Looking for ways to improve your thinking ability? Last October I wrote a blog with a list of books for thought. Check it out below.

Recently a friend of mind sent me an email asking me what books I would recommend to a 20-year-old who wanted to improve their thinking ability. Turns out, he sent it out to 33 people and pretty much everyone responded enthusiastically with both their recommendations and a desire to see the compiled list once everyone had responded. The list of recommendations turned out, not surprisingly, to be fantastic and provocative. Mostly, it makes me wish I had more time to read because I would love to set aside time to read everything I haven’t already gotten to on the list.

So I am offering the list up here as I assume anything that is interesting to me will be interesting to everyone else on Earth (still working on overcoming that bias). For context, the folks the request was sent out to was heavy with poker players and/or people in finance/traders but also included computer scientists, educators, doctors, lawyers, engineers, decision scientists, non-profit leaders, statisticians, real estate entrepreneurs and someone who recently turned 20.

I did have a conversation the other day with one person included in the original email for whom I have great respect and he voiced the opinion that the compiled list would be too heavy or serious for a 20-year-old. He thought offering up something in the vein of Zen and the Art of Motorcycle Maintenance or anything by Vonnegut would make more sense and be more likely to actually get read. That did make me think about my own college education where one of my majors was English Literature. I will say that learning to read a novel and then write a good paper on it, which is really just about constructing a good argument to support your thesis, did get me a long way in my critical thinking skills.

I personally wish every 20-year-old would read some selection of the books below, although I think that some of the philosophers mentioned would make for tough reading without guidance from a teacher or mentor if not simply because the language is arcane.

My personal favorite answer is number 21. So simple yet, so powerful. Read some stuff about something you like and then debate with someone who disagrees with you.

I leave the list relatively unedited mainly so that you can see which books are repeated.


1) I think of two kinds of books:

Books about identifying and eliminating cognitive biases, like:

Fooled by Randomness

How What We Know Isn’t So

Thinking, Fast and Slow

Books about creativity in logical thought, like:

Godel, Escher, Bach: An Eternal Golden Braid

Raymond Smullyan puzzle books (which are often hiding nice mathematics behind the puzzles)

How to Solve It (Polya)

Also I think it’s a great exercise to diligently read original works by philosophers (modern or historical), and carefully construct their arguments, attacking them where possible.

2) My own experience has been that very few books get embedded in me and, therefore, affect my thinking. On this subject, the exception has been Daniel Kahneman’s Thinking, Fast and Slow. But I should warn you that I’ve recommended the book to five people and only one of them felt about it the way I do.

3) Interesting question. I’m not sure I have an answer that addresses it directly, but the first thing that comes to mind is to recommend reading The Elements of Style by Strunk and White. This is the greatest little book on how to write well and it addresses a lot of subtleties that people overlook in everyday communication. My thinking here is that being able to formulate a clear sentence is a key prerequisite to clear thinking. (By the way, both times I took the LSAT exams I prepared by rereading this book.) Reading the recreational math books by Martin Gardner could certainly be helpful, and I think Ray Smullyan wrote some nice logic puzzle books.

4) I have two books at home I like for simple understanding of economics. They are Economics in One Lesson and Economics for Dummies.

Another I like is Predictably Irrational by Dan Ariely.

I know this may sound like a stock answer but Atlas Shrugged is a must.

5) There’s a book called Good to Great.

6) Sway and Predictably Irrational are the most popular and engaging with our interns.

7) Thinking, Fast and Slow is excellent, but the sheer size of the book might seem overwhelming and intimidating. Therefore, I would suggest either:

a) start with a shorter book that includes interesting anecdotes to illustrate the principles (such as How We Decide by Jonah Lehrer orPredictably Irrational by Dan Ariely) and then build on to other reading from there if the interest is there; or

b) start with only a handout copy of an interesting chapter of Thinking, Fast and Slow and see if that whets the appetite for more reading.

Also if I’ve learned nothing else, it’s that you need to keep re-reading these concepts (either the same book, or similar material reconfigured by another author) in order to stay sharp and avoid “relapse”…

Finally, while Lehrer’s originality was somewhat discredited, the principles illustrated in his book have not (to my knowledge) been discredited.

8) I’m going to give a somewhat radical response. Have a look at the site Autonomy and Life and see if you think it would have any value. Arnold Seigel teaches a course that embraces creative thinking as a way of life. I think he is sharp as they come in this area. He encourages his students to think for a minimum of an hour a day, I think he is a great example of the results of his work. Arnold is in his 70s, and keeps improving on and expanding the work that he does; he spends 6–7 hours a day thinking. Obviously any seminar is going to raise some eyebrows and skepticism and is a natural response, but this man is a wonder to see in action.

9) I love the Freakonomics books and all of Malcom Gladwell’s books. The teach you to think in a “numerate” way in a very entertaining style.

10) I like Thinking, Fast and Slow by Kahneman, Innumeracy by Paulos, Money Ball by Lewis, and The Bible. Maybe some Malcolm Gladwell books.

11) Against The Gods: The remarkable Story of Risk by Bernstein. Might be a little dense for a 20-year-old but enough history to make it fun. All things Malcolm Gladwell — my 20-year-old loves his stuff.

12) I’ve read a few books that have a big effect of my way of thinking. Certainly, something like Freakonomics is a good choice. Another book that’s a little more obscure but quite good is The Jungles of Randomness. It deals with the concept of what true randomness means. Until you really understand what randomness means, you get fooled by all those silly media stories about “trends” that aren’t really trends.

13) I guess my initial reaction is to think of books that teach mathematically sound thinking and how to be hyper logical and effective but that may be a pretty confined way to answer your question.

14) The God Delusion and/or The Greatest Show on Earth, The Drunkard’s Walk, Thinking, Fast and Slow

15) Excellent question. Off the top of my head, and ones I have read:

The Bible. Proverbs in particular.

The Social Animal, David Brooks

The Art of War, Sun Tzu

The World is Flat, Thomas Friedman

The Celestine Prophecy, James Redfield

How to Win Friends and Influence People by Dale Carnegie The Seven Habits of Highly Effective People by Stephen Covey

16) The only book that immediately comes to mind for me is the oldDecision Traps.. Others, which might be a little bit just math, would be Fooled by Randomness, The Black Swan, Getting the Best of It, The Signal and the Noise.

17) I would suggest “looking over the shoulder” of a good thinker. For me, that means reading. The book that jumped to mind, and that I can’t displace with a better example is Goedel, Escher, and Bach by Douglas Hofstadter. As I recall, it won him a Pulitzer. My second would be Churchill’s The Second World War. That exposes the holistic and strategic thinking, in the face of politics, that Churchill practiced. It’s like swimming, you have to try, emulate, try again.

18) One book! Consilience by Edward O. Wilson

19) Generally, I would suggest that the person think about something that he really enjoys, and read whatever the best meta- is on that subject. I know that I read and loved a lot of graphic novels without thinking deeply about them, but then hearing Art Speigelman talk about how he put Maus together and the choices he made; and then reading Understanding Comics (McCloud) really made me critical and understanding of the form. So, movies — read Ebert and some approachable literary theory on film. Video games — read a good history on them or a good insider article about the choices and why they were made, etc. I’d vaguely steer away from biographies and towards what-makes-this-tick kinds of behind-the-scenes histories and more interpretative or critical or explanatory takes. Once you do this with a subject you love, I think it makes you a better thinker about all kinds of other things you are presented with in life and how they work.

What If? by Randall Munroe. Kind of similar to the above except you don’ t need a starting point, takes weird thoughts/questions and takes them seriously, including some interesting ways of thinking about and explaining things. Not as a reading-through-it book but looking to see which questions interest him and seeing what got done with them.

20) My completely honest answer is that I think it is very, very difficult to become a better thinker at 20. Most of it is genetic, and what isn’t probably has its effects at earlier ages. I could be wrong. Still I might recommend a book on logic. Aristotle codified all of this stuff 2,500 years ago but it’s worth reviewing given the state of education today. In college I read Copi I believe. It exposes fallacious arguments, which is probably of great practical use.

To pitch Peikoff and Ayn Rand a bit, I really think Objectivism: the Philosophy of Ayn Rand is a very closely reasoned, clear and educational book on basic philosophical issues. Understanding that book might make you a better thinker as an adult.

21) I am not sure there are books to teach how to be a better thinker per se (though decision science certainly might be a good place to try). As an educator, I start with an assumption that I need to engage the 20-year-old — and that the best learning comes when someone (a teacher, a peer, or even a father) pushes the student to defend their point of view, explain their reasoning, and examine their assumptions, etc. So, I would ask what the 20-year-old is interested in. Then find two books with opposite conclusions on the same topic. You both read them. Then take him/her out to dinner frequently and argue.

22) For Moral thinking, Dostoyevsky–Crime and Punishment and The Brothers Karamazov; and the French: Zola, Therese Stendahl, etc. Reading American detective novels are probably the best and most entertaining way to play with evidence-based thinking, but you have to read the greats: Raymond Chandler, James M. Cain. Great science fiction also fosters thinking in terms of consequence, societal structures and individual choices such as Arthur C. Clarke and Isaac Asimov. The Philosophers: Bertrand Russell, if you want a real challenge Ludwig Wittgenstein, Kant and Hegel. Aristotle always a favorite, but he’s more of a moralist.

23) Freakonomics. I like biographies, Walt Disney was great. He was creative smart , and successful. I also liked What They Don’t Teach You at Harvard Business School.

24) Since it is a boy and not girl, I favor a few of the true stories of gallantry written by good historians because they appeal to boys and they can read about decisions and outcomes to momentous events. It will also improve their vocabulary without them knowing it. Path Between the Seas (fascinating story of the building of the Panama Canal) by David McCullough; Undaunted Courage (Lewis and Clark excursion) by Steven Ambrose; Ghost Soldiers (raid on Cabanatuan) by Hampton Sides; The Three Musketeers by Alexandre Dumas (easier but great for boys); Unbroken (WWII survival) by Laura Hillenbrand; Lone Survivor by Marcus Luttrell.

25) Very well. I look forward to the list, and will name just name a few then…

Learning and Leading with Habits of Mind: 16 Essential Characteristics for Success by Costa and Kallick

Intuition Pumps and Other Tools for Thinking by Daniel Dennett

Thinking, Fast and Slow by Daniel Kahneman

The Structure of Scientific Revolutions by Thomas Kuhn

Against the Gods: The Remarkable Story of Risk by Peter L. Bernstein

Images of Organization by Gareth Morgan

Okay, that seems like enough to start, but you’ll notice the absence of real mathematics (especially Abstract Algebra) or the use of any novels. Perhaps the list should be thematically grouped; meta-cognition — thinking about your thinking, understanding and improving the brain as a physical thinking tool, ways of thinking about different domains of knowledge, thinking via different practices — contemplation, writing, and drawing, and explorations of ways of thinking from the primary works of standout thinkers.

26) Any programming book which teaches decision-making through a flow charting methodology. Project management books might also be good where the goal is to achieve a desired result with finite time and resources (e.g., people, money, etc.).

27) Wow, what an amazing question. I’m spinning in circles “thinking” about what it even means to be a “better thinker” and what you/they mean by “thinking.” So in the interests of being helpful to what I feel is the underlying purpose here, my gut tells me to share with you books that I wish I had read at 20-years-old that would positively impact my life as a cognitive being:
Don’t Sweat the Small Stuff (Carlson)
Philosophy in the Flesh (Lakoff & Johnson)
The Power of Now (Tolle)
Complexity (Waldrop)
Black Swan (Taleb)
Fortune’s Formula (Poundstone)
Singularity is Near (Kurzweil)

28) Depends a bit on the kid…

Some ideas:

Darwin’s Dangerous Idea by Dennett

Thinking, Fast and Slow by Kahneman

The Blind Watchmaker by Dawkins

The Halo Effect by Rosenzweig

Against the Gods by Bernstein

The Black Swan by Taleb

Moneyball by Lewis

Complexity by Waldrop

29) Readings in Decision Analysis

The Worldly Philosophers by Robert Heilbronner

Practically Radical by William Taylor

The Halo Effect by Phil Rosenzweig

30) So I included (what I believe to be) two different types of books. It’s been a while since I’ve read some of them, but I think they hold up.

A Whole New Mind by Daniel Pink

Mindset by Carol Dweck

How Children Succeed by Paul

And, I’d imagine Annie would insist on including Dan Ariely’sPredictably Irrational

Then there are these:

The Miracle of Mindfulness by Thich Nhat Hanh

The Alchemist by Paul Coelho and Alan C. Clarke

The Prophet by Kahlil Gibran

31) Being Logical: A Guide to Good Thinking by D.Q. McInerny
Why People Believe Weird Things by Stephen Jay Gould
Searching for Certainty: What Scientists Can Know About the Futureby John Casti

32) Predictably Irrational by Dan Ariely (priceless)

Stumbling on Happiness by Dan Gilbert (perhaps not what you had in mind, but very thought provoking)

Freakonomics by Levitt and Dubner

That being said, the most helpful thing for me in improving my thinking has always been competitive endeavors — particularly games. If a 20-year-old came to me and asked me how to get better at thinking, I would suggest to them that they pick a game with some complexity and attempt to master it (Poker, Backgammon, Hearts, Bridge all come to mind — there are many others). I particularly recommend games with a defined chance element in it, but chess is good too.

If they don’t want to learn to play a game by doing, they can watch others and opine — but in some kind of meaningful way. For instance, try this exercise. Watch a game of jeopardy on DVR. Before every wagering decision is made (Double Jeopardy, Final Jeopardy), pause the game and decide what you think is the right amount for each contestant to wager and why. Then discuss.

Another idea: Learn how to play a game at a rudimentary level, and then read strategy guides on the game (or follow detailed replays with quality commentary). David Sklansky’s books, or the daily bridge column in a newspaper can work here. Avoid mass marketed commentary (anything broadcast on TV or Radio is suspect) as its goal is to entertain, not to educate.

Also — Pick one game (any game) and get as good at it as you can. In my opinion that will teach someone more about how to think then any book.

33) Anger: Wisdom for Cooling the Flames by Thich Nhat Hanh

Mastermind: How to Think Like Sherlock Holmes by Maria Konnikova

Author of Thinking in Bets and How to Decide. Co-founder of The Alliance for Decision Education

Author of Thinking in Bets and How to Decide. Co-founder of The Alliance for Decision Education