Reading List: How to Think for Yourself (December 2021)

You’ve found my all-time reading list on critical thinking, philosophy and storytelling. I’ve put together the most inspiring books, insightful essays, revealing papers and thought-provoking blogs. The ones that have inspired this blog and my free Substack Newsletter featuring 3 Ideas in 2 Minutes.

I’ve arranged them into seven categories, from thinking like an analyst to writing and communicating better to works of fiction and entertainment. The Reading List is updated monthly.

What do you want to do today?

Table of Contents

  1. Think Like an Intelligence Analyst
  2. Make Better Decisions
  3. Write & Communicate Better
  4. Stand up for Yourself and Others
  5. Dive Into Human Psychology
  6. Philosophise About Life
  7. Be Amazed and Entertained

Disclaimer: Some of the book links below are Amazon Affiliate links. I earn a small commission
if you make a qualified purchase through those links. At no extra cost for you.

Think Like an Intelligence Analyst

A Tradecraft Primer: Structured Analytic Techniques for Improving Intelligence Analysis by the US Government

Don’t let the intelligence background of this publication put you off. The freely available Tradecraft Primer is a concise and useful collection of structured analytic techniques. It features diagnostic, contrarian and imaginative thinking methods from academia as well as the corporate sector. Learn how to challenge assumptions, reduce uncertainty, kick-start creativity and make better decisions.

Black Swans: How to Predict the Unpredictable

The Tenth Man Rule: How to Take Devil’s Advocacy to Another Level


Applied Thinking for Intelligence Analysis by Charles Vandepeer

A practical guide covering all the basics of critical thinking and more. From the definition of your problem to dealing with different types of knowledge and biases to being able to justify your judgements. Vandepeer is a senior lecturer in Intelligence Studies at Charles Sturt University, Australia. If you consider yourself a budding analyst and problem solver, Applied Thinking for Intelligence Analysis is your treasure trove and should go on your reading list.

The Tenth Man Rule: How to Take Devil’s Advocacy to Another Level

The Intelligence Cycle: How to Process Information Like an Analyst


Handbook of Analytic Tools & Techniques by Randolph H. Pherson

The Handbook of Analytic Tools & Techniques is a must-read for anyone interested in qualitative analysis. Pherson is a former three-letter agency employee and has put together a remarkable collection of comprehensive and innovative methods.

His book is packed with 33 Structured Analytic Techniques. Explore competing arguments, review your key assumptions or anticipate the future. It’s well-illustrated, full of examples and even maps relevant cognitive biases and misapplied heuristics to each of the techniques.

Mental Shortcuts: 5 Ways Heuristics Can Lead to Poor Decisions

Intuitive Traps: 5 Common But Hidden Barriers to Critical Thinking

Deception Detection: How to Anticipate Deceit

Make Better Decisions

The Almanack of Naval Ravikant: A Guide to Wealth and Happiness by Eric Jorgenson

Naval Ravikant is an angel investor with a talent to distil life-changing wisdom into simple words. Jorgensen’s Navalmanack chronicles the philosopher’s writing, tweets and talks. The book is a detailed guide on how we can create wealth, learn to be happy and live a more fulfilled life in general. Buy a hard copy or audiobook of The Almanack of Naval Ravikant through my affiliate link or download it for free.

Circle of Competence: How to Escape Competition Through Authenticity

21 Memorable Aphorisms About Life: How to Become an Aphorist


The Black Swan: The Impact of the Highly Improbable by Nassim Nicholas Taleb

The metaphor of a black swan, unexpected high-impact events, is hundreds of years old but was popularised by this very book. Taleb’s is an essayist, former trader and risk analyst. His way of thinking about the world truly stands out.

In The Black Swan: The Impact of the Highly Improbable, he explores and critiques how people cope with extremely rare yet unpredictable high-impact events such as 9/11. He offers a different solution grounded in building robustness and anti-fragility. As usual, Taleb doesn’t pull any punches.

Black Swans: How to Predict the Unpredictable

OODA Loop: How to Make Fast Decisions in Disorienting Situations


fs

Farnam Street is the address for mental models and food for thought on how to make better decisions. The blog was founded by Shane Parrish, a former intelligence analyst. fs has since expanded to include a newsletter and a podcast. Their work is also available in book form as The Great Mental Models. Volume 1 on General Thinking Models, Volume 2 on Physics, Chemistry and Biology and Volume 3 on Systems and Mathematics.

Top 25 Interesting Ideas and Concepts Everyone Should Know

Linguistic Oddities: 9 Peculiar Ideas of the English Language


The Decision Book by Mikael Krogerus & Roman Tschäppeler

This classic book on mental models predates fs. Krogerus and Tschäppeler have put together 50 Models for Strategic Thinking. Whether it’s the lesser-known “Making-of Model” or the “Eisenhower Matrix”, the descriptions are succinct and well-illustrated. Perfect for a quick and easy primer.

Black Swans: How to Predict the Unpredictable

The Tenth Man Rule: How to Take Devil’s Advocacy to Another Level

Write & Communicate Better

Never Split the Difference: Negotiating As If Your Life Depended On It by Chris Voss

Would it be ridiculous to think that your negotiation skills could be improved? Chris Voss is a former FBI hostage negotiator who tweaked his lessons learned to everyday applications and packed it all into one thrilling book: Never Split the Difference: Negotiating As If Your Life Depended On It.

If you want to change the way you deal with people on an everyday basis, put it on your reading list. Find out what makes ‘tactical empathy’ an absolute game-changer, why you should start with a ‘No’ and what the Late Night FM Dj voice can do for you. If you’re still undecided, start with my book review below.

Never Split the Difference: Jedi Mind Tricks for Negotiators

Yeah, Nah…: How to Say No Without Feeling Guilty (3 Ways)


Essay Writing Guide by Jordan B. Peterson

This is the most practical guide on how to write essays I’ve come across so far. Whether you need a primer or want to become a more efficient writer, the Essay Writing Guide by Canadian psychologist Jordan B. Peterson is for you. It’s an exercise in first principles thinking, analysis and creation. If you’re looking to learn how to write better essays, put this guide on your reading list.

Yak Shaving: How to Stop Procrastinating

Graham’s Hierarchy of Disagreement: How to Argue Like an Expert

Stand up for Yourself and Others

12 Rules for Life: An Antidote to Chaos by Jordan B. Peterson

Canadian psychologist Jordan B. Peterson also wrote this self-help bestseller about the significance of taking personal responsibility. It features 12 concise rules for a meaningful life, such as “Tell the truth. Or at least don’t lie.” Peterson unpacks each of his rules, weaving together research, mythology and personal anecdotes to explain the seemingly obvious. At the core of 12 Rules for Life: An Antidote to Chaos is the relationship between chaos and order in everyone’s life. His latest book, Beyond Order: 12 More Rules for Life, expands on this theme even further.

The Ship of Theseus: How to Solve the Paradox of Who We Are


On Liberty by John Stuart Mill

Mill’s classic philosophical essay On Liberty is probably best known for his immortal statement that those of us who know only our “own side of the case, know little of that”. Published in 1859, it emphasises the importance of freedom of thought and open debate.

Mill makes a compelling case for individuality, which he considers a pillar for personal wellbeing, and explores the relationship between authority and liberty. It belongs on everyone’s reading list.

Mill’s Trident: The Most Powerful of Arguments on Freedom of Speech?

Steelmanning: How to Discover the Truth by Helping Your Opponent

Strawmanning: How to Use the Straw Man Fallacy to Our Advantage


The Power of the Powerless by Václav Havel

Václav Havel was a Czech writer and dissident turned President. He wrote The Power of the Powerless in 1978. It would later mark a turning point in the fight against the communist regime. The essay is perhaps best-known for Havel’s greengrocer motif. In painful detail, he lays out the implications of a salesman putting a seemingly innocent slogan in the shop window; a sign of fear and obedience to ideology. The essay shows beautifully how the powerless are not as helpless as they seem.

Hard and Soft Power: What Makes You More Powerful Than You Think?

Stanford Prison Experiment: The Power of Perceived Power

Dive Into Human Psychology

Thinking, Fast and Slow by Daniel Kahneman

Thinking, Fast and Slow is a fascinating and comprehensive read on how we think by Israeli psychologist Daniel Kahneman. The winner of the 2002 Nobel Memorial Prize in Economic Sciences details the two systems that function in our brain: The one that allows you to think fast, intuitive and emotional. And the s-l-o-w-e-r and logical one. Each one comes with its own advantages and disadvantages for our everyday lives. A must-read for anyone interested in decision-making and cognitive biases.

Mental Shortcuts: 5 Ways Heuristics Can Lead to Poor Decisions

Intuitive Traps: 5 Common But Hidden Barriers to Critical Thinking

The Mind Palace: How to Memorise Information Like Sherlock Holmes


The Invisible Gorilla by Christopher Chabris and Daniel Simons

It seems obvious that you can’t hit what you don’t aim at. What’s less obvious is what you’re missing out on when you do aim at something.

The Invisible Gorilla: How Our Intuitions Deceive Us is named after the famous attention experiment in which participants are asked to observe a group of people passing a ball. Focused on their task many of them are oblivious to the person in the gorilla costume dancing through the scene. The book goes to show that all too often we miss a whole lot more of the world than we think.

Bikeshedding: Why Meetings Can Be Awful and What to Do About It

Intuitive Traps: 5 Common But Hidden Barriers to Critical Thinking

Philosophise About Life

Bullshit Jobs: A Theory by David Graeber

Would it be ridiculous to think that you’re stuck in a job that’s killing your soul? In a job that is so pointless, you cannot even justify its existence yourself? If your answer is ‘No’, David Graeber’s book might speak from your heart.

With Bullshit Jobs: A Theory, the late anthropologist expanded on his popular work rant in essay form. He was flooded with letters from his readers, which he turned into a handy categorisation of the most pointless jobs out there. Do you know a flunky, a duct taper, a goon, a taskmaster or even a box ticker?

Chmess: How to Spot a Bullshit Job

The Peter Principle: Why the World Is Full of Incompetence

The Science of Bullshitting: Notes from the Frontier of a Research Field


Zen Mind, Beginner’s Mind by Shunryū Suzuki

If you have an interest in Zen Buddhism, this modern classic by Shunryū Suzuki belongs on your reading list. The Japanese Zen monk popularised the philosophy in the United States. Zen Mind, Beginner’s Mind documents his “informal talks on Zen meditation and practice”. It’s a highly instructional piece, inspiring and often mind-bending. You can read it ten times and discover a new perspective and new insights every time. Hence the title.

21 Memorable Aphorisms About Life: How to Become an Aphorist

Dead Horse Theory: What to Do When Your Project Is on Life Support?

Dukkha Bias: Why Nothing Is Ever Good Enough to be Published


The Bed of Procrustes by Nassim Nicholas Taleb

“Procrastination is the soul rebelling against entrapment,” is one of the “philosophical and practical aphorisms” featured in Taleb’s book. The essayist and former risk analyst is known for his thought-provoking, witty and counterintuitive wisdom.

The title goes back to Greek mythology. Procrustes was known for abducting travellers and making them fit his bed. Whatever it took… So be warned, The Bed of Procrustes: Philosophical and Practical Aphorisms pops more than a few bubbles of human self-delusion.

21 Memorable Aphorisms About Life: How to Become an Aphorist

Linguistic Oddities: 9 Peculiar Ideas of the English Language


Higher-Order Truths About Chmess by Daniel C. Dennett

This essay by American philosopher Daniel Dennett will make you see chess differently. Dennett explores how students can avoid dedicating their lives to “artifactual puzzles of no abiding significance” in contemporary philosophy. In Higher-Order Truths About Chmess, he invents the game of chmess to illustrate his point. Put it on your reading list as a quick read. But be careful, it might cause you to see games of chmess everywhere.

Chmess: How to Spot a Bullshit Job

The Peter Principle: Why the World Is Full of Incompetence

Be Amazed and Entertained

1984 by George Orwell

This classic by English novelist George Orwell is an absolute must-read. The story explores the intricacies of totalitarianism through the eyes of the protagonist, Winston Smith. In 1984, Orwell coined infamous phrases such as ‘Big Brother’, an omniscient apparatus of surveillance and control. Or the concept of ‘Doublethink’, the ability to hold to contradictory statements in one’s mind while considering both to be true. It’s dystopian fiction, albeit one that never seems to lose its relevance.

Propaganda in North Korea: Dissecting a Story About Love & Special Aircraft

Deception Detection: How to Anticipate Deceit


Waiting for Godot by Samuel Beckett

When was the last time you were waiting for an event that was definitely and in all likelihood soon going to never happen? Chances are you were waiting for Godot. Waiting for Godot is a play by Samuel Beckett about two characters, Vladimir and Estragon, waiting for an ominous person, not knowing if he will ever arrive. It’s an absurd play with an unfathomably valuable…wait for it…

Stream of Consciousness: How to Make Sense of Our Messy Thoughts

Waiting for Godot: When Tomorrow Never Comes

Chekhov’s Gun: How to Ruin a Story in a Perfect Way


There’s No Such Thing as a Dragon by Jack Kent

There’s No Such Thing as a Dragon is a charming children’s book about the dangers of ignoring problems. The tale follows little Billy Bixbee as he discovers a tiny dragon in his bedroom one morning. But since dragons do not exist, the family soon turns their home into a fixer-upper. Great for kids, but also a surprisingly useful addition to any adult’s reading list. Something tells me it was actually written for grown-ups.

The Boiling Frog: 5 Toxic Leadership Behaviours and How to Handle Them

Dead Horse Theory: What to Do When Your Project Is on Life Support?