Here’s a list of books that I’ve found particularly thought provoking. Each of them has a wealth of insight, wisdom, and knowledge to share. Many of them are worth reading a few times.

I was going to sum up what each of them meant to me in a paragraph or two, but I quickly realized that it would no longer be a paragraph or two then. Instead I have included a quote from each book that I really liked.


Antifragile cover

Few understand that procrastination is our natural defense, letting things take care of themselves and exercise their antifragility; it results from some ecological or naturalistic wisdom, and is not always bad – at an existential level, it is my body rebelling against its entrapment. It is my soul fighting the Procrustean bed of modernity.

Nassim Nicholas Taleb

Don’t Sleep, There Are Snakes

Don't sleep there are snakes cover

They have no craving for truth as a transcendental reality. Indeed, the concept has no place in their values. Truth to the Pirahãs is catching a fish, rowing a canoe, laughing with your children, loving your brother, dying of malaria. Does this make them more primitive? Many anthropologists have suggested so, which is why they are so concerned about finding out the Pirahãs notions about God, the world, and creation.

But there is an interesting alternative to think about things. Perhaps it is their presence of these concerns that makes a culture more primitive, and their absense that renders a culture more sophisticated. If that is true, the Pirahãs are a very sophisticated people. Does this sound far-fetched? Let’s ask ourselves if it is more sophisticated to look at the universe with worry, concern, and a believe that we can understand it all, or to enjoy life as it comes, recognizing the likely futility of looking for truth or God?

Daniel L. Everett

Talent is Overrated

Talent is overrated cover

Landing on your butt twenty thousand times is where great performance comes from.

Geoff Colvin

Excellent Sheep

Excellent Sheep cover

The system manufactures students who are smart and talented and driven, yes, but also anxious, timid, and lost, with little intellectual curiosity and a stunted sense of purpose: trapped in a bubble of privilege, heading meekly in the same direction, great at what they’re doing but with no idea why they’re doing it.

William Deresiewicz

Weapons of Mass Instruction

Weapons of Mass Instruction cover

School trains children to be employees and consumers; teach your own to be leaders and adventurers. School trains children to obey reflexively; teach your own to think critically and independently. Well-schooled kids have a low threshold for boredom; help your own to develop an inner life so that they’ll never be bored.

John Taylor Gatto


Outliers cover

The lesson here is very simple. But it is striking how often it is overlooked. We are so caught in the myths of the best and the brightest and the self-made that we think outliers spring naturally from the earth. We look at the young Bill Gates and marvel that our world allowed that thirteen-year-old to become a fabulously successful entrepreneur. But that’s the wrong lesson. Our world only allowed one thirteen-year-old unlimited access to a time sharing terminal in 1968. If a million teenagers had been given the same opportunity, how many more Microsofts would we have today?

Malcolm Gladwell

Blink cover

Often a sign of expertise is noticing what doesn’t happen.

Malcolm Gladwell

The Wayfinders

The Wayfinders cover

If diversity is a source of wonder, its opposite - the ubiquitous condensation to some blandly amorphous and singulary generic modern culture that takes for granted an impoverished environment - is a source of dismay. There is, indeed, a fire burning over the earth, taking with it plants and animals, cultures, languages, ancient skills and visionary wisdom. Quelling this flame, and re-inventing the poetry of diversity is perhaps the most importent challenge of our times.

Wade Davis

Cave in the Snow

Cave in the Snow cover

Normally we are so identified with our thoughts and emotions, that we are them. We are the happiness, we are the anger, we are the fear. We have to learn to step back and know our thoughts and emotions are just thoughts and emotions. They’re just mental states.

Vicki Mackenzie

Bones of the Master

Bones of the Master

To a spiritual skeptic like myself, Tsung Tsai was too good to be true, a Renaissance man: monk, poet, philosopher, house builder, scientist, doctor, and when necessary, kung fu asskicker. It would spoil everything if he began proselytizing. I was constantly on the look-out for him to begin trying to convert me to devotion and practice. But he never did.

George Crane

Thinking in systems: A Primer

Thinking in Systems cover

People who cling to paradigms (which means just about all of us) take one look at the spacious possibility that everything they think is guaranteed to be nonsense and pedal rapidly in the opposite direction. Surely there is no power, no control, no understanding, not even a reason for being, much less acting, in the notion or experience that there is no certainty in any worldview. But, in fact, everyone who has managed to entertain that idea, for a moment or for a lifetime, has found it to be the basis for radical empowerment. If no paradigm is right, you can choose whatever one will help to achieve your purpose. It is in this space of mastery over paradigms that people throw off addictions, live in constant joy, bring down empires, get locked up or burned at the stake or crucified or shot, and have impacts that last for millennia. In the end, it seems that mastery has less to do with pushing leverage points than it does with strategically, profoundly, madly letting go.

Donna Meadows

An Introduction to General Systems Thinking

An Introduction to General Systems Thinking cover

If you cannot think of three ways of abusing a tool, you do not understand how to use it.

Gerald Weinberg

Deep Work

Deep Work cover

To remain valuable in our economy, therefore, you must master the art of quickly learning complicated things. This task requires deep work. If you don’t cultivate this ability, you’re likely to fall behind as technology advances.

Cal Newport

Thinking Fast and Slow

Thinking Fast and Slow cover

Odd as it may seem, I am my remembering self, and the experiencing self, who does my living, is like a stranger to me.

Daniel Kahneman

Radical Honesty

Radical Honesty cover

Bullshit is a sales pitch for an interpretation of reality that comes with any interpretation of reality. All interpretations of reality are bullshit. Freedom is not being dominated by your own bullshit.

Brad Blanton