“The difference between you and the people you admire, is books.” — Paul Provenza
What follows are the best of the books I’ve read since 2013. For me, the regular input of this high-quality information transformed my effectiveness and added velocity to my career. It’s been like an OS upgrade for my brain, so I like to refer to this as “Brain 2.0”. Enjoy.
While these sections are in no particular order, I have ordered the book recommendations within each section in the order I’d recommend reading them. I’ve also linked to each title on Amazon.
Leadership
Leaders Eat Last by Simon Sinek
Simon Sinek does a better job than anyone else I’ve read at capturing the human components of work, strategy, and leadership. Where most people think about leadership as tackling objectives through a team, Sinek disagrees with this model of leadership. The team is doing the thing, so your job as the leader is to make sure they’re taken care of, supported, and most importantly made to feel safe in their work so that they are actually free to do the things they’re responsible for from a place of confidence and collaboration. If that sounds touchy-feely that’s because it is. This is emotional territory and the sooner we quit pretending that there isn’t a very real, very scary dimension to work the better off we’ll be.
Sinek uses neuroscience to help us understand the relationship between how safe we and our teams feel at work and our ability to do our best work and especially our ability to work together and collaborate. Safety breeds trust and creativity and innovation inevitably follows. Try to innovate without that sense of belonging and you’ll still get somewhere, but you won’t get where you could have gone if your people felt safe and appreciated.
Not simply a guide to emotional intelligence at work, Sinek also gives an important history lesson about how things like using layoffs to balance the books has only recently become accepted practice and are not the default business practices they’re made out to be. He gives multiple case studies of businesses that instead of choosing their quarterly profit margin instead chose their people and went on to succeed because of it.
The Infinite Game by Simon Sinek
A worthy follow up to Leaders Eat Last, Simon Sinek is back and he’s zoomed out from the team level to the business world at large drawing a clear difference between leaders and companies who have a clear mission and those who are simply chasing quarterly profits. The key difference: the kind of game they think they’re playing. If a company is trying to “win” at business and just use profits as their scoring system then they’re playing a finite game, like football. Sinek thinks companies playing a finite game won’t last, and gives many compelling case studies.
By contrast, leaders and companies that are on a worthwhile mission look at the game of business not from a place of high scores, but from one of sustainability, more like Tetris. Because the business has an important mission, it’s more concerned with sustainable practices, more invested in its people and fundamentally playing the game of business as an “infinite game” — one where winning doesn’t mean that you defeated your competition, it means that you get to keep playing. You get to stay in business and continue striving towards your mission.
The main benefit: sustainability. Sinek posits that mission-driven organizations have greater longevity because they are striving towards a larger ideal and have structured themselves in such a way that the goal is not to “win” at business, but to “stay” in business. Less like football, and more like Tetris.
Extreme Ownership by Jocko Willink and Leif Babin
This is the single most concise, practical, no-nonsense writing on leadership I’ve ever read. Not only does it cut to the core of what leadership is, it provides simple, powerful principles of leadership that are immediately useful. These principles were proven effective amidst the chaos of wartime combat, the complexity of military bureaucracy, and the seriousness of life and death operations. While it may not be obvious how combat principles apply to non-military situations, the authors have successfully translated these principles into real-world examples in the world of business.
Much like Ryan Holiday’s duo of The Obstacle is the Way and Ego is the Enemy, I’ve found the principles of Extreme Ownership immediately useful. Read this book, and you’ll be hard pressed not to be a better leader afterwards. “Get some!”
Tribes by Seth Godin
A primer on building and then leading a community of cohorts and customers. Not to be confused with Sebastian Junger’s book Tribe, this book is about a tribe in the sense of a customer base, although many of the underlying principles are the same. This book pairs very nicely with Seth’s other book, The Dip, which is recommended below.
Personal development, effectiveness, meta-learning and stress management
The Obstacle is the Way by Ryan Holiday
Ego is the Enemy by Ryan Holiday
This pair of books are not sequels of each other, but they pair very nicely. Both are intensely practical and grounded in time-tested, mostly ancient philosophies on how to live, how to think, and how to overcome external obstacles (The Obstacle is the Way) and how to overcome internal obstacles (Ego is the Enemy).
The Effective Executive by Peter Drucker
I estimate that roughly 75% of the best productivity advice circulating today has its roots in this book. If you read this, you’ll hear it echo through many of the books that follow in this list.
The 4-Hour Workweek by Tim Ferriss
This book covers a lot of ground, but most critically it focuses on using the Pareto Principle (the 80/20 rule) to organize whatever you’re doing so that you’re spending most of your time doing things that make the biggest difference in your endeavors. It helps teach you how “urgent” and “important” are not synonyms, and it provides dozens of tips and techniques to help you spend your time moving the ball forward rather than simply dribbling the ball crossing off to-do items.
I have not yet read The 4-Hour Chef or Tools of Titans or Tribe of Mentors, but these are obvious follow-ups to Tim’s debut work.
(Unrelated to any specific books, listening to Tim’s podcast, The Tim Ferriss Show, is what introduced me to nearly all of the books in this list.)
How to Stop Worrying and Start Living by Dale Carnegie
We’ve all heard of Carnegie’s other book, How to Win Friends and Influence People, but this book takes on a more critical area of self-care that there just aren’t many good, practical guides out there for this kind of thinking. It’s mostly a terrific deconstruction of how numerous well-known, highly successful people achieved what they did without it taking over their life in a negative way. What’s fun though, is that because it’s from a completely different era, it’s the same kind of business success anecdotes that one would read about today, but using the titans of business from just after the turn of the 20th century instead of Silican Valley tech leaders or empire builders of today.
Essentialism by Greg McKeown
A great, deeper dive into many of the concepts in The 4-Hour Work Week, this book teaches how to stop dividing and start conquering. For example, there is no real plural for the word “priority” even though we have “priorities” as a common word in English. One thing is most important right now, and that should be your focus. “Instead of going a millimeter in a million directions, go a kilometer in one direction.” Not only does this essentialist thinking help me get more done, by focusing on only one thing at a time, I am a lot less stressed.
The Art of Learning by Josh Waitzkin
If The 4-Hour Work Week is about how to use your most potent 20% of inputs to get 80% of your outcomes, this book is about how to go after that last 20% of outcomes.
Do the Work by Steven Pressfield
This is essentially an abridged version of Pressfield’s The War of Art. For me, this book is the other side of the Big Magic equation. If “big magic” is the creative force that’s trying to give you great ideas and feed your soul, “the resistance” is the opposing force that’s trying to stop your best work from starting, continuing or finishing. Obviously, it pairs very well with Big Magic.
The World Beyond Your Head by Matthew B. Crawford
This is a deep dive into how one of the primary causes of stress in our lives is the fragmentation of our attention — much of which happens without our permission. The more distracted we are, the more stressed we are and the less attention we have leftover to focus on things we actually care about. This, and some other things I’ve read of late, treat attention as a finite commodity that you spend throughout the day. You don’t have much of it, so spend it wisely.
Understanding people, community and creativity
Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert
Creativity can feel like an elusive force of nature, and this book dives deep into not only the other-worldly nature of inspiration, but many of the inelegant realities of living out our creativity in our daily lives. It’s a treasure trove of practical, inspiring ways to have a better relationship to one’s art and work. This book pairs very nicely with Steven Pressfield’s Do The Work.
Daring Greatly by Brené Brown
Like Amanda Palmer’s The Art of Asking, this book is a follow up to a viral TED talk given by the author. In this case, Brené Brown is a qualitative researcher who studies vulnerability and shame. Her book explores those topics and shows us how to not simply push through our shame, but how to cultivate vulnerability and make it a force for good in our lives and in our work. This book pairs really well with Big Magic.
The Four Tendencies by Gretchen Rubin
This is a book about expectations and how we meet them. That might not sound sexy at first, but this book deserves your attention as it will help you make immediate sense of yourself and the people around you. Rather than being some sort of holistic, all-encompassing personality framework, The Four Tendencies is only about how we relate to internal and external expectations. According to the author, we all fall into one of four common patterns and understanding these patterns can help us manage ourselves and others much more effectively. They also help us understand each other and why, for example, some of us excel at getting stuff done while others struggle.
Influence by Robert B. Cialdini
This book is a great overview of several psychological techniques that help people agree with you. It also contains interesting psychological triggers that people have regarding pricing, reciprocity, and peer pressure. There are a lot of shortcuts that we use to help us make decisions. This book identifies many of these triggers and helps the reader understand how to use them ethically, but also how to avoid falling for them.
Tribe by Sabastian Junger
This book explores the foundations of human community. In short, we long for meaningful connections with each other, and modern life is structured toward individualism. These two things are in constant conflict. This book is a great way to identify and reconcile those aspects of modern living that while they cater to our comfort, seem to subtract from our happiness.
Permission Marketing by Seth Godin
A primer on the underlying strategies behind marketing to the customers who have opted-in to hearing from you, and how to not screw up that relationship.
The Art of Asking by Amanda Palmer
While mostly a musician’s memoir, this book has gem after gem about what goes into building a community of fans and then how to leverage that community for things like crowdfunding and word-of-mouth marketing. People thought AP went from zero-to-$1MM on Kickstarter overnight, but it was actually a success more than decade in the making. Also, this book is an expanded version of Amanda Palmer’s incredible TED talk.
Who: The A-Method for Hiring By Randy Street and Geoff Smart
This book presents a framework for hiring people that, according to the authors, has a very high success rate in finding the right fit for a given role. This is a how-to guide for anyone trying to pursue a “hire slow / fire fast” approach to staffing.
On systems-first thinking:
How to Fail at Almost Everything and Still Win Big by Scott Adams
This book is an entertaining, approachable primer on systems-first thinking. The primary lesson is that your chances of success go up exponentially when you concentrate on systems rather than goals. “Goals are for suckers.”
Please note, my endorsement of this book should not be construed as alignment with Scott Adams’s political views. We can all be really smart and really stupid all at once, and he’s a good reminder that sometimes we should all probably stay in our lane.
The Power of Habit by Charles Duhigg
The benefits of this book are two fold. First, it will help you get your own shit together in your personal life and business. Second, it will help you understand your customers better and how if you can intersect what you do/sell with habits they already have (or help them create habits that include what you do), then their adoption of what you offer has way more potential.
Fooled by Randomness by Nassim Nicolas Taleb
The Black Swan by Nassim Nicolas Taleb
Anti-Fragile by Nassim Nicolas Taleb
These three books were written as a set, however if you were only going to read one, Anti-Fragile is the one to grab. The other two books are great, but are in many ways simply deeper foundation work for the conclusions and concepts in Anti-Fragile. What’s particularly interesting to me is seeing the way the high-level concepts of this book play out and intersect the smart thinking of other authors in this list. I also return to this book’s risk assessment framework whenever I’m trying to make a big decision.
I Will Teach You To Be Rich by Ramit Sethi
Don’t let the infomercial-sounding title scare you away from this one. This is the single best collection of personal finance advice I’ve ever come across. Most importantly, it’s about creating a financial system for yourself where your money more or less manages itself.
Foundations of business, marketing, and innovation
The 22 Immutable Laws of Marketing by Al Ries, Jack Trout
(get the old version, not the new version with web stuff)
The timeless primer on what does and does not work in marketing.
The E-Myth Revisited by Michael E. Gerber
For anyone who has, or aspires to create their own business, E-Myth is required reading. Especially so if the business you wish to create involves some skill or craft that you as the business owner possess. The transition from practitioner to business owner is the primary inflection point at which most small businesses succeed or fail. This book is about how not to fail at that critical moment.
The Lean Startup by Eric Reis
If E-myth teaches us how optimizing our business is our job as an entrepreneur, then The Lean Startup is the book that teaches us how to go about it. Don’t let the word “startup” turn you away either. In this context, a startup is “any human organization trying to build a sustainable business in an environment of extreme uncertainty.” That describes more businesses than it doesn’t, I think. A more descriptive, if more verbose title could have been How to Use Testing and Science to Build Products and Services Your Customers Will Actually Pay For.
Zero to One by Peter Thiel
This book grew out of the notes of an Ivy-league Entrapreneurship course taught by Peter Thiel, who is one of the co-founders of PayPal and a serial builder of billion dollar businesses. It’s one of the few books about innovation that, I think, actually provides a useful framework for exploring new ideas. Of particular interest is his reframing of competition as a bad thing, and using “the contrarian question” to look for new opportunities in plain sight.
Anything You Want by Derek Sivers
A lightweight story of how one successful business got built, with some surprising advice that applies to all businesses. Derek is a unique voice in the world of business and even philosophy and his TEDx talks are delightful.
The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz
This is a book about all the difficult things that make up any professional venture that really fall into the cracks between the big pieces of advice or case studies you typically find in business books. Besides that, any business book that prefaces its chapters with quotes from hip hop lyrics instead of Steve Jobs is worth your attention.
The Dip by Seth Godin
A primer on having the right kind of perseverance in your projects or your business. Not successful right away? You might just be in the dip. Also, there may be opportunities to create a dip for your competition that is so deep and so wide it’s a valley of death they’ll go broke trying to cross and compete with you. This book pairs very well with Godin’s other book Tribes.
Cautionary tales
What I Learned Losing a Million Dollars by Brendan Moynihan, Jim Paul
This is a long read for no more than there is to this story, but it’s a really good lesson on making big decisions before you’re in the thick of a situation, not during. Choose your in and out points before you have money in the market, then stick to them. Be smart and good, but stop chasing perfect. Perfect is a trap. It doesn’t matter that you “could have” made more.
Intellectual honesty
Waking Up by Sam Harris
While Sam Harris is perhaps best known for his work dismantling religion in books like The End of Faith, this book is about seeking the spiritual without religion. Mostly a primer on mindfulness, the book also takes some very interesting journeys through what we do and do not understand about human consciousness, and how things like psychedelic drugs can play into a non-religious exploration of spirituality.
Lying by Sam Harris
More of an essay than a book, Lying systematically deconstructs all the bullshit reasons we’ve come up with to not simply tell the truth, and why in the end, lying never works.
—Nathaniel Salzman