Editor's Choice

Iterate: Ten Lessons in Design and Failure

May 10, 2019


John Sharp and Colleen Macklin explore iteration and creativity in both an academic and intensely human manner through ten case studies.

Iterate: Ten Lessons in Design and Failure by John Sharp & Colleen Macklin, The MIT Press,

I have become very wary of the fetishization of failure and the “fail fast, fail often” ethos in business and business literature, especially in the tech sector. Luckily, it seems to be somewhat on the wane. And yet, I understand that there is a baby in that bathwater that shouldn’t be thrown out—the importance of prototyping and iteration that is at the heart of the creative process itself.

On a personal level (and since it’s what I do to make a living, on a professional level, as well), I consider every book review I do a failure in some way. I never quite capture the spirit of the book I’m reviewing, and since I only review books I believe in and actually want to get others interested in, I usually end up walking away from every week’s review feeling a little worse for the wear and effort, rather than patting myself on the back for a job well done. And so I’ve come up with a process to make it easier. It’s not perfect. It’s actually kind of a mess. I always wish I had more time. I always wish I did better. But by the end of the week, there is an imperfect review of a book to share with the world.

So the lines with which John Sharp and Colleen Macklin open their new book, Iterate, immediately resonated with me:


Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.


Those lines from Samuel Beckett begin a discussion on the inevitability of failure in creative work, and the important role it plays.


Most creative projects emerge from film scraps on the cutting room floor, waste baskets overflowing with crumpled paper, and abandoned prototypes. Even though these failed experiments are swept out of view once the work is complete, creative practitioners all know they exist, and that they were an integral part of the process.


This book is, early on at least, rather academic—introducing us to various concepts and theories of creativity, and the scholars and practitioners who developed them. It ranges from Joy Paul Guilford (the “father of modern creativity research”) to professor Teresa Amabile (The Progress Principle) to cartoonist Scott McCloud (Understanding Comics). It draws on the work of economist Amy C. Edmonson (The Fearless Organization) and engineer Henry Petroski (To Engineer is Human), psychologist Carol Dweck (Mindset) and architect Kyna Leski (The Storm of Creativity). They take an interdisciplinary approach, and while sticking to creative fields and practitioners, they include some that aren’t usually seen as creative—quoting, for example, physicist Richard Feynman:


“What do we mean by ‘understanding’ something? We can imagine that this complicated array of moving things which constitutes “the world” is something like a great chess game being played by the gods, and we are observers of the game. We do not know what the rules of the game are; all we are allowed to do is watch the playing.”


We are also, of course, active participants with some agency of our own. The point the authors are making here is that “science observes a phenomenon—hopefully multiple times—in order to learn the underlying rules.” Add in the testing of those observations—and of the hypotheses and theories derived from them that lead to new tests and new theories—and you have the scientific method as an ongoing, creative, iterative process. You can see Copernicus and Newton as failures, because pieces of their theories ended up proven wrong, or you can see them as a part of a process, contributing valuable new ideas and pieces to further humankind’s understanding of the universe. “In other words,” the authors write, “science is an iterative process of theorizing, prototyping, testing, and analyzing.”

In business, they point to processes like Toyota’s “kaizen”—literally “continuous improvement”—manufacturing process. They briefly discuss Buddhist sand mandalas that explore the “conception of life as ephemeral,” and Oulipo writing exercises created “to explore and expand literature.”

This all provides the “conceptual scaffolding” of both the field and the book. I am not going to be able to get into each piece of that structure, but it builds up to a basic tenet and understanding that runs through the rest of the book.


In this book, we see creativity as a process, not a characteristic or a capacity.


They explore the various approaches, practices, and perspectives on iteration and what it looks like in different contexts. They provide the reader with “tools for failing better.” They explain how “a key characteristic of iterative process is that it is cyclical,” why it requires not only a consideration of intention, process, outcome, and evaluation, but exists in the world in a specific context and relies on available resources, why:


Despite our culture’s love of the myth of the lone genius, few creative practitioners operate in total isolation.


Rather, every creative person, and creative field, is “part of a community of practice.”

And the real bulk of the book is made up of their 10 case studies of creative practitioners—which are fascinating—in various communities of practice, including Jad Aumrad and Robert Krulwich of Radiolab, comedian Baratunde Thurston, filmmaker Miranda July, and pianist Andy Milne. There is also a winemaker, animator, chef, game designer, architect, toy designer, and skateboarder.

The study of comedian Baratunde Thurston demonstrates an example of external evaluation, which he employs through his audience to iterate both on stage and online. The explanation of his writing process—which involves a feedback loop of paper, computer, recordings of his performance, and deliberate time away from it all—provides helpful insight and instruction. But my mind couldn’t help but find in Thurston’s telling of his family’s history in Washington D.C. a profound example of how our government—and our family history—is an iterative process of its own:


I have ancestors who belonged to the government, who rebelled against it in the form of literacy. My grandmother went on to work for the government—she was actually the first black employee at the Supreme Court building. My mother protested outside of its walls, but also entered it as an employee. And then she gave birth to my older sister who would chronicle government as a journalist, and then me, who takes all that and comments on it, through satire and technology.


You could say that the American Dream—regardless of its often ugly origins and precarious state—is iterative, that what we learn and inherit and pass down to the next generation is iterative too. Reading about what Thurston's mother introduced him to, and how it shaped him, made me reflect on how I was raised, and how I can better raise my own children.

I also found that the last case study, Miranda July, acts almost as a microcosm of the book’s breadth of fields and explorations. As a conceptual artist, she works in and across many different mediums, and explores territory—”the hopelessness of connecting with others, whether or not we can really know someone, the impact of chance occurrence in our lives, and the impermanence of life”—that is as existential and potentially unresolvable as any. (The authors explain how she was also influenced by her parents, and the “get-it-done mindset” they had in founding and running North Atlantic Books, an independent book publisher, out of their home.)

July’s work is used to discuss the idea of Divergent Outcomes, at the heart of which lies doubt. As July says:


“What I’m trying to do is, in the process of making things, I’m having to live with doubt. To me, that is so essential to the creative process. I mean, if you try to stamp that out or try to make everything tidy and doubtless, then you’re done.”


Allowing in that doubt led to her PennySaver project, which came about while struggling on the screenplay for her film, The Future. Instead of locking herself in a room to finish writing, she went on the road with a videographer to interview people about the items they were selling in classified ads. That work not only ended up a part of the film, but in a book, It Chooses You, as well as a standalone series of interviews. It also led indirectly to an idea that resulted in her opening a charity store pop-up in Selfridge’s—the London department store you may know from the PBS series Mr. Selfridge—operated jointly by and benefitting four different religious (and four different religions’) charities. As the authors note:


The project picks picks up a number of threads from the Pennysaver project and its publication, It Chooses You—the forced interaction of people from different walks of life, the role of commerce in human interaction, the peculiarity of money as a social instrument.


The lesson of the book, if there is any, is summed up in the title of Chapter 2, “Failure Is Not the Opposite of Success.”


It’s the quality of failure, and the impetus and persistence to try again, that often determines whether something—whatever it is—will find a place in the world. Indeed, much of culture—from the Mona Lisa to Levi’s 501 jeans to the U.S. Constitution—wouldn’t have been possible without plenty of failure along the way.


Although they provide the “conceptual scaffolding” to better understand different perspectives, practices, and processes, what the authors end up demonstrating through their case studies is that iteration itself is iterative, that it is a combination of and an exploration of many approaches and methods, and there is no “one way” or right way to do it. If you can hold onto that idea, embracing that you’ll experience failure leads to freedom:


In all sorts of contexts, from creativity to solving society’s most vexing problems, iteration is an antidote that can convert our fear of failure into a prepared openness for making the most of failure.


Whether it’s in your own work, in the organization you work in, in your family, or in society, iteration is about interacting with the world around you as an individual, and iterating on yourself. As Baratunde Thurston says: “I have learned what I do well, I have learned a bit about how I do it.” Knowing that, you can offer it to your work, to those around you, to your community, to the world.

I know I have failed to convey everything I want to about this book, and this week I am okay with that. I hope to fail better next week.

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