The Best of the Best Books I Read in 2019

The best of the best books I read in 2019 cover image

Last year I finally cracked my goal to read 100 books. After completing the challenge, I reflected thusly:

So I’m not going to get too hung up on the number this year. My preferred style of reading involves taking copious notes, writing reviews, and scribbling in the margin. I don’t want to feel the slightest pressure to just tag ‘em and bag ‘em.

Sure enough, I dialled it back this year. I only got through 56 books, which feels a little disappointing.

But having looked through my list, I realised that 2019 was still a great year for quake reading.

As always, it was agonising trying to choose between a worthy field, but I’ve winnowed it down to my top 10.

These are the books that blew my mind, made me howl, or filled my notebook to overflowing. In no particular order:

The public library will loan you these books for free. If you’d rather buy them, the affiliate links on this page send a few pennies to support this site, at no extra cost to you (read more here).

Range: Why Generalists Triumph in a Specialized World — David Epstein

Range David EpsteinThis is the Malcolm Gladwell-esque airport book of the year. It’s full of catchy case studies on the rambling career paths of generalists—Vincent van Gogh, Johannes Kepler, the guy who invented GameBoy—but the difference is, it doesn’t rely on them. In fact, instead of creating cute narratives from whole cloth, Range unpicks a bunch of myths perpetuated by previous airport book gurus: the 10,000 hours of deliberate practice, the Tiger Mom, the idea that you ought to relentlessly specialise from childhood.

My overwhelming feeling throughout was one of jealousy. This is exactly what I was getting at in Specialisation is for Insects, but Epstein’s book-length treatment is a million miles better (duh). He also touches on the optionality philosophy that I’ve started laying out: we live in an increasingly volatile and ‘wicked’ world which doesn’t conform to a neat set of rules. That makes life much riskier for narrow specialists, while conditions are perfect for curious and flexible generalists.

Finally, it’s more evidence against long-term planning: successful careers, businesses, and interests tend to emerge organically from the bottom-up, rather than being meticulously planned from the top-down.

I think this is a terrific book that deserves its success. You’ll probably have to skim a bunch of ideas you’ve heard before, but there’s a ton of value in the synthesis.

Barbarian Days — William Finnegan

What’s this memoir about? Mostly surfing, with a side order of surfing. Then it moves on to another course—surfing—before finishing up with a generous helping of surfing. Finnegan dissects every wave down to the level of its component molecules. We hear about every feathering crest, every close-out, the interplay of currents and coastlines and endless unexplained jargon and technical details.

The ravings of hobbyists are usually deathly boring, but I loved this book. It might be because I used to be into surfing, and didn’t have to learn a whole new vocabulary just to understand what he was frothing about. But many non-surfers also love this book, to the point where it won the Pulitzer Prize. Why?

Partly it’s the prose. Finnegan is a staff writer at the New Yorker, and he has some serious chops. His writing is so vivid that it feels like you’re right there with him, experiencing the panic of being rag-dolled over a reef, tripping on acid out the back at Honolua Bay, bashing through Fijian jungle looking for uncharted breaks.

But mostly, it’s the sheer fascination of watching an auto-vivisection of a broken brain—of a person so fanatically devoted to a cause that they will risk death and social isolation and financial ruin, entirely decoupled from the benefits of said cause. It’s a glimpse of the singular madness that makes humans so brilliant, and so absurd. Thanks to my two favourite Pauls (Barnes and Graham) for the recommendation.

The Righteous Mind: Why Good People Are Divided by Politics and Religion — Jonathan Haidt

I’m WEIRD! Chances are, so are you: Western, Educated, Industrialized, Rich, Democratic. As it turns out, the full palate of human morality is much richer than the acquired tastes of our weird little bubble.

Reading this book is like taking an empathy pill. It gets you inside the heads of people from various political tribes, so you can see the world through their eyes. Your opponents are not stupid, or wrong, or evil. They just have a different set of moral taste-buds. 

Haidt isn’t a happy-clappy cultural relativist, though. His theory is an explanation of what is—instincts bestowed upon us by the blind idiot god of evolution—not what ought to be. 

But even that’s enough to be incredibly useful: first, for understanding the culture wars that are raging right now, and second, for refusing to participate. Political partisanship turns your brain into cabbage, and makes you increasingly incapable of seeing reality as it is.

More jarring for me, on a personal level: Haidt argues that the pursuit of rationality through reasoned argument and logic is largely (but not entirely) futile, which is something I’ve reluctantly come to agree with, having initially been big into the rationalist movement.1

But also uplifting! I read part of this book after I’d eaten some THC-infused ice cream, and had a blazing epiphany: humans are the only ultrasocial primates. The group-level cooperation of the social insects—bees, ants, termites—was such a killer innovation that they now make up the majority, by weight, of all insects on Earth. Similarly, the social primates (us) dominated every other mammal on Earth through the ability to cooperate at scale. This really is unique: it would be unheard of for two chimps to carry a log.2 As Haidt puts it, we’re “10 per cent bee”. I think this is cool.

Thanks to Kate and Jonathan for the recommendation. See also: The Happiness Hypothesis, which was one of my top picks last year.

Risk Savvy: How to Make Good Decisions — Gerd Gigerenzer

Remember all the popular behavioural economics research on how we’re all hopelessly biased and irrational? Gerd Gigerenzer is not a fan. He sounds like a fictional villain invented by J.K. Rowling, but he’s the real-life nemesis of Daniel Kahneman and friends.

Gigerenzer argues that our ‘fast and frugal’ heuristics are often superior for decision-making, that intuition serves us very well indeed, and that too much information makes us worse off in conditions of uncertainty.

Risk Savvy is mostly just a solid primer on risk analysis and statistical literacy— which leads to counterintuitive ideas, like why screening for breast or prostate cancer does more harm than good, and terrorism has such an amazing return on investment.

Here’s a taste of some of the heuristics from the book:

  • Don’t ask your doctors what they recommend to you— ask them what they would do if it were their mother, brother, or child
  • Don’t buy financial products you don’t understand
  • If you are highly proficient at a sport, don’t think too long about the next move. If you are a beginner, take your time in deciding what to do
  • Try to get the partner that your peers desire

None of this is to say the ‘biases’ crowd are completely wrong. But it’s an important counterpoint to popular books like Thinking Fast and Slow, which definitely overstated the case.

The Gervais Principle — Venkatesh Rao

Yes, this is a sociological model built around fictional characters from a popular TV show (The Office). Yes, it feels like Rao is just making shit up from the comfort of his couch: arbitrarily dividing the world into Sociopaths, Clueless, and Losers. But who cares! All models are wrong; at least this is one is entertaining and insightful.

I hadn’t even seen The Office, but I still got a lot out of this book stitched-together series of blog posts. Rao is brilliant at surfacing subterranean status dynamics and office politics. One section in particular sent shivers down my spine: the hollowness that comes from seeing social reality as theatre, and running out of masks to paper over the void.

This just so happened to be perfect timing for me, which means it’s probably not a great mass-recommendation. But it’s a cheap and quick option to take out, and if you’re a fan of The Office, surely worth a shot.

Impro: Improvisation and the Theatre — Keith Johnstone

This unassuming little book was published in 1979, and has since become a cult classic. It’s not really about acting, but breaking down the dynamics of status games. Johnstone, a theatre educator, explains the concepts of ‘space’, status roles, body language, and how to play higher or lower, using examples drawn from his improv practice.

The first 50 pages alone are worth the price of admission—the rest of the book is a little repetitive (pages of students’ writing exercises) and I mostly skimmed it, but it’s mercifully short anyway.

Pairs well with The Gervais Principle, and with Kevin Simler’s essays on Status as Space, and Prestige vs Dominance.

How to Take Smart Notes — Sönke Ahrens

Several years ago, I noticed that after reading a fantastic book or blog post, I’d struggle to remember anything about it. Maybe I’d recall the vague outline, or a snippet. But mostly, all that knowledge slipped out of my colander-brain. So I started a methodical system of note-taking, which I only recently learned has a proper name: Zettelkasten.

Even though I was doing it ‘wrong’, Zettelkasten profoundly changed my life as a reader and as a writer. I now have ~7,500 interconnected notes and ideas, going back six years. This is my single most treasured possession, and my ‘secret sauce’ (to the extent that I have any).

If you’re a writer, researcher, or student, I can’t recommend a practice like this strongly enough. Here’s what you need to get started:

  1. An explanation of the system and its benefits. I’m planning to write about this next year, but if you want a book-length treatment, Sönke Ahrens nails it.
  2. A storage system. The classic set-up involves a physical slip-box of index cards. But we can do so much better than that!

My most exciting side-project in recent years has been helping out with a startup called Roam Research, which aims to bring Zettelkasten to the people. If you’ve never used knowledge management tools before, the learning curve will be steep, but it’s worth it.

Roam is now an indispensable part of my life: for time management, note-taking, lists, gratitude journaling, morning pages, structuring writing, and everything in between. Obviously I’m biased, but I think this is something special.3

Calypso — David Sedaris

David Sedaris is the funniest and most ridiculous essayist I’ve ever come across. I’ve already bought at least six copies of Calypso to foist upon friends and family.

This collection is bursting with his trademark pith and gleeful savagery, but it’s also unusually dark and thoughtful: delving into the suicide of his sister, Tiffany, the process of aging and mortality, and of course, the backroom surgery performed by a fan so he could feed his tumour to a snapping turtle:

I got into the express line behind a middle-aged man in a T-shirt…the back pictured a Labrador retriever standing on the beach with a bikini top in his mouth. Below him were the words GOOD DOG. Some people, I thought, opening the wet wipes so I could wash the tumor off my hands before I touched my wallet.

Sedaris has a funny high-pitched voice + buckets of charisma, and Caroleen reports that the audio version is fantastic.

Joan Didion — Slouching Towards Bethlehem

“Once, in a dry season, I wrote in large letters across two pages of a notebook that innocence ends when one is stripped of the delusion that one likes oneself.”

This is my go-to example of how New Journalism (creative nonfiction) ought to be done. It’s inspiring to see cultural criticism dished out without going down the route of the sneering, hardened cynic. Instead, Didion is vulnerable about her own rage and doubts and struggles to make it in a man’s world—but she avoids turning it into the narcissistic All-About-Me! gonzo show.

With that being said, my favourites were her personal essays on self-respect—read the 1961 Vogue original here—and on journaling, which could have been written yesterday. I can’t recommend the collection as a whole, because some of it is too specific to the context of the time.

The other unmissable piece is the titular essay on the degeneracy of San Francisco during its countercultural heyday. This was particularly interesting for me to compare and contrast, as I spent the summer in the Bay Area with my own degenerate friends. I think we’re slouching in the right direction, but it’s jarring how little has changed in half a century (and on some dimensions, has gotten worse).

Circe — Madeleine Miller

Billed as a ‘feminist retelling’ of the Odyssey from the perspective of the witch-goddess Circe, but not at all heavy-handed: Circe is granted the dignity of being a complex character with all her own flaws and reckonings.

I loved the writing, the expanded universe, and the moral ambiguity: it reminded me how dramatically the notion of godhood and heroism has changed over the millennia. Reading The Odyssey around the same time, I couldn’t get over Odysseus’ rat-bastard nature: he’s a cheating, stealing, hubristic, privileged crybaby, and gets everyone around him killed. 

This is the whole point of the story, but man, it makes the Marvel superhero stuff look like tiddlywinks. Thanks to Lindsay for the recommendation.

Honorary Mentions

Some of these could have equally well made it into the top 10, but were narrowly edged out. Briefly:

Evolution of Everything — Matt Ridley

An argument against top-down design in education, law, markets, etc. There’s only room for a quick dip into each field, but it strengthened my confidence in bottom-up tinkering and trial-and-error exploration, and my suspicion of High Modernism and central planning.

The Hungry Brain — Stephan Guyenet

This is far and away the best explanation I’ve come across for unpacking the causes of obesity, calories in calories out, low carb vs low fat, and a bunch of other long-running nutritional debates. The neuroscience stuff is intense, so I skimmed quite a bit. It gets digestible again towards the end, and wraps up with some simple takeaways.

Tenth of December — George Saunders

These grimly uplifting short stories are so good that I read the collection twice in three months. Recently found out that George Saunders is a MacArthur fellow (i.e. received a ‘genius’ grant). Story checks out.

Digital Minimalism — Cal Newport

Mostly preaching to the choir, but I have a slightly rosier view of social media. See my full review here.

The School of Life: An Emotional Education — Alain de Botton

Flowery and melancholic, often insightful. See my review/profile, and full interview with Alain.

When — Daniel Pink

Cute, short pop science book about optimal timing: when to eat, work, sleep, make decisions, etc. Inspired a half-written post that I’ll throw up next year.

Wool — Hugh Howey

Self-published phenomenon, sold a million copies. The anthology drags on (it’s ~80 per cent climbing stairs) but if you stop after Part 1, it makes for a perfect self-contained short story.

Still hungry? Check out the best books I read in 2016, 2017 and 2018.

I notice that more than half my 2019 favourites were recommended by Deep Dish readers, so please drop a comment below! What’s the best book you read this year? 


  1. Intuitions come first, then we backfill accordingly. With a few important exceptions, it seems like rationality skills mostly just make the conscious part of our minds better at coming up with elaborate stories to explain the movements of the enormous subconscious elephant we’re pretending to pilot.

    My guess is that the next big breakthroughs in rationality will come from practices that change the elephant’s course through embodiment and direct experience, rather than reasoned argument—for example, psychedelics, meditation, various forms of therapy, and most importantly, just doing the thing in question, instead of talking about it.

  2. I didn’t realise this—you might see what looks like cooperation, like chimps hunting together, but they’re really all just going after a monkey that they happen to see at once. There’s no strategy at play, and questionable theory of mind: they can’t really model what their fellow chimps are thinking or planning.
  3. The beta is open now if you’re interested. Here’s the white paper I co-authored, which lays out some of the underlying philosophy, and here’s a recent interview/debate between Conor and Tiago Forte of Building a Second Brain.

Not Sure What the Future Holds? Get Your Copy of Optionality Now.

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Kate Stern
Kate Stern
4 years ago

Thanks for the shoutout and the good book ideas 🙂

Just signed up for Roam. I use Workflowy for notes and I love it, but this sounds intriguing!

Another awesome book is Debt: The First 5,000 Years by David Graeber. I wrote about four of his books here (they’re all great).

Kate Stern
Kate Stern
4 years ago

Yeah, you don’t need the book if you already agree with the essay. I just like the way he writes! (Although my friend read Democracy Now on my recommendation and said she hated the rambling, naive idealism, and sweeping declarations with no backup.) Interested to hear what you think of it.

Ah okay. Currently I find Workflowy more aesthetically pleasing, but I’ll have to find out what transclusion means 😛

Tyler Weaver
4 years ago

Range sounds like a good read for some self-worth gratification. My 2019 reading list has been very heavy in the specialization since birth camp. They focus too much on the one in a million. Without success, many of the case studies seem quite miserable. I bet Range ties in pretty well to the book stillness is key by Ryan Holiday.

Vince R
Vince R
4 years ago

Figuring by Maria Popova is one of the best books I’ve read in a long time. It’s hard to explain, but so beautiful.

If you’re feeling like history: King Leopold’s Ghost, Killers of the Flower Moon, and The River of Doubt are a few that I’ve really enjoyed recently.

Jon S
Jon S
4 years ago

You’re welcome 🙂

4 years ago

Hey I read this just a month ago and I was a huge fan, but everyone’s mileage may vary. It was definitely a book that I was almost mad that I read because I knew I was going to like it and I ended up reading it and loved it but it didn’t exactly expand my world view. Because I already agreed with everything already haha. Almost felt a little bit too self-indulgent

Paul Barnes
Paul Barnes
4 years ago

This is my favourite post of yours to read each year.

Notwithstanding my wariness of being taken in by Malcolm Gladwell’s writing, I really liked Talking to Strangers. It created self-understanding by highlighting that understanding reality comes at the cost of fitting in socially with the rest of the world.

I love F1. But it was on the strength of a recommendation by Shane Parrish of Farnam Street that I read Adrian Newey’s How to Build a Car: The Autobiography of the World’s Greatest Formula 1 Designer. Newey is deeply insightful about what it takes to deliver high performance by continuously seeking improved performance. It’s an engineer’s version of Andre Agassi’s Open.

My happiest reading this year has been your material. I feel so damn smug that I will be able to say I know you when you become famous for your coming book.

I’m glad you like Matt Ridley’s book. The key idea from his earlier book The Rational Optimist is the notion of ‘ideas having sex’. And it’s the synthesis of ideas across domains that I find so compelling about your work. So I’m naturally keen to hear more about Zettelkasten and how you use Roam. It does feel like you have some secret sauce.

4 years ago

Stuart Russell’s Human Compatible was quite good. I also enjoyed all the biographies I read this year and last (Steve Jobs, Elon Musk, Benjamin Franklin) and the history of technology books The Idea Factory, The Innovators, and Arsenals of Folly. Also my number one recommendation for a self-help book is Bonds That Make Us Free, which legit changed my life.

4 years ago

My recommendation is the Passion Paradox by Brad Stulberg and Steve Magness. A fairly easy read, but something I’ve found personally valuable.

4 years ago

Thanks, the Zettelkasten stuff sounds really life-changing, I will check it up soon!

4 years ago

I’m really looking forward to your future content on Zettelkasten! I read the white paper you co-authored and this stuff sounds like it could be revolutionary if it’s implemented in a way that’s easyish to learn and visually appealing. I’m struggling with information overload too. I’ll have some recent insights swimming around in my head from reading books or listening to podcasts, but they evaporate or get shoved out by newer content. File storage is getting more difficult too…I’m a digital hoarder who likes to save content I find insightful in case it gets removed from the Web, but I’m now spending more time trying to remember where I stored the content. Tools like GrandPerspective approach something of a bird’s eye view, but without any useful connectivity between content.

4 years ago

Always love receiving an email that you have another post up. I’ll be sure to get some of these books.

Looking forward to your book eventually!