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Stoic Virtue Series #4
Wisdom Takes Work: Learn. Apply. Repeat.
In this much-anticipated final installment in the Stoic Virtues series, Ryan Holiday makes the case for the virtue on which all other virtues depend.
Of all the stoic virtues - courage, discipline, justice, and wisdom - wisdom is the most elusive. This is especially apparent in an age where reaction and idle chatter are rewarded, and restraint and thoughtfulness are unfashionable. The great statesman and philosophers of the past would not be fooled, as we are, by headlines or appearances or the primal pull of tribalism. They knew too much of history, of their own flaws, of the need for collaboration to do any of that. That's wisdom - and we need it more than ever.
Wisdom is Ryan Holiday's guiding principle, and Wisdom Takes Work is the culmination of all his work. Drawing on fascinating stories of the ancient and modern figures alike, Holiday shows how to cultivate wisdom through reading, self-education, and experience. Through the lives of Montaigne, Seneca, Joan Didion, Abraham Lincoln, and others, Holiday teaches us how to listen more than we talk, to think with nuance, to ruthlessly question our own beliefs, and to develop a method of self-education. He argues convincingly for the necessity of mental struggle and warns against taking shortcuts that deprive us of real knowledge. And he shows us how dangerous power and intelligence can be without the tempering influence of wisdom.
An absence of curiosity and prudence is a catastrophe for all of us, argues Ryan Holiday. This incredibly timely book both diagnoses the greatest problem of our current moment and offers solutions for the way forward. Wisdom is work - but it's worth it.
Of all the stoic virtues - courage, discipline, justice, and wisdom - wisdom is the most elusive. This is especially apparent in an age where reaction and idle chatter are rewarded, and restraint and thoughtfulness are unfashionable. The great statesman and philosophers of the past would not be fooled, as we are, by headlines or appearances or the primal pull of tribalism. They knew too much of history, of their own flaws, of the need for collaboration to do any of that. That's wisdom - and we need it more than ever.
Wisdom is Ryan Holiday's guiding principle, and Wisdom Takes Work is the culmination of all his work. Drawing on fascinating stories of the ancient and modern figures alike, Holiday shows how to cultivate wisdom through reading, self-education, and experience. Through the lives of Montaigne, Seneca, Joan Didion, Abraham Lincoln, and others, Holiday teaches us how to listen more than we talk, to think with nuance, to ruthlessly question our own beliefs, and to develop a method of self-education. He argues convincingly for the necessity of mental struggle and warns against taking shortcuts that deprive us of real knowledge. And he shows us how dangerous power and intelligence can be without the tempering influence of wisdom.
An absence of curiosity and prudence is a catastrophe for all of us, argues Ryan Holiday. This incredibly timely book both diagnoses the greatest problem of our current moment and offers solutions for the way forward. Wisdom is work - but it's worth it.
400 pages, Hardcover
Published October 21, 2025
917 people are currently reading
3075 people want to read
About the author
Ryan Holiday
80 books18.1k followersRyan Holiday is media strategist for notorious clients like Tucker Max and Dov Charney. After dropping out of college at 19 to apprentice under the strategist Robert Greene, he went on to advise many bestselling authors and multi-platinum musicians. He is the Director of Marketing at American Apparel, where his work in advertising was internationally known. His strategies are used as case studies by Twitter, YouTube, and Google, and have been written about in AdAge, the New York Times, Gawker, and Fast Company. He is the author is *Trust Me, I'm Lying: Confessions of a Media Manipulator*, which is due out in July. He currently lives in New Orleans, with his rebellious puppy, Hanno.
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Displaying 1 - 30 of 168 reviews
October 26, 2025
Even after I've read the 3rd part in the series and evaluated it 2/5, I knew I'll go for the final one. The world's most famous neo-stoic - Ryan Holiday - doesn't write good books, but they are useful if you treat them as a trigger for self-assessment and deeper consideration of your everyday actions.
Truth to be told, it's damn hard to write a book on "wisdom" and capture the essence of what wisdom is, even without the stoicism lens. So it was quite clear that RH is on his "mission impossible" here. Nevertheless, it was his decision and he should be fairly evaluated (on whether he has delivered or not).
TBH there's surprisingly little actual stoicism here. RH is looking for some individuals that exemplify "wisdom", but his choices are ... controversial. When it come to positive cases, he's very skewed to "US-centric" perspective (that feels a bit grotesque) and for the negative ones, he has spent a lot of keystrokes on a single figure of ... Elon Musk and his publicly visible stunts. That's be still kinda OK, but the analysis is very shallow and feels like taken from tabloids (e.g., take-over of Twitter, relation with his trans-gender kid). The effect is caricature - instead of proving some point or helping the reader read something, I couldn't wait to get through to the next section.
In the end, yes, this book has made me thing a bit on the nature of wisdom: what it really is, how to recognize it, what we could do to "boost"/help wisdom. But I'd lie if I've told you there are more answers than questions here ...
Truth to be told, it's damn hard to write a book on "wisdom" and capture the essence of what wisdom is, even without the stoicism lens. So it was quite clear that RH is on his "mission impossible" here. Nevertheless, it was his decision and he should be fairly evaluated (on whether he has delivered or not).
TBH there's surprisingly little actual stoicism here. RH is looking for some individuals that exemplify "wisdom", but his choices are ... controversial. When it come to positive cases, he's very skewed to "US-centric" perspective (that feels a bit grotesque) and for the negative ones, he has spent a lot of keystrokes on a single figure of ... Elon Musk and his publicly visible stunts. That's be still kinda OK, but the analysis is very shallow and feels like taken from tabloids (e.g., take-over of Twitter, relation with his trans-gender kid). The effect is caricature - instead of proving some point or helping the reader read something, I couldn't wait to get through to the next section.
In the end, yes, this book has made me thing a bit on the nature of wisdom: what it really is, how to recognize it, what we could do to "boost"/help wisdom. But I'd lie if I've told you there are more answers than questions here ...
October 23, 2025
There was a time when Ryan Holiday stood as one of the most compelling modern interpreters of Stoic philosophy—bridging ancient wisdom with contemporary relevance in a way that felt urgent, accessible, and above all, apolitical. With Wisdom Takes Work, that era appears to be over.
This latest installment in Holiday’s long-running project to bring Stoicism to the masses is not just a disappointment—it’s a misfire that undermines its own thesis. What should be a timeless reflection on character, resilience, and moral discipline instead reads like a politically narrow treatise filtered through personal grievance. The book’s title promises hard-earned truth. What it delivers feels more like a vendetta masked as virtue.
The core flaw lies in Holiday’s jarring choice of modern figures to represent “evil.” Instead of drawing from history’s deep well—where tyrants, narcissists, and warmongers abound—Holiday trains his fire on Elon Musk and Donald Trump. Agree with his politics or not, these selections are clumsy and alienating. It’s not that critique of the powerful is off-limits—it’s that Stoicism, properly practiced, demands restraint, humility, and perspective. Here, Holiday seems to reach not for Marcus Aurelius, but for MSNBC.
The irony is suffocating. In a book about wisdom and inner discipline, Holiday’s own lack of detachment becomes the loudest voice in the room. There’s a performative certainty to his condemnation of present-day figures whose legacies are still unfolding—a certainty unbecoming of someone who purports to champion nuance and long-term reflection. It’s not that his targets are above criticism; it’s that their inclusion does the very thing Stoicism warns against: reducing complex matters to emotional impulse.
For longtime readers who once turned to Holiday as a rare voice of clarity in a cultural landscape of division, this feels like a betrayal. His previous books, while increasingly slick and brand-conscious, at least aspired to universalism. Wisdom Takes Work narrows the field, drawing hard lines between the virtuous and the damned—lines that just happen to align with the author’s politics.
In doing so, he’s abandoned what made his work resonate with such a broad audience. The true gift of Stoicism is that it transcends ideology. It’s why a Roman emperor and a former slave could teach the same values across centuries. Holiday, once a student of that school, now appears more interested in wielding Stoicism than embodying it.
This may well be the last time many of his fans—this reviewer included—engage with his work. Not out of spite, but out of disappointment. Because wisdom does take work, and this book, for all its ambition, doesn’t do the work. It preaches where it should question. It alienates where it should invite. And it politicizes what should be sacred.
In the end, Wisdom Takes Work proves Holiday’s own point—but perhaps not in the way he intended.
This latest installment in Holiday’s long-running project to bring Stoicism to the masses is not just a disappointment—it’s a misfire that undermines its own thesis. What should be a timeless reflection on character, resilience, and moral discipline instead reads like a politically narrow treatise filtered through personal grievance. The book’s title promises hard-earned truth. What it delivers feels more like a vendetta masked as virtue.
The core flaw lies in Holiday’s jarring choice of modern figures to represent “evil.” Instead of drawing from history’s deep well—where tyrants, narcissists, and warmongers abound—Holiday trains his fire on Elon Musk and Donald Trump. Agree with his politics or not, these selections are clumsy and alienating. It’s not that critique of the powerful is off-limits—it’s that Stoicism, properly practiced, demands restraint, humility, and perspective. Here, Holiday seems to reach not for Marcus Aurelius, but for MSNBC.
The irony is suffocating. In a book about wisdom and inner discipline, Holiday’s own lack of detachment becomes the loudest voice in the room. There’s a performative certainty to his condemnation of present-day figures whose legacies are still unfolding—a certainty unbecoming of someone who purports to champion nuance and long-term reflection. It’s not that his targets are above criticism; it’s that their inclusion does the very thing Stoicism warns against: reducing complex matters to emotional impulse.
For longtime readers who once turned to Holiday as a rare voice of clarity in a cultural landscape of division, this feels like a betrayal. His previous books, while increasingly slick and brand-conscious, at least aspired to universalism. Wisdom Takes Work narrows the field, drawing hard lines between the virtuous and the damned—lines that just happen to align with the author’s politics.
In doing so, he’s abandoned what made his work resonate with such a broad audience. The true gift of Stoicism is that it transcends ideology. It’s why a Roman emperor and a former slave could teach the same values across centuries. Holiday, once a student of that school, now appears more interested in wielding Stoicism than embodying it.
This may well be the last time many of his fans—this reviewer included—engage with his work. Not out of spite, but out of disappointment. Because wisdom does take work, and this book, for all its ambition, doesn’t do the work. It preaches where it should question. It alienates where it should invite. And it politicizes what should be sacred.
In the end, Wisdom Takes Work proves Holiday’s own point—but perhaps not in the way he intended.
December 7, 2025
⭐️⭐️⭐️⭐️⭐️ 5 Stars — Holiday’s Best, and a Personal Gratitude
Wisdom Takes Work is the final installment in Ryan Holiday’s Virtue series, and in my opinion, it’s the best in the bunch. This book hit me right where I am in life — and I feel like I owe the author a sincere debt of gratitude.
About a year and a half ago, I retired from full-time teaching and felt a bit of a void. I started exploring Stoicism as a way to find grounding and purpose in this new phase. Holiday’s podcast was one of the first things that put me on a solid path — encouraging me to read more, think deeper, and find a sense of tranquility in daily life. Now, 18 months later, I’ve worked through a stack of books, gained some real insight, and feel more centered than I have in years. This book feels like the culmination of that journey.
Holiday’s style remains what it has always been: highly accessible, reader-friendly, and polished. His books are meant to be springboards — not dense philosophical tomes — and that’s a strength. He has introduced Stoicism to a wide audience and made these timeless ideas feel both practical and deeply needed today. Sure, the series may lack the heavy academic heft of ancient sources, but that simply isn’t its goal.
I used immersive reading again for this one, and Holiday’s own narration is excellent — intimate and energized without being preachy. Some readers may bristle at a few of the contemporary examples he brings into the discussion, but Holiday has always called things as he sees them. The Stoics weren’t shy about applying philosophy to real life, so why should he be? Yes, he really rakes a few subjects over the hot coals. So be it.
This book is ultimately about putting wisdom into practice — daily, deliberately, and with humility. And that message resonated powerfully with me. Now, if I can just get my sons to read it…
A terrific finish to an impactful series. Highly recommended for anyone seeking a more thoughtful, grounded, and purposeful way to live. I wonder what’s next?
Wisdom Takes Work is the final installment in Ryan Holiday’s Virtue series, and in my opinion, it’s the best in the bunch. This book hit me right where I am in life — and I feel like I owe the author a sincere debt of gratitude.
About a year and a half ago, I retired from full-time teaching and felt a bit of a void. I started exploring Stoicism as a way to find grounding and purpose in this new phase. Holiday’s podcast was one of the first things that put me on a solid path — encouraging me to read more, think deeper, and find a sense of tranquility in daily life. Now, 18 months later, I’ve worked through a stack of books, gained some real insight, and feel more centered than I have in years. This book feels like the culmination of that journey.
Holiday’s style remains what it has always been: highly accessible, reader-friendly, and polished. His books are meant to be springboards — not dense philosophical tomes — and that’s a strength. He has introduced Stoicism to a wide audience and made these timeless ideas feel both practical and deeply needed today. Sure, the series may lack the heavy academic heft of ancient sources, but that simply isn’t its goal.
I used immersive reading again for this one, and Holiday’s own narration is excellent — intimate and energized without being preachy. Some readers may bristle at a few of the contemporary examples he brings into the discussion, but Holiday has always called things as he sees them. The Stoics weren’t shy about applying philosophy to real life, so why should he be? Yes, he really rakes a few subjects over the hot coals. So be it.
This book is ultimately about putting wisdom into practice — daily, deliberately, and with humility. And that message resonated powerfully with me. Now, if I can just get my sons to read it…
A terrific finish to an impactful series. Highly recommended for anyone seeking a more thoughtful, grounded, and purposeful way to live. I wonder what’s next?
October 28, 2025
I've read most - if not all - of Holiday's books, and this book is completely on par with the rest.
However, Holiday completely lost the plot in his pages-long rant about Elon Musk. I'm not a Musk fan by any means; but ranting for 15 pages about the things Musk has been posting about on X (many of the things Musk said even turned out to be completely accurate and true) completely derailed the book for me.
The point about hubris (still related to the core of the book at this point) was made on the first page. But for some reason Holiday still decided to spend page after page summing up tweet after tweet after tweet from Musk in an almost fanatical rant.
What's even more jarring is the fact that certain chapters are hastily written in 2 or 3 pages (ironically the chapter preceding Musk's, which he could easily have written 5+ pages about), in favor of political rants of 20+ pages.
And ofcourse, after Musk, Holiday will rant about Trump. Take this quote: "[his staff] have begged him to spend time with his wife or children, but Trump prefers to spend the mornings (and evenings) with TiVo". Seriously, where does Holiday even come up with this nonsense?
Ironically, Holiday obviously still needs to read and apply the lessons from his own book.
For the love of God; leave your own political views out of books that are not actually about politics. We do not care about your personal views.
However, Holiday completely lost the plot in his pages-long rant about Elon Musk. I'm not a Musk fan by any means; but ranting for 15 pages about the things Musk has been posting about on X (many of the things Musk said even turned out to be completely accurate and true) completely derailed the book for me.
The point about hubris (still related to the core of the book at this point) was made on the first page. But for some reason Holiday still decided to spend page after page summing up tweet after tweet after tweet from Musk in an almost fanatical rant.
What's even more jarring is the fact that certain chapters are hastily written in 2 or 3 pages (ironically the chapter preceding Musk's, which he could easily have written 5+ pages about), in favor of political rants of 20+ pages.
And ofcourse, after Musk, Holiday will rant about Trump. Take this quote: "[his staff] have begged him to spend time with his wife or children, but Trump prefers to spend the mornings (and evenings) with TiVo". Seriously, where does Holiday even come up with this nonsense?
Ironically, Holiday obviously still needs to read and apply the lessons from his own book.
For the love of God; leave your own political views out of books that are not actually about politics. We do not care about your personal views.
October 25, 2025
Wisdom does, take work Mr. Holiday. I usually don't take time to review books I won't be finishing. BUT- when I pre-order a book and pay Amazon's inflated, stupid license to read price for it and receive this level of crap you, the author, Mr. Holiday get a one star review.
Mr. Holiday claims to be a stoic. He in fact thinks that he is great at being a stoic and knows how to share the philosophy with the rest of the world. I was aware of the author's political views before purchase. With this book I was giving him a chance to show me that politics could stay out of this. Based on one chapter - the chapter I quit this book over- he needs some more time with Marcus before writing anymore books.
The chapter I quit with is " The Storm Within Us". I made it a third of the way through this book and realized that this chapter was written with more energy then the rest of the book together up to this point. And it is a rant about how awful Elon Musk is. Now, stoicism is about not letting others get to us. Mr Holiday seems to have a very serious problem with Elon Musk. Mr. Musk is definitely under the author's skin and living rent free in his brain. He used this chapter as a political and personal rant. I suspect there is a fair amount of jealousy along with the hate being spewed in said rant.
Now- I do agree with some of Holiday's observations about Musk but a book titled "Wisdom Takes Work" is not the place for this. It feels like a bait and switch to get a political beef into my hands. I already pay for my husband's DISH habit. I can watch CNN if I want thoughtless political beef without investing $16 more dollars for a worthless kindle license to read it. I won't be giving Mr. Holiday anymore money, time or thought. That is what Stoicism is really about.
Mr. Holiday claims to be a stoic. He in fact thinks that he is great at being a stoic and knows how to share the philosophy with the rest of the world. I was aware of the author's political views before purchase. With this book I was giving him a chance to show me that politics could stay out of this. Based on one chapter - the chapter I quit this book over- he needs some more time with Marcus before writing anymore books.
The chapter I quit with is " The Storm Within Us". I made it a third of the way through this book and realized that this chapter was written with more energy then the rest of the book together up to this point. And it is a rant about how awful Elon Musk is. Now, stoicism is about not letting others get to us. Mr Holiday seems to have a very serious problem with Elon Musk. Mr. Musk is definitely under the author's skin and living rent free in his brain. He used this chapter as a political and personal rant. I suspect there is a fair amount of jealousy along with the hate being spewed in said rant.
Now- I do agree with some of Holiday's observations about Musk but a book titled "Wisdom Takes Work" is not the place for this. It feels like a bait and switch to get a political beef into my hands. I already pay for my husband's DISH habit. I can watch CNN if I want thoughtless political beef without investing $16 more dollars for a worthless kindle license to read it. I won't be giving Mr. Holiday anymore money, time or thought. That is what Stoicism is really about.
November 5, 2025
⭐⭐“A bit of a stumble at the finish line”
I’ve really enjoyed Ryan Holiday’s Stoic Virtue series, but Wisdom Takes Work felt like the weakest entry for me. It didn’t quite live up to the clarity and balance of the earlier books. At times, it felt like Ryan wasn’t following the very Stoic principles he’s spent years writing and teaching.
Some chapters felt rushed, while others, like the first chapter in Part 2 dragged on, especially the long section about Elon Musk. There are still a few valuable takeaways I’ll carry with me, but overall, this one didn’t land as powerfully as I hoped. A disappointing end to what’s otherwise been a thoughtful and inspiring series.
I’ve really enjoyed Ryan Holiday’s Stoic Virtue series, but Wisdom Takes Work felt like the weakest entry for me. It didn’t quite live up to the clarity and balance of the earlier books. At times, it felt like Ryan wasn’t following the very Stoic principles he’s spent years writing and teaching.
Some chapters felt rushed, while others, like the first chapter in Part 2 dragged on, especially the long section about Elon Musk. There are still a few valuable takeaways I’ll carry with me, but overall, this one didn’t land as powerfully as I hoped. A disappointing end to what’s otherwise been a thoughtful and inspiring series.
July 18, 2025
As a follower of Ryan Holiday's podcasts and particularly his virtue series, I have perhaps been the most excited for this final installment on wisdom. I might contend of the four virtues wisdom is often the most overlooked or, at least, it is not often written about. In his typical Holiday fashion, Ryan navigates us through insightful takeaways while employing biographical stories to make the content really stick. His examples within Wisdom Takes Work are both historical and poignant.
As I began to read through the fourth book in the virtue series, I feared that Holiday might fall short of my expectations on the subject. Using Montaigne and others as examples, there was a great discussion on knowledge, in particular. Sure, knowledge is important, but is that wisdom? Well, it turned out only to be a launching pad into the deeper discussion of wisdom itself. I think one of Holiday's strongest and most relevant arguments throughout this book is that one can be full of knowledge and yet incredibly unwise. One could be successful and even arguably one of the smartest individuals of our time, and yet a complete fool. What a travesty!
This book, then, is not only to inform and teach us as to what wisdom entails, but it is to point us in a different direction so we might not waste our knowledge and expend our potential in folly.
If you have read any of Ryan's other books, you will be familiar with his style. Always informative and well-researched. Full of character portraits and examples, and immensely practical. Given the density, but also the subject, I could see this being a book to which I return on more than one occasion.
I do want to thank NetGalley and Portfolio for the advanced readers’ copy and opportunity to offer my honest review of Wisdom Takes Work.
As I began to read through the fourth book in the virtue series, I feared that Holiday might fall short of my expectations on the subject. Using Montaigne and others as examples, there was a great discussion on knowledge, in particular. Sure, knowledge is important, but is that wisdom? Well, it turned out only to be a launching pad into the deeper discussion of wisdom itself. I think one of Holiday's strongest and most relevant arguments throughout this book is that one can be full of knowledge and yet incredibly unwise. One could be successful and even arguably one of the smartest individuals of our time, and yet a complete fool. What a travesty!
This book, then, is not only to inform and teach us as to what wisdom entails, but it is to point us in a different direction so we might not waste our knowledge and expend our potential in folly.
If you have read any of Ryan's other books, you will be familiar with his style. Always informative and well-researched. Full of character portraits and examples, and immensely practical. Given the density, but also the subject, I could see this being a book to which I return on more than one occasion.
I do want to thank NetGalley and Portfolio for the advanced readers’ copy and opportunity to offer my honest review of Wisdom Takes Work.
Read
November 3, 2025Was very excited for this book and as this Series has been great. All other books in this series have been 5 stars. This book had a very political agenda which is simply not what I expected from this author and series. Normally I don't give ratings under 3 stars, as I simply don't finish books that I don't like, in this case I preorder this book since the rest of the series was so good.
November 3, 2025
Ryan Holiday is (by far) one of my favorite authors. So, I'm really looking forward to reading is new book!
November 15, 2025
I have been excited to read this book since June. I thoroughly enjoyed the previous three books in the series and was expecting a genuine finale. I made sure I was in line to purchase an autographed first edition that’s how much I love his books. Sadly, it delivers a pile of disappointment and questions as to why this book feels so out of character for Holiday. Very bizarre. It started strong and then fell off a cliff when the longest chapter wasn’t anything full of wisdom but literally a giant Elon Musk rant. (And NO I’m not a Musk/Trump supporter being critical of this) By the end of that chapter I sat there asking myself, “this is so weird, what did I just read?” The vibe turned into: “I think I just found out Elon’s d!ck is bigger than mine so I’m ditching stoicism and now I’m going to rant through the rest of this book while trying to insert wisdom once in a while.”
I feel a second-hand embarrassment for Holiday when reading this book and now I’m struggling to finish it.
I feel a second-hand embarrassment for Holiday when reading this book and now I’m struggling to finish it.
November 12, 2025
I'm not sure what happened with this book, but the first half is nothing but reminders to read, slow down, and partisan critiques. Holiday dedicates 3 straight chapters to criticizing Elon Musk and Donald Trump, often confusing political opinions with character flaws (of which there are plenty). But disagreements on transgender policies or how one views climate activists does not indicate a lack of stoic virtues.
This book is also repetitive of the first 3 in the series. Ryan Holiday is capable of much better work.
This book is also repetitive of the first 3 in the series. Ryan Holiday is capable of much better work.
May 21, 2025
Be wise through reading
November 2, 2025
The last of the virtue series- books make you wise. And stoic. And also changing your mind. And don’t think you’re so smart. I lived the Montaigne references and the Elon references but was sort of over the Lincoln references. Recommend.
June 9, 2025
"From The Ancient to The Present"
After unwrapping Courage, Justice, and Discipline, Ryan Holiday is now ready to uncover the long-awaited Wisdom – the fourth virtue of Stoicism. Often seen as a pathway to enlightenment in religious contexts, Ryan Holiday narrows its scope through the timeless stories of renowned world public figures. Wisdom Takes Work delivers its grounded approach in three chapters: The Agoge, The Sirens, and The Apotheosis. The journey begins with the cultivating the right mindset through education, contemplation, endurance, and understanding. Moreover, the author warns us of the two obstacles, power and intelligence, that might lead us off track to wisdom.
Despite the complexity of the subject, the author’s extensive research is deeply respected. Rather than relying on a single source or text, Ryan Holiday also puts together other sources, creating a trustworthy and thoughtful narrative. The curation of words is notable –carefully chosen, bold, a bit poetic, yet clear and easy to understand. The author also openly admits that he is still on the journey toward wisdom, despite having written the book. This admission makes the readers feel more connected to the authors, as we are on the same journey. Although it is my first read from Ryan Holiday, his storytelling style effectively builds intrigue and keeps the reader engaged.
However, some parts of the book are harder to digest due to the abundance of references. It felt like being bombarded with too much information all at once. Additionally, the book would benefit from greater consistency if the subchapters were more uniform in length.
Ryan Holiday’s narrative successfully unpacks the complexities of wisdom, bridging the ancient with the present. With its simplicity, honesty, and well-researched content, the book is recommended for readers who are new to the philosophy genre or curious about Stoicism.
It is a well-written, well-researched, and engaging read for those seeking to be wiser.
Thank you Portfolio Publisher and Ryan Holiday for the opportunity to read the e-ARC in exchange for honest review
After unwrapping Courage, Justice, and Discipline, Ryan Holiday is now ready to uncover the long-awaited Wisdom – the fourth virtue of Stoicism. Often seen as a pathway to enlightenment in religious contexts, Ryan Holiday narrows its scope through the timeless stories of renowned world public figures. Wisdom Takes Work delivers its grounded approach in three chapters: The Agoge, The Sirens, and The Apotheosis. The journey begins with the cultivating the right mindset through education, contemplation, endurance, and understanding. Moreover, the author warns us of the two obstacles, power and intelligence, that might lead us off track to wisdom.
Despite the complexity of the subject, the author’s extensive research is deeply respected. Rather than relying on a single source or text, Ryan Holiday also puts together other sources, creating a trustworthy and thoughtful narrative. The curation of words is notable –carefully chosen, bold, a bit poetic, yet clear and easy to understand. The author also openly admits that he is still on the journey toward wisdom, despite having written the book. This admission makes the readers feel more connected to the authors, as we are on the same journey. Although it is my first read from Ryan Holiday, his storytelling style effectively builds intrigue and keeps the reader engaged.
However, some parts of the book are harder to digest due to the abundance of references. It felt like being bombarded with too much information all at once. Additionally, the book would benefit from greater consistency if the subchapters were more uniform in length.
Ryan Holiday’s narrative successfully unpacks the complexities of wisdom, bridging the ancient with the present. With its simplicity, honesty, and well-researched content, the book is recommended for readers who are new to the philosophy genre or curious about Stoicism.
It is a well-written, well-researched, and engaging read for those seeking to be wiser.
Thank you Portfolio Publisher and Ryan Holiday for the opportunity to read the e-ARC in exchange for honest review
December 8, 2025
Animar a alguien. Hacer que se sienta mejor. Ayudarle a recuperar la calma. Las personas divertidas son luces que brillan en la oscuridad. Iluminan el mundo. La vida es dolorosa y absurda. También es risible y ridícula. Todo depende de cómo la veamos.
November 13, 2025
Terrible book out of the whole series. He went on a long excruciating rant about Elon Musk almost as if Elon personally hurt him. That wasn’t very stoic of him. Also too many political statements and ideologies in the book. Every other book in the virtue series has been a re read for me, this one will go in the trash.
November 10, 2025
Too much social commentary, not enough philosophy
Too much social commentary, not enough philosophy. Elon Musk surely lives rent free in the author’s head. It was a very disappointing read.
Too much social commentary, not enough philosophy. Elon Musk surely lives rent free in the author’s head. It was a very disappointing read.
November 21, 2025
This is one of those books where it documents current relevant events and compares it to the past yet will become applicable at any time in history. I have enjoyed all of Holiday's books and I was worried this fourth book would be a bit repetitive of the previous three and I am quite pleased this is not the case. You can tell Holiday has done his work in researching the figures he discusses in the chapters. I was surprised to walk away learning so much of what I thought I already knew and EAGER to learn more. This book has opened my eyes to what it really means to be wise and to be dissatisfied just getting the "gist" of something. This book is going to upset some people, its news they don't want to hear but those who strive to uphold virtue will take it like its medicine.
November 26, 2025
I want to spend some time writing a full review, but the TLDR is that I thought this book and the series overall are excellent.
Wisdom on every page, and it's a series that I'll revisit, for full rereads, but also even over the last few weeks I've found myself searching them, rereading passages, as something I read pops back into my mind.
Wisdom on every page, and it's a series that I'll revisit, for full rereads, but also even over the last few weeks I've found myself searching them, rereading passages, as something I read pops back into my mind.
December 31, 2025
Ryan Holiday did it again. I see myself going back to this one, heck the entire series because the Stoics had it right. I felt seen in Wisdom Takes Work. Ryan’s voice is powerful and if you don’t read, try listening to the audiobook because his voice and way with words will get to you. Thank you Ryan for this gift!
November 28, 2025
excellent book with great topics. The people used to prove points were powerful examples. Sad to see the virtue series ending. Look forward to re-reading the series.
December 27, 2025
Good read but the constant Elon bashing was a bit unnecessary and feels like quick wins on the pages. His other work in the series is a lot better.
January 6, 2026
Last book of his series. I have marked up several pages of this book including giving me the inspiration for the word(s) of the year for me… Disciple of Experience.
December 24, 2025
He repeat everything he said before, he milk his own brand. Funny how it talks about not following a guru...but become one.
And obviously, he is obsess with Elon Musk
Talk about him all the time. Again and again.
bizarre
To read if you didn't read nothing else from him
And obviously, he is obsess with Elon Musk
Talk about him all the time. Again and again.
bizarre
To read if you didn't read nothing else from him
October 4, 2025
I really enjoyed working my way through this thoughtful and practical guide on wisdom. Wisdom Takes Work by Ryan Holiday closes out his Stoic Virtues series by highlighting the virtue that makes all the others possible. Through stories ranging from ancient philosophers to modern thinkers, he shows that true wisdom is built slowly through curiosity, self-education, and the discipline of listening more than we speak, a refreshing reminder in a world that seems to reward noise over nuance.
I found myself nodding along to his call for filling our minds with the right kinds of books, the ones that stretch our thinking and push us into unfamiliar territory. The first few chapters were packed with quotable lines, and there were so many that this book deserves its own quote journal. Some of the people he used as examples felt a little outdated, and I wished he had included fresher public figures we could relate to today, though I loved seeing Joan Didion included.
Overall, this felt like the perfect conclusion to his Stoic Virtues series, tying everything together in a way that is both inspiring and practical. It is the kind of book that encourages reflection, careful thought, and applying wisdom in our own lives.
Thank you to NetGalley and the publisher, Portfolio Books, for the advanced copy in exchange for my honest review. All opinions are my own.
I found myself nodding along to his call for filling our minds with the right kinds of books, the ones that stretch our thinking and push us into unfamiliar territory. The first few chapters were packed with quotable lines, and there were so many that this book deserves its own quote journal. Some of the people he used as examples felt a little outdated, and I wished he had included fresher public figures we could relate to today, though I loved seeing Joan Didion included.
Overall, this felt like the perfect conclusion to his Stoic Virtues series, tying everything together in a way that is both inspiring and practical. It is the kind of book that encourages reflection, careful thought, and applying wisdom in our own lives.
Thank you to NetGalley and the publisher, Portfolio Books, for the advanced copy in exchange for my honest review. All opinions are my own.
December 24, 2025
Read all of the four books and they are probably my favorite book series I have read so far.
Courage to go out there.
Discipline to elevate oneself by controlling ones lower self.
The book on virtue made me have a whole life crisis, trying to devote my life to help others, then got depressed by living this way and found that living for oneself, while helping others along the way probably is the way to go.
And now finally this elusive thing called wisdom.
"Courage and wisdom are related - the former allows for the latter. If you can't bear to engage with ner information, you can't learn. Cowards are fools, and fools are usually cowardly."
All of these book really lay out an ideal way to live and spend ones time. These books are filled with role-models of actual character which one does not find many of in the current media landscape.
I liked them a lot. Definitely had a huge impact on me over the last few years.
Grateful that they exist.
Courage to go out there.
Discipline to elevate oneself by controlling ones lower self.
The book on virtue made me have a whole life crisis, trying to devote my life to help others, then got depressed by living this way and found that living for oneself, while helping others along the way probably is the way to go.
And now finally this elusive thing called wisdom.
"Courage and wisdom are related - the former allows for the latter. If you can't bear to engage with ner information, you can't learn. Cowards are fools, and fools are usually cowardly."
All of these book really lay out an ideal way to live and spend ones time. These books are filled with role-models of actual character which one does not find many of in the current media landscape.
I liked them a lot. Definitely had a huge impact on me over the last few years.
Grateful that they exist.
November 9, 2025
Anyone who knows me well knows that Ryan Holiday is one of my favorite nonfiction authors. In fact, I'd be hard-pressed to name a nonfiction writer whose works I enjoy more than Holiday's books on Stoicism. So, I guess he IS my favorite nonfiction writer.
Consequently, I couldn't wait to read his four-book series on the cardinal virtues of Stoicism: Courage, Temperance (or Discipline), Justice, and Wisdom. I thought his first book on Courage was okay. Parts I and II were excellent, while Part III felt rushed and not up to his usual standard. Consequently, I gave it four stars.
Holiday redeemed himself in his second book on the cardinal virtues: "Discipline is Destiny." The writing was classic Holiday...part history lesson, part Stoicism textbook, part self-help book, part inspirational literature. So, I gave it five stars.
"Right Think, Right Now" fell in between those two. It was better than "Courage" - but not quite as good as "Discipline." And because 4.5 stars wasn't an option, I gave it four stars.
This final book in the series was similar to that work. It was really good, but not great - something I'll explain more in a bit.
As was the case with the first three books in the series, Holiday separated his essays into three parts:
Part 1: THE AGOGE (YOUR TRAINING GROUND)
Part 2: THE SIRENS (THE PERILOUS ROCKS YOU MUST BEWARE)
Part 3: THE APOTHEOSIS (TOUCHING THE DIVINE)
In terms of his specific content, here's the marketing blurb/jacket description:
"Wisdom has been called the mother of the virtues - for good reason. Courage, discipline, and justice all descend from first knowing what's what. Wisdom gives us perspective, uncovers truth, shows us how the world works, and guides us where to go. This critical and all too rare ability - discernment - is not something anyone is born with.
No, wisdom is cultivated. Wisdom is earned. Wisdom is hard-won. Just as it was for all the people we admire and the heroes who make up this book: Montaigne, whose most unusual education created an open and empathetic mind in a time of division and disruption; Marcus Aurelius, perhaps the only 'philosopher king' to ever live; Abraham Lincoln, a self-taught and self-made man who led our nation out of its worst crisis. We learn from Joan Didion's lifelong practice of keeping notebooks, and from Maya Angelou's habit of active listening. We learn from Zeno and General Patton, whose love of reading allowed them to bend space and time and speak with the dead. We learn cautionary tales from figures like Elon Musk, whose brilliance was turned against itself and the world.
In this fourth and final installment in the best-selling Stoic Virtues series, Ryan Holiday shows how to cultivate wisdom through reading, self-education, and lived experience. He teaches us how to listen more than we talk, to think with nuance, and to ruthlessly question our own beliefs. He argues convincingly for the necessity of mental struggle and warns against taking shortcuts that deprive us of real knowledge. And he shows us how dangerous power and intelligence can be without the tempering influence of wisdom.
This incredibly timely book both diagnoses the greatest problem of our current moment and offers solutions for the way forward. Wisdom is work. But it's worth it."
Again, I enjoyed this work a lot. However, I thought that it got repetitive at times. And his focus and constant return to a discussion of Elon Musk bordered on obsessive. Finally, it seemed more dense than the first three works - even after Holiday cut 20,000 words from it, according to his Afterword!
Still, this is yet another of Holiday's works that I will reread again and again. And I encourage anyone with the courage for deep self-reflection to read it.
I'll close this review with a few of my favorite excerpts. (I ended up with 18 pages of typed notes from it!)
"Just as no one is born wise, no one is born dumb – ignorant, sure, but remaining so is a choice. What will we choose?” [p. xix]
“How can you lead if you haven’t listened to the people you’ll be leading? Why are you trying to solve a problem before you’ve asked what others have already tried? What information are you crowding out with all your chatter?” [p. 51]
“The world is very big. Our culture is but one of many. There is wisdom in geography, wisdom in the generations of people who have lived in one place, adapting to the land and the environment around them. If only we are curious enough to learn it.
So hit the road! Travel to the well-known places and the little seen. Travel by boat and by car and by train and by plane and by foot – do as much as you can on foot. Read the signs. Struggle with the language barrier. See things from the other side of the road. Eat the food. Go to museums. Hike the mountains. Sit at sidewalk cafes. Watch a concert. See the ancient hieroglyphs and notice graffiti on city streets. Listen to people chatter. See the cemeteries. Visit the battlefields. Tarry for a while...
There are a million excuses not to travel, but that’s what they are, excuses…exploration is an important step in growing up. It will change you for the better. You don’t have to spend a fortune traveling to become a worldly person...but you do have to check out what is on the other side of the hill a couple times.” [p. 89]
“A strong mind needs a strong body and vice versa. In fact, to the Romans, a poorly educated person was someone who hadn’t learned to read or swim.” [p.100]
“You need both the mental and the physical. A person is incomplete and unbalanced if they neglect one in favor of the other.” [p. 100]
“We must be strong mentally, physically. Brains and courage. Brawn and kindness. Only a fool neglects the body in favor of the mind, or the mind in favor of the body. Virtue – excellence – is the cultivation of all these traits, the aspiration to be a complete and well-rounded person. Smart and strong. Strong and smart.” [p. 101]
“It’s very difficult, it’s been said, to reason your way out of a position you didn’t reason yourself into.” [p. 179]
“You’re not special. You’re also not a delicate little flower that needs to be protected.
Political correctness. Censorship. Shouting people down. This doesn’t make anyone smarter or better or safer. In fact, it makes us weaker, more susceptible to groupthink, more delusional, more likely to overreach or misread…
Snowflakes make bad decisions because every decision is decided by the least consequential variable: Does this align with what I want to be true?
No wisdom is possible for the fragile. No growth. No truth.” [pp. 193-194]
“There is no freedom without wisdom, there is no wisdom without freedom.” [p. 305]
“You can’t attain happiness or wisdom by making it a bull’s-eye…We must embrace the paradox that happiness is essential but not something we can aim at. We get it indirectly by living well and doing good. Like wisdom itself, happiness is the result of a process, of doing the right things in the right way. It’s something that ensues as opposed to something we pursue. Instead of trying to get it, we’re better when we try to give it.” [p. 312]
“In fact, philosophy had taught Seneca the most important lesson about our mortality: Death is not something we do once, at the end of life. In fact, Seneca knew that life is death. We are dying every day, Seneca understood, for every moment that ticks by on the clock is dead and gone. So is the person we were in that moment. He understood that he had been in this situation before, as we all are, for we don’t die once but countless times, with a shrug. The death to be worried about is not the one you meet as an old man in exile, but the one you refused to see when you were young and thought you had all the time in the world.” [p. 341]
“Whether it’s from the Bible or from Hercules or East of Eden or Faust, the parable’s message is the same: We have a choice. We choose between wisdom and ignorance, cowardice and courage, discipline and excess, right and wrong, virtue and vice.” [p. 351]
“Each of us has a calling, the task of our lives is to listen to it…and be brave enough to follow.” [p. 360]
“Just because the world seems to be cruel and stupid these days doesn’t mean we have to be. Just because some people seem to revel in the fantasy world they have created, preferring fictions to complicated reality, doesn’t mean we should. That was the whole point of philosophy, Chrysippus said, to not be part of the mob and rabble.” [p. 368]
“How is a person supposed to know if they’re making progress if wisdom is so elusive? The same way it works with the horizon. We’re never actually getting closer to it, but we can look behind us and see that we are at least covering serious distance – we can see how far we’ve come from where we started.” [p. 369]
“Ignorance is a solvable problem…but it requires admitting the problem first.” [p. 229]
Consequently, I couldn't wait to read his four-book series on the cardinal virtues of Stoicism: Courage, Temperance (or Discipline), Justice, and Wisdom. I thought his first book on Courage was okay. Parts I and II were excellent, while Part III felt rushed and not up to his usual standard. Consequently, I gave it four stars.
Holiday redeemed himself in his second book on the cardinal virtues: "Discipline is Destiny." The writing was classic Holiday...part history lesson, part Stoicism textbook, part self-help book, part inspirational literature. So, I gave it five stars.
"Right Think, Right Now" fell in between those two. It was better than "Courage" - but not quite as good as "Discipline." And because 4.5 stars wasn't an option, I gave it four stars.
This final book in the series was similar to that work. It was really good, but not great - something I'll explain more in a bit.
As was the case with the first three books in the series, Holiday separated his essays into three parts:
Part 1: THE AGOGE (YOUR TRAINING GROUND)
Part 2: THE SIRENS (THE PERILOUS ROCKS YOU MUST BEWARE)
Part 3: THE APOTHEOSIS (TOUCHING THE DIVINE)
In terms of his specific content, here's the marketing blurb/jacket description:
"Wisdom has been called the mother of the virtues - for good reason. Courage, discipline, and justice all descend from first knowing what's what. Wisdom gives us perspective, uncovers truth, shows us how the world works, and guides us where to go. This critical and all too rare ability - discernment - is not something anyone is born with.
No, wisdom is cultivated. Wisdom is earned. Wisdom is hard-won. Just as it was for all the people we admire and the heroes who make up this book: Montaigne, whose most unusual education created an open and empathetic mind in a time of division and disruption; Marcus Aurelius, perhaps the only 'philosopher king' to ever live; Abraham Lincoln, a self-taught and self-made man who led our nation out of its worst crisis. We learn from Joan Didion's lifelong practice of keeping notebooks, and from Maya Angelou's habit of active listening. We learn from Zeno and General Patton, whose love of reading allowed them to bend space and time and speak with the dead. We learn cautionary tales from figures like Elon Musk, whose brilliance was turned against itself and the world.
In this fourth and final installment in the best-selling Stoic Virtues series, Ryan Holiday shows how to cultivate wisdom through reading, self-education, and lived experience. He teaches us how to listen more than we talk, to think with nuance, and to ruthlessly question our own beliefs. He argues convincingly for the necessity of mental struggle and warns against taking shortcuts that deprive us of real knowledge. And he shows us how dangerous power and intelligence can be without the tempering influence of wisdom.
This incredibly timely book both diagnoses the greatest problem of our current moment and offers solutions for the way forward. Wisdom is work. But it's worth it."
Again, I enjoyed this work a lot. However, I thought that it got repetitive at times. And his focus and constant return to a discussion of Elon Musk bordered on obsessive. Finally, it seemed more dense than the first three works - even after Holiday cut 20,000 words from it, according to his Afterword!
Still, this is yet another of Holiday's works that I will reread again and again. And I encourage anyone with the courage for deep self-reflection to read it.
I'll close this review with a few of my favorite excerpts. (I ended up with 18 pages of typed notes from it!)
"Just as no one is born wise, no one is born dumb – ignorant, sure, but remaining so is a choice. What will we choose?” [p. xix]
“How can you lead if you haven’t listened to the people you’ll be leading? Why are you trying to solve a problem before you’ve asked what others have already tried? What information are you crowding out with all your chatter?” [p. 51]
“The world is very big. Our culture is but one of many. There is wisdom in geography, wisdom in the generations of people who have lived in one place, adapting to the land and the environment around them. If only we are curious enough to learn it.
So hit the road! Travel to the well-known places and the little seen. Travel by boat and by car and by train and by plane and by foot – do as much as you can on foot. Read the signs. Struggle with the language barrier. See things from the other side of the road. Eat the food. Go to museums. Hike the mountains. Sit at sidewalk cafes. Watch a concert. See the ancient hieroglyphs and notice graffiti on city streets. Listen to people chatter. See the cemeteries. Visit the battlefields. Tarry for a while...
There are a million excuses not to travel, but that’s what they are, excuses…exploration is an important step in growing up. It will change you for the better. You don’t have to spend a fortune traveling to become a worldly person...but you do have to check out what is on the other side of the hill a couple times.” [p. 89]
“A strong mind needs a strong body and vice versa. In fact, to the Romans, a poorly educated person was someone who hadn’t learned to read or swim.” [p.100]
“You need both the mental and the physical. A person is incomplete and unbalanced if they neglect one in favor of the other.” [p. 100]
“We must be strong mentally, physically. Brains and courage. Brawn and kindness. Only a fool neglects the body in favor of the mind, or the mind in favor of the body. Virtue – excellence – is the cultivation of all these traits, the aspiration to be a complete and well-rounded person. Smart and strong. Strong and smart.” [p. 101]
“It’s very difficult, it’s been said, to reason your way out of a position you didn’t reason yourself into.” [p. 179]
“You’re not special. You’re also not a delicate little flower that needs to be protected.
Political correctness. Censorship. Shouting people down. This doesn’t make anyone smarter or better or safer. In fact, it makes us weaker, more susceptible to groupthink, more delusional, more likely to overreach or misread…
Snowflakes make bad decisions because every decision is decided by the least consequential variable: Does this align with what I want to be true?
No wisdom is possible for the fragile. No growth. No truth.” [pp. 193-194]
“There is no freedom without wisdom, there is no wisdom without freedom.” [p. 305]
“You can’t attain happiness or wisdom by making it a bull’s-eye…We must embrace the paradox that happiness is essential but not something we can aim at. We get it indirectly by living well and doing good. Like wisdom itself, happiness is the result of a process, of doing the right things in the right way. It’s something that ensues as opposed to something we pursue. Instead of trying to get it, we’re better when we try to give it.” [p. 312]
“In fact, philosophy had taught Seneca the most important lesson about our mortality: Death is not something we do once, at the end of life. In fact, Seneca knew that life is death. We are dying every day, Seneca understood, for every moment that ticks by on the clock is dead and gone. So is the person we were in that moment. He understood that he had been in this situation before, as we all are, for we don’t die once but countless times, with a shrug. The death to be worried about is not the one you meet as an old man in exile, but the one you refused to see when you were young and thought you had all the time in the world.” [p. 341]
“Whether it’s from the Bible or from Hercules or East of Eden or Faust, the parable’s message is the same: We have a choice. We choose between wisdom and ignorance, cowardice and courage, discipline and excess, right and wrong, virtue and vice.” [p. 351]
“Each of us has a calling, the task of our lives is to listen to it…and be brave enough to follow.” [p. 360]
“Just because the world seems to be cruel and stupid these days doesn’t mean we have to be. Just because some people seem to revel in the fantasy world they have created, preferring fictions to complicated reality, doesn’t mean we should. That was the whole point of philosophy, Chrysippus said, to not be part of the mob and rabble.” [p. 368]
“How is a person supposed to know if they’re making progress if wisdom is so elusive? The same way it works with the horizon. We’re never actually getting closer to it, but we can look behind us and see that we are at least covering serious distance – we can see how far we’ve come from where we started.” [p. 369]
“Ignorance is a solvable problem…but it requires admitting the problem first.” [p. 229]
November 24, 2025
A large portion is book is just praising and roasting Elon Musk. I didn’t feel like it belonged. I don’t want to read about Elon Musk.
September 9, 2025
3.5⭐️ While this was not my favorite of this author’s books, I did still enjoy it and had multiple takeaways. My main reason for not loving it was the examples used for each chapter. They felt rather repetitive instead of a through line. I also personally like the examples of people who are a little more recent as they feel more applicable. Still recommend!
ARC was provided by the publisher via Netgalley in exchange for an honest review.
ARC was provided by the publisher via Netgalley in exchange for an honest review.
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December 20, 2025"Wisdom Takes Work: Learn. Apply. Repeat." by Ryan Holiday explores the idea that wisdom is not something we inherit, stumble upon, or achieve once and for all, but something we must practice repeatedly throughout our lives. Drawing on ancient philosophy, historical examples, and modern reflections, the book argues that wisdom is earned through effort, reflection, humility, and action. From the very beginning, the message is clear: wisdom demands commitment. It is not the glamorous or easy path, but it is the one that leads to clarity, purpose, and a deeper form of happiness.
The book opens by grounding its philosophy in a timeless image from ancient Greece: a young Hercules standing at a crossroads, faced with two paths. One offers comfort, pleasure, and ease; the other promises difficulty, discipline, and virtue. This choice mirrors the central question of the book - whether we are willing to do the hard work required to live wisely. Wisdom, as Holiday presents it through Stoic thought, is not passive knowledge but the ability to consistently make sound judgments in complex situations. It is the guiding force behind justice, courage, and self-control, and without it, these virtues cannot exist in a meaningful way.
Wisdom is difficult to define precisely because it encompasses many qualities at once. It includes intelligence, experience, emotional awareness, moral judgment, and perspective, but it is more than the sum of these parts. At its core, wisdom is knowing what to do, when to do it, and how to do it. Importantly, it is never complete. No one ever reaches a final state of wisdom, and this is not a flaw but a feature. Growth remains possible at every stage of life. Ignorance may be unavoidable early on, but remaining unwise is framed as a choice - a failure to reflect, learn, and adapt.
To show how wisdom is cultivated in practice, the book turns to historical figures who embodied lifelong learning. One of the most prominent examples is Michel de Montaigne, a French thinker who lived through political chaos and personal crisis. From his early upbringing, which emphasized humility and shared humanity, to his near-death experience that reshaped his priorities, Montaigne’s life demonstrates how wisdom is often forged through discomfort and self-examination. Retreating to his library to read, think, and write, he questioned everything, including his own assumptions. His guiding principle, 'What do I know?', captures a core Stoic idea: certainty is dangerous, and humility is essential.
Montaigne’s wisdom was not confined to isolation. He remained engaged in public life, serving as a mediator during religious conflicts when rigid ideology threatened to tear society apart. His ability to hold nuance, resist extremes, and see shared humanity in opposing sides illustrates how wisdom operates in real-world situations. The lesson is not to withdraw from life, but to participate thoughtfully, informed by reflection rather than ego.
The book expands this idea by emphasizing that life itself is the classroom for wisdom. Formal education can help, but it is not sufficient. Many of history’s wisest figures learned through experience rather than instruction. Artists, leaders, and philosophers often developed their insight by immersing themselves in environments that challenged them. Wisdom grows when people take responsibility for their own learning, choosing paths that suit their nature rather than blindly following conventional expectations. The value lies not in how impressive the path looks, but in how deeply it teaches.
A crucial part of wisdom, according to the book, is empathy. Understanding others does not mean agreeing with them, but it does require the ability to step outside one’s own perspective. Every person experiences the world differently, shaped by circumstances, biology, and history. Without recognizing this, judgment becomes shallow and conflict becomes inevitable. Empathy allows wisdom to function socially, helping individuals navigate disagreements, relationships, and moral dilemmas with fairness and care. It transforms wisdom from a private virtue into a communal one.
Equally important is the acceptance of limitation and uncertainty. The book repeatedly warns against the dangers of overconfidence, using historical failures to show how catastrophic certainty can be. Many disasters were caused not by lack of intelligence, but by leaders who believed they fully understood situations that were far more complex than they realized. True wisdom remains cautious, aware of blind spots, and open to correction. This humility does not weaken decision-making; it strengthens it.
At the same time, uncertainty is not portrayed as something purely negative. The ability to live comfortably with unanswered questions is framed as a mark of maturity and intelligence. Great art, philosophy, and leadership often arise from ambiguity rather than rigid conclusions. Wisdom allows for contradiction, context, and flexibility. What is right in one situation may be wrong in another, and the wise person adjusts accordingly rather than clinging to fixed rules.
The book ultimately connects wisdom to happiness, redefining what happiness truly means. Rather than chasing pleasure, success, or external approval, Stoic philosophy links happiness to inner stability and moral clarity. Happiness is not something granted by circumstances but something generated through wise judgment. By focusing on what we can control - our actions, values, and responses - we free ourselves from dependence on outcomes beyond our power. In this sense, wisdom and happiness are inseparable. To live wisely is to live well.
In conclusion, "Wisdom Takes Work: Learn. Apply. Repeat." by Ryan Holiday presents wisdom as an active, lifelong pursuit rather than an abstract ideal. It teaches that wisdom grows through practice, empathy, humility, and the willingness to question oneself again and again. By embracing uncertainty, learning from experience, and choosing the harder but more meaningful path, individuals can develop the clarity needed to navigate life’s challenges. The book reminds us that wisdom is not about having all the answers, but about continuously learning how to live better - and that this ongoing effort is what ultimately leads to fulfillment and peace.
The book opens by grounding its philosophy in a timeless image from ancient Greece: a young Hercules standing at a crossroads, faced with two paths. One offers comfort, pleasure, and ease; the other promises difficulty, discipline, and virtue. This choice mirrors the central question of the book - whether we are willing to do the hard work required to live wisely. Wisdom, as Holiday presents it through Stoic thought, is not passive knowledge but the ability to consistently make sound judgments in complex situations. It is the guiding force behind justice, courage, and self-control, and without it, these virtues cannot exist in a meaningful way.
Wisdom is difficult to define precisely because it encompasses many qualities at once. It includes intelligence, experience, emotional awareness, moral judgment, and perspective, but it is more than the sum of these parts. At its core, wisdom is knowing what to do, when to do it, and how to do it. Importantly, it is never complete. No one ever reaches a final state of wisdom, and this is not a flaw but a feature. Growth remains possible at every stage of life. Ignorance may be unavoidable early on, but remaining unwise is framed as a choice - a failure to reflect, learn, and adapt.
To show how wisdom is cultivated in practice, the book turns to historical figures who embodied lifelong learning. One of the most prominent examples is Michel de Montaigne, a French thinker who lived through political chaos and personal crisis. From his early upbringing, which emphasized humility and shared humanity, to his near-death experience that reshaped his priorities, Montaigne’s life demonstrates how wisdom is often forged through discomfort and self-examination. Retreating to his library to read, think, and write, he questioned everything, including his own assumptions. His guiding principle, 'What do I know?', captures a core Stoic idea: certainty is dangerous, and humility is essential.
Montaigne’s wisdom was not confined to isolation. He remained engaged in public life, serving as a mediator during religious conflicts when rigid ideology threatened to tear society apart. His ability to hold nuance, resist extremes, and see shared humanity in opposing sides illustrates how wisdom operates in real-world situations. The lesson is not to withdraw from life, but to participate thoughtfully, informed by reflection rather than ego.
The book expands this idea by emphasizing that life itself is the classroom for wisdom. Formal education can help, but it is not sufficient. Many of history’s wisest figures learned through experience rather than instruction. Artists, leaders, and philosophers often developed their insight by immersing themselves in environments that challenged them. Wisdom grows when people take responsibility for their own learning, choosing paths that suit their nature rather than blindly following conventional expectations. The value lies not in how impressive the path looks, but in how deeply it teaches.
A crucial part of wisdom, according to the book, is empathy. Understanding others does not mean agreeing with them, but it does require the ability to step outside one’s own perspective. Every person experiences the world differently, shaped by circumstances, biology, and history. Without recognizing this, judgment becomes shallow and conflict becomes inevitable. Empathy allows wisdom to function socially, helping individuals navigate disagreements, relationships, and moral dilemmas with fairness and care. It transforms wisdom from a private virtue into a communal one.
Equally important is the acceptance of limitation and uncertainty. The book repeatedly warns against the dangers of overconfidence, using historical failures to show how catastrophic certainty can be. Many disasters were caused not by lack of intelligence, but by leaders who believed they fully understood situations that were far more complex than they realized. True wisdom remains cautious, aware of blind spots, and open to correction. This humility does not weaken decision-making; it strengthens it.
At the same time, uncertainty is not portrayed as something purely negative. The ability to live comfortably with unanswered questions is framed as a mark of maturity and intelligence. Great art, philosophy, and leadership often arise from ambiguity rather than rigid conclusions. Wisdom allows for contradiction, context, and flexibility. What is right in one situation may be wrong in another, and the wise person adjusts accordingly rather than clinging to fixed rules.
The book ultimately connects wisdom to happiness, redefining what happiness truly means. Rather than chasing pleasure, success, or external approval, Stoic philosophy links happiness to inner stability and moral clarity. Happiness is not something granted by circumstances but something generated through wise judgment. By focusing on what we can control - our actions, values, and responses - we free ourselves from dependence on outcomes beyond our power. In this sense, wisdom and happiness are inseparable. To live wisely is to live well.
In conclusion, "Wisdom Takes Work: Learn. Apply. Repeat." by Ryan Holiday presents wisdom as an active, lifelong pursuit rather than an abstract ideal. It teaches that wisdom grows through practice, empathy, humility, and the willingness to question oneself again and again. By embracing uncertainty, learning from experience, and choosing the harder but more meaningful path, individuals can develop the clarity needed to navigate life’s challenges. The book reminds us that wisdom is not about having all the answers, but about continuously learning how to live better - and that this ongoing effort is what ultimately leads to fulfillment and peace.
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