The GY20R Book Club
We long for the world to be simple and formulaic.
And because we only see the world from one perspective, it can often look that way.
But the world is complicated. This is why we need books.
Books to show us the world from another perspective. Books that allow us to make some sense of life’s complexity.
Getting Your 20’s Right requires books.
Below, you will find the books that have helped me and the GY20R community make sense of the world. Some will interest you and some won’t. Don’t try to read them all. But start somewhere. Because we could all use a little better perspective.
The Defining Decade
Why Your Twenties Matter—And How to Make the Most of Them Now
by Meg Jay
As a psychotherapist who has worked with twentysomethings for decades, Meg Jay draws on her experiences as a counselor to deliver an urgent, thoughtful, and actionable message to millennials. She has made a career of asking twentysomethings hard questions about work, love, and risk. She will highlight the decisions you need to make that will have the greatest impact on your lifelong happiness.
The book is broken into three sections: work, relationships, and your brain.
Concerning work, she will talk about the need to develop “identity capital” and how it is your greatest asset in the job market. Concerning relationships, she will help you see that your “weak ties” are the people who will have the greatest impact on the course of your life. Concerning your brain, she will help you see just how unique of a time the twentysomething years are for learning and developing.
If your life is not currently on a trajectory to be the most awesome person ever, read this book. I’ve already read it three times.
“Twentysomethings who use their brains by engaging with good jobs and real relationships are learning the language of adulthood just when their brains are primed to learn it.”
“But while the urban tribe helps us survive, it does not help us thrive. The urban tribe may bring us soup when we are sick, but it is the people we hardly know—those who never make it into our tribe—who will swiftly and dramatically change our lives for the better.”
“Twentysomethings who don’t feel anxious and incompetent at work are usually overconfident or underemployed.”
“Like with work, good relationships don’t just appear when we’re ready. It may take a few thoughtful tries before we know what love and commitment really are.”
“The more you use your brain, the more brain you will have to use.”
Mastery is a book about power and experiencing reality to its fullest.
It is about how focused practice changes the brain to be more observant. It is about how the cultivation of social intelligence allows us to see people as complicated and multi-faceted, which is the only way to achieve mastery. It is about how rigid generalizations of the world distance us from reality and the (attainable) status of “genius.”
In true Robert Greene fashion, he makes the case that mastery is the ultimate form of power—and how that power is available to everyone.
It sounds like something written by a cult leader or self-help guru, but it isn’t. This is the book every self-help book wants to be.
“It is time that the word ‘genius’ becomes demystified and de-rarefied. We are all closer than we think to such intelligence.”
“Do not envy those who seem to be naturally gifted; it is often a curse, as such types rarely learn the value of diligence and focus, and they pay for this later in life.”
“In this new age, those who follow a rigid, singular path in their youth often find themselves in a career dead end in their forties, or overwhelmed with boredom. The wide ranging apprenticeship of your twenties will yield the opposite – expanding possibilities as you get older.”
“The need for certainty is the greatest disease the mind faces.”
“And so the extreme paradox is that those who impress the most with their individuality—John Coltrane at the top—are the ones who first completely submerge their character in a long apprenticeship.”
“There is nothing that becomes repetitive and boring more quickly than free expression that is not rooted in reality and discipline.”
“The time that leads to mastery is dependent on the intensity of our focus… We don’t simply absorb information—we internalize it and make it our own by finding some way to put this knowledge to practical use.”
How to Read a Book
The Classic Guide to Intelligent Reading
by Mortimer J. Adler and Charles Van Doren
I know what you’re thinking. A book on how to read a book? This is a joke.
It isn’t. It’s actually a guide to taking your reading abilities to the next level. So how do we do that?
It’s all about answering the four questions:
- What is the book about as a whole?
- What is being said in detail, and how?
- Is the book true, in whole or part?
- What of it? (How should this book influence the way I live every day, if at all?)
Whether poetry, philosophy, or business, the authors show that you can (and should) ask these questions of everything you read.
They also explain the four levels of reading: elementary, inspectional, analytical, and syntopical reading. The bulk of the book is on analytical reading, a level of reading they believe every person should reach. Essentially, if you have reached the analytical level of reading, you will be able to aptly answer the question of, “what was that book about?” (Which is harder to answer than you think.)
Since books are the most valuable and accessible sources of wisdom and knowledge, harnessing their power is an incredible skill. This book is about harnessing that power.
(Review by Kyle Downey)
“Good books are over your head; they would not be good for you if they were not.”
“No one who looks upon disagreement as an occasion for teaching another should forget that it is also an occasion for being taught.”
“The great writers have always been great readers, but that does not mean that they read all the books that, in their day, were listed as the indispensable one. In many cases, they read fewer books than are now required in most colleges, but what they did read, they read well. Because they mastered these books, they became peers with their authors. They were entitled to become authorities on their own rights.”
“To become well-read, in every sense of the word, one must know how to use whatever skill one possesses with discrimination – by reading every book according to its merits.”
How to Fail at Almost Everything and Still Win Big
Kind of the Story of My Life
by Scott Adams
There’s this incredible moment at the beginning of J.K. Rowling’s Harvard commencement address. It begins with her statement, “I have decided to talk to you about the benefits of failure.”
The incredible part, though, is not what she says next. The incredible part is that an audible group of people laugh. Like she is making a joke. They laugh at the idea of failure having any benefit.
If you’re the kind of person that would laugh at J.K. Rowling for talking about the benefits of failure, you should not read this book. But if you fail often, this book is probably for you.
Scott Adams is an incredible failure. He’s also an incredible writer, entrepreneur, and comedian. But he’s all of those things because of his track record with failure. He knows how to milk failure for all it’s worth. With an incredibly refreshing lack of B.S., he is willing to tell you how. And it’s good.
So if you think that failure is what will prevent you from being successful in life, Scott is here to tell you that you’re thinking about it all wrong.
“Success caused passion more than passion caused success.”
“To put it bluntly, goals are for losers. That’s literally true most of the time. For example, if your goal is to lose ten pounds, you will spend every moment until you reach the goal—if you reach it at all—feeling as if you were short of your goal. In other words, goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary.”
“There are three kinds of people in the world: 1) Selfish 2) Stupid 3) Burden on others… Your best option is to be selfish, because being stupid or a burden on society won’t help anyone. Society hopes you will handle your selfishness with some grace and compassion. If you do selfishness right, you automatically become a net benefit to society. Successful people generally don’t burden the word.”
“Where there is a tolerance for risk, there is often talent.”
“Success isn’t magic; it’s generally the product of picking a good system and following it until luck finds you.”
“I think it’s important to think of each new skill you acquire as a doubling of your odds of success… quantity often beats quality.”
If you like being an American, you should read this book. I’m not saying it’s your civic duty to know the history of our Founding Fathers, but I’m implying it.
And if you’re not an American, you should still read this book. Ben is an endlessly interesting man. He was a reader, writer, philosopher, speaker, persuader, entrepreneur, diplomat, politician, inventor, scientist, and thinker. Tell me that you wouldn’t want to sit next to him at a party.
Read this book for thoughts on the importance and role of virtue.
Read it for political and economic ideas that will make both conservatives’ and liberals’ blood boil.
Read it for the story of an individual striving to reach his fullest potential (the real American Dream).
To make America great again, read about and emulate a man who made America great.
(Review by Ryan Downey)
“Those who would give up essential liberty to purchase a little temporary safety deserve neither liberty nor safety.”
“Industry and constant employment are great preservatives of morals and virtue.”
“In free Government the rulers are the servants, and the people there superiors and sovereigns.”
“[Those who] drink to the bottom of the cup must expect to meet some of the dregs.”
In America: “People do not inquire of a stranger, ‘What is he?’ but, ‘What can he do?’”
“Silence had often been [Franklin’s] best weapon, making him seem wise or benign or serene.”
“American democracy was built on a foundation of unbridled free speech”
Hollywood is crazy about dystopia right now. Specifically, George Orwell’s 1984 brand of dystopia.
We are drawn to the kind of dystopia where the government rules with an iron fist. We like the irony of “Peace-keepers” wielding guns. We like a dystopia where rebels can shoot down the Death Star. We like a dystopia where truth, above all else, can inspire the masses to reclaim their freedom.
But what if dystopia was not the result of force, but pleasure? What if “Peace-keepers” wielded the perfect drug, not the perfect weapon? What if the masses were conditioned from birth to willingly discard truth and beauty for the sake of happiness? What do you do when no one wants freedom?
That is the dystopia of Brave New World. And it’s incredible.
No work of fiction has caused me to think so deeply as Brave New World. While it is not a page-turner like The Hunger Games, it is an incredible thought-experiment on the condition of the human soul and the incredible (and horrifying) power of consumerism. If you like to think about big ideas (or “intellectually necessary evils” as they’re called in the book), Brave New World is your jam.
“Happiness is a hard master—particularly other people’s happiness. A much harder master, if one isn’t conditioned to accept it unquestioningly, than truth.”
“You can’t consume much if you sit still and read books.”
“It was the sort of idea that might easily decondition the more unsettled minds among the higher castes—make them lose their faith in happiness as the Sovereign Good and take to believing, instead, that the goal was somewhere beyond… that the purpose of life was not the maintenance of well-being, but some intensification and refining of consciousness, some enlargement of knowledge.”
“Universal happiness keeps the wheels steadily turning; truth and beauty can’t. And, of course, whenever the masses seized political power, then it was happiness rather than truth and beauty that mattered.”
“And that’s why we went to bed together yesterday—like infants—instead of being adults and waiting.”
“Sixty-two thousand four hundred repetitions make one truth.”
The Road Back To You
An Enneagram Journey to Self-Discovery
by Ian Morgan Cron and Suzanne Stabile
The Enneagram has single-handedly been the most helpful personality tool I’ve ever come across.
This book taught me what it was, helped me identify my type, helped me learn about what helps me thrive and what brings out my darker shadow side, and gave me tools for understanding both myself and the people around me, all through a Christian lens that helps me grow as a human and as a believer.
It wasn’t until I read this book that I really started to peel back the deepest layers of my heart, mind, and soul. It’s changed me forever (in the best way possible) and I want every single person to read this book and be changed, too.
Taking a close, hard look at all the things that shape who you are leads to growth—and we all could use a little bit of that. Let’s be better, healthier, happier, more grounded people, yeah?
(Review by Rachel Dawson)
“The purpose of the Enneagram is to develop self-knowledge and learn how to recognize and dis-identify with the parts of our personalities that limit us so we can be reunited with our truest and best selves, that ‘pure diamond, blazing with the invisible light of heaven,’ as Thomas Merton said.”
“Spiritually speaking, it’s a real advantage to know what happens to your type and the number it naturally goes to in stress. It’s equally valuable to learn the positive qualities of the number you instinctively move toward in security as well. Once you become familiar with this material, you can know and catch yourself when you’re heading in the direction of a breakthrough or a breakdown, and make wiser choices than in the past.”
“As long as we are unaware of our deadly sin and the way it lurks around unchallenged in our lives we will remain in bondage to it. Learning to manage your deadly sin rather than allowing it to manage you is one of the goals of the Enneagram.”
You will utter these five words at some point in your life: “How did I get here…” How you punctuate the end of that sentence will say a lot about your life. Will it be with an exclamation point? (“How did I get here!“) Or will it be with a question mark? (“How did I get here?“)
Jon wants you to end that sentence with an exclamation point.
He does this by drawing a map of the hard-to-follow Road to Awesome. On Jon’s map, you’ll see that this “Road” travels through five different “Lands”: Learning, Editing, Mastering, Harvesting, and Guiding. Each of these Lands has its own distinct psychological traps and pitfalls. (He knows this because he’s fallen into all of them.)
No matter which Land you’re in right now, Jon has helpful insights to help you stay on the Road and not return to the Land of Average.
So basically, if you like metaphors, laughter, and success, you’ll like this book.
“I only had two speeds; waste all my time or try to be impossibly perfect with my time.”
“Why do most people decide to travel down that average path? The truth is that they don’t decide.”
“Be brutally realistic about your present circumstances… Be wildly unrealistic about your future circumstances.”
“Purpose usually finds you. Purpose is attracted to motion.”
“Luck is a word people who are lazy use to describe people who are hustling.”
“You can’t be ‘anything you want,’ but you can be something even better: the best version of you.”
“Critic’s Math: 1 insult + 1,000 compliments = 1 insult”
This book will teach you a lot about what it means to be vegan and why it’s an important and worthwhile lifestyle to consider. (I promise I’m not just saying that because I’m a vegan.)
Veganism is often seen as a trend, a silly fad, or only for those tree-hugging activists. But there’s solid reasoning behind it. It’s worth reading about if you’ve never actually taken time to understand why someone would cut all animal products out of their life.
This book is incredibly informative. It’s written very conversationally and honestly, it’s bold, and it’s really eye-opening—no matter what your stance. It’s thorough and presents a solid argument for veganism. So even if you don’t agree, I think you’ll be able to respect the lifestyle more after reading this one.
(Review by Rachel Dawson)
“Veganism as a process and as a way of life is all about asking you to rewrite those internal scripts to recognize the inherent worth of animals. Coming to this awareness is complex and at times frustrating, making ethical veganism a complex gift.”
“Veganism is not only an affirmation about how we want the world to be, it is a lived form of protest, and our reminding people that everything is not quite right when it comes to how we treat animals.”
“When it comes down to it, people need to know that you’re a vegan. If people don’t know what veganism is, and they seem genuinely curious, tell them. If you’re afraid that the very idea of calling yourself a “vegan” might make others wary of you, or scare people off, the solution isn’t to run from veganism. The solution is to live your life in a way that proves to people that veganism is not the equivalent of joining a cult.”
The Curated Closet
A Simple System for Discovering Your Personal Style and Building Your Dream Wardrobe
by Anuschka Rees
If you’ve ever been on Pinterest for more than five minutes, chances are, you’ve seen something about a capsule wardrobe. Maybe you’re a guy who never browses Pinterest so that terms sounds super weird… but let me explain. Capsule wardrobes are an experimental, minimalist method of choosing and wearing clothes– you pick a specific number of pieces, put everything else away, and only wear those pieces (your capsule) for a predetermined length of time (usually a season). It seems a little extreme, but I’m in the middle of doing my first one now, and it’s actually pretty great.
I grabbed this book after seeing many bloggers talk about how helpful it was in creating their own capsule wardrobes, or even just in simplifying their closets and defining their personal style. I think this book would apply to both men and women in many ways, but it’s clearly written for the female audience. Sorry, guys. Feel free to sit this one out.
(Review by Rachel Dawson)
“The perfect wardrobe isn’t something that you can cook up in a weekend. Your personal style is the result of many different influences, all the people you have met over the years, all the places you have traveled. It’s a truly personal thing that can take a little digging to fully uncover. But don’t worry: the process is a lot of fun too!”
“Our clothes tell a story. Our clothes reflect our personality and what’s important to us.”
“Building a great wardrobe is not just about making sure you have enough clothes for whatever you want to do; each individual piece in your wardrobe should also be functional and work well for whatever activity you’re dressing for.”
“Life is too short for uncomfortable clothes.” (PREACH.)