I've tracking books that I've read since 2013 or so, and writing about it since 2020 (2020, 2021). This year, I read 30 books, graphic novels, and related publications.

Top Picks & Honorable Mentions

NonFiction

It's hard to pick a "best of" list of nonfiction books because most of the books I finished were pretty good. If they weren't, I would have left them half-read!

That said, I found myself repeatedly coming back to the ideas in these books throughout the year. Because of that, I've ended up recommending them over and over to friends and colleagues.

• F.I.R.E. - How Fast, Inexpensive, Restrained, and Elegant Methods Ignite Innovation by Dan Ward (2014)
  I bought this on a whim with little expectation, and I was wildly surprised at just how readable, practical, and useful it was. Written primarily with government/military-style projects as the primary case studies, but they are relevant to working in any business or product management role.
• The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success by William Thorndike (2012)
  I picked this up on a recommendation while trying to learn more about finance and cash flow management, and I wasn't disappointed. It was a crash course on how financing and cash flow works and I learned just how central cash flow is to healthy business decision-making.
• Quit by Annie Duke (2022)
  I enjoyed Annie Duke's "Thinking in Bets" and found myself struggling a lot with "should I quit [thing]"-type questions this year. This book gave me the emotional and cognitive foundation to figure out why I was struggling with the decisions, and the analytical framework for how to actually make a call. Really useful, and lots of great anecdotes and case studies to call back on.
• Runners Up: Creative Selection by Ken Kocienda, Write Useful Books by Rob Fitzpatrick.

Fiction

I read fiction mostly for entertainment, but every once in a while a story manages to leave an imprint that doesn't go away. I found myself regularly recommending:

• Tomorrow & Tomorrow & Tomorrow by Gabrielle Zevin (2022)
  Friendship, creativity, and how people grapple with their identities and work, told during the rise of videogames as art. It's immensely readable and a lot of fun.
• When We Cease to Understand the World by Bejamin Labatut (2020)
  A series of haunting historical vignettes about how science escapes our ability to control and comprehend it. Both about the consequences of scientific pursuit for the sake of knowledge, and about the joy, wonder, beauty, and horror of discovery.
• The Mountain in the Sea by Ray Naylor (2022)
  A slow and careful story about studying emergent animal behaviors while reflecting on what it means to be conscious and intelligent. Also a deep look into how humanity struggles to interact with things that challenge its monopoly on intelligent thought – whether that be animals, artificial intelligence, or anything else.

Some Reflections

Half-Read Books

I had left my employer to focus on my own businesses in 2022 and expected to have a lot more time to devote to reading and learning this year. In some regards, this was true – I've started, flipped through, or referenced in passing at least 50 different books during the last 12 months. Many of those now sit half-read or dog-eared, waiting for me to get back to them. Many have been technical or business books, which explains why I never finished them... I got what I needed and moved on.

Other books sit half-read because they weren't that great. Maybe it was my head space at the time, or maybe the books themselves weren't quality. I'm never quite sure whether I should add a 1/2 or 3/4ths-completed book that I've stopped and won't complete to my "read" pile. Over the years I've been pretty diligent about finishing books and only adding finished books to my list. But that also means the list itself isn't an accurate reflection of my reading... just my completion rate.

Other times still, I'll read half-way through a book and come back months or years later to finish it. A few of books I've started in years past were "finished" in this year by that count.

All in all, this is a taxonomy problem – how do you categorize things, and what does that categorization reflect for you? What makes one particular system valuable for you, and what does it hide?

Books and Pictures

Another taxonomy problem is on how to "read" and record image-based books. Whereas a "words" books might take hours, days, or weeks to complete, an "image" book takes me take only hours or days. Is a photo retrospective equivalent to a novel or technical manual? Does it need to be?

I try to "read" and record image books the same way as any other books. Maybe because of my art-school-adjacent upbringing, I devote quite a bit of time to looking at and reading each image. I get just as much out of them as I do other books, but other folks might look at my list and wonder if calling a catalogue of national park brochures and design systems therein (Parks) counts as a "book read". It does for me. Plus, it was super useful as a reference for a project I was working on at the time!

However, I don't record movies or TV shows I watched. Why not? Should I? I suppose I've not taken them as seriously as I do books and watch them mostly in the background. But maybe it's worth noting the full "media" diet each year. Should podcasts then also make the list? For some people, I suppose it should. What about magazines? Articles?

What's Valuable is the Specifics

One of the things I've found most valuable in my reading was specificity. Books that are more abstract (such as Dalio's Principles or philosophical tomes) have not been useful and I've struggled to apply the lessons from them. But reading through case study-oriented books has been wildly useful, especially when the cases are written with a lot of specific and operational details. The Outsiders was a good example of this, as was Ken Kocienda's Creative Selection. Cedric Chen's recent case studies collections (which were probably book-length but didn't make it in to the list) were another example.

I find myself drawing multiple lessons from each case, including operational lessons that the author may not have intentionally been meaning to convey. "Focus on the Cases" by Cedric Chen and "Reality Has a Surprising Amount of Detail"  by John Salvatier do a much better job than I do explaining why this is so.

Lindy Effect vs. Recency Bias

In recent years, I've focused on buying less books and reading more of what I already had. It paid off this year as most of my books were catch-ups on previous years' worth of acquisitions. I try to track this with the publication year as a proxy for my acquisitions (though I might also start adding acquired, started, and finished dates to the ex libris pages).

While I'm a firm believer in the Lindy Effect, I've noticed that I have a bias towards newer books, especially with technical books. To that end, only five books (13%) were not from the last decade, and only one (Douglas Adams, much overdue) was from before the year 2000.

When dealing with the specifics of technology, most books end up being out of date quite quickly. On one hand, this is the perfect example of the aforementioned Lindy effect – books that have aged well continue to be useful long into the future. It's worth seeking those out because "things that have stood the test of time" are also often the things worth studying – or as Jeff Bezos/Amazon says, "focus on things that don't change".

Yet too much of business operations and technology have changed over the past twenty years, making some business "classics" appear quite dated or no longer useful. This is something I picked up on last year, and continue to find true:

I found that overly technical guides might be referencing long-unused frameworks and paradigms, while business books might be holding up as a case study a business that has aged extremely poorly. Branding agency Red Antler's Emily Hayworth alluded to the speed with which her examples might fade out of relevancy in the first pages of her book – 'Some of these brands might be under fire or pariahs due to missteps of their founders by the time you read this' (and it was true - Away Luggage was under fire while other startup brands had faded from relevance).

That makes me question the core principles that are being communicated. After all, why trust the premise of building towards longevity if the examples you use don't last more than a year's worth of time?

Even older 'classics' such as "Built to Last", "Good to Great", "Positioning", "22 Laws of Marketing", and others of that vein have not aged particularly well, and I found myself putting them down with some disappointment as to the value of insights they purported to offer. Part of this is natural – it's a process of cultural reflexivity and raising standards. [In business,] Michael Mauboussin calls this the "paradox of skill": "As people become better at an activity, the difference between the best and the average and the best and the worst becomes much narrower. As people become more skillful, luck becomes more important."

Business and technology are reflexive in that an innovative practice today becomes a best practice tomorrow, and a baseline the week afterwards. The baseline continues to rise and new practices are introduced. When you're working with systems – business, technology, or otherwise – you're finding ways to work within and around that system. Those systems eventually catch up to you – that's the reflexivity – and you need to come up with new strategies to achieve results.

So one of the things I've sought out – in conjunction with aforementioned specificity – is replicability. One of the reasons why The Outsiders was such an interesting read is because it focused on business operators that have repeatedly delivered high-performing results across a number of different industries and market conditions.

I want to unpack that: what I mean is that most case studies tend to have a bias towards market exceptions. These books/case studies are written about as if they were standard-bearers, when instead they tend to be exceptions to the rule. This is a backwards way of going about things. An exceptional case is one that has succeeded in spite of its circumstances and it is extremely hard to untangle what was causal, what was correlational, and what was luck. Exceptional cases are often not reproducible and so there are few "useful" lessons to take away from that.

As someone wiser than me remarked, focusing on exceptional cases is like asking a lottery winner to tell you what their lucky number was and how they walked to the bodega to buy a ticket. That's great for them and might make for a good story, but you don't really learn anything useful from that. What's more useful is to focus on why almost all people win very little at the lottery (that's the group you're in, statistically speaking), and what people who win multiple times understand about the lottery that other people don't seem to.

So rather than seeking out exceptional cases, I'm more interested in understanding reproducible results. Most of the time this manifests as case studies of failure – why most businesses fail to find product market fit, or the cause behind why so many companies are firing folks today. The lessons there are often what not to do, which is still valuable; as Charlie Munger remarked, “It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”

But every so often – and again, this is where The Outsiders and Creative Selection (or Legacy about the All-Blacks, or Creativity Inc about Pixar) are worthwhile  – you get case studies of success that were reproduced over different periods with different people and different conditions. This tends to isolate the consistent variables across those periods, without conflating situational idiosyncrasies to a level of causality. But I'm getting off on a tangent here.

Anyway, the Lindy-vs-Recency issue is also true for speculative fiction and science fiction, which I'm an avid reader of. It's worth teasing out that a lot of "classics" can be split into historically important novels (valuable because they represent a clear paradigm shift or before/after in how/what stories are told) and others are great stories that have stood the test of time (often because they focus less on technology and more about how technology or some other macguffin changes how people relate to each other). I find most of the historically important novels to not age too well, and love the timeless tales.

But with Sci-Fi/Spec-Fi, I also find that the recency bias – books that are contemporary, fun, but might not be groundbreaking – are still valuable to read because they tend to be mirrors to today's preoccupations and concerns. Similarly, most of today's business books are a reflection of today's business landscape and concerns. Both will likely go out of date quite quickly but that's not a complete-enough deterrent from always staying away from them, especially when they may have interesting perpectives and reveal your own blind spots about the present and near future.  

A Diversity of Perspectives

I've tried to be intentional the last few years about picking up books from perspectives unlike my own – non-white/male/European perspectives. Here's last year:

Thirty percent of books I read were by not by men, and only thirteen percent were by nonwhite authors. [In 2020], only six percent were not by men, and twelve percent by nonwhite authors. It's progress, but it's not great.

This year was roughly the same as last year. Eight out of thirty books (25%) were by women, and six (20%) were by non-white authors. However, books by non-white/non-male authors were in my top 3 best books in both fiction and nonfiction.

I take full accountability for the books selections I make. Still, there remain two challenges. First is that I pick books up primarily because of the content and not the author. I also don't know the author's background beyond what they choose to present and make a part of their explicit biography.

Secondly, part of the challenge seems to be in structural inequalities in publishing – the choices we make are constrained by the available selection. For many technical subjects (especially in business, computer sciences, and older Lindy-validated books), this means a bias towards white and male authors.

While it's immediately clear the benefit of having a diverse perspective brings to things such as social sciences or narrative fiction, I've heard some hang ups from folks about more technical work. If you're writing a guide to managing python-based deployments of data models, does it really matter who is doing the telling?

The answer is yes, for many different reasons. I can't offer a comprehensive list, but the benefits I've seen from having diverse perspectives on even technical subjects include:

• Clearly identifying ethical and moral concerns that are implicit in the work being done, and strategies for mitigation.
• A plurality of examples for how to relate to both abstract and technical concepts, which resonate differently across populations. These semantic differences manifest in increasing accessibility and comprehensibility.
• It introduces a diversity of teaching techniques and practical examples to work through. I find practical examples to be my own preferred way of learning, and I also know that a good study-project can spur my imagination to other applications within my own life. Good practice cases offer immediate and practical benefits to folks.
• Given that most work is done in collaboration with other people, strategies for relating and working with other people/teams/contributors are wildly different. Groups of people who experience structural inequalities have wildly different techniques for negotiating those spaces compared to people in an in-group.
• It exposes biases that you may not have known existed – the "unknown unknowns".

How true is this in practice? I think that Marianne Bellotti's "Kill it With Fire" (on managing aging computer systems) is wildly different to somewhat comparable/overlapping dev-ops and change management books such as "The Phoenix Project" (Gene Kim) or "An Elegant Puzzle" by Will Larson (again – where those books overlap topically). It's almost incomparably different from anything that the HBR may have written on the topic as well. I believe this is partially because Marianne Bellotti is really good at what she does and partially because her background as a woman in tech leadership means that she doesn't have all of the affordances that a more commonly represented background might experience, and therefore needs different strategies to approach her subject matter.

Similarly, in Mismatch, Kat Holmes writes about inclusion and how most accessible design ends up benefiting a much broader population than what they intended to serve for. Sidewalk cutaways, keyboards, TV captions, and many other innovations are the direct result of designing for inclusivity and accessibility, which is another way of saying that it's design for people outside of the most-commonly-represented-stereotypes. So again – diverse backgrounds benefit everyone.

I also look at Cedric Chen's Commoncog blog and know for a fact that we all benefit from his first-hand experience managing software projects in Southeast Asia even if  at first glance the specific challenges are not the same as where I work. Simply put, the world gets richer from a plurality of examples and I'm glad to not reread the same three case studies of US-based venture companies over and over when people write about growth in software.

So looking into 2023, I want to continue being more intentional with my selections, and I'm going to try to make an effort to feature such perspectives. Please reach out if you're interested!

And Now, the Complete List

(In no particular order)

Narrative & Technical Non-Fiction

Tape Sucks by Frank Slootman (2011)

F.I.R.E. - How Fast, Inexpensive, Restrained, and Elegant Methods Ignite Innovation by Dan Ward (2014)

The Principles Sequence by Cedric Chen (2019)

Burnout: A Guide by Cedric Chen (2022)

The Founders by Jimmy Soni (2022)

The Man Who Solved The Market: How Jim Simons Launched the Quant Revolution by Gregory Zuckerman (2019)

Write Useful Books by Rob Fitzgerald (2021)

Analogia: Emergence of Technology Outside of Programmable Control by George Dyson (2020)

The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success by William Thorndike (2012)

How to Do Nothing by Jenny Odell (2019)

The Toaster Project by Thomas Thwaites (2011)

Philosophy for Polar Explorers by Erling Kagge (2006)

Quit by Annie Duke (2022)

Creative Selection by Ken Kocienda (2018)

Fiction

The Murderbot Diaries, Books 1-5 (Artificial Condition, Rogue Protocol, Exit Strategy, Networks Effects, Fugitive Telemetry) by Martha Wells (2018-2020)

The Mountain in the Sea by Ray Naylor (2022)

Hummingbird Salamander by Jeff Vandermeer (2020)

When We Cease to Understand the World by Bejamin Labatut (2020)

Valuable Humans in Transit (and other stories) by qntm (2006-2022)

The Hitchhiker's Guide to the Galaxy by Douglas Adamas (1979)

Tomorrow & Tomorrow & Tomorrow by Gabrielle Zevin (2022)

The Lying Life of Adults by Elena Ferrante (2019)

Art, Design, and Image Mediums

Abandoned Moments by Ed Kashi (2021)

Parks by Standards Manual (2018)

A Man & His Cat, Vol 1-3 by Umi Sakurai (2021)

Opus by Satoshi Kon (2014)