It’s that time of year again, where we’re all socially pressured into spending an inordinate amount of time around people that we’ve kinda-sorta known our whole lives, but who also drive us insane and make us feel like there’s no point to it all.
It’s in that warm holiday spirit, then, that I present to you, six books that will hopefully make those close to you (or perhaps you, yourself) slightly-less-horrible people this holiday season. These are good books to help increase empathy and gain a better understanding of all the beautiful flaws in yourself and in the humans around you. They’re also ways to avoid talking to your family.
So Merry Holidays and Happy Who Gives a Fuck. Let’s read.
Tiny Beautiful Things
by Cheryl Strayed
What it’s about: Few people know that before the world famous novels and the big budget film featuring Reese Witherspoon clomping around in hiking boots, Strayed wrote an anonymous advice column for a small literary website. The questions sent to her were pretty standard fare for the genre: break ups, coping with death or trauma, abusive family members, struggling with addiction, and so on.
What’s not generic at all are Strayed’s responses. First of all, they’re long. Often stretching out for 20-30 pages apiece. Second, they’re intense, personal and raw. Strayed’s lived a fucked up life and somehow come out the other end. Rather than wax philosophic about theories and silly shit like affirmations, she does something much better in Tiny Beautiful Things: she drags the reader back through the mud she lived through, reminding them that they are not alone and that yes, they will be all right.
As a person who exists in this genre and often writes articles or emails responding (whether directly or indirectly) to people’s personal problems, this may be the only book that I have found that I look up to as a role model. Responses and writing like Strayed’s here are something I aspire to and hope to achieve one day in my own work.
Notable quotes: “I’ll never know, and neither will you, of the life you don’t choose. We’ll only know that whatever that sister life was, it was important and beautiful and not ours. It was the ghost ship that didn’t carry us. There’s nothing to do but salute it from the shore.”
“You cannot convince people to love you. This is an absolute rule. No one will ever give you love because you want him or her to give it. Real love moves freely in both directions. Don’t waste your time on anything else.”
“Nobody will protect you from your suffering. You can’t cry it away or eat it away or starve it away or walk it away or punch it away or even therapy it away. It’s just there, and you have to survive it. You have to endure it. You have to live through it and love it and move on and be better for it and run as far as you can in the direction of your best and happiest dreams across the bridge that was built by your own desire to heal.”
How it will make you a less horrible person: There are two ways to help people in this world: 1) give them specific, tangible advice on what they should do to fix their problems, and 2) normalize their suffering to simply remind them that they are not as alone or as hopeless as they think they are.
Strayed’s work here is light on the first and heavy on the second. But she’s an expert at the second. In fact, her book is probably the best example I’ve ever seen of the, “Hey, sometimes life is shit; let’s talk about it” variety.
Often what we need the most is not more “tools” and “tips” to get through our hardest hours. What we need is someone who simply understands our pain, and is able to clearly and beautifully articulate that it will one day be OK again.
A great gift idea for…: That awkward cousin who cries when you carve the turkey; your friend who has said for a decade plus she was going to write a screenplay but is still waiting tables; family members who have made a sport out of feeling sorry for themselves; abuse survivors.
Between the World and Me
by Ta-Nehisi Coates
What it’s about: There’s a lot of hype and hate around this book. It’s about racism in the United States, so obviously, it’s been politicized to hell and back. It also won the National Book Award, garnered Coates the MacArthur Fellowship Grant (also referred to as “The Genius Grant”), Nobel Prize laureates in literature have called it “required reading for humanity” and the New York Times, Washington Post, and Chicago Tribune all nearly crapped their pants screaming that it was the best book of 2015 — so you can imagine how it’s been a lightning rod for a lot of nitpicky criticism.
First, let’s get the most obvious and important facts out of the way: Ta-Nehisi Coates is black. He also has a regular column at The Atlantic and has become (in)famous not only for his powerful prose, but for some of his more radical and unconventional ideas about US history and race.
Between the World and Me is relatively short at 163 pages. It’s an open letter from Coates to his 13-year-old son. After seeing the news that George Zimmerman had been acquitted for shooting and killing Trayvon Martin, an unarmed black teenage boy in broad daylight, Coates watched his son — who was now old enough to understand such racial injustices — retreat to his room and lock the door and proceed to cry uncontrollably in solitude. Coates, standing outside of his son’s door, wanted to say something to make his son feel better, but he realized there was nothing he could say because there was no reason to feel better about it. Instead, he sat down and wrote this book.
The book doubles as both a memoir of Coates’ experiences with racism, black culture, and growing up in the ghettos of Baltimore, as well as a political commentary on the history of race in the United States. Coates seamlessly weaves between the ideas of black intellectuals such as James Baldwin, Malcolm X, and Martin Luther King Jr., and much of the violence, frustration and prejudice Coates experienced in his own life. It is political. But it’s also personal. It is a love letter, not just to Coates’ son, but to black people and even the United States, in the truest sense of the genre.
It’s also gorgeously written. Coates is so gifted that it makes the injustices he’s lived through that much more difficult to read. It’s at times an emotional scree of a concerned black father terrified for the safety of his son and, at other times, a highly reasoned political argument. It’s both a radical and unconventional criticism of the injustice bred into American society as well as a work of art. It’s like nothing else I’ve ever read.
Notable quotes: “But race is the child of racism, not the father. And the process of naming ‘the people’ has never been a matter of genealogy and physiognomy so much as one of hierarchy. Difference in hue and hair is old. But the belief in the preeminence of hue and hair, the notion that these factors can correctly organize a society and that they signify deeper attributes, which are indelible—this is the new idea at the heart of these new people who have been brought up hopelessly, tragically, deceitfully, to believe that they are white.”
“Hate gives identity. The nigger, the fag, the bitch illuminate the border, illuminate what we ostensibly are not, illuminate the Dream of being white, of being a Man. We name the hated strangers and are thus confirmed in the tribe.”
“But all our phrasing—race relations, racial chasm, racial justice, racial profiling, white privilege, even white supremacy—serves to obscure that racism is a visceral experience, that it dislodges brains, blocks airways, rips muscle, extracts organs, cracks bones, breaks teeth. You must never look away from this. You must always remember that the sociology, the history, the economics, the graphs, the charts, the regressions all land, with great violence, upon the body.”
How it will make you a less horrible person: As an upper-middle class white boy from the suburbs who pretty much always thought he had the whole racism thing figured out from an early age (cheat sheet: don’t be mean to black or brown people; don’t use “n-word;” rinse and repeat), this book changed my mind about a lot of things. It also showed how horribly naïve I was to how a large percentage of people in my country live.
Coates’ writing is all at once beautiful, political, personal, historical and urgent. But unlike his columns at The Atlantic, here he has no clear thesis. There’s not some overarching political argument here. Rather, it’s a stark and unflinching reflection on both his life as a black man and the state of race-relations in the US. Although less directed, this ends up feeling far more powerful. It was what books were made for: an opportunity to inhabit, albeit briefly, the mind and experiences of another person, and to exercise our muscle to expand our empathy.
A great gift idea for…: That racist uncle who doesn’t realize that he’s racist; anyone who speaks about ‘trigger warnings’ and ‘safe spaces’ unironically; Trump voters.
Fooled By Randomness
by Nassim Taleb
What it’s about: Nassim Taleb was a successful bonds trader in Chicago. He made a killing in the 80s, but did so because he developed an unconventional philosophy around finance and trading: to bet on the most unexpected occurrence possible, that the entire market is random and anyone who believed they had any sort of skill or predictive power was merely deluding themselves and would eventually go broke.
After the dot-com bubble burst and 9/11 happened, Taleb wrote his odd philosophy down and Fooled by Randomness is what emerged. And although the book primarily uses financial markets in its examples, the concepts and principles have wide applications in life as well. Taleb shows us that much of what we think we know — about skill about success, about important figures in history, even about mundane things such as dietary habits, athletic performance or business success — is to largely be the product of chance.
Notable quotes: “Reality is far more vicious than Russian roulette. First, it delivers the fatal bullet rather infrequently, like a revolver that would have hundreds, even thousands of chambers instead of six. After a few dozen tries, one forgets about the existence of a bullet, under a numbing false sense of security. Second, unlike a well-defined precise game like Russian roulette, where the risks are visible to anyone capable of multiplying and dividing by six, one does not observe the barrel of reality. One is capable of unwittingly playing Russian roulette – and calling it by some alternative “low risk” game.”
“Mild success can be explainable by skills and labor. Wild success is attributable to variance.”
“Probability is not a mere computation of odds on the dice or more complicated variants; it is the acceptance of the lack of certainty in our knowledge and the development of methods for dealing with our ignorance.”
How it will make you a less horrible person: It will (hopefully) humble you. It will expose you to how much you don’t know. It will show you that many of the greatest qualities you assume about yourself are likely deluded or, at best, the result of a streak of luck. This is a good thing, as you’ll be less up your own ass and more comfortable with failure as a result.
A great gift idea for…: Anyone who has won money in the stock market lately; anyone who has lost money in the stock market lately; anyone who takes themselves and their money a little bit too seriously.
Ego is the Enemy
by Ryan Holiday
What it’s about: Ryan is like my brother from another philosophical mother. Despite the fact that we pretty much have completely opposite personalities, writing styles, and lifestyles, intellectually, he and I tend to always end up at the same place.
Ego is the Enemy is Holiday’s second philosopho-self-help title. And although The Obstacle is the Way probably got more media hype, I think this book is the better one. It’s more focused and more personable. It takes an age-old message, a message you see bandied about in a million self-help books about the ego, but gives it a serious philosophical treatment and grounds it with countless historical examples.
The result is a book about ego that isn’t so much dramatic as it is practical. Our egos are here to stay. They are an inherent effect of our wiring. The question isn’t so much quashing the ego, as much as wrestling with it, taming it and ultimately managing it.
Notable quotes: “Impressing people is utterly different from being truly impressive.”
“Almost universally, the kind of performance we give on social media is positive. It’s more ‘Let me tell you how well things are going. Look how great I am.’ It’s rarely the truth: ‘I’m scared. I’m struggling. I don’t know.’”
“People learn from their failures. Seldom do they learn anything from success.”
How it will make you a less horrible person: It’s a classically-driven, philosophically-minded argument against self-absorption and entitlement. It’s the manual for mastering your own mind and coming to terms with your ego without indulging in all the pseudo-spiritual bullshit of other books. It’s a no-nonsense book about your relationship with yourself, and how you should probably cool it and keep your pants on a bit more often.
(Well, actually, you can keep the pants off if you’d like… you know, if you’re into that sort of thing.)
A great gift idea for…: That cute guy/girl in your classical literature class who quotes Aristotle at keg parties and is strangely sexy in a nerd-chic kind of way; your friend who just torpedoed his fourth business idea in a row and doesn’t think it’s his fault; people who want practical life advice but hate the “woo woo” stuff of typical self-help; anyone who is really into men wearing togas.
Thinking, Fast and Slow
by Daniel Kahneman
What it’s about: Daniel Kahneman is a Nobel prize-winning psychologist and possibly one of the most influential academics and thinkers in the past 50 years. Kahneman, along with his colleague Amos Tversky, are the godfathers of behavioral economics — a branch of psychology/economics that shows how humans often make irrational economic decisions, and in many cases, even make decisions against their own interest, despite the information available.
Thinking, Fast or Slow is a layman’s summary of this entire body of work. In the book, Kahneman argues that our brains have two forms of thinking. The first is “fast thinking,” or what many of us consider intuition or a “gut feeling.” Fast thinking allows humans to arrive at conclusions extremely quickly despite complicated circumstances or lots of information. Fast thinking is unconscious. It’s quick. It feels obvious and automatic.
Slow thinking, on the other hand, is that shit you had to do in school. Slow, methodical, rational analysis. Test conclusions, weigh evidence, make judgments.
The problem is that our fast thinking often hijacks our slow thinking. In fact, our fast thinking often kicks in without us even realizing it, and so our slow thinking operates from shaky ground to begin with. Not only does the book spell out, meticulously, the flaws in your own brain, but it also gives you insight into how to notice those flaws, and act against them.
Notable quotes: “A reliable way to make people believe in falsehoods is frequent repetition because familiarity is not easily distinguished from truth. Authoritarian institutions and marketers have always known this fact.”
“The confidence that individuals have in their beliefs depends mostly on the quality of the story they can tell about what they see, even if they see little.”
“We can be blind to the obvious, but we are also blind to our blindness.”
How it will make you a less horrible person: You’ll realize the dozens of ways your brain sucks. You’ll be a little bit less sure of yourself, a little bit more aware of your own biases and mental flubs, a little more skeptical of all the bullshit being shoveled your way.
That and you’ll hopefully be better at managing your money, second-guessing many of your assumptions, and maybe not being such a pious dick all the time.
A great gift idea for…: That obnoxious family member, who after too much eggnog, thinks he knows exactly what the government is up to, and can’t be talked out of it nor be ignored; that Aunt who unironically talks about her “intuition” and how wise it is.
The Subtle Art of Not Giving a Fuck
by Mark Manson
What it’s about: I know this is cheating and you’re never supposed to include your own book on these lists, but guess what? Yeah, yeah… that’s right, I don’t give a fuck.
What’s this book about? Well, basically some douchebag with a blog wrote a book and now he won’t shut up about it.
Oh, and he likes to quote himself a lot too…
Notable quotes: “The desire for more positive experience is itself a negative experience. And, paradoxically, the acceptance of one’s negative experience is itself a positive experience.”
“Life is essentially an endless series of problems. The solution to one problem is merely the creation of another.”
“We suffer for the simple reason that suffering is biologically useful. It is nature’s preferred agent for inspiring change. We have evolved to always live with a certain degree of dissatisfaction and insecurity, because it’s the mildly dissatisfied and insecure creature that’s going to do the most work to innovate and survive.”
How it will make you a less horrible person: You will probably still be a horrible person afterward. But hey, I tried.
A great gift idea for…: Everyone; seriously, buy a copy for your entire family, the dog, your parakeet, the pet hamster in your kid’s third grade classroom; re-mortgage your house and buy 100 copies for the whole neighborhood; send a copy to the moon with a monkey; I’m serious guys; Hey, why are you walking away? Wait, no, come back; You forgot your book; Guys? … Guys?
Looking for more books to read?
The School is a collection of 6 brand-new video courses each with a pretty printable workbook, plus 3 bonus courses, ebooks on my favorite topics, commentaries on all my books, and a “library” of best books to read. Oh, did I mention I also do a live monthly webinar with members where I’ll answer all your questions and talk about tacos?
I also have an all-time recommended reading list which non-members can access. You’re welcome.