My Top Books of 2019

December 28, 2019,


It’s the end of 2019, which means I’ve started my yearly cycle of review and resolution. I call them resolutions because that’s the word people know, but it’s really a series of habits and foci with corresponding goals to keep my competitive mind motivated.

Something I refocused on in 2019, without it being a resolution, was reading. My writing has increased in both volume and complexity, which is good, but I’ve been pulled away from the books that compelled my own words in the first place. Being frank, a large part of that has been the daily siren call of my phone. Like everyone, I’m almost always connected to it. I’ve been trying to sever that connection, which has had fits and starts but has been somewhat successful. (My wife may disagree.)

Some of my friends recently discussed kids and tech on an email conversation. One friend shared a picture of her 12 year old daughter with her nose buried in a book while waiting for her ride at the front door. Every free second she’s reading. Then my friend remarked, “My cousin said just the other day that this was her daughter until the day ‘she got her phone’”.

This was me too for years and years. Every spare moment I was spent reading. If I was walking, I was reading. If I was sitting in the car, I was reading. In bed before falling asleep, I was reading. Waiting in line at the store, I was reading. During breakfast, I was reading.

You can now replace ‘I was reading’ with ‘I was on my phone’ in every one of those sentences.

And this is all of us. All of the time. It’s grand and frightening and glorious and terrible all at the same time. Our society seems to be asymptoting towards a maxima of cultural change and our technology has created what Venkatesh Rao coined the “Global Social Computer in the Cloud (GSCITC)”. We are computing the future nearly as fast as we can.

The problem with this is two-fold. First, the overall speed and volume of human thought has dramatically increased, but our capacity to ingest and understand it all has remained static. This leads to a local-maxima problem where we efficiently hone in on the local solutions to questions based on all of our small bits of data - tweets and likes and other atomic cultural constructs - but miss dramatic and sweeping changes in our thought that can only be captured in the length of a book. The most important ideas, the most fleeting and achingly beautiful arcs of human thought, can only be explored in longer forms. Some of the most important ideas can’t be contained in our working memory; they need to be written on hundreds of pages to be absorbed and poured over and explored before being understood.

The second side of this problem is synthesis. The human mind is strange and fickle and we don’t really understand how we think or how we generate our ideas. When we keep only to our areas of expertise we lose the ability to synthesize information across fields, which is often where original ideas really come from.

Charlie Munger said it best:

“In my whole life, I have known no wise people (over a broad subject matter area) who didn’t read all the time — none, zero. You’d be amazed at how much Warren reads—and at how much I read. My children laugh at me. They think I’m a book with a couple of legs sticking out.”

I’ve been thinking about this quote a lot. I believe it to be true. But the following quote from Boyan Slat - the founder of the Ocean Cleanup project - is also true:

“Technology is the most potent agent of change. It is an amplifier of our human capabilities.”

The ability to think and absorb information across many fields is one key to humanity. Books are the best medium for this capability. To use Peter Thiel’s metaphor, this kind of information synthesis and idea generation is the foundation of being able to go from Zero to One.

Technology, most potently in computers and the Internet and the GSCITC, is the amplifier. But we still need the original signal to amplify.


Holy shit, Greg, this was just supposed to be a list of some interesting books you read in 2019 - what are you doing to me? Well, what strikes me when I look at this list is that the books seem to be spread across a variety of topics. I’m happy not only about reading a lot again, but also about reading different things, and I wanted to explain why I believe that’s important. So without further ado, here they are:

  • The Pendulum: A Granddaughter’s Search for Her Family’s Forbidden Nazi Past, Julie Lindahl: Strictly speaking I have a few pages left in this one, but 2019 isn’t over. The Pendulum is Julie Lindahl’s magically intimate retelling of the research she did into her family’s Nazi past. She grew up in Brazil - where her family had fled in 1960 - with strange holes and disconnections about her family’s past. There are many memoirs from the perspective of Jewish descendants, but few that I’ve seen from Nazi descendants. From her relationship with her loving but Nazi-sympathetic grandmother to the encounters with old men who still remember her cruel and fanatical SS grandfather, this book holds nothing back and is absolutely beautiful.

  • The Alternative: Most of What You Believe About Poverty Is Wrong, Mauricio Miller: I tend to have my head in the clouds, which means I don’t pay enough attention to the practical problems of the day. Things like poverty and social welfare systems and immigration. I also assume that mainstream left and right perspectives on the solutions to problems like this are fundamentally flawed. Mauricio Miller’s book on poverty and social service demonstrated a vastly different approach to poverty that is frightening in efficiency and devastating to the philosophies of both left and right. He constructed a very successful social service system where the social workers were forbidden to help people and were, in fact, fired if they did. They became simply observers. What happens next is that communities learn how to help themselves and repeat it over and over. The concept of “positive deviancy” Miller illuminates is beautiful and requires a maturity and trust I’m not sure we’re ready for as a society, although I wish we were.

  • Range : Why Generalists Triumph in a Specialized World, David Epstein: Do you forgive me for having a best-seller on here? I continually worry about some of the side-effects of specialization in our modern world, and Range provided needed ammunition for me to understand why it bothers me. It also provides iconoclastic perspective that we all should apply to our parenting.

  • On Writing, Stephen King: This isn’t just the best book I read this year, it’s also probably one of my top five books ever. Part of the book is honest autobiography and part is a lesson in craft. I don’t want to do it any injustice, so I will just say go read it. Whether you have an interest in writing or not. It is an opus.

  • Cool It: The Skeptical Environmentalist’s Guide to Global Warming, Bjorn Lomborg: Depending on who you hang out with, simply reading this could get you excommunicated. I’m a fan of Lomborg and the Copenhagen Consensus, but I still think it’s important to approach a book like this with some healthy skepticism. The biggest takeaway for me is that the climate debate is so reductionist that we miss entire suites of solutions for some problems. For example, the proximate problem with polar bear populations in the 70s and 80s was not warming but hunting.

  • The Consuming Fire, John Scalzi: The first book in this trilogy, The Collapsing Empire, was good but not great. It took awhile to get going and felt like mostly setup. Book 2 was the pay off. Scalzi paints political and human problems in a fascinating sci-fi world the same way GRRM does this on a fantasy canvas.

  • The Personal MBA, Josh Kaufman: The publishing date of this book represents the end of the era of the MBA. Nobody ever needs one ever again. It’s the physical manifestation of Will Hunting saying:

    “You wasted $150,000 on an education you coulda got for $1.50 in late fees at the public library.”

  • Tomorrow 3.0: Transaction Costs and the Sharing Economy, Michael Munger: I listen to a lot of EconTalk which means I’ve listened to quite a few interesting debates involving Mike Munger; this is my first book. It’s a good one. Munger describes how transaction costs are changing in the modern world and what it means for the future.

  • Killing Floor, Lee Child: I’d never picked up a Jack Reacher novel, so I started at the beginning and went straight through 4 or 5 of them in as many weeks. They’re great rides, but the first was probably the best. Reacher is raw and visceral and Child’s writing matches. Lots of fun.

  • Lock In, John Scalzi: Ever since I read Old Man’s War - another book on my all-time list - I’ve been a big Scalzi fan. This one started out slowly but soon became wildly interesting as a cautionary tale about how the physical and virtual worlds can interact.

Bonus: Two Short Stories

These two aren’t books, but they were both new to me in 2019 and had a strong impact. I’ve never been a big fan of Hemingway at book length, but it turns out that I find his short stories both more dramatic and more compelling. These two are gems. Hills Like White Elephants in particular is striking. If you don’t follow what it’s about after reading it, go look it up, then read it again.

Greg Olsen
Hi I'm Greg. Occasionally, I do things.ArchiveTumble