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A Few Books that Changed My Life
Welcome to my library of recommendations.
Jack Raines
September 15, 2022
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A few months ago, I mentioned that the two most important inputs for any writer are "the things you read and the experiences you have."
I'm constantly asking for book recommendations, and people often ask me for book recommendations as well. Today, I wanted to share a few books that have changed my life. I hope you enjoy it.
Man's Search for Meaning
Everything can be taken from a man but one thing: the last of the human freedoms—to choose one’s attitude in any given set of circumstances, to choose one’s own way.
The most important book I've ever read, period. I read Man's Search for Meaning for the first time when I was in Budapest last September. The reason? I was visiting Auschwitz a week later, and Man's Search for Meaning is Dr. Viktor Frankl's story of his experience in Auschwitz, as well as his thoughts on how man can find meaning in his existence despite his circumstances.
We know about the Holocaust from history books, but you can't fully grasp the horror of camp inmates' realities until you read a personal account.
Your friends and family marching to their deaths every single day, as you wonder if you'll be next.
The dehumanizing, grotesque treatment you receive from the guards.
Your body deteriorating as it struggles to survive on a few daily bites of stale bread.
These experiences aren't captured in history books. They can only be understood through the accounts of survivors.
But the most shocking aspect of Frankl's book isn't the horrors of the Holocaust. It's the ability of man to overcome the horrors of the Holocaust.
Man's resilience in spite of these horrific circumstances and Frankl's commentary on finding purpose make this book a must-read for anyone.
Greenlights
Life is our resume. It is our story to tell, and the choices we make write the chapters. Can we live in a way where we look forward to looking back?
I've always been a big McConaughey fan. Dazed and Confused. Dallas Buyers Club. The Lincoln Lawyer. All phenomenal films. So when McConaughey wrote a book, I figured why not read a sort-of autobiography written by one of my favorite actors?
And man oh man, was my mind blown.
Greenlights is an autobiography. A comedy. A love story. A work of philosophy. A book on living and dying and everything in between.
Matthew McConaughey has a better grasp on life and living than anyone that I've ever encountered, and Greenlights is the author's invitation to come along for the ride.
As someone who found myself struggling with some of the "what am I doing with my life" questions that persist among 20-somethings, I found that Greenlights provided both clarity and inspiration.
The Psychology of Money
Risk is what’s left over when you think you’ve thought of everything.
To date, Morgan Housel's The Psychology of Money is the greatest finance book that I have ever read. Finance is a quantitative field largely saturated by quantitative books, but Housel's magnum opus turned this dynamic on its head.
The Psychology of Money isn't a book on stock picking, market behavior, or "how to make more money," as so many finance books are.
Housel tells 18 stories about our relationship with our money. The Psychology of Money isn't a book about finance. It's a book about people, about you and me. He just happens to convey his messages through the lens of markets and investors.
Outside of The Psychology of Money, Housel is one of the few writers whose content I read every time he posts, and I have incorporated his style in my own writing. He's that good.
Vagabonding
“There’s a story that comes from the tradition of the Desert Fathers, an order of Christian monks who lived in the wastelands of Egypt about seventeen hundred years ago. In the tale, a couple of monks named Theodore and Lucius shared the acute desire to go out and see the world.Since they’d made vows of contemplation, however, this was not something they were allowed to do. So, to satiate their wanderlust, Theodore and Lucius learned to “mock their temptations” by relegating their travels to the future. When the summertime came, they said to each other, “We will leave in the winter.” When the winter came, they said, “We will leave in the summer.”They went on like this for over fifty years, never once leaving the monastery or breaking their vows. Most of us, of course, have never taken such vows—but we choose to live like monks anyway, rooting ourselves to a home or a career and using the future as a kind of phony ritual that justifies the present. In this way, we end up spending (as Thoreau put it) “the best part of one’s life earning money in order to enjoy a questionable liberty during the least valuable part of it.”We’d love to drop all and explore the world outside, we tell ourselves, but the time never seems right. Thus, given an unlimited amount of choices, we make none. Settling into our lives, we get so obsessed with holding on to our domestic certainties that we forget why we desired them in the first place.
This is the book that caused me to live out of a backpack across 20+ countries for the last year.
We're all born with this intrinsic desire to travel and explore. A desire to see the world around us. Is there a dream more widely-shared than that of exploring foreign lands with no rush to return home?
But somewhere along the way, we begin suppressing that desire. We say, "We can't go just yet! The timing isn't right."
Instead of long-term traveling and actually experiencing new places, we condense our travel into week-long blocks where we rush to visit as many tourist sites as possible. We have commoditized travel to fit our work-centric culture, to the point that our trips abroad are just another bullet point on the to-do list.
Vagabonding showed me that the timing is never right, and the costs aren't all that expensive. That we should travel for travel's sake, and we should expand our time abroad.
Travel shouldn't be a luxury reserved for the twilight years of our lives. It should be an ongoing experience that we incorporate into every stage of life.
Vagabonding is one of the few books that I have read 3+ times over.
If you have that urge to explore, but you can't quite pull the trigger, this is the book for you.
The War of Art
Are you paralyzed with fear? That’s a good sign. Fear is good. Like self-doubt, fear is an indicator. Fear tells us what we have to do. Remember one rule of thumb: the more scared we are of a work or calling, the more sure we can be that we have to do it.
If you are a creator, from a writer to an artist to an athlete to an entrepreneur, you need to read this book. Pressfield does a masterclass job of illustrating the internal battle that we all face while creating: the struggle against Resistance.
Resistance is that invisible force always lurking around the corner. That unnamed figure that conspires against your success. Resistance has many names, such as "fear", "procrastination", and "doubt". But all of these negative forces are simply the different facades of Resistance.
Pressfield's The War of Art helped me define "Resistance" and continue to work in spite of it.
Models
Intentions are always speaking ten times louder than your actual words. What are they saying?
I thought I was going to hate this book. In fact, I originally thought I would hate all of Mark Manson's stuff.
Can you blame me? The guy has written books called The Subtle Art of Not Giving a F*ck and Everything Is F*cked, A Book About Hope.
So yeah, I thought I would hate Manson's stuff. I thought it would be the cringe, in-your-face sensationalistic self-help content that you see plastered across social media.
But I was wrong.
I found Manson's blog back in June, and I was enthralled. He has written more about relationships, traveling, self-confidence, internal demons, sex, and psychology than pretty much anyone else out there.
But the most interesting thing about Manson isn't his library of blog posts. It's that the F-bomb-loving self-help author got his start as a writer by giving guys advice in online dating forums. In bro talk: he helped dudes get chicks.
Six weeks into his first (and only) job with a prestigious bank in Boston, he quit. Around this time, his girlfriend cheated on him. Manson took a healthy approach to the breakup by trying to sleep around as much as physically possible (no better way to suppress those negative emotions!). He started posting in online dating forums, and guys began paying him to go out to bars with them to see how he did it.
Pretty wild career pivot from investment banking, no?
Eventually, Manson compiled everything that he knew about guys, girls, and dating into a book, Models: Attract Women Through Honesty.
Given Manson's backstory, I was intrigued. While most "dating advice," especially advice aimed at guys, consists of shallow gimmicks and tricks to "get" girls, Manson's book clearly defined the roles that emotional connections, honesty, and confidence play in the dating process.
Whether or not you are single or taken, guy or girl, I think you'll find this book interesting.
The Alchemist
It's the possibility of having a dream come true that makes life interesting.
A young man in search of a hidden treasure, a side quest that becomes a life's calling, wise mentors from foreign lands, an unexpected romance, and countless conflicts that almost keep our protagonist from reaching his destination.
The stereotypical Hero's Journey.
And yet, Coelho wrote such a compelling narrative that this "stereotype" melts away. I found myself immersed in the story from page one. The Alchemist set the standard for "Hero's Journey" fiction.
The 48 Laws of Power
When you show yourself to the world and display your talents, you naturally stir all kinds of resentment, envy, and other manifestations of insecurity... you cannot spend your life worrying about the petty feelings of others.
This book is controversial for many. Some view it as manipulative, while others see it as merely describing the realities of power and human interactions.
I thought The 48 Laws of Power was fascinating.
Greene explains the dynamic of power and the means by which it shifts from person to person through stories from history.
Greene is a master historian and storyteller, and I learned as much about human behavior as I did about Napoleon's reign, the rise and fall of Chinese empires, and the fatal blunders of Italian and French monarchs.
Each chapter left me wanting more.
The Order of Time
Because everything that begins must end. What causes us to suffer is not in the past or the future: it is here, now, in our memory, in our expectations. We long for timelessness, we endure the passing of time: we suffer time. Time is suffering.
I still can't wrap my mind around this book. Rovelli is an Italian theoretical physicist who, through this book, explains the realities of "time" to mere mortal readers like me. I don't know what's more impressive, his understanding of time or his ability to explain such an insane phenomenon to someone like me.
A few takeaways:
Time isn't linear.
Everything that will happen has happened, and everything that has happened is happening.
The only thing "linear" is our perception and experience of time itself.
This book is a mind b-e-n-d-e-r.
$100M Offers
Hormozi Law: The longer you delay the ask, the bigger the ask you can make. “The longer the runway, the bigger the plane that can take off.
$100M Deals is the most important book any entrepreneur can read. Hormozi wrote a masterclass work on maximizing the profitability of one's product, service, or business by clearly conveying just how valuable it is to the client.
Is this easy in theory? Probably, but it's excruciating in execution.
Hormozi bootstrapped his way from broke gym owner to multi-millionaire in just a few years thanks to his ability to clearly convey value to clients. Through $100M Deals, he shares his best insights with the world.
Considering that this book is literally $1, you would be crazy not to read it.
A Cook's Tour
I wanted adventures. I wanted to go up the Nung river to the heart of darkness in Cambodia. I wanted to ride out into a desert on camelback, sand and dunes in every direction, eat whole roasted lamb with my fingers. I wanted to kick snow off my boots in a Mafiya nightclub in Russia. I wanted to play with automatic weapons in Phnom Penh, recapture the past in a small oyster village in France, step into a seedy neon-lit pulqueria in rural Mexico. I wanted to run roadblocks in the middle of the night, blowing past angry militia with a handful of hurled Marlboro packs, experience fear, excitement, wonder. I wanted kicks – the kind of melodramatic thrills and chills I’d yearned for since childhood, the kind of adventure I’d found as a little boy in the pages of my Tintin comic books. I wanted to see the world – and I wanted the world to be just like the movies.
It's a damn shame I didn't read/watch more of Bourdain's stuff while he was still alive (RIP). I never realized that it was possible to tell the stories of the world through food, but Bourdain proved that there was no better way to do it.
Bourdain's willingness to travel to the ends of the earth, to share a meal or take a shot with anyone and everyone, is the kind of energy I desire in my life.
And his blunt, comical, sometimes condescending tone of writing makes you feel like you are sitting at the table with him on the other side of the world.
How to Live
Please read slowly.
One line at a time.
I don't know how I found Sivers' book, How to Live, but I remember when I found it. I was on a train from Naples, Italy to London, England (yes, you read that correctly), and I think I saw someone mention the book on Twitter.
I checked out Derek's website, found myself intrigued, and bought his newest work. And I spent the next six hours, between a couple of train rides and a McDonald's in rural Switzerland at 4 AM, reading every page.
How to Live is 27 conflicting tales, poems really, of how one could live their life.
I'm honestly not sure how to describe the book, but each chapter peeled back a layer of my own life.
Shoe Dog
I’d tell men and women in their midtwenties not to settle for a job or a profession or even a career. Seek a calling. Even if you don’t know what that means, seek it. If you’re following your calling, the fatigue will be easier to bear, the disappointments will be fuel, the highs will be like nothing you’ve ever felt.
A former collegiate track star fresh out of Stanford's Graduate School of Business, Phil Knight has no idea what he wanted to do with his life. Nothing except for a half-baked idea for some Japanese running shoes and a desire to see the world.
So he took off to travel the world, and he made a pitstop in Japan to pitch this crazy shoe idea of his.
If you've ever worn a pair of kicks emblazoned with that white Nike swoosh, you know how this story ends.
Knight's entrepreneurial journey is one of my favorites, because the reader sees the full progression of how a disheveled 24-year-old with a sense of wanderlust ends up changing the world.
(It makes sense that I like Knight's memoir, I am partial to a good travel story.)
- Jack
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Jack's Picks
While I don't work for a startup (do I?) I am very interested in the startup scene. CJ Gustafson recently wrote a great piece about the reality of cash burn with startups, check it out here.
For the active investors in the reader base: Contrary Capital has started publishing deep dive pieces on different private tech companies, and the memos are fantastic. If you want to peel back the layers on the business models of some of the biggest private companies like Discord and Canva, check out there site here.
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