If someone told me to choose the best twenty books to read in your twenties, I don’t know where I would begin. I might point to Augustine’s Confessions. Likely Newman’s Apologia. Maybe some plays of Shakespeare, novels of George Eliot, dialogues of Plato, essays of Joseph Mitchell, Pnin—but this is quickly becoming just a list of the things I myself have enjoyed reading in the first half of my third decade. For a serious answer, I’d have to think about it more. And I haven’t had the chance because about six months ago, an anonymous Twitter account called Art of Life composed a comprehensive list for twenty-somethings that has since consumed my attention. The terminally online know exactly the list to which I am referring, and those who have a more healthy relationship with the internet will likely recognize its general outlines anyway. Art of Life is one of those big accounts that posts motivational exhortations. This one was titled Twenty Books to Read in Your Twenties (although it actually consisted of about forty), all of which were self-help manuals. The account claimed that the reader who completed them would “Become your best self,” “Live a happier and healthier life,” and “Grow mentally and emotionally.” Twitter spent several days mocking the conceit, but I resolved to read the whole list and—who knows?—maybe change my life for the better.
When I sat down to my task, I surrounded myself with the tools of success: a double shot of espresso, a bowl of Jordan almonds, and a pack of Winston Red 100s. I think it was Christian Lorentzen who said that all you need to motor through a stack of books on deadline is a comfortable chair and a quiet place to chain-smoke. I had both. Everything was in place. Well, everything except for the motivation to begin. Each time I opened Atomic Habits, Make Your Bed, or Start With Why, I lost interest after a few pages. I never had read a self-help book before, and I didn’t have the hunger for improvement that a reader of the genre must possess to get anything out of it. Worse, I was easily distracted, and, in truth, I felt like I was wasting my time. I knew for a fact that a colleague down the hall was leaning back in an office chair, feet propped on his desk, reading Proust. That’s what I wanted to be doing. So I drank my espresso, ate the almonds, and moved over to cigarillos. The books sat piled against the wall for several weeks, untouched.
But then I started taking the Metro to work. Each day for about a month, I rode from East Falls Church to Brookland, which is a fifty-minute trip during peak ridership hours. Although I was constantly surrounded by noisy commuters on screeching, often un-airconditioned trains, I finally found the focus that eluded me in my office. I devoured Art of Life’s list, sometimes reading half a book on the way into work and finishing up on the way home. I never felt unmotivated. In fact, for the first time in a while, I felt satisfied. Like living in a dream. I discovered what many other self-help readers already know: the books themselves were all the help I needed. They soothe your anxieties and flatter your intelligence in a way that makes you feel that simply by finishing you have already progressed far down the road of improvement. Even when they take a harsh tone, they are quick to reassure you that the criticism is loving and necessary. Of course, the advice in each book is usually impossible to follow, so the only way to feel like you’re still improving is to read another one. When I at last had no more, I felt like Caliban shaken from his visions of riches pouring out of the heavens: I cried to dream again.
And if it weren’t for my other responsibilities—and an overlong interlude in the Midwest—I probably could have dreamed indefinitely. There are thousands of self-help books published every year. Many are bestsellers. But I knew that by the end of Art of Life’s list, I was bumping up against the outer limits of the genre. I’m twenty-four, and there are many other things I’d like to read in this decade. It was time to move on. After all, there are only five major categories of self-help, and I found that once you have identified them, it’s hard to read another book in the genre, except, perhaps, as a connoisseur.
The classic form is the most recognizable. These are the books that propose comprehensive plans of life, usually arranged in a series of rules that the author insists must be followed rigorously for success. The most famous is Dale Carnegie’s How to Win Friends and Influence People, which, nearly ninety years after its publication, still towers over every other self-help book. Carnegie’s main point is that the path to success—financial or otherwise—is flattery. Most people want a “feeling of importance,” he writes, and if you want something out of them, that’s the least you could give in return. There’s nothing wrong with this sort of behavior, he adds, because it gives everyone involved in the transaction a sense of empowerment. Win-win. Carnegie’s manual forms something of a triptych with the two other bastions of classic self-help: Think and Grow Rich by Napoleon Hill and The Power of Positive Thinking by Norman Vincent Peale. Hill’s book rests on the idea that you can become fabulously wealthy so long as you have a BURNING DESIRE for money. He recommends that you set your mind on a fixed amount of cash, and when you rise in the morning and retire at night, recite twice the plan for acquiring it. This advice, however, comes with a caveat. Only those with a true obsession for wealth will find it:
You may complain that it is impossible for you to “see yourself in possession of money” before you actually have it. Here is where a BURNING DESIRE will come to your aid. If you truly DESIRE money so keenly that your desire is an obsession, you have no difficulty in convincing yourself that you will acquire it. The object is to want money, and to become so determined to have it that you CONVINCE yourself you will have it.
A good friend of mine keeps Think and Grow Rich and the Catechism on his bedside table. He often jokes that one is his temporal, the other his spiritual guide to success. (Curiously, Hill actually was a moralist as well: in Outwitting the Devil, a book unpublished until long after his death, he uses the same logic of Think and Grow Rich to prove the evil of masturbation.) Peale’s advice is similar to Hill’s, but with an explicit religious dimension. Simply desiring wealth is not enough, he writes. You must also believe that God favors you and will shower you with earthly riches. He recommends you repeat two mantras adapted from Scripture ten times daily: “If God be for us, who can be against us?” and “I can do all things through Christ which strengtheneth me.” Although Peale still has many followers (the former president of the United States, for instance, is a big fan), The Power of Positive Thinking remains controversial and is frequently savaged both by theologians and mental health experts, as well as other plan-of-life authors embarrassed by his quackery.
The tripartite skeeviness of Carnegie, Hill, and Peale prompted some of these dissatisfied writers to publish a number of books emphasizing morality, a subject uninteresting to their forebears. The most famous is Stephen R. Covey’s 7 Habits of Highly Effective People, a diagram-heavy book that argues that “personality growth, communication skill training, and education in the field of influence strategies and positive thinking” are ultimately short-sighted paths to success. The truly successful man, Covey says, is someone with a strong character who lives by a series of unchangeable principles, which just so happen to be his seven habits. A score of imitators have followed 7 Habits—four of the books in Art of Life’s list riff on its title—but none with so much success as Jordan Peterson in 12 Rules for Life and its sequel, Beyond Order: 12 More Rules for Life. Like Covey, Peterson positions himself above the hucksters by playing ethicist. Peterson’s teachings are severe, and he identifies personal responsibility as the best way to find meaning in life. His books are engaging and at times literate, but their framing as a series of “rules” keeps them definitively in the realm of self-help. No number of references to Carl Jung can change that.
Not for lack of trying, though. For decades, many self-help authors have attempted to reinforce their credibility by aligning themselves with the wisdom of the fathers, such that an entire cross section of texts from the ancient, medieval, and early modern world have been recast as a subgenre within self-help. The most obvious examples are Marcus Aurelius’ Meditations, which frequently tops best-of self-improvement lists, and Sun Tzu’s Art of War, which half of lower Manhattan has at least halfway memorized. (When my brother worked briefly at a private equity firm, at the end of his first week, his boss gave him a copy of Sun Tzu and instructed him to study it carefully.) The Prince and The Book of the Courtier also remain popular among young strivers, to the point that in Washington, D.C. even some twenty-three-year-olds without a lick of Italian can deliver long discourses on the meaning of sprezzatura. None of these books, however, would have much purchase with the self-help set if it weren’t for the fact that nearly every successful author claims one as his inspiration. This convention, like many in the genre, began with Carnegie, who says that he derived his philosophy of agreeableness from Socrates:
His whole technique, now called the “Socratic method,” was based upon getting a “yes, yes” response. He asked questions with which his opponent would have to agree. He kept on winning one admission after another until he had an armful of yeses. He kept on asking questions until finally, almost without realizing it, his opponents found themselves embracing a conclusion they would have bitterly denied a few minutes previously.
The next time we are tempted to tell someone he or she is wrong, let’s remember old Socrates and ask a gentle question—a question that will get the “yes, yes” response.
Well and good, but we all know where a lifetime of that behavior got Socrates. Certainly not to the top of the corporate ladder.
While plan-of-life literature often relies on the classics for authority, another species within the genre attempts to mimic them outright. These are mindset books, whose rise in popularity over the last decade has coincided with the increased ability for mindset gurus to hold court on social media. The most popular ones tend to push a religious dedication to order—books such as Think Like a Monk and The Monk Who Sold His Ferrari detail the successes of white-collar men who embraced Eastern asceticism—but without the faith commitment to any particular religion. Others make similar recommendations about discipline but leave off the religious stuff entirely, opting instead for a vague sort of mysticism. A typical example is The 5A.M. Club, whose author, Robin Sharma, promises to give his readers the ability “to wake up early feeling inspired, focused, and flooded with a fiery drive to get the most out of each day,” so long as they rise at five every morning and follow his 20/20/20 Formula:
There are three twenty-minute pockets to install and then practice to mastery-level. The first twenty minute pocket of The 20/20/20 Formula requires that you Move. Simply put, doing some sweaty exercise first thing every morning will revolutionize the quality of your days. The second pocket encourages you to Reflect for twenty minutes. This segment is designed to help you re-access your natural power, boost self-awareness, dissolve your stress, fuel your happiness and restore your inner peace in an era of acute overstimulation and excessive activity. And you’ll round out this sixty-minute Victory Hour of personal fortification with twenty minutes centered around ensuring that you Grow, whether that means investing some time reading a book that will improve your understanding of how the best lives were made or an article that will refine your professional prowess or listening to an audio session on how the virtuosos accomplish their unusual results or watching an educational video that will show you how to lift your relationships or increase your finances or deepen your spirituality.
Although that formula isn’t quite the same as rising for Lauds (let alone Matins, which is the real sacrifice), I think any reasonable person would agree that its broad outlines are unobjectionable. Waking up early is good. So are exercise, silent reflection, and reading. I’ve found that the weakness of mindset literature isn’t so much its prescriptions as the fact that there’s no motivating factor behind the advice except for the promise of personal growth. For most people that’s not too compelling. Besides, if you’re not already motivated, it’s unlikely that any book will invigorate your will. For myself, I’ve found that the only way to do anything is by necessity. And I believe others are the same way. I was conversing recently with an old college professor who, since the mid-1990s, has woken up every morning at 5:00 A.M. and knocked out several hours of writing before the workday begins. I asked how he did it. His response: “Well, I set an alarm.” Don DeLillo, I have heard, has a similar approach to writing novels. When he needs to finish one, he turns on his word processor and begins typing.
Of course, it’s much more fun to believe that there are bizarre and arcane shortcuts to success. It’s no surprise that the same people who enjoy mindset literature also often enjoy mind-altering narratives. These are the books most commonly found in airports. They’re all about the same in structure: the author states an absurd claim and then spends much of the book meticulously defending it. In Outliers, Malcolm Gladwell attempts to prove that no one can be the master of any subject unless he spends a minimum of ten thousand hours practicing it. In Everything is F*cked, Mark Manson attempts to prove that despair is actually hope. In Freakonomics, Stephen J. Dubner and Steven Levitt attempt to prove that more abortions reduce crime. This sort of book is the literary equivalent to Charlie Day’s mailroom freak-out.
The most respectable form of self-help—the one type that respectable people will read openly—is the book that only claims to offer practical advice. These tend to be memoirs or biographies. Recent popular examples include Phil Knight’s Shoe Dog, about how he transformed Nike into a Fortune 500 company, or Ashlee Vance’s biography of Elon Musk, which attempts to explain the tech CEO’s seemingly unbroken string of successes. There are also a series of often goofily titled guidebooks that illustrate a simple point of prudence. Who Moved My Cheese? reminds you to remain nimble and adaptable to changes in the workplace. Eat That Frog! offers some tips for beating procrastination.
Out of all these books, however, I can’t think of a practical wisdom manual that has been better received among young professionals than Cal Newport’s Deep Work. It is likely the most influential self-help book being read today and for good reason. Newport structures it according to the Carnegie model, but is very careful not to overstate his case or make any ridiculous claims about his methods. The argument is simple: most “knowledge workers” (people in tech, finance, and academia) waste a lot of time on “shallow work,” among which Newport classes emails, meetings, and time spent on social media. If you want to be productive, he says, you have to shut that stuff out and do “deep work” instead. Deep work can vary in meaning from job to job, but essentially all Newport means by the term is “the ability to focus on the task at hand.” There are many ways to learn deep work—and Newport outlines a few—but he doesn’t privilege any one over the other and repeatedly acknowledges that his book will only be helpful for people who have the leisure to ignore the outside world for days, weeks, or months at a time.
Newport is also careful not to make any moral claims. He’s skeptical of Twitter’s usefulness, for instance, but he never launches into an invective against its existence. He maintains a similar attitude toward email and open plan offices. He also never claims that doing deep work will necessarily make you a better person. The furthest he goes down that road is when he makes the case that the best deep workers treat their tasks as a craftsman treats his art. He cites several examples of blacksmiths and farmers whose radical attention to their work has given them a greater sense of satisfaction in the rest of their lives. There’s no reason why office workers can’t have that too, he says.
It is at this point that Deep Work begins to wobble. The knowledge workers Newport praises generally seem like miserable people. I was surprised, for example, when he pointed to Woody Allen as a model of deep work. Twenty-three Academy Award nominations and “an absurd rate of artistic productivity” are great, but Allen would probably be better off if he had relaxed his work on, say, Radio Days, to reassess his parenting style. And when he was in his prime, Allen had a reputation for absolute obsession. On the set of Crimes and Misdemeanors, Philip Roth observed that Allen “bore so little resemblance to a human being. The man, if that is the word, is a fake from top to bottom.” The same probably could be said of Newport’s ultimate deep worker, Bill Gates. Although Newport repeatedly praises Gates’s famous “Think Weeks,” when the CEO departs into the woods and does nothing but “read and think big thoughts,” I was left wondering whether some of the results of those sessions are worthy of the same praise. Gates is the guy after all, whose big-brained contributions to society include curbing population growth in Africa and encouraging people to drink their own urine. But these sorts of concerns fall outside of Newport’s purview. He concludes the book by wrapping his arguments in the safety blanket of pragmatism:
A commitment to deep work is not a moral stance and it’s not a philosophical statement—it is instead a pragmatic recognition that the ability to concentrate is a skill that gets valuable things done. Deep work is important, in other words, not because distraction is evil, but because it enabled Bill Gates to start a billion-dollar industry in less than a semester.
This conclusion seems to cut against all the arguments made earlier in the book. Newport had said that deep work is practiced by those who treat their office jobs with a certain dignity, the sort that these days is associated with medieval craft guilds. But then he concludes that it’s a get-rich-quick scheme like any other: valuable because a few billionaires do it. The tension does not need to be there. If the craftsman element of deep work were really important, then Newport could simply say that the profit-driven side is a secondary concern. Or vice versa. But instead, by not addressing it at all, Newport leaves the casual reader with the hope that his work can be somehow sublimely fulfilling and get him filthy rich, two goods that rarely come together. In the end, the book isn’t substantially different from any other self-help book—only tonally a few notes off of Think and Grow Rich.
But I suppose that’s how you write a bestseller. Very few people would spend thirty dollars on an improving book if they didn’t also think that it could make them a little more money. And very few people would read these things if they had more imaginative fantasies. (In another world, millions of people turn to Invisible Cities and Tristram Shandy to indulge their self-help dreams.) After I finished Art of Life’s list, I checked the account’s other content to see what the typical mindset guru has on offer these days. It’s mostly encouragement to “Stop overthinking things” and “Live with intention” and “Believe in yourself.” Fine aspirations, all. But I don’t need a self-help book to do that. I already have my almonds and cigarillos.
