I’ve previously (2019, 2018, 2017, 2013) compiled lists of some the books and articles I most enjoyed during the year. Thanks to the pandemic, I read more in 2020 than usual. In no particular order, here are the books and posts that I enjoyed and/or learned from most during the year. (Note: these weren’t all published in 2020 — that’s just when I got to them.)


On Having No Head by Douglas Harding

A short treatise on the experience of consciousness and being. Reconnected me with Zen Buddhism, a great influence in my late teens and early 20s.

I have never been anything but this ageless, measureless, lucid and altogether immaculate Void: it is unthinkable that I could ever have confused that staring wraith over there with what I plainly perceive myself to be here and now and always!


Doughnut Economics: Seven Ways to Think Like a 21st-Century Economist by Kate Raworth

An invitation to lead generative lives within the bounds of planetary systems. The doughnut is a “21st Century compass” — a visual prompt that articulates these boundaries clearly and simply.

what enables human beings to thrive? A world in which every person can lead their life with dignity, opportunity and community — and we can all do so within the means of our life-giving planet.


The Universe of Design: Horst Rittel’s Theories of Design and Planning by Jean-Pierre Protzen and David J. Harris

A collection of Rittel’s writings — essential if you’re dealing with wicked problems.

A model can be defined as a suitable abstraction of reality, presenting the essential structure of a problem, a representation of a subject of enquiry into objects, processes, or systems, for prediction and control. It can be used if the manipulation of the represented entity itself is too expensive or impossible.

(This is one of the best definitions I’ve found of models.)

The innovator, or designer, or planner acts politically in all cases where he is producing essential innovation — even though he may not know it — though he should!


The Image: Knowledge in Life and Society by Kenneth E. Boulding

A short treatise on “the image”: “the sum of what we think we know and what makes us act the way we do.” Provides insights on mental models.


Competing Against Luck: The Story of Innovation and Customer Choice by Clay Christensen, Karen Dillo, Taddy Hall, and David S. Duncan

Go-to book for the Jobs-to-be-done theory. JTBD has become very popular, and this book is a good articulation of the theory. (I was also pleased by its defense of theory itself.)

New products succeed not because of the features and functionality they offer but because of the experiences they enable.

Data is always an abstraction of reality based on underlying assumptions as to how to categorize the unstructured phenomena of the real world.

Organizations typically structure themselves around function or business unit or geography—but successful growth companies optimize around the job.”

If you can’t describe what you are doing as a process, then you don’t know what you are doing.


High Output Management by Andrew S. Grove

The best book I’ve read about management. My career would’ve been very different had I read High Output Management twenty years ago.

All managers in such companies need to adapt to the new environment. What are the rules of the new environment? First, everything happens faster. Second, anything that can be done will be done, if not by you, then by someone else. Let there be no misunderstanding: These changes lead to a less kind, less gentle, and less predictable workplace. Again, as a manager in such a workplace, you need to develop a higher tolerance for disorder.

A manager’s output = the output of his organization + the output of the neighboring organizations under his influence.

The art of management lies in the capacity to select from the many activities of seemingly comparable significance the one or two or three that provide leverage well beyond the others and concentrate on them.

My book notesAmazon

Figure It Out: Getting From Information to Understanding by Stephen Anderson and Karl Fast

Great book on how we make sense of the world. Lots of useful implications for designers. (Disclosure: both co-authors are friends and I received this book for free as a previous Rosenfeld Media/Two Waves author.)

Rosenfeld MediaAmazon

Reagan: The Life by H.W. Brands

One of several books about U.S. politics I read during this election year. This biography gave me a new appreciation of President Reagan’s leadership during a critical period in world history. (I came of age during the years portrayed in the book, and remembered many of the book’s episodes from the news.)

Reagan wasn’t acting when he spoke; his rhetorical power rested on his wholehearted belief in all the wonderful things he said about the United States and the American people, about their brave past and their brilliant future. He believed what Americans have always wanted to believe about their country, and he made them believe it too.


On Writing: A Memoir Of The Craft by Stephen King

A combination memoir and instruction manual on better writing from a master storyteller. I loved the image of the story as a fossil to be unearthed.

write with the door closed, rewrite with the door open. Your stuff starts out being just for you, in other words, but then it goes out. Once you know what the story is and get it right — as right as you can, anyway — it belongs to anyone who wants to read it. Or criticize it. If you’re very lucky (this is my idea, not John Gould’s, but I believe he would have subscribed to the notion), more will want to do the former than the latter.

Some people don’t want to hear the truth, of course, but that’s not your problem.

Good fiction always begins with story and progresses to theme; it almost never begins with theme and progresses to story.


Good Strategy, Bad Strategy: The Difference and Why it Matters by Richard Rumelt

Strategy is a key, yet elusive, concept. This book clearly defines what constitutes “good” strategy by showing lots of examples of good and bad strategies.

The core of strategy work is always the same: discovering the critical factors in a situation and designing a way of coordinating and focusing actions to deal with those factors.


Mornings on Horseback: The Story of an Extraordinary Family, a Vanished Way of Life, and the Unique Child Who Became Theodore Roosevelt by David McCullough

A compelling biography of the young Theodore Roosevelt by one of my favorite writers on U.S. history. The Roosevelt family’s aristocratic milieu feels at times like an alien world; McCullough takes us there and makes us care.


Children of Dune by Frank Herbert

This year I read the first three Dune books. I’d read the first one in the mid-80s, when the David Lynch movie came out, but I hadn’t read Dune Messiah or Children of Dune. I thought I’d tackle the trilogy now that a new movie is imminent. I especially liked the third book.

“The purpose of argument is to change the nature of truth.”

He had to be as precise as possible. At the same time, he knew that precise thinking contained undigested absolutes. Nature was not precise. The universe was not precise when reduced to his scale; it was vague and fuzzy, full of unexpected movements and changes.

Good government never depends upon laws, but upon the personal qualities of those who govern. The machinery of government is always subordinate to the will of those who administer that machinery. The most important element of government, therefore, is the method of choosing leaders.

Is your religion real when it costs you nothing and carries no risk? Is your religion real when you fatten upon it? Is your religion real when you commit atrocities in its name?


Mastery: The Keys to Success and Long-term Fulfillment by George Leonard

Don’t be put off by the cheesy title. This is a good book on the lifelong journey of mastery, inspired by Aikido and Zen.

How do you best move toward mastery? To put it simply, you practice diligently, but you practice primarily for the sake of the practice itself.

My notesAmazon

The Overstory: A Novel by Richard Powers

Pulitzer-prize winning novel about the relationship between humans and the environment, the tension between individual drive and the common weal, and the allure (and perils) of groupthink. Wise, engaging, layered.

His brow crumples. He shrugs. What else is there to say, to a bear? “Apologize! I tell him, people very stupid. They forget everything—where they come from, where they go. I say: Don’t worry. Human being leaving this world, very soon. Then the bear get top bunk to himself again.”

The confirmation of others: a sickness the entire race will die of.

“Then why doesn’t the market respond?” Because ecosystems tend toward diversity, and markets do the opposite. But she’s smart enough not to say this. Never attack the local gods. “I’m not an economist. Or a psychologist.”


Posts, Essays, Interviews

Turn-by-turntables: How drivers got from point A to point B in the early 1900s by Larry Printz

How to Get Started Designing for Developers by Tim Sheiner

The 20 Levers for Return on Design by Enrique Allen

A history of Simlish, the language that defined The Sims by Brennan Kibane

How to Write Usefully by Paul Graham

Wikipedia Is the Last Best Place on the Internet by Richard Cooke

68 Bits of Unsolicited Advice by Kevin Kelly

Investing in Figma: The Decade of Design by Peter Levine

How Coronavirus Mutates and Spreads by Jonathan Corum and Carl Zimmer

How would Jane Jacobs design a social media platform? by Jasmine Sun

In a Crisis, Ecosystem Businesses Have a Competitive Advantage by Mark J. Greeven and Howard Yu

When SimCity got serious: the story of Maxis Business Simulations and SimRefinery by Phil Salvador

What a Prehistoric Monument Reveals about the Value of Maintenance by Ahmed Kabil

Welcome to the 21st Century: How To Plan For The Post-Covid Future by Tim O’Reilly

Liquid Cities by William O. Gardner

Idea Generation by Sam Altman

How You Should Read Coronavirus Studies, or Any Science Paper by Carl Zimmer

Peer Review by Rodney Brooks

Taming Complexity by Martin Reeves, Simon Levin, Thomas Fink and Ania Levina

The Long Shadow Of The Future by Nils Gilman and Steven Weber

An Opinionated Guide to ML Research by John Schulman

Researchers and Founders by Sam Altman

Game Design as Narrative Architecture by Henry Jenkins

The silence is deafening by Devon Zuegel

Why Figma Wins by Kevin Kwok

The Lure of New Features and Products by John Cutler

We Change By Slowly Changing Everything, an interview with Bruce Mau

Make me think! by Ralph Ammer

Human-scale digital spaces by Alexis Lloyd

Six Ways to Think Long-term: A Cognitive Toolkit for Good Ancestors by Roman Krznaric

The UX of LEGO Interface Panels by George Cave

How the Blog Broke the Web by Amy Hoy

The relevance of cybernetics to design and AI systems by Hugh Dubberly

Why Gregory Bateson Matters by Ted Gioia

Milestones of User Interface Design by Boris Müller

Complex systems science allows us to see new paths forward by Jessica Flack & Melanie Mitchell

Revisiting Adaptive Design, a lost design movement by Matt Webb

Seamful Futures by Brian Dell

An uneven history of content strategy by Rahel Anne Bailie

Hopeful and Powerless? Design in a Crisis by Stephen P. Anderson

Christopher Alexander’s Battle for Beauty in a World Turning Ugly by Per Galle

Applying Ancient Chinese Philosophy To Artificial Intelligence by Bing Song

Navigating Organizational Transformation: Let Buildings Be Your Sensei by Ganesh Sankaran

Thinking in maps: from the Lascaux caves to knowledge graphs by Anne-Laure Le Cunff

How to Build a Digital Brand That Lasts by William Collis and David Collis

How Apple Is Organized for Innovation by Joel M. Podolny and Morten T. Hansen

The Analog City and the Digital City by L. M. Sacasas

When Managing Through Ambiguity, Develop a Clear Vision by Cheryl Strauss Einhorn

What complexity science says about what makes a winning team by Jessica Flack and Cade Massey

How to Think for Yourself by Paul Graham

Why Technology Has a Will, an interview with Kevin Kelly

The Social Life of Forests by Ferris Jabr

Camera Obscura: Beyond the lens of user-centered design by Alexis Lloyd, Devin Mancuso, Diana Sonis, and Lis Hubert

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