Ryan Holiday Shares The Secrets Of Stoic Parenting, One Day At A Time

Talking to Ryan Holiday furnishes you with enough wisdom to fill a library. During our Zoom call, he references luminaries from Leo Tolstoy to Pete Holmes, often with the preface: “There’s this great quote by…” He’s able to select just the right words from a mind teeming with bon mots; fittingly, his backdrop is a literal wall of books.

An author, philosopher, marketer, media strategist, podcast host, and bookstore proprietor, Holiday reads, writes, and generally outputs more than you would think possible for a father of two young children. In the past decade, the 35-year-old has written 13 books — including two for kids — that have collectively sold more than 6 million copies. His bookstore, the Painted Porch, in Bastrop, Texas, about 30 miles outside Austin, carries only titles he’s read and thinks you should read, too.

Holiday’s newest book, The Daily Dad: 366 Meditations on Parenting, Love and Raising Great Kids, draws its inspiration from his email, the Daily Dad. (He also produces a monthly email recommending the best books he’s read recently.) The idea behind the Daily Dad is that you read one page, or “meditation,” a day, which is hopefully doable even for the fathers of young children.

Holiday struggled with most parenting books, “which I think is not an indictment of the writers so much as it is the medium,” he says. The idea that you read one book over a week or a month that covers the whole fatherhood journey and still applies when you and your kid are both 10 years older? It didn’t work for him. Whereas the page-a-day format, he says, stays with you for a year, if not longer: Some people have read his book The Daily Stoic — also the name of his other daily email and podcast — every day for eight years. Most days, if he remembers, Holiday reads Tolstoy’s A Calendar of Wisdom. The same entry read over the years can, at another life stage, hit him “totally differently.”

One of the things my wife and I have thought a lot about is just: Do they love books? That seems to be a much more important skill than whether they’re good at reading or not.

As a 19-year-old college student, Holiday read Meditations by the Roman emperor and Stoic Marcus Aurelius four times in a row. He dropped out of college to apprentice under Robert Greene, author of The 48 Laws of Power, which updated Machiavellian lessons from history for contemporary movers and shakers, including Jay-Z. (Greene is now a client of Holiday’s creative agency, Brass Check.) Holiday launched the Daily Stoic following the breakout success of his 2014 book The Obstacle Is the Way, which introduced modern readers to ancient ideas that still apply today. Founded in Athens more than 2,000 years ago, Stoicism teaches that we don’t control events, only our response to them, and has influenced everything from ancient Roman governance to Christian theology to cognitive behavioral therapy.

After the births of his sons, in 2016 and 2019 respectively, Holiday decided to apply the same methodology of writing concisely and daily to being a dad. “It’s been a really wonderful experience to sit down and think every day about some kind of universal parenting principle or reminder,” he says. The commitment has helped him “a ton” as a father.

Before they became parents, Holiday and his wife had already made “maybe the most important decision” of parenting: where to bring up their kids. They relocated from New York to Texas, where the family raises cattle, donkeys, and goats on a 20-acre ranch that’s cheaper than their former Midtown apartment, and where Holiday has more freedom financially to decide what professional commitments he takes on. There’s a “terrible irony,” he says, in working hard for your kids when what they really want is you.

Holiday’s admittedly privileged position presents a different challenge: Can you say no, for your kids, to something that’s potentially lucrative, career-advancing, exciting, rewarding, validating? “I struggle with that choice all the time,” he says. Speaking engagements are hard to turn down, but Holiday — who has addressed pro sports teams, special forces operatives, and sitting senators — tries to measure lost income against lost bedtimes.

While writing demands blocks of uninterrupted concentration, says Holiday, kids demand to interrupt. He used to work from home more, but accepting his kids’ interruptions — how stoic — so he could spend time with them only made it harder for him to wrap up at the end of the day. At the start of the pandemic, he set up an office above his nearby bookstore; he can drop his kids off at school in the morning, be at work, and then pick them up in the afternoon. Another big parenting question, says Holiday, is how to design your life so you waste as little time as possible. He thinks about his ideal day, which always includes spending time with his kids, and with that in mind, makes decisions: some easy, some “expensive.”

I once heard Pete Holmes say, “Watch all the movies where bad things happen to kids while you still can.” Having kids has made me a total softy in that sense.

The Stoics sought ways to navigate turbulent times, including pandemics. Holiday became a father the day after the 2016 U.S. election. In an open letter to his own father asking him to not vote for Donald Trump, Holiday wrote that he’d developed as a writer “sitting alone in my room as a kid, trying to respond to your overwhelming parental logic.” Holiday was attracted to writing, he says, as many creatives are to their medium, “as a way of having a voice.” It was an outlet that has served him well professionally, but personally he’s “come to understand with sort of a sadness” that there’s a “tragic element” driving a lot of successful people: “You shouldn’t need to go become world-class at something so you can finally get your dad to see you or hear you or be proud of you.”

In 2020, having turned down a communications job in the Trump administration, Holiday again wrote his father an open letter asking him not to vote for Trump and articulating the “real grief” of discovering that the values your parents told you they believed in, by which you set your moral compass, were not sincere. That, says Holiday, is “a disorienting place to be.”

The author of Ego Is the Enemy, Stillness Is the Key, Courage Is Calling, and Discipline Is Destiny seems very different from the one smoking a cigarette on the cover of his first book, Trust Me, I’m Lying: Confessions of a Media Manipulator, which brought to light the PR dark arts the 20-something Holiday performed at the controversy-courting L.A. label American Apparel. It was, he says, “a weird time.” But the values and perspective you pass on to your kids come from your understanding of the world and from your mistakes.

While the world can be heartbreaking and hard to understand, The Daily Dad offers wise counsel and the consolation that, more than 2,000 years ago, fathers also worried about their kids. Holiday says he has his moments of despair and anger but tries to focus his attention where it can have the greatest impact: on two impressionable adults in the making. “I have seen a lot of examples of what I want to raise my kids to not do and be,” he says.

Holiday has a great quote tattooed on his forearm as a reminder: “The obstacle is the way.” It comes from another philosopher: himself.

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What’s your favorite thing to do together as a family?

I like when we go on walks. I’ve said before: I don’t think walking will solve every problem, but there’s few problems that are made worse by going for a walk. Anytime we’re being crazy, anytime we’re not getting along, anytime we’re grouchy, anytime we don’t feel connected, I’ve found that getting outside and walking around works some magic.

What’s your favorite piece of clothing or accessory that you own?

My old band T-shirts. I have an Iron Maiden shirt that I bought at a concert when I was in high school that I wear pretty often. One of the perks of being a writer is that you can wear whatever you want. And there’s that Thoreau quote where he says “Beware of all enterprises that require new clothes.” Whenever I find myself going “Oh, I don't have clothes for that,” I go, “Do I actually need to do that?”

Name the most important skill you’re passing down to your kids.

Well, I don’t know if any of the skills have taken root yet, so I feel like that might be too early to say. Reading? I would like reading to be that. We’re still working on it here! My kids are just at reading age right now, and there’s a lot of: “How are they comparing to other kids? Are they doing it fast enough? Could we have started sooner?” One of the things my wife and I have thought a lot about is just: “Do they love books?” That seems to be a much more important skill than whether they’re good at reading or not. Because you can always get better at reading, but if you don’t like books, if you don’t understand what books could do for you, it doesn’t really matter how technically proficient you are.

Give us a book, record, movie, or TV recommendation.

One book that really helped me is Adult Children of Emotionally Immature Parents by Lindsay Gibson. Because if you didn’t have parents who were particularly good with their emotions, it’s very hard for you to be good with yours. Not only did you not get what you needed, but you didn’t see them being what they needed for themselves. I’ve taken a lot out of that book.

If you have an hour yourself, what are you doing?

I’m probably going to go for a run or a swim or do something physical but solitary.

If you could give one piece of advice to your former kid-free self, what would it be?

I once heard Pete Holmes say, “Watch all the movies where bad things happen to kids while you still can.” Having kids has made me a total softy in that sense.

But I’d probably say — I think I say this is in The Daily Dad — but having kids is one of the few things in my life that I wish I did sooner. And I didn’t have kids late, so it’s not like, “Oh, I’m going to be old when I have kids.” I’ve just so enjoyed it; it’s made me better in so many ways. I think I was intimidated by it, and thought I’d be giving up so much stuff, that I was hesitant for longer than I needed to be.

So I might have told myself, “You’re going to figure it out; you’re going to handle it. Everyone does, ultimately. So what are you waiting for?”