People think that leadership is something that just happens. One is anointed a leader. One is promoted to leadership. One is born into leadership. And of course, this is not the case.

“Leadership,” Eisenhower said, “is the art of getting someone else to do something that you want done because he wants to do it.” Which means that, like any art, leadership is something that has to be studied. You have to practice and develop skills. Like an apprentice, you have to get yourself in the vicinity of the greats. You have to, as Marcus Aurelius wrote of his own development as a leader, “go straight to the seat of intelligence.”

No one comes out of the womb a leader. And yet we’re all leaders in one way or another—of families, of companies, of a team, of an audience, of a group of friends, of ourselves. So there’s no one who wouldn’t benefit from learning some of the essential lessons on the art of leadership from some of history’s greatest leaders. Lessons on how to inspire people, lessons on how to survive crises, lessons on how to treat people, lessons on how to learn. These 18 by no means make a complete list, but if you implement even a couple of them, I’m comfortable guaranteeing you’ll be a better leader for it. But perhaps the first and most important lesson we learn from the leaders I talk about below is that leadership is a skill that one could refine over multiple lifetimes—so the sooner you start the better.

A Leader Is A Reader

Harry Truman famously said that not all readers are leaders but all leaders are readers—they have to be. And they certainly aren’t reading to impress people or for the mental gymnastics. It’s to get better! It’s to find things they can use. Not at the dinner table or on Twitter, but in their real lives. “One common characteristic of virtually all great leaders I have known is that they have been great readers,” Richard Nixon would write later in life. “Reading not only enlarges and challenges the mind; it engages and exercises the brain. Today’s youth who sits mesmerized by a television screen is not going to be tomorrow’s leader.” Great advice… that a reader of history also knows that Nixon did not quite live up to. In all, Nixon watched over 500 movies while in office in less than 6 years. Might he have been better served by engaging and exercising his brain? Might he have been better off if he’d had more of his assumptions challenged? A leader must learn from the experiences of others. A leader must be challenged. A leader must prepare themselves for the things they’ll only be able to experience once, by learning from the experiences of others. Because, to paraphrase the soldier-philosopher General James Mattis, it is unconscionable to fill up body bags while you get your education solely by experience, one mistake at a time. A leader must be a reader. It’s not just the best way, it’s the only way. 

A Leader Knows What They Stand For

There’s a story of Mattis, as a very senior officer, who took over guard duty on Christmas so a soldier could be home with his family. These types of gestures abound in the lore around Mattis. There’s the story of Mattis exposing himself to the elements and danger in Iraq like a common soldier and countless other incidents. With modesty, he would attribute these examples of leadership to a philosophy he picked up in his early years as a Marine. “Know what you will stand for and, more important, what you won’t stand for,” Mattis wrote. “State your flat-ass rules and stick to them.” Marcus Aurelius called them “epithets for the self.” Upright. Modest. Straightforward. Sane. Cooperative. Disinterested. Those were his non-negotiables. “If you maintain your claim to these epithets,” Marcus wrote, “without caring if others apply them to you or not—you’ll become a new person, living a new life.” That’s what Mattis believed too. He said having character is harder than having physical courage. The less disciplined, more self-centered, more power-obsessed types of people are everywhere and try everything to make you those things too. Draw the bottom line, Mattis said, remove any uncertainty, clear out the ambiguity until they don’t “come as a surprise to anyone.”

A Leader Accepts Reality On Reality’s Terms

When James Stockdale was shot down over Vietnam and taken prisoner, he knew he would be the highest-ranking POW the North Vietnamese had ever captured. That meant that at the Hỏa Lò Prison, victory for his captors was getting Stockdale to break. He was deprived and tortured and beaten and stripped of his possessions and forced to wear leg irons in solitary confinement for two of the seven years he ultimately spent in solitary confinement. But when later asked if he had it the worst in Hỏa Lò, Stockled said no. Who could have possibly had it worse? “Oh, that’s easy,” Stockdale answered, “the optimists…The ones who said, ‘We’re going to be out by Christmas.’ And Christmas would come, and Christmas would go. Then they’d say, ‘We’re going to be out by Easter.’ And Easter would come, and Easter would go. And then Thanksgiving, and then it would be Christmas again. And they died of a broken heart.” When things are hard, when things are scary, when we’re tired, when we’ve had a run of bad luck, that’s what happens: magical thinking kicks in. This will all be over soon, we convince ourselves. Great leaders resist this kind of thinking. Whether they’re facing a crisis or a downturn or a disruptive competitor or a spectacular losing streak, hope and denial and running away are never part of their strategy. As Jocko Willink told me on the Daily Stoic podcast a few months into the pandemic, the only type of people among his client base of businesses and nonprofits and military leaders who had managed to thrive were the ones who accepted the reality of the situation immediately. Unflinchingly. That’s what Stockdale said too:  “You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be.” It doesn’t matter if you’re in the Hỏa Lò Prison or the midst of the biggest economic crisis of our generation, that’s the only way through. 

A Leader Puts Everything In The Calm and Mild Light

The job of a leader, George Washington said, was to look at all events, all opportunities, all people through the “calm light of mild philosophy.” The phrase comes from the play Cato, about the Roman Senator and Stoic philosopher by Joseph Addison. In a single two week period in 1797, Washington quoted that same line in three different letters. And later, in Washington’s greatest but probably least known moment, when he talked down the mutinous troops who were plotting to overthrow the U.S government at Newburgh, he quoted the same line again, as he urged them away from acting on their anger and frustration. “It shapes and builds up the soul,” Seneca wrote of the calm lights of mild philosophy, “it gives order to life, guides action, shows what should and shouldn’t be done—it sits at the rudder steering our course as we vacillate in uncertainties…Countless things happen every hour that require advice, and such advice is to be sought out in philosophy.” 

A Leader Seeks To Serve Others

Eleanor Roosevelt said that the surest way to happiness was to seek it for others. She was referring to doing good, to being of service. It’s how she found happiness despite the tragic loss of her father, her painful childhood, her troubled marriage. And it’s how she became one of the most powerful and influential female activ­ists in history and America’s most important First Lady. She did good. She made herself useful. She sought relief for others. Marcus Aurelius said that his only job was to do works for the common good. That is: a leader’s only job is to do good. To help others. To be of service. To think less of your problems and try to help others with theirs.

A Leader Is Not Passionate 

A young basketball player named Lewis Alcindor Jr., who won three national championships with John Wooden at UCLA, used one word to describe the style of his famous coach: “dispassionate.” As in not passionate. Wooden wasn’t about rah-rah speeches or screaming from the sidelines. He saw those extra emotions as a burden. Instead, his philosophy was about being in control and doing your job and never being “passion’s slave.” The player who learned that lesson from Wooden would later change his name to one you remember better: Kareem Abdul-Jabbar. 

A Leader Knows What To Prioritize

Success, money, and power can intoxicate a leader. The great ones stay sober because they know what to prioritize. One look at Angela Merkel, one of the most powerful women on the planet is revealing. She lives in an apartment rather than a palace. She is plain and modest—one writer said that unpretentiousness is Merkel’s main weapon—unlike most world leaders intoxicated with position. Or look at Warren Buffett, whose net worth is approximately $65 billion, lives in the same house he bought in 1958 for $31,500. Or San Antonio Spurs star Kawhi Leonard, who gets around in the 1997 Chevy Tahoe he’s had since he was a teenager, even with a contract worth some $94 million. Why? It’s not because Merkel, Buffett, and Leonard are cheap. It’s because the things that matter to them are. It’s not an accident that they’ve become who they are. It’s the result of prioritizing, which allows them the freedom to pursue the things they most care about.

A Leader Sets High Standards 

Football coach Bill Walsh took the 49ers from the worst team in the league to Super Bowl champions in just three years. How? He created a culture of excellence and instilled what he called his “Standard of Performance.” That is: How to practice. How to dress. How to hold the ball. Where to be on a play down to the very inch. Which skills mattered for each position. He knew that by upholding these standards, “the score would take care of itself.”

A Leader Persists 

“Two words,” Epictetus says, “should be committed to memory and obeyed by alternatively exhorting and restraining ourselves, words that will ensure we lead a mainly blameless and untroubled life.” Those two words were ‘persist and resist.’ A leader knows that an obstacle standing in their way isn’t going anywhere on its own. A leader is in it for the long haul. Others might give up but the leader says, as Margaret Thatcher famously did: “You turn if you want to. The lady’s not for turning.” A leader knows that genius often really is just persistence in disguise.

A Leader Does The Right Thing

When the Antonine Plague hit Rome and plunged its economy, fundraising efforts began with a masterstroke of inspirational leadership. As one biographer wrote, the emperor Marcus Aurelius “conducted a two-month sale of imperial effects and possessions, putting under the hammer not just sumptuous furniture from the imperial apartments, gold goblets, silver flagons, crystals and chandeliers, but also his wife’s silken, gold-embroidered robes and her jewels.” Funerals for plague victims were paid for by the imperial state. He audited his own officials and allowed no expenditures without approval. In a crisis, people must trust that their leaders are doing the right thing and that they are bearing the same burden as the citizens—if not a greater one.

A Leader Listens To Feedback

The great ancient Roman historian Cassius Dio contrasted Marcus Aurelius’ greatness against his son Commodus’ fatal flaw. Marcus famously surrounded himself with brilliant public servants and talked about how he would gladly change if anyone could show him he were looking at things the wrong way. Commodus, on the other hand, had “many guardians, among whom were numbered the best men of the senate. But their suggestions and counsels Commodus rejected.” Dio adds that “[Commodus] was not naturally wicked, but, on the contrary, as guileless as any man that ever lived.” This innocent young man became one of history’s most wicked beings because he made the deliberate decision to reject his advisors advice and feedback. As Dwight D. Eisenhower, one of the best commanders of the last century, said of the necessity of listening to feedback: “I have no sympathy with anyone, whatever his station, who will not brook criticism. We are here to get the best possible results.”

A Leader Stands Up and Stands Out

In a famous exchange, the lesser known philosopher Agrippinus said he was spurning an invitation to attend some banquet being put on by Nero. A fellow philosopher, one who had felt inclined to attend, asked for an explanation. Agrippinus responded with an interesting analogy. He said people are like threads in a garment. Most people see it as their job to match the other threads in color and style. They want to blend in, so the fabric will match. But “I want to be the red,” Agrippinus said, “that small and brilliant portion which causes the rest to appear comely and beautiful…’Be like the majority of people?’ And if I do that, how shall I any longer be the red?” He wanted to be red even if it meant being beheaded or exiled.  Because he felt it was right. Because he wouldn’t be anything other than his true self. That’s the leader’s job. It is not to go along to get along. It is not to be another replaceable thread in an otherwise unremarkable garment. The leader’s job is to stand up. To stand out. To speak the truth. As Sam Walker writes in his wonderful book The Captain Class about the unsung leaders who have taken their teams on incredible championship runs, one of the traits great leaders share is they have “strong convictions and the courage to stand apart.

A Leader is Always Composed 

“The first qualification of a general is a cool head,” Napoleon once said. Remaining cool-headed in times of crisis and adversity is one of the most critical skills. The worst that can happen is not the event itself but the event and you losing your cool.

A Leader Doesn’t Make Problems Worse

Chris Hadfield, the astronaut, reminds us that there is “no problem so bad that we can’t make it worse” (and panicking is often a way to do that). Yet how many of us have had bosses we didn’t want to keep informed about problems because if we did, they’d only make solving them harder? Leaders have to be a source of good energy and solutions. They can’t make hard things harder—they need to make hard things easier for their employees or followers. That’s the job.

A Leader Prepares  for Chaos 

As the legendary coach Phil Jackson would explain, “Once I had the Bulls practice in silence; on another occasion I made them scrimmage with the lights out. Not because I want to make their lives miserable but because I want to prepare them for the inevitable chaos that occurs the minute they step onto a basketball court.”

A Leader Has a Guiding Philosophy

I mentioned Bill Walsh’s “Standard of Performance” philosophy above. Seahawks coach Pete Carroll is known for his “Win Forever” philosophy—the winning mindset he aims to instill in his staff and players. The great coach John Wooden had his “Pyramid of Success” philosophy. These philosophies and frameworks are critical as they codify the principles and rules by which a team will make decisions and operate on a day-to-day basis. If you don’t have a philosophy, how do you expect to know what to do in tough situations? Or when things are confusing or complicated? Being reactive is never a position of strength. It is not a position a leader should find themselves in.

A Leader Gets The Best Out Of People

Aside from Marcus Aurelius’ 3-page recount of everything he learned from his mentor, Antoninus Pius is largely forgotten by history. Ernest Renan wrote that if he hadn’t groomed Marcus so successfully, his name would today be to us what Marcus’ is. All his adult life, Marcus strived to be a disciple of his adopted step-father, to whom he saw, according to the french philosopher Ernest Renan, as the “the most beautiful model of a perfect life.” What was the most important lesson he learned from Antoninus? “This in particular,” Marcus said, “his willingness to yield the floor to experts—in oratory, law, psychology, whatever—and to support them energetically, so that each of them could fulfill his potential.” This in particular because it would have been more natural for him to have often been frustrated and disappointed with people. It’s something that lots of brilliant leaders and talented people have wrestled with through the centuries—they expect of others what they expect of themselves, so they are constantly upset and let down. We know that Marcus found a better way through. “So long as a person did anything good,” Cassius Dio wrote, “he would praise him and use him for the service in which he excelled, but to his other conduct he paid no attention.” That’s key for anyone in any position of leadership. Your standards are for you. You only control your behavior. You have to meet everyone else where they are. Get as much as you can from them and of them. See the good in them. Lean into their strengths rather than disdain their weaknesses. Focus on what is special and unique about them instead of zeroing in on the ways they are not as good as you. That’s not only the kind way to lead, it’s the only effective way.

A Leader Isn’t All About Business

Randall Stutman has been a coach to some of Wall Street’s biggest CEOs for decades. His clients have included Goldman Sachs, Morgan Stanley and Bank of America. His consulting and advising agency, CRA, has worked with thousands of executives at hundreds of hedge funds and banks. These are people whose entire livelihood depends on them being perpetually ready to respond to the daily, hourly, sometimes even minute-by-minute volatility of the world’s financial markets. Stutman surprised me when he told me that he often asks these very busy executives how they recharge, given the all-consuming nature of their work. The best, he found, have at least one hobby that gives them peace — things like sailing, long-distance cycling, listening quietly to classical music, scuba diving, riding motorcycles, and fly fishing. There is a surprising commonality between all the hobbies: An absence of voices. For leaders, people who make countless high-stakes decisions in the course of a day, a couple hours without chatter, without other people in their ear, where they can simply think (or not think), is essential.

P.S. On Monday, we announced what is the longest and most in depth course ever built over at Daily Stoic. It’s one I’ve been working on for 6 months, The Daily Stoic Leadership Challenge: Ancient Wisdom For Modern Leaders. It features 63 total emails, packed with the best wisdom from the Stoics on what it takes to become a great leader. I also assembled some of today’s great leaders to be for you what Antoninus was for Marcus, as I mentioned above. Once a week, there will be a Leadership Deep Dive—a live video session where I’ll be interviewing a guest with expertise on that week’s theme before we open it up to questions from course participants. Randall Stutman is actually one of those leadership experts. He’s been a coach and a mentor of mine over the years, so I’m excited to be able to bring him—as well as military generals and pioneering businesswomen and CEOs of professional sports teams, among others—into the Daily Stoic community. I’m really excited about this course. I think it’s going to be one of our best. I would love to have you join us—you can learn more at dailystoic.com/leadershipchallenge

It is with some pride that I can think of some “big” things I have passed on doing.

Tickets to the Super Bowl.

A trip to Necker Island.

More than a few different book deals.

I’m not proud because I think I am better than those things, it was just that I had better things to do with that time, at that time. Sometimes it was family, sometimes it was cooler work opportunities, sometimes it was just because I was exhausted and I needed to rest. 

Just because you’re offered something that might be good for your career, that would definitely feel good to your ego, that most people would have said yes to, doesn’t mean you have to listen to your ego and accept the offer. You can say NO.

It’s easy to forget that, especially with peer pressure and FOMO, but it’s true. 

There’s a great quote from Nassim Taleb:

“You are rich if and only if money you refuse tastes better than money you accept.”

I didn’t need it. I had competing interests. I could say “No,” so I did. 

That’s a rich feeling, that’s only tangentially related to money.  

Yet if I am being honest, like most people, it’s not one I indulge myself in enough.

In the last year, as the pandemic radically reoriented so many parts of everybody’s lives, I was reminded painfully of what economists call opportunity costs. I’ve always been productive and disciplined, so I was under the impression that even with all my traveling and various projects, I wasn’t suffering much for it. 

I was producing books, after all. I spent lots of time with my kids. I was exercising. I was writing my daily emails for Daily Stoic and Daily Dad, my Reading List Email each month and this email each week. Obviously there was no problem with the things I had been accepting to that point. But in having so much suddenly taken away, I was given the gift of seeing what all the busyness was actually costing me.

The last twelve months have been the most creatively fulfilling and productive months of my life. It turns out (surprise!) that being home for bath and dinner every single night had a massive impact on my relationship with my young children, their behavior and my marriage. 

Obviously the costs of this had been there all along, I just wasn’t aware of them—or I was denying them. Even if you’re aware that you’re, say, 80% as effective while on the road as you are when you’re at home, in your routine, it’s easy to miss the simple math: Four days of traveling is the equivalent of taking a full day off…without the benefits of, you know, a day off. 

So while I do take pride in some of the things I’ve said no to over the years, the reality is that I have been undisciplined more often that I was disciplined. I may have been producing…but it wasn’t as good as it could be. And when it didn’t feel like work was suffering, it was only because other parts of life were.

All those meetings I didn’t really need to go to. Those clients I really didn’t respect or like that I worked with anyway. Interview or press that I did because it was flattering. The time when my kid wanted my attention, but I was glued to my phone, to some email—so glued that my “no” was implicit. I didn’t have to be somewhere else. I was home…and yet I was gone all the same. 

You have to understand: Everything you say “YES” to in this life means saying “NO” to something else. 

The decision to agree to that coffee meeting means saying no to an hour of reading. The decision to hop on this Zoom call means not hopping on the bike and getting some exercise in . The decision to stay up late to watch another episode of some mindless television show or scroll on your phone is saying no to a productive early morning. The decision to go to some conference across the country means missing one of those meaningful developmental moments with your young kids right there at home.  

Which of these will you get more out of? Which will produce the growth you seek? Which will you remember ten years, ten weeks, hell, ten days from now?

Why is it so hard for us to see this? Inertia for one. Ego for another. We identify with being busy, we think it’s taking a step towards our best work, but that’s because we’re blinded to the long-term costs. 

There is a haunting clip of Joan Rivers, well into her seventies, in which she is asked why she keeps working, why she is always on the road, always looking for more gigs. Telling the interviewer about the fear that drives her, she holds up an empty calendar. “If my book ever looked like this, it would mean that nobody wants me, that everything I ever tried to do in life didn’t work. Nobody cared and I’ve been totally forgotten.” 

That’s an attitude that creates a lot of work, but does it create anybody’s best work? No, desperation stinks. It corrupts. It wears you down. 

What kind of rich life is that? 

You have to be able to say no. You have to be able to pick your shots. And if success doesn’t earn you that right, what kind of success is it? If you’re not strong or free enough to pass on things, are you really that strong or free?

In fact, really caring about your work is a great reason to need to be able to say no to stuff. 

A pilot gets to say, “Sorry, I’m on standby,” as an excuse to get out of things. Doctors and firemen and police officers get to use being “on call” as a shield. But are we not on call in our own lives? Isn’t there something (or someone) that we’re preserving our full capacities for? Are our own bodies not on call for our families, for our self-improvement, for our calling? 

I want to remind you (and myself) to always think about what you’re really being asked to give. Because the answer is often a piece of your life, usually in exchange for something you don’t even want. Remember, that’s what time is. It’s your life, it’s your flesh and blood, that you can never get back.

And when we get better at saying “No,” we get to experience the benefits of the flip-side of what I said above. Because everything we say “No” to means you’re saying “Yes” to something else. 

To your important work.

To your health.

To the people you love.

Even to just a moment of stillness in a busy life.

You deserve that. You’ll be proud of yourself if you do it. 

P.S. For a limited time, the ebook edition of my book Stillness is the Key is nearly 90% off! Whether you want to get better at saying NO or at knowing what to say YES to, whether you’re overwhelmed with opportunities or with problems and uncertainties and emails and notifications and alerts and one thing after another—Stillness is the Key is for you. It is a formula for keeping steady, disciplined, focused, and at peace, so you can access your full capabilities. It was an instant #1 bestseller and will not be on sale for long so grab it now! Or if you prefer hardcover, you can order those in the Daily Stoic store, where you can also get a personalized signed copy.

Warren Buffett considers the foundation of his multi-billion dollar empire to be a book. At 19 years old, he bought a copy of The Intelligent Investor by Benjamin Graham. We don’t know exactly what he paid for it, but in the early 1950s, a hardcover typically went for $1.30. Today, Buffett’s worth $108.7 billion, having given away some $37 billion to charitable causes. 

Not a bad ROI!

Some people might recoil at categorizing a book that way, but as a lover of literature, I have no problem with it. I myself wouldn’t be writing this to you today if I hadn’t bought a copy of Meditations in 2006 for $8.25 on Amazon. That book of philosophy taught me not just about life, but also schooled me in the art of writing, in working with and managing people, and gave me the speciality which I now write my own books about. Again, not a bad ROI!

One of the questions I get most is about business and marketing books specifically. In school, kids are already assigned literature and history. But about books that teach you about business? About money? About building something? About getting people interested in what you’ve built? 

There are some amazing, life-changing books in these categories, some of which also rank among the best investments I’ve made in my life. I returned to many of them during the crazy twelve months of renovating and opening our new bookstore during the pandemic. And now, we carry many of the books below at The Painted Porch.

If you’re looking for a business education, these 18 books are a lot cheaper than an MBA.

Enjoy!

Billion Dollar Lessons: What You Can Learn from the Most Inexcusable Business Failures of the Last 25 Years by Paul B. Carroll and What I Learned Losing a Million Dollars by Jim Paul and Brendan Moynihan 

Any fool can learn by experience, I prefer to learn by the experiences of others, is how Bismark put it. Most business books are about what went right. This one isn’t. It’s about painful failures. The ones that get repeated over and over and over. This book will humble future CEOs and keep them conservative—which is an important balance for any ambitious person. Pair Carroll’s book with the story of Jim Paul, who made some successful moves to become the Governor of the Chicago Mercantile Exchange, which convinced him that he was special, different, and exempt from the rules. Once the markets turned against his trades, he lost it all — his fortune, job, and reputation. That’s what makes this book a critical part in understanding how letting arrogance and pride get to your head will ruin your business. Learn from stories like this instead of by your own trial and error. Think about that next time you believe you have it all figured out. (Tim Ferriss produced the audiobook version of this, which I recommend.)

The Fish That Ate the Whale: The Life and Times of America’s Banana King by Rich Cohen  

This book tells the incredible story of Sam Zemurray, the penniless Russian immigrant who, through pure hustle and drive, became the CEO of United Fruit, the biggest fruit company in the world. The greatness of Zemurray, as author Rich Cohen puts it, “lies in the fact that he never lost faith in his ability to salvage a situation.” For Zemurray, there was always a countermove, always a way through an obstacle, no matter how dire the situation. That’s why, although he was a morally complicated man, I used his story in The Obstacle is the Way. You can listen to my interview with Rich Cohen here as well.

Shoe Dog: A Memoir by the Creator of Nike by Phil Knight  

This is the memoir of the founder of Nike, it’s really the story of a lost kid trying to find meaning in his life and it ends with him creating a multi-billion dollar company that changes sports forever. What I love about this book is that 90% of it is about the early years. It’s not about how to sign Jordan, but about how he sold shoes out of the trunk of his car. The main thing I took from it? You actually have to love the thing you’re going into business to sell. Live and love it and breathe it.

Essentialism: The Disciplined Pursuit of Less by Greg McKeown  

This is a book that focuses you, that makes you question many of the projects and commitments and assumptions you’ve said yes to over the years. Though the book is about applying design-style thinking to your life, I really think it is just a solid book of philosophy, stories and anecdotes that make you reconsider your priorities. That’s all you can hope for from a book and it more than delivers, as Greg did when he came on the Daily Stoic podcast.

Good to Great: Why Some Companies Make the Leap and Others Don’t by Jim Collins 

There is a little pseudo-science to Collins’ research but I don’t care about that. This is a great book. He creates a framework for how to think about building a great company. You get the right people on the bus, you spend time and energy winding up the flywheel and if you’re lucky you break through. It’s not a complicated formula but the examples in this book are helpful. Even if you don’t read it, the title is helpful. You don’t want to be good, you want to be great.

Purple Cow: Transform Your Business by Being Remarkable by Seth Godin 

You wouldn’t tell anyone that you saw a cow. You would tell them if you saw a purple cow. Seth wrote this book many years ago but it’s a classic because it says something basic, timeless and important. Make remarkable things, do remarkable marketing. It’s the best way to grow. It’s the best way to sell. Even Jay-Z has recommended this book—to Oprah no less! As a marketer, the clearest takeaway from the book is: Represent people who stand out, it makes it easier to do what you do. 

The 22 Immutable Laws of Marketing: Violate Them at Your Own Risk! by Al Ries and Jack Trout 

It’s a quick read, but I think you’ll come away with one or two key lessons that with stick with you. Personally, I found the valuable lessons were a bit front loaded (the first couple laws are the best). In short: turns out the best “marketing” decisions you’ll make come long before the paint is dried (or even applied) to the product. Forget the notion that marketing is something that is applied after the product is completed and aim to achieve Product-Market Fit. As I write in Growth Hacker Marketing, the single worst marketing decision you can make is to work on a product that nobody wants.

Blue Ocean Strategy: How to Create Uncontested Market Space and Make Competition Irrelevant and Blue Ocean Shift: Beyond Competing – Proven Steps to Inspire Confidence and Seize New Growth by W. Chan Kim and Renee Mauborgne  

The best law in the 22 Immutable Laws of Marketing is “invent your own category.” Well, Blue Ocean Strategy is entirely about that. It’s about competing where there is the least amount of competition. It teaches you how successful businesses focus on being different, about carving out a new space for themselves. Instead of battling numerous competitors in a contested “red ocean,” it’s far better to seek fresh, uncontested “blue” water. If Blue Ocean Strategy is the what behind the theory of creating new markets rather than competing in crowded ones, then Blue Ocean Shift is the how and the mindset required to do so. Lots of good examples in this book, including a bunch that are not from business (“blue ocean” thinking also applies to government, NGOs, leadership, etc.).

The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future by Chris Guillebeau

This book is my favorite of Chris’s and a must read. You don’t have to have a lot of money to start a company, and not every idea has to be some massive world changing thing. Start small. Be smart. Be creative. I talked about those themes and more when I interviewed Chris in early April of 2020 while he was feeling the fresh sting of having to cancel a 40-city tour for his then just-released book, The Money Tree.

Leadership: In Turbulent Times by Doris Kearns Goodwin

This is an absolutely incredible book—a study of Abraham Lincoln, Theodore Roosevelt, FDR and Lyndon Johnson. It is so clearly the culmination of a lifetime of research… yet somehow not overwhelming or boring. Distillation at its best! Even stuff I already knew about those figures, I benefited from Goodwin’s perspective. This is the perfect book to read right now—a timely reminder that leadership matters. Or as the Stoics say: character is fate. Or as I wrote about in this piece about leadership during the plague in ancient Rome: when things break down, good leaders have to stand up.

The Hard Thing About Hard Things: Building A Business When There Are No Easy Answers by Ben Horowitz 

Ben Horowitz wrote a fantastic book. If it was the only thing he’d ever done, I’d consider him a master. But it’s not. Building billion-dollar companies, slogging through the depths of multiple recessions, mentoring hundreds of entrepreneurs—these are the things Ben does for his day job. Writing for him is just a side project distilling that hard won experience into lessons we can use. This book is inspiring, it’s honest, it’s practical and it’s actually real. There’s a reason Horowitz’s essays have taken hold online second only to those of Paul Graham. 

Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers by Tim Ferriss  

We talked about ROI at the beginning of this piece. The question to ask yourself with this book is, What’s one life-changing tool worth? What’s one solid new habit worth over the course of a life? Because that’s what you will find in here. Emerson talked about how we can learn something from everyone we meet, because everyone is better than us at something. Tim is a master at learning something from everyone he meets, interviews, works with and then sharing that wisdom with us. 

Titan: The Life of John D. Rockefeller Sr. by Ron Chernow

I found Rockefeller to be strangely stoic, incredibly resilient, and, despite his reputation as a robber baron, humble and compassionate. Most people get worse as they get successful, many more get worse as they age. In fact, Rockefeller began tithing his money with his first job and gave more of it away as he became successful. He grew more open-minded the older he became, more generous, more pious, more dedicated to making a difference. And what made Rockefeller stand apart as a young man was his ability to remain cool-headed in adversity and grounded in success, always on an even keel, never letting excessive passion and emotion hold sway over him. That’s why I used his story to open the discipline of perception section of The Obstacle is the Way. 

The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success by William N. Thorndike

This book is also one of Warren Buffett’s favorite books. Instead of focusing on celebrity business figures who were good at self-promotion, it studies the heads of companies like the Washington Post, Berkshire Hathaway, General Dynamics, Capital Cities Broadcasting, TCI, and Teledyne who created billions of dollars of wealth through a series of unorthodox business and leadership strategies we can all learn from. I discovered the book after reading Katharine Graham’s epic autobiography—an exceptional leader and CEO.

Empire State of Mind: How Jay Z Went from Street Corner to Corner Office by Zack O’Malley Greenburg

This is a biography that also functions as a business book. It shows how as a young man in Brooklyn, Jay applied hustling techniques to the music business and eventually built his empire. A true hustler, he never did only one thing — from music to fashion to sports, Jay dominated each field, always operating on the same principles. As he puts it, “I’m not a businessman, I’m a business, man!” And related to that, I also recommend The 50th Law, which tells the stories of many such individuals and will stick with you just as long.

Oh and one more book…by me.

Perennial Seller: The Art of Making and Marketing Work That Lasts by Ryan Holiday

Perennial sellers are books like What To Expect When You’re Expecting, Good to Great, The Great Gatsby, movies like “The Shawshank Redemption” or “A Christmas Story,” or songs like “Happy Birthday” or “Candle In The Wind.” It’s products like Red Wing’s 1907 Work Boot (which confusingly only dates back to the 1950s) or restaurants like The Original Pantry, which has been open every single day since 1924. People think that perennial sellers are created by accident. The truth is that when you study them, there are all sorts of lessons to be learned from the classics, there are timeless principles to be applied in your own pursuit to make something that lasts.

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Of course there are many other books that belong on this list. If you want some more related book recommendations, here is a list of essential strategy books, biographies and you can get books recommended each month by signing up here.