Ryan Holiday loves to write. He has published several books within the past decade, including “The Obstacle Is the Way” and “Ego Is the Enemy”. One of his more prominent pieces of work ‘The Daily Stoic’ was published in 2016 after our mutual connection Steve Hanselman began encouraging him to write a one-page-a-day philosophy book. An interesting take on the traditional one-and-done reads he had explored before, Ryan decided to do that by creating a compilation of over 360 daily insights derived from Stoicism. Two million copies translated into 30 languages later, ‘The Daily Stoic’ was a success. In addition to writing and publishing books, Ryan also has an impressive portfolio of work as a media strategist. Just some of his past clients include Google, TASER, and Complex, as well as prominent bestselling authors including Neil Strauss, Tony Robbins, and Tim Ferriss. An expert in expert guidance to say the least.
Creating ‘The Daily Stoic’ and ‘The Daily Dad’
Around the same time that ‘The Daily Stoic’ began to take off, Ryan and his wife learned that they were expecting their first child. Exciting for anyone, but just as much so daunting. Forget publishing globally-acclaimed books – how on Earth do you take care of one of these things? That’s the exact question he took to the bookstore in search of answers; now on the other side of the dynamic, Ryan found himself buying and reading all the parenting titles he could find.
But they just weren’t helping. Every book was like a summary of EVERYTHING you can expect when raising a kid, from one week old to eighteen years. Sure, the first few pages are helpful, but how are you supposed to remember specific anecdotes five or ten years down the road? It’s like being given instructions for IKEA furniture that won’t hit the shelves until 2027. Frustrated by this lack of options, Ryan ended up turning back to the principles of ‘The Daily Stoic’. He, like so many other expecting and established parents, recognized that making it through would take much more ongoing learning. No one knows what they’re doing at first, so maybe a day-by-day walkthrough would offer more value.
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This thought eventually led to the creation of a newsletter, which Ryan emailed to dads looking for support daily for months. He found it just as helpful of a tool for his own journey – an opportunity to put his thoughts and new experiences in writing to look back on later. These notes accumulated from 2017 up until today and are now published in ‘The Daily Dad: 366 Meditations on Parenting, Love, and Raising Great Kids‘.
Stoicism and Parenting: Applying Ancient Wisdom to Modern Life
The prospect of becoming a parent is tiring enough, so why would Ryan want to spend his finite energy on anything else during these first years? Blame it on natural entrepreneurship. Creators are a unique bunch of people who thrive upon self-expression and problem-solving. We look at things a bit differently; ‘no existing solution available to meet my needs? Might as well make one and scratch my creative itch in the process’. That’s exactly how Ryan explains why he did what he did.
But the value of ‘The Daily Dad’ extends far beyond filling a void for him. The book’s concept ties back to the principles covered in ‘The Daily Stoke’ – making some kind of minimum commitment to growth every day.
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“We all spend a lot of time and energy trying to get better at things in our lives,” he says. “The time you put in at the office, the time you put in at the gym, self-help. We all spend time trying to get better”. So why not apply it to parenting? It seems to be the one area of life where accountability to one’s commitments isn’t policed nearly enough. And this goes in both an external and internal sense; not only are you expected to literally show up and be present for your child when they need you, but also offer the support and guidance critical to their development. You need to be stoic in more ways than one.
The Importance of Daily Practice
All of this is easier said than done, of course. Ryan acknowledges the expectations parents – or scratch that – anyone can feel when trying to improve themselves in a big way. His best advice? Just find one thing a day.
Life’s largest challenges aren’t overcome in one sweep of action. They require ongoing commitment and effort, that is at least if you want long-term change. It’s about looking at things cumulatively and thinking ‘what initiative, however small, can I regularly take to improve my daily mindset?’
The answer isn’t reading a specific self-help book or going to therapy once.
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That’s not how it works. Transformation is a process “like the way that a bank balance grows by making deposits every day, and then the compounding effect of the interest on top of that”, Ryan illustrates.
So don’t get overwhelmed. Start small with one doable daily goal. Maybe it’s reading one page of a book, or watching one five-minute Ted Talk. Or perhaps it’s as passive as a 30 second break every morning to pause and take a few deep breaths. When practiced regularly enough, you’ll find the benefits stack up and feel like dedicating more time to it.
Neither life or parenting come with a perfect point-by-point instruction manual. And they shouldn’t. Everyone’s situation is different, only made the most of when lived and learned at the same time. Ryan hopes to provide parents of all stages with guidance from his own experiences in ‘The Daily Dad’. While far from a blueprint for success, it will hopefully serve as a support for those who feel daunted, and just as much a reminder that the best kids are raised one day at a time. I highly recommend reading ‘The Daily Dad: 366 Meditations on Parenting, Love, and Raising Great Kids’ when it hits shelves May 2nd.