Skip to content

The Best Books I Read In 2021

8 min

Better Questions is supported by readers like you. If you get value from my writing, consider becoming a supporting member. Exclusive content, weekly deep-dives, free beta-access to future courses and more. Thanks.


Cold weather calls for reflection. Maybe it’s the shortening days, or the nostalgic mood. Maybe it’s just because I’m spending more time inside.

Whatever the reason, I spend a lot of time at the end of each year reflecting back on what was.

(By the way, a HUGE thank you to everyone who supported the launch of my Personal End of Year Review course! It did way better than I was expecting, and that means the world to me.)

And a large contributor to the “texture” of every year is the books I read. I read nearly everyday, following wherever my interests lead me. I also tend to read in “chains,” checking out several books on a topic at once.

This means that years tend to have emergent “themes.” 2020, for example, took a massive detour into neuroscience after I read - and was floored by - The Master and His Emissary.

Being as books are so important to me (and to this blog, which acts as a forcing function for me to better internalize what I read), I’d like to make a tradition out of sharing my favorite books from the year.

Please note that most of the books didn’t actually come out in 2021; i anything, I try to avoid newer books.

All the links go over to Goodreads so you can learn a bit more about the books. These are all easily available at Amazon or your local bookstore. :-)

Let’s get to it!

The Best Books I Read In 2021

Thinking In Systems, by Donella Meadows.

Donella Meadows (pictured above) was one of the popularizers of systems thinking, and this book is, in my opinion, the single best primer to the discipline. Meadows is approachable, fun, and sincere - she deeply believes in the transformative power of systems thinking to change our relationship with the natural world. Meadows was an environmental scientist who worked on “The Limits To Growth,” which did a great deal to shape the ways we think about environmentalism in the US.

This is one of those books that I highlighted so much it probably would have been easier to highlight the passages I didn’t get value out of.

Meadows has sadly passed away, but her work continues through the institute that bears her name. I highly recommend Thinking In Systems as a guide to her thinking.

Drift Into Failure, by Sidney Dekker

Systems, systems, systems. Thinking In Systems is all about understanding complex systems and the ways in which they work. Drift Into Failure, on the other hand, is about how complex systems can explode…despite everyone doing their absolute best to ensure they don’t.

Fair warning: I haven’t finished this one yet (I move slowly through individual books since I tend to read several books at once). However, this book has done the most of anything I read all year to really light my brain on fire. From oil spills to plane crashes, Dekker’s thesis - that systems create the environments for their own collapse - is powerful. You’ll start to see the symptoms of “drift” everywhere.

To Dekker’s credit, he specifically asks you not to do this, arguing against the use of drift into failure as a “folk model,” a pat and easy way of explaining incredibly complex things. With that chastisement in mind, this book is probably the one that did the most to “nudge” the way I see the world.

Maxims for Thinking Analytically: The wisdom of legendary Harvard Professor Richard Zeckhauser by Dan Levy

This book is what it says on the tin: a collection of maxims to help you think rationally.

While I love a good maxim, the real attraction of this book is the fond stories and deep respect these people - all influential academics and professionals in their own right - have for a beloved teacher and mentor. The emotion is palpable throughout the book, which left me with a real desire to meet Richard Zeckhauser - or to at least enroll in some of his courses.

The maxims themselves are quite good, and form a useful checklist for ensuring you approach your problems, big and small, with a rational bent. It’s a quick, pleasant read. Recommended.

A Distant Mirror: The Calamitous 14th Century, by Barbara Tuchman

Barbara Tuchman is my favorite historian (or Abe she’s tied with Modris Eksteins, also on this list - don’t make me choose). This rollicking, sometimes hilarious, often maddening book is one of her best.

How to describe this book? It’s the book that made me realize that medieval knights were complete assholes - literally just riding around and killing innocent people in their own countries because they were…bored?

When Tuchman says the 14th century was calamitous, she ain’t kidding. The Black Death, religious hysteria, governmental collapse, constant and fruitless war, political misdeeds, a complete lack of faith in the institutions of the day - the 14th century has it all.

If you’re ever tempted to bemoan the times we live in, I STRONGLY encourage you to pick up this book. Tuchman is highly readable, deeply researched, and doesn’t hesitate to call them like she sees them (want to know who the worst Pope was? Check out this book).

The Body, by Bill Bryson

Can Bill Bryson make a whole chapter about the liver fun, and interesting, and funny? Yes. Yes, he can.

This book was just a pure joy. So many facts! Dry humor! Untold stories of the men and women who made scientific breakthroughs, only to have their work stolen by their professors!

This book became a problem in my marriage, because I couldn’t stop turning to my wife and saying “Did YOU know that…” and then spitting out some random fact about the human body. I literally had to write an entire blog post about it just so I would stop bothering her.

Anything Bryson writes is good, and everyone’s got an inherent interest in bodies - after all, we’ve all got one.

Yes To Life, by Victor Frankl

Frankl, a holocaust survivor, is best known for his book Man’s Search For Meaning, but I actually found this collection of early lectures a more approachable introduction.

Frank’s story is, as you might imagine, harrowing. His approach to survival - a focus on controlling his own thoughts first and foremost, a call to appreciate the smallest pleasures and victories in life - is powerful, and easily applicable in everyday life.

This book had an impact on me, and I think of it often. Particularly, I found this passage moving:

What did the men mainly dream of in the camp? Always the same: bread, cigarettes, decent ground coffee, and, last but not least, a nice warm bath (and I personally always dreamt of a very particular gateau).

It reminds me that the things I experience every day - and take for granted - were the most-longed-for dreams of people living lives I could barely imagine. I think of them often as I make my coffee in the morning, and it helps me bring me out of my head a bit.

Priming: Programming the Mind for Habit Change and Success by Clifton Mitchell

I wrote a bit about the central lesson of this book in "Ironic Processes" this year, so I won't belabor the point again. This book isn't exactly going to win any literary prizes - it's very to the point. The value is in the method described. To put it succinctly: repeat a mantra to yourself hundreds of times a day in order to subtly shift hard-to-change behaviors.

I experimented with this early this year and had a surprising amount of success with it. It's not often that I find a simple technique that had such impact.

Solar Dance: Van Gogh, Forgery, and the Eclipse of Certainty by Modris Eksteins

OK, maybe Modris Eksteins is my favorite historian. Rites of Spring rates as one of my favorite books of all time, so I'm not sure why it took me so long to get around to Solar Dance. I think I just thought Van Gogh wasn't terribly interesting.

I should have known better. While Eksteins DOES deal with Van Gogh (in his typically fascinating way), this book is more about Van Gogh idea than it is about Van Gogh the man.

WHY, exactly, is Van Gogh the world's most famous artist? How, exactly, did that happen? We cover the lives, not just of Van Gogh and his contemporaries, but those who made his reputation - the art dealers, thieves, and critics that turned the man into an icon.

Everything Eksteins writes is awesome. This book seems to have received mixed reviews, but don't listen to the haters.

Cynefin - Weaving Sense-Making into the Fabric of Our World by Dave Snowden and others

This particular book is OK - it's more on here to represent my discovery of Cynefin, a mental model that had a profound effect on how I see the world.

Strangely, there is no good introduction to Cynefin in book form. Instead, to get the whole picture you'll need to attend a workshop online (as I did). This is a book aimed mainly at people who are already in the know, detailing some specific applications of the framework.

There's some interesting stuff in here, but here's my real recommendation: research Snowden and Cynefin (the original articles are available online for free). We've mentioned systems multiple times in this note - clearly, systems thinking weighed heavily on my mind this year. Cynefin did the most to help me quickly classify the kinds of systems dynamics I see, and figure out the best way to approach improving things.

How to Measure Anything: Finding the Value of Intangibles in Business by Douglas W. Hubbard

OK, yes - this book sounds extremely boring. I know.

There are some really insightful ideas in here, however, namely: a measurement is just something that reduces your uncertainty. There is NO "real measure" of anything - no way to really "get it right." Instead, we need to judge our measurements by the extent to which they reduce our uncertainty, and operate in the full understanding that 100% clarity is never truly possible.

This book is as much about risk and uncertainty as it is about "measuring stuff," and it provides an extremely straight-forward and practical framework for applying that mindset to every day life. If you're looking for an immediately-applicable way of improving your predictions and decision-making, this book is it.

Digital Gold: Bitcoin and the Inside Story of the Misfits and Millionaires Trying to Reinvent Money by Nathaniel Popper

I went from 100% crypto skeptic to 50/50 skeptic and optimist this year. I'll likely be dedicating a good chunk of the next quarter into experimenting in that space (so expect to see at least a blog post or two on that).

While speculating in memes and JPEGs isn't particularly interesting to me, I'm pretty convinced that blockchain - the underlying technological innovation that allows for cryptocurrencies to exist - will end up eating the world.

Digital Gold provides an excellent history of the creation and spread of Bitcoin. For a topic that could be incredibly dry (there are MANY scenes of people sitting in front of computers), the book is highly engaging and reads like a thriller.

If you're at all interested in understanding this wave of technology (as I am), this is a great place to start.

Here's to another great year of reading!


P.S. What was the best book YOU read last year? I'd love to know - reply to this email and I'll share reader suggestions!


20 Years After The End of The World.

Members of Radiohead reflect back on the release of Kid A and Amnesiac. These records hit me like a ton of bricks when they came out - and they're worth revisiting.

Subscribe to receive the latest posts in your inbox.