Can This Two-Week Program Make You a Better Reader—And Do You Want It To?

I did self-improvement guru Ryan Holiday's "Read to Lead Challenge," and I learned... well, something

Pile of self-help books including The Daily Stoic by Ryan Holiday
Photo by Shiromani Kant
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At some point in the past few years, I’ve noticed that a certain kind of wildly popular self-help guru—male, young, obsessed with optimizing one’s life—has gotten particularly intense about reading. James Clear, the author of Atomic Habits, reads 20 pages of a book every morning and maintains several “Best Books of All-Time” lists, including a list of “Books with the Most Page-For-Page Wisdom.” Mark Manson, author of The Subtle Art of Not Giving a F*ck, lays out in one of his blog posts how to read faster and remember more of what you read. “Scan for important words only,” he advises. “You get 90% of the meaning with about 50% of the words.” Manson, too, maintains his own lists of “Best Books of All Time.” 

The king of reading as a form of self-improvement, though, is undoubtedly Ryan Holiday, the author of Ego Is the Enemy, The Obstacle Is the Way, and Stillness Is the Key, as well as books on marketing, “media manipulation,” and the trial that ultimately took down Gawker Media. He’s also a vocal proponent of Stoicism—as in, the ancient Greek school of philosophy. He runs a website called The Daily Stoic, which publishes articles on “How to Plan Your Day Like Marcus Aurelius,” and from which you can buy a pewter bust of Seneca or a medallion that says “Memento Mori” on it. Holiday writes about his own reading habits with messianic fervor. He advocates reading extremely long books, buying books over borrowing them from libraries, and taking extensive notes by hand on index cards, which he then files away into categories. “Wisdom, not facts,” he writes. “We’re not just looking [sic] random pieces of information. What’s the point of that?” 

What would I be like when I emerged from this 13-day course a fully optimized reading bodhisattva capable of absorbing a book’s infinite wisdom with a single glance?

Ryan Holiday is also the creator of Read to Lead: A Daily Stoic Reading Challenge, a $50, 13-day course developed in 2019 whose promotional page promises that the course will teach me how to “Remember more of what you read to reach your true potential” and “Make more time for reading by replacing dead time with reading.” The page features no less than four red “Buy now” buttons. Months into a pandemic that seemed to have no end, I stumbled across this course and wondered: How exactly would a self-help bro teach me how to read better? Might I gain some clarity on what life-improving benefits we actually derive from reading? And what would I be like when I emerged from this 13-day course a fully optimized reading bodhisattva capable of absorbing a book’s infinite wisdom with a single glance? I got out my credit card.

Day 1: Start A Commonplace Book

You may be wondering what on earth I—someone who, insofar as I’ve made a professional name for myself, has done it as a book critic—was even doing in this part of the internet. Mostly, it started with a bad relationship. Circa 2017, I spent day after day reading shitty blog posts that doled out relationship and self-improvement advice—guiltily, by myself, and in an incognito tab, the way most people consume porn. Eventually, I stumbled across a whole ecosystem of self-help bros telling me how I might fix my life, and started reading them religiously. Something about the way they looked at life resonated with me, probably because I was dating an extremely troubled tech bro who was also constantly telling me how I might fix my life (and his). 

Back then, in those miserable days of 2017, I had also started writing book reviews. Maybe if I just read more, I thought then, I might get closer to figuring out what it is I actually wanted to do with my life, or at least more closely align the disappointing external trappings of my life with what I felt inside (sad and literary). 

If the purveyors of self-help are talking about something, it’s a good bet that the subject has become a source of guilty, deep-rooted despair.

These days, I no longer read articles dispensing relationship advice in a private tab on my phone late into the night, but the way gurus like Ryan Holiday think about reading—as a “habit” to be “optimized”—has lingered. If the purveyors of self-help are talking about something, it’s a good bet that the subject has become a source of guilty, deep-rooted despair in American life. And the way Holiday has talked about reading for years now seems to have been prescient: he, and this course, tap into the fact that reading is something we’re now all deeply anxious about.

Consider that the internet now seems to be filled with advice on how to read (more mindfully, more diversely, more quickly, more lengthily, more weekly, but mostly just more), and with people writing about their monumental pandemic reading projects and far more people beating themselves up because they can’t bring themselves to read anything at all, which means they’ve failed in some vague but definite way. All these lists and tips—“Read during commercial breaks!”—don’t make sense unless we’re haunted by an ambient conviction that however much we’re reading, it’s not enough. (Unless you get to 100 books a year, upon which I hear you instantly attain enlightenment.)

And there are all those vexed questions about format: do audiobooks “count”? Do e-readers “count”? Despite the lists’ assurances that actually there are no rules when it comes to reading, we can’t shake the feeling that there’s something simply more virtuous about glue bindings and dog-eared pages. That reading is now an oddly sanctified and protected activity, something that exalts and improves the person who can muster up the willpower to crack open a book.

I consider myself an earnest book-reading type as much as anything else, but something about this blunt insistence on reading as an undifferentiated good doesn’t quite sit right with me. Isn’t it an oversimplification to say that reading any book, regardless of its content, is a good thing—and even, as these tips suggest, the best thing one can do with one’s time? I worry that the way we talk about reading now has taken a turn for the sentimental: it’s reading as lifestyle signifier or personality indicator, reading as a fetishy idea, instead of something that people just, you know, do. 

I suppose what I’m skeptical of is the notion that the mere act of reading can “improve” anyone. It feels a little more complicated than that. Back in 2017, I started reading books for money out of a vague sense that I might gain a clearer idea of myself and my own mind—that I might, in some way, become better. So, if anything, I’m the perfect counterexample: If reading a lot is really supposed to improve and exalt us, why do I still feel totally inadequate all the time?  

I get an email from “Read to Lead: A Daily Stoic Challenge.” It is festooned with pithy quotes, generic book-themed line drawings, and illustrative anecdotes about great men of history, a regular sausage-fest: Ronald Reagan, Marcus Aurelius, H.L. Mencken, Charles Darwin, Beethoven, Mark Twain.

The email itself provides unobjectionable advice: start taking notes on the books you read and collect those notes in a single place (your “commonplace book”) for easy reference. I do this already—I’ve developed a byzantine yet highly technological system that involves the notes app on my phone, my email, and an inordinate number of text files—and so the email tells me I should “make a commitment to refresh how you use your commonplace book.” 

“If you don’t find anything in your current book multiple days in a row,” the email continues, “consider discarding it and picking a new book, one that you’ve chosen specifically because it promises to impart lessons. Think of specific topics you want to cover: devote the next ten pages of your book to leadership, or examples from history, or the price of arrogance.”

There’s something off to me about the idea that anyone would choose a book “specifically because it promises to impart lessons,” as if the keys to life could be neatly extracted, lifted clean out of a book’s pages to be dutifully copied down. Obviously books can teach us things, but it seems to me that often this type of learning—“wisdom, not facts,” as Holiday himself puts it—is a slower, more difficult process, one where insights arise from the way a book’s language and plot and grammar act on your mind. I think of that highly-shared Lauren Michele Jackson piece about anti-racism reading lists, which themselves are explicitly compiled to “impart lessons.” These reading lists, Jackson writes, fail the very people who ask for them, “for they are already predisposed to read black art zoologically.” In a very real sense, actively looking for “lessons” might fail precisely because of how ham-handed the looking is.

Day 2: Calculate How Many Books You Have Left To Read in Your Life

After answering questions in a handy worksheet about whether anyone in my family had heart problems before 50, and whether I know my blood pressure, and whether I always buckle my seatbelt, I am given an estimated life expectancy of 90 years. That means, given my current rate of book consumption (around 60 books a year, if you must know), I have about 3,720 books to read before I die. 

Counting the number of books one reads has always felt like a bookworm’s version of a dick-measuring contest.

This number is supposed to frighten me into reading more—it’s a “Stoic memento mori exercise,” Ryan Holiday tells us in an accompanying video. Looking at it, though, I don’t really feel much of anything, though I also sincerely doubt my 89-year-old self will be reading 60 books a year. Counting the number of books one reads has always felt beside the point and slightly suspect to me, like a bookworm’s version of a dick-measuring contest. It’s what you do with the pages that counts. 

Day 3: Re-Read a Book You Love; Day 4: Read a Work of Fiction; Day 5: Read a Banned Book

Day 3’s email tells me I need to pick a favorite book and give it another go. (“It’s only through true study and depth of knowledge that one builds expertise and mastery.”) Day 4’s email is about the benefits of reading fiction—gaining insight into the human condition, understanding other perspectives, empathy, etc.—and it includes a quote from Adolf Hitler: “I’ve never read a novel. That kind of reading annoys me.” Day 5’s challenge is to read a banned book. Or rather, it’s to “pick a book that has been banned, and ruminate on its ideas. Take notes on the messages its author intended to send. Absorb its knowledge, knowledge that was forbidden by certain people; fight back against their censorious urges.”

I’ve decided to reread Madame Bovary, which checks all three boxes. When I first read the novel, I was subletting a dingy but incredibly cheap room in a Chicago apartment the summer after graduating college, with no real plans for the rest of my life. Every night before I went to sleep I’d lie on my thin, lumpy mattress and crack open Flaubert. I might have been paralyzed by the thought of my own appallingly vacant future, but my problems paled in comparison to Emma Bovary’s. I read with delight as she marries a disappointing man, takes two very different but equally disappointing lovers, and then—after some mind-blowingly gorgeous passages about the nature of fantasy and reality—dies. 

When the novel was originally published, it was considered obscene enough by the French government to be put on trial in 1857, mainly for its frank, impersonal depiction of adultery without helpful moralizing from the narrator to show readers the errors of Emma’s ways. (Flaubert was eventually acquitted, and he dedicated the novel to his lawyer.) As a fallen denizen of the 21st century, I find it easy to dismiss this attempted censorship as futile pearl-clutching. What I’m more interested in is that Madame Bovary is just one of many instances of literature that plays on the dangers of consuming literature. Along with books like Don Quixote and Northanger Abbey, it gestures towards fears that novels were in fact so seductive that they could seriously confuse a person, render them incapable of discerning what was real and what was fantasy. Which stands in stark contrast to the soft-focus image that “reading is our compass, our guiding light” and that “it’s what we owe our ultimate devotion.” Which are actual quotes from a “Read to Lead” email.

Day 7: Review A Book Like A Critic

I am, for better or for worse, a professional book critic, and today I received a worksheet that renders my profession obsolete.

Each little sheet—which prints four to a page and looks a bit like the tiny surveys you get at fancy restaurants asking how the service was—says “Read Like a Critic!” in flowy script at the top, flanked by two drawings of open books. There are spaces to fill out the book’s title, author, and genre. The question afforded the largest amount of space (four blank lines) is: “Sum up the book in one or two sentences.” Below that is “Do you agree with the author’s thesis?” with two Scantron-type bubbles labeled “YES” and “NO.” Then there are questions about what the author’s strongest and weakest points are, and what they got wrong, and what they could’ve improved. On the very bottom is “Rating:” and five blank stars you can color in. I can’t decide if I find the whole thing adorable, as one would a child’s crayon rendering of the interior of the Sistine Chapel, or appalling, as one would if everyone thought that was actually what the interior of the Sistine Chapel looked like.

Mostly my notes are me copying out deliciously snarky or luminously precise passages and writing ‘whoa’ next to them.

To be fair, it’s not like reading as an actual critic is particularly glamorous. Certainly not the way I do it. I have finally begun to reread Madame Bovary, and mostly my notes are me copying out deliciously snarky or luminously precise passages and writing “whoa” next to them, or recording brilliant witticisms of my own devising, like “if I ever became a rapper my rapper name would be Flow-bear.” 

But I also have a lot of unresolved questions bouncing around in my head. What’s with that weird first person plural the book starts out with, and why does it just fade away? Why does Emma’s perspective start so late; why do we get the life story of her boring husband in so much detail first? There’s page after page of description so crystalline that everything else I read feels vague and baggy for a while, but why is it written that way? Does it have anything to do with the act of looking or seeing (“His own eye would lose itself in these depths, and he could see himself, in miniature, down to his shoulders, with his scarf on his head and his nightshirt unbuttoned”)?

What I’m mostly trying to do is figure out what exactly Flaubert is up to, to try to understand the novel’s language and plot and grammar. Simultaneously, armed with index cards, I’ve been dutifully scanning Madame Bovary to extract “information that strikes you, quotes that motivate you, stories that inspire you for later use in your life, in your business, in your writing, in your speaking, or whatever it is that you do,” as I was advised to do in that first email about commonplace books. But I’m not quite sure what to write down to save for myself for posterity. Every sentence seems both incredibly stylish and completely meaningless taken out of context. Flaubert isn’t going to come out and drop some hard-earned truths on us outright, it turns out. Whatever lessons there are, they seem baked into the style itself—and nearly impossible to articulate on a worksheet.

Day 8: Replace Screen Time with Book Time

Today’s task is: read all the goddamn time. “When you sit down with your coffee and some breakfast, don’t watch the news. Read a book. When feel [sic] the urge to reach for the phone, don’t open Twitter. Open the kindle app. When you’re commuting to the office, or you’re at the gym, or you’re on a run, don’t listen to music. Listen to an audio book. When you’re eating lunch, don’t catch up on your social media feeds. Read. When you’re waiting at the airport, waiting at the gate, waiting to takeoff, waiting for the pilot to permit electronic devices, don’t just sit and kill time. Read. When you get home from work or when you have spare time on a weekend, don’t binge-watch Game of Thrones. Binge-read it.”

We’ve agreed that reading is categorically better than the way we’re actually spending our time, which is mostly dicking around on social media.

In some respects, this email directly addresses the main reason we’re so anxious about reading: because we’ve agreed that reading is categorically better than the way we’re actually spending our time, which is mostly dicking around on social media. Reading is “hard” now, something we have to convince and/or trick our lazy animal selves into doing instead of shopping online or looking for fulfillment at the bottom of an endless newsfeed or letting the “Next Episode” button on Netflix fill rightward with unstoppable speed. Reading is now seen as precisely the opposite of dicking around on social media, something that might just save us from the forces of the corrupting internet/everything that makes us dumb. It’s the argument Nicholas Carr articulated a decade ago in his book The Shallows: that we’re slowly forgetting how to read and grapple with difficult texts, and that our dwindling attention spans put us at risk of losing a grand but infinitely fragile intellectual tradition at the core of everything that makes Western civilization great.

When I was a kid, I would have made Ryan Holiday proud. I read on the toilet, I read in the moments immediately before and after showering, I read while I was supposed to be practicing the piano (I’d put my book in front of the sheet music), I read during meals. My sister and I even brought books to restaurants to read while our parents talked to each other, and it took me a long time to realize that this was something other people didn’t do. I did become a very good reader, but I was also an awkward shy kid who remained completely clueless about the state of the actual world well into my twenties. 

Which is why I’m not convinced that reading is strictly more valuable than, like, the vast breadth of all other human activities. How exactly is reading better than staying informed or listening to music or talking to your friends or parents or a stranger or just having a silent moment to yourself? It makes no sense to consider reading the “opposite” of any other activity; doesn’t it all depend on the experience of what you’re actually doing and what you’re getting out of it? Exclusively exalting one category over another means ceding your own judgment to mere differences of form—and I’ve seen TikToks that contain more poetry than some books. I get that mindlessly scrolling through Twitter or watching people yell at each other on cable TV can corrode one’s soul. But surely you need some sort of healthy mix. The ancient Greeks were always going on about moderation.

I’m not convinced that reading is strictly more valuable than, like, the vast breadth of all other human activities.

“You’ve converted minutes and hours that you used to spend passively into something else: time spent acquiring wisdom,” the email says. But this line of reasoning presumes that there’s only one correct way to read, i.e. to acquire wisdom, instead of perhaps to experience beauty or joy or a certain heady pleasure, which I’m beginning to realize is why I read. (And anyone who thinks all books are founts of wisdom clearly hasn’t read enough books.) The aggressive pursuit of “wisdom,” in fact, strikes me as a distinctly unwise, almost naïve way to go about your life. Aren’t there profound truths you can’t glean from books, things you can really only learn from experience and the passage of time? I think of a line I read once in a Geoff Dyer book: “How can you know anything about literature if all you’ve done is read books?”

Day 11: Read A Book That’s Above Your Level

“You’re here because you’re a good reader,” today’s email begins, encouragingly. “But you want to become a great reader. Well there is a harsh truth at the center of all improvement: you will not get better by doing what is comfortable and convenient. Progress demands conquest.” 

That “conquest” is triumphing over books we’re intimidated by because we think they’re intellectually over our heads or too long to actually make it through. I decide to read Edward Said’s Orientalism, a book that’s been on my list for years, and then I feel extremely uncomfortable about the notion of “conquering” Orientalism

I’ve been thinking, in any case, about reading not as conquest but as something quite the opposite: freedom. I find it depressing that so many people feel a sense of obligation about reading—something they “should” do because it’s “good for them”—because part of reading’s appeal to me is that it feels fundamentally not coercive, an escape hatch from social pressures and other people’s expectations. Reading lets me make my own quiet decisions about whether I agree with an idea or not; I can vacillate in indecision (my typical state) for as long as I need to without anyone demanding that I come down on a side. Forcing yourself to read almost feels like destroying the spirit of the whole enterprise. Read hard books, by all means, but do it because you actually enjoy it, not because of some underbaked sense that it will turn you into “a gladiator of the written word” (gross; actual quote).

Day 12: Build and Organize Your Library; Day 13: Start Your “Anti-Library”; Wrap up Day (plus bonus content)

The email helpfully suggests a list of books that are designed to be worked through one day at a time, starting with two books by Ryan Holiday.

I organize my books (“You want everything about your library to facilitate your future use of it as a developmental tool”), buy ten more books on the internet (“An anti-library ensures that our weaknesses, our island of ignorance, is always in plain sight”), and the course is over. The next day, I receive an email that contains three extra, longer-term challenges, one of which makes me roll my eyes so powerfully that I’m in danger of pulling a muscle. It’s to “pick a book of wisdom and read one page per day.” The email helpfully suggests a list of books that are designed to be worked through one day at a time, starting with The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living by Ryan Holiday and Stephen Hanselman and The Daily Stoic Journal by Ryan Holiday and Stephen Hanselman. The Daily Stoic consists of quotes and themed meditations for every day of the year, with headings like “Be Ruthless to the Things That Don’t Matter” and “Cut the Strings that Pull Your Mind.” 

“One of the reasons we wrote The Daily Stoic,” reads the email, seamlessly transitioning into an advertisement, “was that we thought it was pretty remarkable that despite more than two thousand years of popularity, no one had ever put the best of the Stoics in one book for ease of study.” The idea is that day by day, the reader focuses on integrating a tiny aspect of Stoic philosophy into their own life. If that works for you, great! Meaningful direction on how we should live our lives is hard to come by nowadays. But I find it hard to accept that wisdom is simply a series of injunctions that sages came up with thousands of years ago, a list of “do this, do that” that can be catalogued in what is essentially a desk calendar masquerading as a book. If wisdom were that easy to access and simply difficult to put into practice, why struggle through War and Peace at all? 

I have finally finished rereading Madame Bovary. I didn’t remember it being so accessibly funny, nor so dark at the end. I also didn’t remember identifying with Emma quite so much, which says something about how I’ve spent the six intervening years between readings. When I read it for the first time back in 2014, I saw a clear-cut distinction in the novel between fantasy (bad) and reality (good), and was astonished by the way Flaubert used the way he was writing, his style, to make his point. But now I kept noticing that coexisting with the narrator’s scathing irony was sympathy and identification—I got the sense that Flaubert was able to so completely skewer Emma’s delusions because he had experienced them, in some form, himself (“Madame Bovary, c’est moi”). The descriptions of Emma’s pastoral surroundings, the ones she scorns, are crisp where her fantasies are vague, but they now seemed to me tinged with their own kind of romance. 

What reading-forward self-help gurus miss is that reading great literature is perhaps the least efficient thing you can do.

But I still feel like I’m barely scratching the surface of this novel. What reading-forward self-help gurus miss, I’ve come to conclude, is that reading great literature is perhaps the least efficient thing you can do. I keep coming back to the word “discernment.” Unlike self-improvement books, literature isn’t full of common sense injunctions that get straight to the point, that give you the answers outright, that tell you exactly what you need to do to change your life. The books I love the most don’t give you very much direction for your own life at all. They show you different ways of looking at human problems—they teach you how to see. That’s the lesson I’ve taken, at least, from the clear and unforgiving narrator of Madame Bovary, who fillets every character and presents them to us for our own judgment. And through that, through a long period of slow discernment that might take as long as life itself—and might, in fact, be life itself—is how I think you might gain wisdom. 

Which, it occurs to me, is also why I still feel totally inadequate all the time, despite all my reading. Because honing your capacity for discernment actually requires that you feel totally inadequate most if not all of the time: because what you’re doing is a ton of self-questioning, constantly reevaluating what you think you know, existing in a state of doubt that might let the nuances in. It was an old Greek dude, after all, who noted that true wisdom means realizing that you know absolutely nothing.

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