2016 was a busy year of writing for me (and reading—but that’s in a different post). Not only did I publish two books, and launch the new daily newsletter for DailyStoic.com, but I wrote something like 100 articles. Back of the envelop math, that comes to roughly 2 articles per week, and ~150,000 words (all in that’s probably 275,000 words not including ghostwriting). There were times where I felt a little bit like I was stretching myself too slim, but I’m actually hoping to do more, and do even better writing in the year to come.
Anyway, in case you missed any of them or are looking for something to read, I thought I would put them here—all in one place. I also recently put up a page on this site that highlights some of my favorite posts I’ve written from the last ten or so years. You can also sign up to get the posts via email when they happen by clicking here.
Every year, I try to narrow down the hundred plus books I have recommended or read down to just the three or four best. I know that people are busy, and most of you don’t have time to read as much as you’d like. There’s absolutely no shame in that–what matters is that you make the time you can and that you pick the right books when you do.
They are books that I and the 70,000 readers on my reading list email have enjoyed and learned from. If they had been all that I had read over the last twelve months, I’d have considered 2016 a successful year of reading.
In January, I picked up my first book in this Caro’s series on Lyndon Johnson. It wasn’t until June that I finished my fourth, but I consider finishing all of them to be one of my proudest reading achievements. (FYI, I started withThe Passage of Power, then read The Path to Power, then Means of Ascent andMaster of the Senate. The order didn’t seem to matter.) It’s unquestionable to me that Caro is one of the greatest biographers to ever live. His intricate, complicated, sprawling investigation into Lyndon Johnson will change how you see power, ambition, politics, personality and justice. If there is one line that sums up the whole series it’s this: It’s that power doesn’t only corrupt. That’s too simple. What power does is reveal. It’s also easy to be disillusioned by politics right now but for me, getting lost in these Lyndon Johnson books has been a helpful and educational process. Because you learn two things 1) that things have always been complicated and confusing but they tend to turn out alright 2) that our system, whatever its flaws, can still produce good results from bad men.
After the Caro series, I started William Manchester’s equally epic three volume set on Winston Churchill (Visions of Glory, Alone, Defender of the Realm) which Robert Greene gave me as a wedding present last year. Like all truly great long reads, you learn not just about the subject but every intersecting one: the history of British peerage, the Victorian era, the British Empire, Colonialism, modern warfare, international relations, evil, the nature of genius, the effects of absent parents. The book is masterfully written about a masterful man—Churchill was a soldier, a writer, a politician, a statesman, a strategist and a true great man of history. Each book in the series is equally distinct and interesting. The first is Churchill as a young, ambitious man. The second is his time in the political wilderness, when his ego has driven him from power and into writing and thinking. The third is his time back on the world’s stage, in what was perhaps the finest hour of any empire in any era. The last book is probably the best. It features the famous bulldog version of Churchill: rescuing the troops at Dunkirk, persevering through the Blitz, vowing to fight on the landing grounds and the beaches and in the streets, whatever the cost may be. The sheer determination of this man, to take an entire country on your back and defy a horde which had overrun the European continent in a matter of months…it’s almost breathtaking to think about.
As I said, if you were to only read one thing in the next year, you could do a lot worse than either of these series. They contain dozens of books within them and will teach you about so much more than just the man they are ostensibly about. Please, please read them.
As a general rule, most new memoirs are mediocre and most business memoirs are even worse. Shoe Dog by Phil Knight is an exception to that rule in every way and as a result, was one of my favorite books of the year and favorite business books ever. I started reading it while on the runway of a flight and figured I’d read a few pages before opening my laptop and working. Instead, my laptop stayed in my bag during the flight and I read almost the entire book in one extended sitting. Ostensibly 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. I’m not sure if Knight used a ghostwriter (the acknowledgements are unclear) but his personal touches are all over the book—and the book itself is deeply personal and authentic. The afterward is an incredibly moving reflection of a man looking back on his life. I loved this book. It ends just as Nike is starting to turn into the behemoth it would become, so I hold out hope that there may be more books to follow. In terms of other surprising memoirs, I found JD Vance’s Hillbilly Elegy to be another well-written gem and despite its popularity, When Breath Becomes Air is actually underrated. It’s make-you-cry good.
I thought I’d read this book before but clearly they gave me some sort of children’s version. Because the one I’d read as a kid wasn’t a 1,200 page epic of some of the most brilliant, beautiful and complicated storytelling ever put to paper. What a book! When I typed out my notes (and quotes) after finishing this book, it ran some 3,000 words. I was riveted from cover to cover. I enjoyed all the stuff I missed as a kid: the Counts struggle with his faith in light of what was done to him, the Hundred Days of Napoleon’s return, his rants against technology, the criticism of newspapers, the influence of ancient philosophy, ultimately, a warning against being consumed by revenge. Please—if you’re going on a long trip or looking to check out of modern events for a while—get this book. I recommend the Penguin Classics edition.
Revenge books seemed to be a trend for me this year. I loved Michael Punke’s The Revenant, about a man who bravely challenged his fate in the wilderness just as Edmond Dantes did in prison. This year I also re-read Walker Percy’s Lancelot, a dark story of revenge and an attempt to go to the heart of evil. Less dark, but equally epic, I also loved (and raved about repeatedly) Aaron Thier’s new novel Mr. Eternity. If you read a lot of non-fiction, do yourself a favor this year and set aside some time for some serious fiction reading. You can learn just as much and be changed just as much by a truly great story as you can by any business or self-help book.
Strategy isn’t something that’s taught well in school. Hell, most people probably couldn’t tell you the difference between “strategy” and “tactics” (or even know there is a difference.)
This is unfortunate, because strategy is something that is critically relevant to all of us – not just those with careers in the military. We all have goals, we all have obstacles to those goals and we all live in a world we do not control. Those things combine to create the necessity of strategy.
The better we are at it – the better we are at doing what we want and need to do.
How do I accomplish what I need to accomplish? How do I find my way, deliberately, instead of stumbling around, in a reactionary fashion? Too many of us live our lives in a sort of haze, acting without a plan or guidance. Too many of us make unnecessary mistakes (costly ones at that), because we lack the ability to craft a strategic vision and a plan.
Like I said, this isn’t exactly our fault. No one taught us explicitly how to do things differently. But the good news is that such instruction is out there. Wise thinkers have been writing and teaching strategic expertise for thousands of years. The problem is knowing where to start.
In this list I want to give you some of the best (and most accessible) books, essays and documents about strategy. Used properly they will help you craft your strategic mind. You were born to be a strategist, it’s up to you to become that destiny.
This book – of a long forgotten war – really functions as a biography and strategic analysis of some of the greatest minds in the history of war. We have Pericles, Brasidas, Alcibiades and many others.
The anecdotes and the stories in this book are timeless. If you make your way all the way through it, I promise you will not forget it. Because the war was so long, involved so many different countries and was so varied (sea, land, siege, politics), it basically covers every type of situation you can think of.
Think of this book as a textbook. Read it. (But it is dense so if you need some help, try this.)
Both Hillary Clinton and Barack Obama studied Alinsky extensively as they mapped their individual paths to power. He is the real originator of the concept of community organization.
Alinsky was also a die hard pragmatist, a man who had ideals but also a sense for working with and through the system to get what he needed. In fact, his best examples in these books is actually how to use the system against itself to get what he needed. These two books are classics and woefully underrated. Read them now.
This is probably the most definitive and comprehensive narrative of power ever written.
It maps the entire career of the city planner Robert Moses. I know that doesn’t seem like a particularly illustrative case study for power and strategy but Robert Moses lived power. He controlled the expansion and the building of civilization’s most advanced and important city–and he did it because he was a strategic genius (and of course, a power addict).
This book will take weeks to read but it will stick with you forever. After you are done, I promise you will not forget or ever underestimate the importance of hidden influence, power and levers again.
Of course, I am biased because I trained under Robert. But if I had not, these books still would have given me a priceless education (as they have for millions of other people).
Robert is a crack researcher and storyteller – he has a profound ability to explain timeless truths through story and example. You can read the classics and not always understand the lessons. But if you read Robert’s books, I promise you will leave not just with actionable lessons but an indelible sense of what to do in many trying and confusion situations. Also the extra benefit of reading Robert is that you get mini-bios of strategic geniuses like Napoleon, Edison, Machiavelli, Caesar, Cortez, and others.
This short essay from Plutarch is about an important strategic (and life) lesson. Our enemies and our obstacles are always teaching us. There is always some lesson or advantage we can derive from them. But we must make ourselves open to this. We must cultivate an attitude that welcomes these lessons rather than fights against them.
Like Greene, Hart has the ability to communicate and explain timeless truths about strategy and power. Reading one of his books is the equivalent of reading many other primary texts because he so expertly synthesizes and communicates what lies within them. He is also eminently quotable–which makes the lessons that much easier to recall. For instance, he reduced Sherman down to a simple line: Attack along the line of least expectation, and tactically along the line of least resistance.
Boyd was a world class fighter pilot who changed warfare and strategy not just in the air, but on the ground and by sea. His concepts pioneered the modern concept of maneuver warfare (and were used for the First Gulf War). His method of problem solving and problem analysis – known as the OODA Loop – is now used in boardrooms and everywhere else. He also perfected the art of “Getting Things Done” whether that was in war or in the bureaucracy of the Pentagon. You need to know and understand John Boyd.
Musashi was a different kind of strategist, which is why his book is so important. Most of us won’t find ourselves leading armies anytime soon. As a swordsman, Musashi fought mostly by himself, for himself. His strategic wisdom, therefore, is mostly internal. It’s about the mindset, the discipline, and the perception necessary to win in life or death situations. He tells you how to outthink and outmaneuver your enemies. He tells you how to fend for yourself. And isn’t that precisely what so many of us need help with everyday?
Of course, this is a must read. Machiavelli is one of those figures and writers who is tragically overrated and underrated at the same time. Unfortunately that means that many people who read him miss the point and other people avoid him and miss out altogether. Take Machiavelli slow, and really read him. Also understand the man behind the book–not just as a masterful writer but a man who withstood heinous torture and exile with barely a whimper.
Machiavelli is a glimpse into a time when power was literal and out for public viewing–when he talks about making an example of someone, he doesn’t mean calling them out, he means putting their head on a pike. Don’t let that scare you because we’re not as far from that world as we’d like to think. Deny that at your own peril.
What’s interesting about Jackson’s approach is how eastern it is–he guides by giving up control, he leads by encouraging other leaders, he favors movement over resistance. He has articulated these concepts in an incredibly accessible way in his most recent book and I strongly suggest everyone read it.
These two books are the two best books of political thinking and theater from both the left and the right.
Regardless of ideologies, both are experts in influencing and leading public perception through image and words. It actually matters whether we’re talking about illegal immigrants or undocumented workers, or whether we describe the problem as climate change or global warming.
Strategists need to understand the power of language and framing–it doesn’t matter how right you are, if you lose this battle it can be impossible to rally people to your cause. Read both these books.
I just finished this book and, goddamn, Washington’s status as an icon shamefully understates his genius as a strategist.
The man had an impeccable intuition for timing, for gestures, for politics, for the moment to strike, not just on the battlefield but in relationships, in office and in his private life.
We must study Washington not only for his nearly unbelievable military victory over a superior British Army, but also for his strategic vision which quite literally was responsible for many of the most enduring American institutions and practices.
I admit this book is long, but it is so good. It is packed with illustrative examples, analysis and stories. Read it.
I know this will offend many strategy purists, but for most audiences I recommend these two books only with a pretty strong disclaimer.
While both are clearly full of strategic wisdom, they are hard to separate from their respective eras and brands of warfare. As budding strategists in business and in life, most of us are really looking for advice that can help us with our own problems. The reality is that Napoleonic warfare does not exactly have its equivalents in today’s society.
On the other hand, Sun-Tzu is so aphoristic that it’s hard to say what is concrete advice and what is just common sense. But the books are so convincing that you might still end up leaving thinking that they can be easily applied. So, again, check these books out if you’re really interested, but I think some of the other books are much better places to start.
This might feel like a weird book to include, but I think it presents another side of strategy that is too often forgotten.
It’s not always about bold actors and strategic thrusts. Sometimes strategy is about subtle influence. Sometimes it is framing and small tweaks that change behavior.
We can have big aims, but get there with little moves. This book has excellent examples of that kind of thinking and how it is changing politics, government and business. My favorite example is about the bumblebee that they started putting on urinals–which drastically reduced the amount of spray and spillage because it changed where men aimed when they peed. It’s not exactly the coolest strategy but it solved a problem. So we can learn from it.
I am putting this book on here as a cautionary tale for all the supposed business strategists out there. Because it turns out that most (if not all) genius business strategies are totally misguided and lead to catastrophic failure.
Your planned merger, roll up, pivot–it’s probably got glaring strategic flaws in it. Why? Because you’re too caught up in your own vision to see what can go wrong, to see where you’ve been overly optimistic, to accept how little you control.
Pairing this book with some of the books on war is a good idea. It will humble you and keep you conservative–which all good strategists are. “Boldness” should be used sparingly because it’s often actually just stupidity in disguise.
It probably seems weird to recommend books on pickup artists, pick pockets and con men (nor am I necessarily equating the three groups) but it fits.
Though I would accept that most of what these guys do is tactical rather than strategic—they are still quite excellent at identifying opportunities and weaving such flawless, enveloping plans that the marks often have no idea that anything is actually occurring.
A favorite con example is the one where the con man sets up a fake boxing match that he agrees to “fix” with his mark. Taking the marks money, he then fakes the fake boxing match so that it appears that one boxers kills the other in the ring. He and the mark then flee the scene in opposite direction to avoid the police–the mark thinking he got away with murder, when really he was robbed.
The Game is about seduction, literally, but the other two books are about seduction in their own way as well. These books are all classics and will help you, no matter what you do.
These two men won the Civil War despite numerous obstacles.
In many ways, the war was the South’s to lose–they possessed all the territory they wanted at the beginning of the war, they faced a divided enemy, and all they had to do was wait the North out.
The America we live in today is what it is because of the strategic genius and partnership of the Grant and Sherman. Sherman understood the grand strategy of the war–that it depended on crushing the morale of the Southern cause. Grant understand and held the determination required to muddle through battle after battle (along with the destructive politics).
Sherman’s march through the South was a masterwork of planning and vision. Grant’s slow maneuvering of Lee, meant that Lee (who I think is massively overrated) could do nothing to stop it. These two books, written by the men themselves, are about totally unique and priceless historical documents.
Strategy is a rabbit hole that never ends. I am not saying that my list is conclusion–I know it doesn’t even come close. I am just trying to get you started.
I hope these books help. I hope they begin to bring out the strategist inside you. Because there is one there–and whatever you’re working on it will benefit from cultivating that side of yourself.
Now get reading and then get working. Because every word you read in these books become more valuable the more experience you combine it with. Don’t just read about strategy, live it.