Lessons about Design Distilled from a Goodreads Challenge

54 insights about design from mostly-not-design books.

Jan 01, 2020

In 2019 I read 54 books, coming through the other side of — if I’m remembering correctly — my only resolution made twelve months ago to read 52 books as part of the Goodreads challenge. This was personally ambitious. I learned a lot about how to read, something I’m interested in sharing in another writeup, but my biggest takeaway has been that reading variety is a kind of combinatory play — think: random word association games — and the connections you’re able to draw between totally disparate subjects can be a source of a ton of a-ha moments.

So, here are 54 lessons about design from my mostly non-design body count.

The services we design have a kind of agency of their own.
The Subtle Knife by Philip Pullman
We waste many good years of our lives caring too much about the quality of design or design thinking in the industry.
The Witch of Lime Street: Seance, Seduction, and Houdini in the Spirit World by David Jaher
J.M. Barrie introduced fairy dust as a component for flight because in an earlier production where only happy thoughts were necessary, children tried flying from their beds and hurt themselves. Test often.
Peter Pan by J.M. Barrie
Human language is an open-source service that adapts to jobs to be done in realtime.
Because Internet: Understanding the New Rules of Language by Gretchen McCulloch
The product is a means to an end that facilitates the service. Sometimes, the service is better served by a different product. In this case, the movie out-serves the book.
The Exorcist by William Peter Blatty
The key to talking to strangers is a foundation in service design. We are very bad at first impressions, judging strangers, but how strangers act is informed by their world: complex ecosystems of pressures and reliefs - jobs - and the services afforded in the environment.
Talking to Strangers by Malcolm Gladwell
An okay product in disciplined hands is better than a great product in any hands less than.
The Revenant by Michael Punke
“Coupling” is a critical component of user behavior. In a moment of grief, you can’t bring someone back from the dead if you don’t have a Pet Sematary in walking distance.
Pet Sematary by Stephen King
Design twitter: “It’s like a bunch of hipstery academic fucks try to have an adventure, and instead spend most of the time discussing the adventure they’re currently having, instead of actually having it.” From a funny comment on Goodreads.
The Haunting of Hill House by Shirley Jackson
The key is to just ask for help. Admit it when you’re scared, or out of your debt. It’s okay. Good folks are out there.
The Art of Asking; or, How I Learned to Stop Worrying and Let People Help by Amanda Palmer
A great service is front-loaded with a metric ton of discovery.
Fire & Blood by George R. R. Martin
Integrity and foundational design principles are difficult — but not impossible — for an individual to adhere to against nuanced, pervasive external pressures. Good systems of work are a better bet.
Truman by David McCullough
Our pseudo-scientific approach to design, hypotheses fine-tuned through trial, error, testing, are still at their core make-believe paintings on the walls of cave. Design now serves the same function as design then.
Midnight Son by James Dommek Jr., Josephine Holtzman, Isaac Kestenbaum
Your product, service, or organization will not only die, it will be forgotten - and you might not even see it coming. Memento mori. Subscribe to Stoic Designer.
The End is Always Near by Dan Carlin
Read the books your mentors read, then the books their mentors read. Try to understand how your own opinion has been shaped over time.
How to be an Epicurean: the Ancient Art of Living Well by Catherine Wilson
Meaningful quotes out of context are both motivating behavioral triggers - and lies. Context is the key. Try to avoid repeating quotes or ideas (or trend hype) without understanding wtf you’re saying.
The Bed of Procrustes: Philosophical and Practical Aphorisms by Nassim Nicholas Taleb
Context is key.
The Adventures of Huckleberry Finn by Mark Twain
Project managers get paid well to use sticky notes. The tools people use say little about their fitness for the job to be done. Focus on people, not tools.
Project Management for Humans by Brett Harned
Ask yourself: how much of your process is in place just because it’s common in the industry? Then, ask yourself: does this process actually work for what I need to do?
Shape Up: Stop Running in Circles and ShipWork that Matters by Ryan Singer
Good design is a value judgment that has a lot to do with the time you’re in. Be sure that the design choices you make actually work for now.
The Fall of Arthur by J.R.R. Tolkien
The temporal midpoint may be one of the most impactful project management tools at your disposal.
When: the Scientific Secrets of Perfect Timing by Daniel H. Pink
You too can write novels with a little time management.
Renegade Star by J.N. Chaney
You too can turn a podcast into a novel with a little time management.
Welcome to Night Vale by Joseph Fink, Jeffrey Cranor
Deliberate practice will rewire your brain, meaning you can train your mood, or even creativity.
The Brain’s Way of Healing by Norman Doidge, M.D.
A real danger of distributed systems of work, such as agile at scale, is that you can be engaged in unethical design work and not know it.
Permanent Record by Edward Snowden
Remember that paleontologists decided the Brontosaurus no longer existed, shattering our childhood dreams - before deciding that, in fact, it did. It is hard to come by objective truth.
A Grown-up Guide to Dinosaurs by Ben Garrod
Hype, expectation, and convention can mute an otherwise positive user experience. A user-experience is not in a vacuum.
World War Z by Max Brooks
The best hypothesis is the one that reflexively accepts its potential wrongness to begin with. Klosterman’s razor.
But what if we’re wrong? Thinking about the present as if it were the past by Chuck Klosterman
Good self-improvement advice earned organically through trials and tribulations are more easily learned by reading the Stoics.
Unfu*k Yourself: Get out of your head and into your life by Gary John Bishop
In some way, everyone you know - especially those you work with - are strangers.
The Golden Compass by Philip Pullman
Commit to re-reading books or articles you read — say — ten years ago. You are a different person, now, and you will see things very differently.
Dracula by Bram Stoker
Deliberately choose the people who you spend your time — especially your time working — with.
Naturally Tan by Tan France
You will be remembered by your actions - not your words. History, likely, will forget you. Glory is ephemeral.
The Pagan Lord by Bernard Cornwell
When you are confronted with a new design problem, tell yourself: “good.” Problems are clarifying. They make your decisions about what to do and how to spend your time easier.
Extreme Ownership by Jocko Willink and Leif Babin
Great content is evergreen.
Alien III by William Gibson
Victory does not come to people who listen to their fears.
Death of Kings by Bernard Cornwell
If you don’t read widely, witticisms, pull-quotes, and a tendency to cite sources in conversation will seem profound. If you read widely, you see these for what they are.
12 Rules for Life by Jordan B. Peterson
Do one thing well rather than two mediocre things.
Good to Great by Jim Collins
Classics are not sacrosanct and exist to be remixed. Remix them.
The Song of Achilles by Madeline Miller
Many of the components of your success are out of your control. Those who are wildly successful are so because of circumstances of luck. They are not the ones to learn from.
Outliers by Malcolm Gladwell
When you innovate successfully, your innovations will become conventions. Given time, your work won’t seem so innovative.
Salem’s Lot by Stephen King
Very complex award-winning designs probably got those awards because the award-givers couldn’t figure out wtf was going on, but wanted to seem smart.
The Three-Body Problem by Liu Cixin
The nueroscience of consciousness is mind-bending. When you try too hard to code a service, identify the most granular job-to-be-done, or understand a “user experience,” you’ll find that the physics of your understanding of design won’t hold up.
Waking Up by Sam Harris
Good service design allows for the product to retire gracefully. The job to be done remains, and a different product becomes a better vector for that service provision.
Tiamat’s Wrath by James S.A. Corey
“I realize that not infrequently books speak of books: it ias as if they spoke among themselves. In the light of this reflection, the library seemed all the more disturbing to me. It was then the place of long, centuries-old murmuing, an imperceptible dialogue between one parchment and another, a living thing.”

Memetics. Design speaks of design. It is also important to not get trapped in the altar of design. Design-thinking is a tool, it is not to be worshipped.
The Name of the Roseby Umberto Eco
There is always a loophole, and always an industry — not just a person — that will accrue around it.
The Dispatcher by John Scalzi
Stoic Design is definitely the way to go.
The Manual by Epictetus
Honestly, if you want to see design lessons learned from the Stoics, read my work doing Stoic Designer.
The Tao of Seneca, Vol. 1 by Seneca (!)
We tend to accept and repeat maxims about actions being louder than words, but words — also — are actions - and they are powerful.
The Raven Tower by Ann Leckie
Plentiful wells empty eventually.
The X-Files: Cold Cases by Joe Harris
It’s services all the way down: functions are services, objects are services, sound software composition is good service design.
Composing Software by Eric Elliott
What stands in the way becomes the way. “Problem” is a perspective, especially in something as — let’s be honest, comparative to the world: — usually low stakes as design work. When you encounter a challenge, whether a bug in the platform or a pain point in a journey, then you can see that as clarifying. You know now what to do: address the problem.
The Obstacle is the Way by Ryan Holiday
Everyone is a stranger subject to behavioral coupling. It is naive to think you have anything better than an educated guess about how a person will act given a specific situation. Check your biases.
The Demon Next Door by Bryan Burrough
Your hands look a lot cleaner when you get to dictate where history begins, and what parts of it count.
Persepolis Rising by James S.A. Corey

This took me a couple of days to write because of some of the mental gymnastics required to mine design insights out — let’s say — The Haunting of Hill House. In some of these cases, like World War Z, my lesson is about the book itself: you’re not going to find lessons about hype in this novel, but hype mutes experience and for as objectively neat and well-composed as that book, I was always waiting for it to rise to expectations.

My main advice is to read widely. Skimming? Go for it. Trash fiction? Awesome. It doesn’t matter. When you read enough, your mind can’t help but draw associations between Composing Software and The Fall of Arthur. These connections, more often than not, are silly, but I hope in this little jaunt 👆 I was able to demonstrate how they can be insightful.

I’m looking forward to another year with you all,
Michael Schofield

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