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Ranking Ryan Holiday’s Books

photo by Christopher Pierznik

Ryan Holiday is my favorite author.

I first became aware of him in 2011 (via Gawker, ironically), but I immediately became a superfan in 2013 after reading his “How I Work” entry for Lifehacker. I’ve been hooked on his work ever since. He’s basically a modern day genius, a deep thinker and strategist who not only philosophizes but also lives what he preaches through his life and business.

He is incredibly prolific – in addition to writing ten books in less than a decade, he has published hundreds of articles, he blasts out three newsletters – two daily; one monthly – that have hundreds of thousands of subscribers, he creates videos for his YouTube channel that is approaching 400,000 subscribers, serves as a ghostwriter for others, and is co-founder of Brass Check, a creative agency that boasts clients ranging from Google and Complex to Neil Strauss, Tony Robbins, and Tim Ferriss.

In some ways, I like his articles even more than his books. I also download and listen to his podcast appearances multiple times, each listen uncovering another gem or insight I missed the first time around. He was profiled in the New York Times in 2016 and his popularity has actually exploded since then – the article mentions his 80,000 Twitter followers; that number has quadrupled in the five years since. His books have been translated into over 30 languages and read by over two million people worldwide.

I was fortunate to get the opportunity to meet him at a book event in New York City in 2017, upon the release of his book, Perennial Seller.

As Holiday embarks on the next segment of his bibliography – his new book, Courage Is Calling, is the first in what is planned to be a four-part series on the Stoic virtues (the other three being wisdom, justice, and temperance), which he referred to as the “next creative mountain” – I thought it was the perfect time to look back at his decade of publishing books and see which of his ten (so far) are the best.

{Note: This list excludes The Daily Stoic Journal as well as numerous books that he has ghostwritten (some of which are known publicly; many are not).}


10. The Boy Who Would Be King (2021)

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By definition, a ranking has to have a last place. The Boy Who Would Be King is not a bad book at all – it’s gorgeously illustrated, well-written, and delivers an important and timeless fable. It’s a children’s book so perhaps it’s a bit unfair to include it here, but Holiday didn’t simply dash off a cartoon book for kids to make a quick buck; this includes all of the things he’s been writing and talking about for over a decade, just in an easier-to-digest, but more visually appealing, format.

9. Growth Hacker Marketing (2014)

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It’s interesting how the attention on Holiday has changed over the years. From a writing standpoint, he’s made his biggest impact regarding Stoicism, but he originally came to prominence – and landed a book deal – through his marketing talents. Growth Hacker Marketing is very insightful and includes numerous gems about the current world of marketing and how to do it on a modest budget. It’s short, which makes sense in a world in which being nimble is essential for survival, but it’s also proof that he was in transition – it is the bridge between a media exposé (Trust Me, I’m Lying) and a Stoic handbook (The Obstacle Is the Way).

8. The Daily Stoic (2016)

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This is the most difficult book to rank, so much so that I even considered excluding it from this list. The Daily Stoic is broken down into three parts – perception; action; will – with each page of the book dedicated to a specific day of the year (including leap day), comprised of a stoic quote from Epictetus, Seneca, or Marcus Aurelius, followed by a short paragraph relating it to our current world. It’s a type of daily devotional, but it’s a powerful one, and is succinct enough to maintain its importance through the year.

7. Lives of the Stoics (2020)

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There are books that you didn’t know you wanted (or needed) until you open them for the first time. Lives of the Stoics fits into that category. Credit the writing for that. I never would have imagined that I’d be interested in two dozen short biographies about a group of individuals that were much more than thinkers and, though they lived more than two millennia ago, faced plenty of problems, large and small, and made plenty of mistakes on their way to greatness. The Stoics – they’re just like us!

6. Stillness Is the Key (2019)

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The third and final work of his first book series, Stillness Is the Key is an important book at the moment, preaching the power of tranquility and solitude in our loud, bright, fast-paced world. Unfortunately, after topics like external obstacles and internal egos, this premise does not have the same heft. The research and writing is just as strong, and it once again includes some great stories from history, but it’s just a step below the other two entries in the series.

photo via Ryan Holiday

5. Trust Me, I’m Lying (2012)

Ryan Holiday understood the world of the internet, particularly how pageviews and virality drove everything, long before most. In his first book, he lays out the modern method of news accumulation (“trading up the chain”) while depicting how his various stunts for Tucker Max, Dov Charney, and others manipulated and gamed the system. Originally intended to be a cautionary tale of what not to do, Trust Me, I’m Lying became a playbook that is assigned in business schools and devoured by a new generation that yearns to be online (in)famous.

4. Perennial Seller (2017)

If the Bible is the best selling book in recorded history, why doesn’t it ever appear on a bestseller list? It turns out that the New York Times and other arbiters of such lists have a methodology of how they count them and it does not include books that sell incredibly well year after year. Such works are called “perennial sellers” and Holiday’s 2017 book of the same title uses his (and Robert Greene’s) method of incorporating historical anecdotes and lessons to a specific topic, in this case making something that stands the test of time. The topic is a personal favorite of Holiday’s and that comes through on the page as he dissects why certain things last and others do not. In a culture in which success is determined by how popular a book/movie/album is within its first days of release, the focus and goal to create something that endures beyond next week’s top ten list is extremely refreshing.

3. Ego Is the Enemy (2016)

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While The Obstacle Is the Way focused on external forces that try to block our success, Holiday’s next book, Ego Is the Enemy, turned inward and examined how we stymie ourselves. While ostensibly part two, it’s clear that it’s more personal than Obstacle and Holiday’s first-hand knowledge of the subject – via both his own experience and others with whom he worked closely – shine through in the writing. It’s just as good as its predecessor and makes for a beautiful symmetry between the two.

2. The Obstacle Is the Way (2014)

When Holiday told his publisher that he wanted to write a book about “a two-thousand-year-old obscure school of ancient philosophy” as a follow-up to his first book on marketing, they were less than enthused. Their feelings soon changed, however, when it became a massive hit, now having sold over a million copies. The Obstacle Is the Way has struck a chord with individuals from all walks of life. The book has “spread so far throughout the sports world,” to the point that it became a focal point in pieces featured on both Sports Illustrated and ESPN. There’s a reason. Its timeless message of “turning trials into triumph” is applicable to anyone at any time, from politicians, entrepreneurs, businesspeople, actors, athletes, and everyone in between.

1. Conspiracy (2018)

The book that Holiday himself believes is his best work is also the one that challenged him the most. Conspiracy is the unbelievable true story of the demise of Gawker at the hands of billionaire entrepreneur Peter Thiel through the silent funding of the sex tape lawsuit starring Hulk Hogan. A nonfiction narrative, it does more than simply recount the timeline of events, but gives it all context and backstory through tireless research of legal documents as well as interviews with Thiel, Hogan, Gawker founder Nick Denton, and the mysterious man who first brought the idea to Thiel. Paced like a thriller novel, it’s a tale that would be perfect for a movie (currently in development) and Holiday showed once again he’s much more than the Stoicism guy.


Christopher Pierznik is the worst-selling author of nine books. Check out more of his writing at Medium. His work has appeared on XXL, Cuepoint, Business Insider, The Cauldron, Fatherly, Hip Hop Golden Age, and many more. Follow him on Facebook or Twitter. Please feel free to get in touch at CPierznik99@gmail.com.

This article contains Amazon affiliate links. Any click may result in my receiving a commission.

By Christopher Pierznik

Christopher Pierznik is the author of 9 books and has contributed to numerous websites on a variety of topics including music, sports, movies, TV, personal finance, and life. He works in corporate finance and lives in northern New Jersey with his family. His dream is to one day be a member of the Wu-Tang Clan.

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