I read all 826 articles by Ryan Holiday. This is what I learned about doing great work.

“I don’t know how to answer that.”

I had just shared my first online writing with my personal coach. 

“What did writing this do for you?” The chills racked my body as I read that question. How did he always know how to ask the one question I wasn’t prepared to answer? How could I respond? The bright blue bubble begged for more context than I could provide on my 2-inch iPhone keyboard.

That first essay was the most vulnerable I’d ever been in public. In trying to make sense of my time flying relief missions over Fukushima, I was trying to find anchors that would ground my life. I was looking for the lived equivalent of Maxwell’s equations, the first principles which underlie my understanding of reality. I’ve been looking for them for a long time. Writing that was my way of dropping those anchors. Writing also helped me find my own voice and the desire to share it through my writing.

There’s no one whose ideas have helped me come to these realizations more than the writings of Ryan Holiday.

Who is Ryan Holiday?

If you’re interested in Stoicism, history, strategy, or being a dad, you’ve probably come across Ryan’s writing. He’s introduced Stoicism to everyone from the NFL to the US Special Operations forces, Silicon Valley executives, And me. He’s written 10 books and over 800 articles, all before I had changed my first diaper. 

If this is your first introduction to Ryan’s writings, lucky you.

The Anchor Principles of Ryan Holiday

I can’t remember when I first read one of Ryan’s books. In my memory, I see a young boy stuffed into that faded green chair at the Naval Academy with The Obstacle is the Way, trying to squeeze in another paragraph before taps announced bedtime. Yet that book wasn’t published until 8 years after I graduated. 

The ideas behind that book, the research that went into it, and the mindset it evokes are older than that book. It’s that mindset that forms the anchor of Ryan’s work, and it’s the mindset that feels like it molded me.

Reading is work. Make it your best work.

If you want to understand Ryan Holiday, start with Read to Lead: How to Digest Books Above Your “Level”.

I remember exactly when this essay released my ambition from the prison of my formal education. Ryan had taken all the rules my parents and teachers had drilled into me and told me to do the exact opposite. He might as well have burned Ms. Kearney in effigy - or not in effigy. 

I had always loved to read, but this essay made me understand that reading this way is work. It’s the devout prayer of a monk in the monastery long after the sun has set and his candle’s wick is about to extinguish. Ryan’s anchor is about the work of reading.

As you read his article, notice that reading is as much a mindset as a process. It’s the mindset of focusing on reasons over facts. When you read The Measure of My Days, you don’t focus on the fact that Florida Scott-Maxwell was 82 or recovering from gallbladder surgery. You read to understand what it feels like to be shattered by life and get back up with even more intense passion. You read it because it helps you make sense of the difficulties still to come. You read it to appreciate what life was like for your 90-year-old grandfather, who couldn’t tell you through the dementia that stole his brain. And maybe you read it to appreciate the beauty on the page.

Notice that reading this way is more of a two-sided conversation than we were taught. When you read The Last Lion series, don’t just listen to Manchester’s words. Cover the page in your own experience. Elbow Manchester aside while you take notes in the margins, and then use those notes to remind yourself how difficult it can be to go against popular opinion in search of the truth. If Churchill had to suffer while standing up to Hitler, surely we can withstand the principal who would rather make a point during the IEP meeting than help our child.

Notice the reading this way doesn’t end when you read the last word. When you read How the Word is Passed, don’t put down the book and feel like your job is done. Go to Monticello and sit at the Burial Ground for Enslaved People. Reckon with the fact that our third President was a slaveowner who wrote about the “moral depravity of slavery” while owning other human beings. Maybe we can forgive him, maybe we can’t, but if we don’t understand how our history is flawed, what hope do we have of improving it for our children?

Read above your level

If Read to Lead is all about reading well, what about the above our level part? Thankfully, Ryan has helped us here too. Go to his Reading Recommendation Email and sign up. You’ll get an email with great books he recommends once a month. 

Those emails you just signed up for are a testament to playing the long game. The emails have no pictures, only text and links. He doesn’t even link to Amazon anymore, instead choosing to link to the Painted Porch (his bookstore in Austin). He has no sponsors and rarely includes his own books in those emails. Yet that email list, which breaks every rule my marketing friends swear by, has continued for 11 years and grown to over 60,000 subscribers. I’m one of them.

What Good Are These Anchors?

Ryan’s work is special, not for what he said to me but for who he introduced me to. 

Without him, I would never have been mentored by Marcus Aurelius as I grappled with the demons of Fukushima. That period of my life wouldn’t be any different, but the stories I tell myself wouldn’t be as honest as they are.

I would never have grounded myself in Viktor Frankl as I grabbed for any identity that would stop me from feeling empty as I left the Navy. I may have collapsed under disillusionment rather than continuing to explore what lifted me up.

I likely never would have started writing. 

To understand why read So You Want To Be A Writer? That’s Mistake #1.

That essay convinced me that I had something interesting to say. I had used Ryan’s work to help interpret my life, but I didn’t believe I had anything to write. I hadn’t studied writing or literature since high school. But I live a life I’m proud of. His article convinced me that it’s worth sharing.

Don’t read Ryan’s work to learn to be a great writer. Read his work to understand how to make sense of the challenges inherent in living a good life. Read it to aspire to live a better life. Read him to explore the edges of your own humanity. While you do, make sure you put in the work.