idea of how I ran our family. And put the actual most important things first like family dinner and like spending time together and having time for self-care and for exercise and the things that help cultivate stillness. And it was a really drastic shift in the family because I was calmer and encouraged the kids to be calmer. We all had so much more bandwidth. But I think you’re right, like motherhood is wonderful for kind of building in some of those lessons of stoicism.
Ryan: Well, so two things. I think one like I don’t think this is just limited to women, but like one of the things that having a newborn really taught me and now my son’s three and my other son’s about four months is like, what we’re doing is what we’re doing, right? Like I don’t think playing in the dirt is fun, but that’s what he thinks is fun. If he can do it for hours and hours, so that’s what we’re doing. Do you know what I mean? That like stillness is just being present and enjoying and finding, you know, experiences in sometimes in the most mundane and ordinary things. And I think one of the things that having kids really teaches you that is such a critical part of stillness is presence and not like you go…so many parents, it’s like, “Oh, now we have to go.”
It’s like, do you really have to go or is this made up thing that you are deciding to do? Can’t you just do this and why don’t you just play? Why don’t you just sit here at the park for three hours instead of running? You know, you think this other thing is more educational and important, but really like sitting here playing in the sand is teaching all sorts of lessons. So I think I learned a lot of presence from parenting and that’s been an important part of stillness in my own life. And you brought up that idea of burnout. Like people think, Oh, I can’t afford stillness. I’m busy. I’ve got a company to run, I have money to make. I’ve books to write, a blog to keep you know, I have a career I’m trying to advance in.
Well, if you ended up working so hard that you work yourself into an early grave, that’s not good for your career, right? If you work so hard that it sucks all the joy and love that you had out of what you were doing, and so you wanna quit, that’s not good for your career. If an athlete is so unable to balance and pace themselves that they injured themselves, that’s not good for their career. Look at Kevin Garnett. He or, sorry, not Kevin Garnett, Kevin Durant. He hurt himself in the playoffs this year. He was recovering. Against doctor’s advice, he rushed back. He played like for like eight minutes in one of the games in the finals and blew out his leg and is now missing an entire season. So, you know, we say we wanna be there for our kids. We wanna provide for them, but if we actively injure ourselves mentally or physically because we can’t find a balance and we are incapable of moderation, one of those keystone virtues, well that’s pretty self-defeating.
Katie: So for you, personally, as both a business owner and a parent, what are some of the ways that these ideas of stoicism manifest in your daily life in a practical way? So how do you implement some of these? What are your own strategies?
Ryan: Sure. Well, give you some, I think some strategies that I’ve tried to practice that I think will be helpful for cultivating stillness and make people a better parent and a more stoic one. Number one is…this comes from Winston Churchill. Winston Churchill said the most important thing that a powerful public person needs to have. He said a good hobby. You need to have hobbies that balance you out, right? You can’t just be all about work. You can’t just be all about family, right? How many stay-at-home moms live and die by their kids and that’s why they hold onto them so tightly and why they get so wrapped up and say their personal lives or, you know, trying to bribe their kids way into college or whatever. It’s like, no, you should have been painting Martha or you should have, you know, gotten into doing triathlons and that would’ve been a good outlet for some of that energy, right. And allowed you to have some more balance and perspective with your kids.
So for me, and this ties into a second part of stoicism like physical exercise almost enduring or seeking out suffering in your life. So I try to swim or run every single day. And that exercise I think makes me a better dad. This morning I gave a talk here in Austin. And so I had to take my son to daycare, in pre-K and then I had to go do this talk and I had to be there by 10:00. And then I’ve been in recording interviews and preparing for the book launch all day. So it was a busy day, right? But it was important for me to exercise. So I got up at 6:30. I did some of my work. My son woke up at 7:30 and I took him on a four mile run in a stroller. And so that was our time together in the morning when we talked. We had fun, we were out in nature, but I was also taking care of myself. Sometimes when we do it in a bike, you know, sometimes I carry him in a backpack, but we experienced that morning together. And I think it’s really important.
Another important habit, and I know you’ve talked about this before, but like the power of journaling. You’re gonna wish in 20 years that you wrote down some of the memories and the experiences that you have while raising your kids, or just that you journaled the difficulties and the tough times that you had. And so, you know, we’re gonna want those journals in the future and your kids and your grandkids and your great grandkids will be grateful, you know, to look at those journals 50 years from now, 100 years from now. And so I’d encourage everyone to grab a notebook and try to jot a few thoughts in it every single day. So those are just be a couple straightforward strategies that I think are pretty practical and usable.
Katie: Those are great.
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Katie: And to circle back to something you said earlier when you were talking about “The Obstacle is the Way,” I think that’s another really profound mental shift that is especially beneficial in our specific period of time. I think at least the social media world that I see people are so easily angered and emotions skyrocket and they escalate and people build on each other for that. And I think that mindset shift of away from the idea that any obstacle is bad and actually to the idea that an obstacle can be very good is really profound. Are there any ways that you, like tangible ways you get people to start implementing that mindset shift because it is a big one?
Ryan: Well, you know, there’s this expression that’s become so popular now. People are like, oh, that’s trigger. You know, you’re like, “I’m triggered.” You know, and we wanna like we wanna sensor unpleasant or offensive viewpoints. And look, I’m not saying anyone should say anything offensive. Like, I try not to hurt people’s feelings. I don’t wanna be rude. I don’t like to just say mean or hurtful things for the sake of it. But I also, at the end of the day, think truth is important and I am not a fan of censorship. So like the idea that we should be teaching our kids to shout “trigger”, you know, that you’re triggering me and close their ears, you know what that’s doing? That’s setting them up to be hurt more because they’re more vulnerable to those things because they have no experience.
Adam Carolla, who I think is hilarious. I don’t agree with him on everything, but I think he’s hilarious. You know, he gave this great talk. I think he was testified before Congress and he was talking about this sort of censorship. It’s popular on college campuses. And he was like, look, this is the parents’ fault. You know, he’s like, this is like parents who have given their kids really bad allergies by not exposing them to things, right? By keeping your kids sheltered, by not, you know, by no nuts allowed or you know, like by overprotecting them, you’re actually made them incredibly vulnerable. By not letting them play in the dirt, they’ve not gotten the antibodies and the sort of exposure to things that they need to build up in a strong immune system.
And so I think one of the things we’ve gotta be really careful with as parents is not sheltering our kids from all the bad offensive things. Like people go, What should I tell my kids about what Donald Trump said on television? What should I say about these, you know, vulgar television shows?” Well, you should have an intelligent adult conversation with your kids about why certain things shouldn’t be said, why it reflects poorly on the person who said them, what it means, you know. It’s your impulse to block them from the unpleasantness of life that will ultimately make life much more unpleasant for them once they leave your house.
Katie: So true. And I love that you brought that up about allergies because that’s been, I think a shift that’s finally happening in the nutrition world is that for so long they had pregnant moms avoid allergens like nuts and avoid giving them to kids and it actually made the kids more likely to have allergies. And now the science is saying actually early careful introduction is much more effective and important. And so we’re starting to see that. And the same with dirt and like how we now know of kids play in the dirt and have pets in the home, they’re less likely to have allergies and less likely to have problems. And then how much of a metaphor for life that is like we can’t protect our kids from the emotionally tough things in the world either. A friend of mine, Aaron Alexander has a quote, he said, “Never waste a trigger.” And he goes onto how that shows you something really important about yourself. Like if someone else doing something that’s not directly aimed at you as causing you to have some kind of really strong emotional reaction, turn that around and figure out why because that’s really enlightening thing to look at.
Ryan: I just wrote that down, never waste a trigger. That’s so good. Well look, and you might agree, you might disagree with this which I, I would be perfectly fine to hear it, but like one of the things like my wife doesn’t eat gluten. I try to eat sort of mostly Paleo, the whole 30, I don’t eat a ton of gluten, but we let our son eat gluten. Like obviously as he gets a little bit older and is sort of more nutritional health matters. Like if he was an athlete or something, we’re gonna try to eat healthy and we don’t just like make him sandwiches all the time. But we didn’t wanna be the parent that says like, don’t give my kid pizza at this party, right? Because one, we didn’t want to be that. But also we know we can’t be there preventing him from eating a cupcake or a cookie at school if someone gives it to him.
So we wanna make sure that he has an, you know, the first five years of his life, he didn’t grow up in a bubble just because we eat healthy and we know what’s good or bad. We wanted to make sure he was prepared for a world in which, you know, stuff gets slipped in your food or you feel pressured to eat something because you don’t want to upset people or somebody doesn’t know. And are you making a mistake? We didn’t want that to be the first time that he, you know, eats this or that and it throws his whole body into shock. We wanted him to have the freedom to know, you know, does that make sense or is that crazy?
Katie: Absolutely. No, and I’m right there 100% with you. I actually invested in a company that’s doing the research on early introduction, introducing gluten, peanuts and dairy to babies starting at six months when they get food, but in very small doses and building because of that exact thing. If they’re not exposed at all, and I’m the same way, I eat, almost never eat those things. I almost never eat gluten or dairy or processed food in general, but I don’t forbid my kids from it and I don’t tell them they can’t eat things and when they’re out in public, they 100% make their own choices about food. And my thought is at home I’m responsible for cooking for the family and I’m gonna cook what I believe to be healthy and good for them. But I’m also not gonna control them when they’re not there. Because if anything, it’s like when you, you know, an alcohol is this completely forbidden thing, then they more likely, you know, to consume that when they’re older. And so having those conversations about it, certainly educating about why they might choose not to do those things, but not forbidding it because I think that can make them more likely to actually want to try the thing.
Ryan: That’s a great point. Yeah. And you don’t like, I think it’s important with kids like, eh, I don’t wanna give them any issues regarding food. Do you know what I mean? Like, I don’t wanna make food an obsession in their lives. I don’t wanna give them body or you know, mental issues pertaining to food. I want them to eat when they’re hungry, eat reasonably, you know. I just, and then we’ll handle it when they’re a little bit more capable of having an adult discussion about it. But I think you’re right. This is a great metaphor for parenting and for life in general. Like I think with this college admission scandal, like introduced a new term to me. Like I was familiar with helicopter parents, right? You don’t wanna be the parent that’s constantly hovering, making sure they don’t fall down, you know, being way too involved in their business, always watching, always observing, spying on them, whatever. That’s helicopter parenting and it’s bad for a lot of reasons.
But what these parents were, was snowplow parents. That’s what I heard. They were constantly, they were in front of their kids removing obstacles, removing difficulties. So they always had a clear and pleasant path to wherever they wanted to go. And that involved cheating on the SATs, that involved bribing their way into college. These kids never experienced difficulty failure, setback. The parents removed obstacles and then wondered why the kids were so fragile and you know, didn’t thrive. And so the job of the parent is not to prevent your kid from experiencing adversity. It’s to equip the kid to know how to respond to adversity because what’s a better strategy for life? Pretend that you can always be there and always eliminate obstacles or help raise and instruct a kid so obstacles never slow them down more than they need to.
Katie: Wow. Yeah, I heard that term as well, snowplow parent. And I feel like I’d be the complete opposite of that because when I look at my own life, I realize a lot of my accomplishments have come as almost a direct result of obstacles and overcoming those obstacles. And some of those things I had to work through where things I would certainly never wish on my child. But obviously as parents we wish our children every success and happiness in life. And that’s something I’ve really wrestled with as a parent is how do I, like, how do I hopefully give them those same skills and lessons without them hopefully having to go through some of those hard things that I did. And also realizing as a parent I can’t purposely make their life hard. That kinda goes against parenting.
And so for us, we tried to find ways to build in natural good challenges in ways that we can tackle as a family and that might be travel, that might be tackling new skills together, like handstands or whatever it may be. I’m curious how you guys approach that with your kids as they start to get older. How do you approach the idea of obstacles and equipping them for those things and also, giving them chances to fail and have obstacles?
Ryan: Well, that’s a funny thing cause I’ve heard from lots of people, adults since the book was written and they go, you know, “Does that mean I should seek out obstacles?” And it’s like, what life is gonna throw enough obstacles at you that you, I don’t know, you need to go seek them out. But I do think making sure that we’re not actively preventing those obstacles from happening is really important for kids and also, putting them in positions or giving them experiences that force them to learn. So like, I think it’s interesting, like obviously you wanna be cognitive of say choking, but like the idea that that you should give two craps what the toy box says, the suggested age for a toy is to me is hilarious. Like, I’m gonna give my kids the toys that challenge them, that make them that they have to figure out. I’m not gonna give them the simplest, easiest toys. Like, that’s not how you learn. That’s not how you get better. You get better by being put out of your comfort zone, by having to figure things out.
So yeah, we’re constant. Like our, you know, our kid was swimming from like, you know, three months on where he likes to wear a life jacket, but we encourage him to swim without a life jacket when we’re in the pool because, you know, if we let him in our pool in a life jacket, we find that the next couple times he’s swimming without a life jacket, he’s too brazen and his skills have atrophied, right? Because he’s gotten used to just jumping in off the side and not having to swim back to the side, right? And so we’re constantly trying to put him in challenging situations and experiences, not like throwing up obstacles in his path, but sort of like you’ve done with your kids. And I’ve seen them, they’re wonderful. Like they’re out there exploring outside, you know, their free range or whatever the expression is, because that’s what’s gonna put them in a position to naturally experience obstacles that they grow and learn from.
Katie: Yeah, exactly. And I think there’s also ways as parents, we can easily let build an obstacles in the form of just natural consequences by not problem solving for them, like you said, or not doing things for them when they could have done it themselves. So for instance, like with our kids, if they don’t like a food that I cook, they don’t have to eat it, but they’re not getting anything else. And our thought is that hunger is a great natural teacher and that is, you know, an obstacle that’s not life-threatening in any way that they will gladly overcome by the next meal. But that they can learn from that scenario. Or now that they all do their own laundry, if they don’t do their laundry, they don’t have clothes, and that’s an obstacle they’ve created and then they have to solve because I’m not gonna solve that problem for them. And so I think you’re right, like all of those things, if we just build in those lessons, life certainly throws plenty of them at all of us.
Ryan: Yeah, I think that’s right. I think that’s right. And not solving the problems for them when they come to you with a, “Hey, fix this.” And it’s like, you know how to fix this. You show me how to fix it. And I think that’s really important.
Katie: So one of the critiques I’ve heard of stoicism is that it’s an ancient philosophy and how can it actually, you know, fit into modern times and that these philosophers didn’t chase a lot of this stuff that we face in the modern world, which I’ll agree with that point. They didn’t deal with social media trolls and they didn’t deal with the constant demands of all of the things that necessarily hit us in modern life. But I’m just curious your take on that. When you hear people say like, you know, how does stoicism really fit in the modern world?
Ryan: To me, people are people. And the more things have changed over the passage of history and time, fundamentally, the more they’ve stayed the same, right? Marcus Aurelius had like 9 or 10 kids, you know, he ran an empire. He had people who worked for him. You know, if he was cold in the winter and hot in the summer, you know he dealt with critics. He dealt with fans, you know, he dealt with plans that he had that fell apart. He was trying to solve the problems of existence just like we are. And he was coming at it from a position of great privilege, which many of us have, right? We’re lucky to be born in America. We’re lucky not to be impoverished. You know, we’re lucky to have our health.
On the other side of the stoke spectrum, there’s Epictetus and Epictetus was a former slave. He was disabled. His leg was sort of all but useless and he walked with a limp all of his life. And yet he was the other famous stoic philosopher so much so that he was probably Marcus’s favorite philosopher. And he has all sorts of interesting things to say about those experiences, which are timeless as well. How many people are disabled? How many people have come from less than desirable circumstances? How many people have anger and resentment about things that people have done to them? Right? Stoicism is ultimately a philosophy that’s I think applicable to whoever you are, whatever you’re doing, wherever you are. Because ultimately those virtues we talked about earlier on, temperance, courage, wisdom, justice, we all need more of these things. And the ancient world has a lot to teach us about them just like the research that we’ve done, you know, in psychology and biology and neuroscience has a lot to teach the Stoics, right?
Like Marcus would have been a better parent, I’m sure if he had John Bowlby’s, you know, breakthroughs about attachment theory pertaining to kids. Maybe his kid, Commodus, wouldn’t have been so messed up if Marcus probably hadn’t had and, you know, had a closer, more involved relationship with him. So it’s not to say stoicism is perfect. No. Nothing is perfect and everything, you know, from the past has biased and flawed assumptions. The stoics didn’t have a problem with slavery, right? Even Epictetus who was a slave never seems to have questioned whether as institution that was okay or not, right? So there’s a lot that needs to be updated within stoicism and I kind of tried to do that in my books, but the idea that you would write it off just because it’s all this ridiculous. The Magna Carta is old, the Constitution is old, you know, Christianity is old. But that doesn’t mean there’s not a lot of good ideas in those things.
Katie: I completely agree. And another thing that you have is you have these coins that I actually keep with me all the time now. Yeah. I have memento mori and I have a amor fati. And so I took Latin all the way through high school and I love Latin phrases, but I love if you could just kind of give us an overview of those two specifically because I just find them really helpful in my own life. And I think it’s so cool that you made those.
Ryan: So I have those two coins. I have in my left pocket, I have the memento mori coin and it comes from an ancient stoic practice. The idea of meditating on your mortality on the back as a quote from Marcus Aurelius, he says, “You could leave life right now let that determine what you do and say and think. And so I think about that always, and I made this coin for Daily Stoke. You can see it if you’ve got a daily stoke.com/store. But the idea of the coin is like a reminder that…a physical reminder can reach in my pocket and touch it. I can spin it around on the table and it’s a reminder to me constantly not to take life for granted and not to take anyone for granted.
One of the, I think the most provocative exercises in all this stoicism, and this might trigger some moms listening, Marcus Aurelius and Epictetus both said that as you tuck your child into bed at night, you should say to yourself this could be the last time that I see them. You know, that they might not make it to the morning. The idea of thinking that your children are mortal is so repugnant and so terrifying that we don’t wanna do it. But the purpose of that exercise is not to detach from your children. It’s to not just go through the motions as you’re tucking them down, not to take them for granted, not to hold a grudge, not to yell at them because they’re, you know, putting on their pajamas too slowly or to get upset that they, you know, they spilled their food on the way into the bedroom or to take it personally that they yelled or got frustrated with, you know, like, enjoy this. Don’t take it for granted. Don’t take anyone for granted. We do not possess the people that we love. They can be taken from us at any moment. And this is an essential part of stoicism.
And then in my other pocket, I have amor fati, which it comes from that other metaphor from Marcus Aurelius we talked about earlier, the idea that, you know, he says what you throw in front of a fire is fuel for the fire. Amor Fati means you just love everything that happens. You embrace all of it. Your family is stuck at the airport for three hours because your flight is delayed. You can sit there and complain or you can go, this is the best thing that ever happened to me. I’m gonna say yes to this and we’re gonna have a fun family experience. Or at the very least, I’m just not gonna yell at anyone. You know, I’m not gonna take this personally. I’m not gonna get upset by it. Just gonna accept it and I’m gonna enjoy it as best I can. And so this idea of memento mori and amor fati to me are two critical practices to parenting, to life, to entrepreneurship because I mean, what else are you gonna do?
Katie: I love both of those so much. And okay, so I always love to ask book recommendations at the end of interviews and your books are actually some of my most recommended, but I’m curious what books besides your own you have really taking like life lessons from or have really been foundational for you?
Ryan: Yeah, so I’ll give you a couple. I think some of these kind of pertain to stoicism. Some of them pertain to parenting. One of my favorite books is a book written by a woman named Totto-Chan who is sort of like the Ellen of Japan. And she wrote this memoir of growing up in Japan as a young girl during the Second World War called “The Little Girl at the Window.” And it’s about this sort of untraditional education that she had, this wonderful school principal who embraced her strangeness and weirdness. She’s clearly a kid with ADHD is what you would call it now. But this teacher instead of trying to change her, embraced her and encouraged her to be who she was, and it’s one of my favorite books and I just absolutely love it. I would recommend “Antifragile” by Nassim Nicholas Taleb. I think that’s an important one. I think that’s what we’re trying to do with kids is not raise fragile kids, but kids who are strong and resilient.
I really like “The Second Mountain” by David Brooks, which I read recently, which is like, so the first mountain we try to climb as career success that’s being famous, that’s being rich. But it says the second mountain is your family is the impact that you have on your community. It’s what you do for other people. It’s figuring out why you were actually put on this planet and what kind of impact and difference you can make. That’s a really important one. And then I have one that I think Seth would like that I just found out about recently. I didn’t know Herbert Hoover, the president, you know, the guy who basically didn’t respond right to the great depression happened to have written a book called “Fishing for Fun” and the subtitle is “How to Wash Your Soul.” And he wrote a book about the therapeutic philosophical and spiritual benefits efficient. And I just I thought it was beautiful. We have a little lake behind our house and I’d love to go out there and fish and my son fishes with me even though he’s three and it’s totally true. You never come back from fishing worse off than you did before you came, even if you don’t catch anything,
Katie: I love all of those and I’ll make sure they are in the show notes as along with links to the Daily Dad and all of your books and all of your sites. But where can people find you online if they wanna follow your work and stay in touch?
Ryan: Well, that would be really cool if they did. So I’m @ryanholiday on pretty much all social platforms. You can go to dailystoic.com/email if you want an email inspired by stoicism every day, dailydad.com if you want a parenting email each day. And then I hope they check out “Stillness is the Key” which is available in bookstores everywhere starting October 1st.
Katie: Awesome. And I got a pre-release copy, which I was really grateful to get and I highly recommend that you guys, it’s awesome. I think it’s especially like we talked about, applicable to parents and I think it’s a really important message in today’s world. But Ryan, like I said at the beginning, you are one of my favorite authors and I have looked up to you for a long time. So I’m really grateful that you took the time to be here today to share with the audience. And I love that we took such a parenting direction because I think that’s such a perfect and applicable way to talk about stoicism.
Ryan: Well, thank you. And I’m so glad. That was very nice of you. I’m so glad we met at John Durant’s event and that I overheard you talking about where you live because that’s a place that my wife and I visited a lot and it happened. I think that’s why we connected and here we are talking. So it’s awesome. And Samantha says hello. I just texted her to say we were talking and she says hello and hopes you’re doing awesome.
Katie: Oh, I love it. And tell her hi for me and your little ones as well. And thank you for your time today and thanks all of you for listening and sharing your time with us today. We’re so grateful that you did and I hope that you will join me again on the next episode of the “Wellness Mama” podcast.