I interviewed Stewart Brand about writing The Maintenance Race.
The Maintenance Race tells the thrilling story of a 1968 solo sailing race around the world, a feat that had never before been attempted. It follows three competitors—the man who won, the man who chose not to win, and the man who cheated—illuminating what their respective journeys reveal about the art of maintenance.
Yes, that’s right, maintenance: the critical but rarely celebrated work of keeping systems running smoothly. We all know we should maintain what we care about: our possessions, our relationships, ourselves—but it’s always tempting to skip to the hot new thing that captures our attention, letting our lives fall into disrepair in the process. The Maintenance Race will show you why maintenance matters and how bringing the full scope of your care and attention to bear on it can be transformative—the story sucked me in from the first sentence and inspired me to apply its ideas to my own projects.
Stewart has led a long and fascinating life that I can’t even begin to summarize here, but that I highly recommend you investigate further—this film and this podcast interview are great places to start. He is the president of the Long Now Foundation (I’m a proud member), the founder of Whole Earth Catalog and the WELL, and the author of many books, including How Buildings Learn.
In the following conversation, we discuss why maintenance matters and the creative process behind The Maintenance Race, which is the standalone opening chapter of Stewart’s forthcoming book.

What is the origin story of The Maintenance Race and the book it may ultimately grow to become? What made you realize this is a story you need to tell? How has the project evolved since you first conceived it?
A friend named Garrett Gruener said “Why don’t you do a book about maintenance?” I replied politely “Yeah, I wish someone would do that, but it’s not me. I have a book I’m working on.” By next morning the book I wanted to write had a title, Maintenance. That was two and a half years ago. The research keeps surprising me. I have to continue it until it doesn’t—until it begins to close on itself, and I know what my news can be.
My discovery of the Golden Globe race came from briefly knowing one the legendary competitors, Bernard Moitessier. Years ago I read his book The Long Way, so I knew about his exemplary maintenance stye. Hugh Howey suggested I compare him to Donald Crowhurst. I had read the book about him too. Rereading them I discovered Robin Knox-Johnston. I had characters. I had saga. The rest was just research and writing.
You released the first chapter, The Maintenance Race, as a standalone Audible Original and asked listeners to share feedback to help inform whether and how you write subsequent chapters. What’s the most surprising thing you’ve learned from listeners so far?
I used to buy Buckminster Fuller’s admonition, “NEVER show half-finished work.” For some writers that means: “Don’t even tell anyone what you’re working on.” I’m now persuaded that the opposite works best, at least for me.
I think it’s worth knowing as soon as possible if the thing you want to build is going to take on a life of its own—if it’s going to “make circuit” with the world (in Gregory Bateson’s terminology). Software developers hasten to build an MVP—Minimum Viable Product—to connect with early users and get a sense of how to shape the product around real use. (Amazon developers prefer test launching of a “Minimum Loveable Product”—a more demanding exercise.)
I saw that the first chapter for my barely-started book Maintenance: Of Everything was working out surprisingly well and looked like it could stand alone. So I polished it up enough to send to some magazines; they weren’t interested. For fact checking I had sent an early draft to a friend, writer Hugh Howey, who was long a professional sailboat skipper. He loved it, critiqued it (overnight!), and sent it to his friend Don Katz, founder and executive chairman of Audible Inc.
Don liked it and sent it to David Blum, editor-in-chief of Audible Originals, who liked it and assigned it to pruducer Rachel Hamburg, who deftly guided me through the process of improving the story’s listenability. When I asked my friend Peter Coyote if he would consider narrating the story, he recommended his beloved acting teacher Richard Seyd (who was born with a British accent appropriate to a mostly-British story).
I specify all this to honor the extensive handing-around by supportive people that is involved in getting any piece of writing into the world.
The most surprising feedback? Many wondered how I could possibly make the rest of the book as gripping as the first chapter. Now I wonder too.
The Maintenance Race is a thriller: it makes you want to find out what happens next even as it makes you think. How do you think about the relationship between stories and ideas? How are you going about weaving them together to create this book?
The start is where you lose or win the reader. My title might as well have been Maintenance: The World’s Most Boring Subject. For most of us, maintenance is only interesting when it is life-critical, like with airplanes. Sailing alone for half a year in the murderous Southern Ocean qualifies. Add competition. Add true-life legends at their mythic best. With luck you might boil the reader’s blood a bit.
My medium is journalistic essays—lots of news, with enough argument to hold it together and maybe give it direction. I try to give the reader sufficient information—all of it hopefully “new, true, important, and well written”—for them to find their own argument in it and disagree with mine if they choose.
Narrative is what our mind craves, but there is a problem. David Krakauer voiced it this month in Parallax—the newsletter of Santa Fe Institute, which studies complexity. He wrote that narrative is “a sequence of limited and dominant cause/effect relations required to explain the present in terms of a contingent past.”
To make a story work, the past is adjusted to explain the present in a satisfying way. The punchline shapes how the joke develops. The moral determines the fable. Narrative is always a simplistic lie, compared with the boundlessly multi-causal-at-multiple-scales real world.
My Chapter 1 is a morality tale where the several outcomes in the infamous 1968 Golden Globe Sailboat Race are explained in terms of differing modes of boat maintenance. Dramatic! Persuasive! True too!—to the facts that are reported. The moral determined the fable. I can’t do that with the rest of the book.
In his Parallax essay, Krakauer goes on to write, “One way to apprehend this complexity is through methods or frameworks that can deal with irreducible complexity, either with coarse-graining observations and understanding how much information is being lost, or by working within methods that eschew easy explanations in terms of patterns and schemes that provide a means of classifying varieties of historical sequence.”
But don’t we ultimately need to derive explanations that are sufficiently straightforward to inform action, and wouldn’t any such explanation fall right back into the clockwork trap (and make for a great story)? If complexity is indeed irreducible, then what we can we learn from it beyond humility?
It’s good to regard narratives with suspicion always. Each is just one path through reality, not reality itself. For those interested in becoming liberated from the narrow-mindedness of stories, explorers of non-narrative understanding include Krakauer’s Santa Fe Institute (where I was a board member for 14 years), Philip Tetlock (trainer of “superforecasters”), and Judea Pearl (author of The Book of Why).
Maintainers are massive scholars of causation. They routinely have to figure out why something stopped working, and it can be maddening. Each success is a compelling detective story. Once they understand the problem (or have a guess they’re willing to work with), they have to figure out what to do about it. Each of those successes is a caper story. In The Maintenance Race an example is Bernard Moitessier figuring out how to fix his disastrously bent bowsprit, at sea, by himself.
Why is it so easy to underinvest in maintenance, whether it’s of physical infrastructure, personal relationships, software, public institutions, or anything else? What can we learn about ourselves and our blindspots from observing maintenance failures?
The short answer is mismanaged priority lists. We tend to let our lists be dominated by things that are urgent, that require immediate action. Things that are profoundly important but don’t require immediate action—like maintenance—go so far down the list they seldom get dealt with, or they get only half-hearted, feeble attention.
What differentiates masters of maintenance? How do maintenance and long-term thinking relate to each other? How is your work at the Long Now Foundation influencing the book, and vice versa?
Maintainers are habitual long-term thinkers. At The Long Now Foundation we’re treating my research on maintenance as an informal Long Now project. A related formal project, led by our executive director Alexander Rose, is the Organizational Continuity Project examining how really long-lived and long-valuable institutions manage to keep themselves useful for centuries. Institutional maintenance.
What’s the most unexpected thing you’ve discovered researching the book? What’s taken you by surprise, and how has it changed what maintenance means to you?
The most news for me keeps coming from software engineers. Yeah, software eats the world, and maintenance eats software developers. The fixing and adjusting never stops. It is so complex and tedious the developers are always trying out better designs to minimize it. When stuck with it they try to automate around it. And still it eats them. The clever results of their inventiveness can help any other maintenance domain that chooses to pay attention.
How are you planning to maintain a book about maintenance? What strategies are you employing in researching, writing, and publishing this book to help it survive and thrive for the long run?
The book will be similar to my How Buildings Learn in some ways. I expect it to be richly illustrated throughout. I was once a photojournalist and still prefer to communicate that way. But a major difference is that this book can’t attemp to be comprehensive the way my buildings book was. (A measure of success with that is that How Buildings Learn continues to sell well 18 years later without revisions, and no other book has tried to replace it. Of course that success may also be a measure of how static the building trades are. Nobody is growing bio-buildings yet.)
Like my buildings-in-time book, this one is introducing a broad topic—maintenance-in-general. But it can only be introductory. Each of its chapter (on vehicles, aerospace, cities, Japan, civilization, planet, etc.) could be, with vast research, an entire book. And to stay relevant each such “book” would have to live online and be updated continuously by a large team. So, forget that. All I can do is introduce. That will make it a short-lived book.
What might last, if I’m successful, is interest in the subject as a general one. I’ve scanned and read hundreds of books so far in my research. In very few of them is “maintenance” even an item in the index. An indication of success for my book would be if “maintenance” starts showing up as an index item in a wide variety of books, the way “infrastructure” now does, for example.
So. The range of my chapters is so wide, I need all the help I can find to fact-check, correct, improve, and comment on what I write. I plan to pre-publish chapter drafts online and sometimes elsewhere—as I did with The Maintenance Race—and invite assistance. Will that help or hurt eventual book sales? Who cares? I just want text and imagery that has been de-bugged by a lot of eyeballs.
What should fans of The Maintenance Race read while they wait for the next chapter? What books have shaped your thinking on this subject in unexpected ways?
The four wonderful Golden Globe books are:
- A Voyage for Madmen by Peter Nichols
- The Long Way by Bernard Moitessier
- A World of My Own by Robin Knox-Johnston
- The Strange Last Voyage of Donal Crowhurst by Nicholas Tomalin and Ron Hall
Some books that have surprised me and shaped where I might go with the book are:
- The Shock of the Old: Technology and Global History since 1900 by David Edgerton
- The Perfectionists: How Precision Engineers Created the Modern World by Simon Winchester
- Working Knowledge: Skill and Community in a Small Shop by Douglas Harper
- Working in Public: The Making and Maintenance of Open Source Software by Nadia Eghbal
- Connectography: Mapping the Future of Global Civilization by Parag Khanna
Can you share anything about the next chapter?
My second chapter is titled “Vehicle,” starting of course with motorcycles. And of course I draw on Robert Persig’s celebrated Zen and the Art of Motorcycle Maintenance. Since my book will be illustrated in color, I looked for imagery.
Most people know that Persig’s brilliant philosophy book is based on a real motorcycle road trip that he and his son took, across the American west. What most don’t know is that their trip companions took a few photos. This is one:

In the summer of 1968 Robert Persig was photographed at a roadside stop (I think in South Dakota) by Sylvia Sutherland. His troubled 11-year-old son Chris is on the back with the camp gear and motorcycle tools. Maintenance of the motorcycle was described in detail throughout the book, but its make and model were never mentioned. It was a 1966 Honda CB77F “Super Hawk”—Honda’s first sport bike. Persig kept it the rest of his life. It is now in the Smithsonian.