Amy Whitaker
Source: Amy Whitaker

​​Even the most fervent defender of the corporate mainstream will have realized by now that business-as-usual is broken. Employee engagement remains scandalously low, and companies are having a hard time changing (that is, staying relevant) and innovating. Many, in fact, are struggling to even imagine their own future.

New technology and processes can fix a few things, but at the heart of the malaise is something else: business thinking. Clearly, business is too important to be left to business people. So what if instead of narrowing options, codifying behavior, and mitigating risk, business leaders thought and acted more like artists? 

This is not a new idea: Andy Warhol famously claimed that “being good in business is the most fascinating kind of art,” David Whyte brought poetry to organizations, Alan Moore has written about beauty and doing business in a non-linear world, and Age of Artists has accumulated an impressive pool of case studies and insights. I explored the concept myself in a blog post a few years ago and have ever since grown confident in calling myself a “strategy artist.”

And yet, the idea needed a mantle, a comprehensive framework, so I was riveted when I read Amy Whitaker’s extremely thorough and eloquent new book, “Art Thinking: How to Carve Out Creative Space in a World of Schedules, Budgets, and Bosses” (full disclosure: she and I have the same publisher, Harper Business). Amy holds an MBA from Yale University and an MFA in painting from the University College London, and she is an assistant professor at NYU’s Steinhardt School. I recently had the pleasure of a brief email exchange with her:

What’s the difference between Design Thinking — promoted by the likes of IDEO or Frog Design and now well established in corporate America — and Art Thinking? Is your vision for Art Thinking to play a similar role in changing everyday business?

Art thinking is a process not of going from point A to point B as well as possible but inventing point B. In the long run, success in business — and in almost any area of life — requires you to take those kinds of risks and leaps, with skill and in service to your highest objectives.

Art thinking and design thinking have similarities, especially as more exploratory fields of speculative design flourish. The key difference is that in design you have a brief. You are trying to ask, how can I make this better? How can I execute on this brief in the best possible way? In art thinking, you are often asking, is this even possible? You are developing the question andanswering it. The two approaches are highly compatible, but art thinking stakes out more space for the unknown, the untested, and the not yet commercialized.

The founders of Airbnb, among others, have proven that designers can succeed as business leaders and in fact become CEOs. Do you think that’s equally true for artists?

I think that everyone is an artist, that the capacity to think open-endedly, from first principle, and to move forward into the unknown, is a basic human quality. So, yes, I think there are many CEOs I would call artists. The idea of inventing point B is to think of art as a process in any area of life. Devising original strategies — that is, accepting the responsibilities of leadership to follow your own compass and to risk the new — can be a deeply artistic process.

I would also like to add that the Airbnb founders were graduating from RISD not long before they founded the company. (Brian Chesky said his first entrepreneurial project was starting a basketball team at RISD. He also busted into full Michael Jackson Billie Jean giving a RISD commencement speech.) I think they were artists as well as designers. They used design skills beautifully in their early projects and in the Airbnb interface. They also imagined something was possible and brought us all into the point-B world of their creation, radically changing a business model along the way.

One idea in the book — in the chapter where Airbnb is discussed — is that there are two kinds of creativity: writing the letter and designing the envelope. Writing the letter is making the work itself — designing a product, executing a strategy. Building the envelope is the process of creating the business model by which the product is possible. The Airbnb founders are excellent envelope-builders. You could call them artists of enterprise. The business model itself is the artistic output.

Is there a danger that we undermine the inherent value of art if we try to make it work in and for business?

Art, by definition, has intrinsic value that can never be reflected accurately by price — a logic that, counter-intuitively, supports astronomical prices for fine art at auction.

Here, the problem we are grappling with is different. We are grappling with the economic belief that markets work well because price equals value. For early-stage creative work, price doesn’t equal value. To explore creative frontiers, we have to invest and to guess the value of things well before we know if they will succeed and what they will be worth. The business tools of art thinking help you to structure ownership and to take risks well, so that if you succeed you own some of the upside you create, and if you fail, you’ve built a sturdy portfolio of projects within which you can weather that setback.

One more point on this question: the mental model of the question itself is probably from the point of view of the art collector, about the assessment of value. In Art Thinking, we are looking from the point of view of the artist — meaning the person creating value and taking risks to put something out into the world. Actively engaging in creating new work, not replicating old projects, never undermines inherent value, but builds it.

“Art is the most important thing we need right now,” Brian Eno said. Do you agree? And if yes, why?

Yes, I think art as a process is the most important thing we need right now. The process can be applied to almost anything — business, politics, seemingly unsolvable social problems, everyday life. The miracle of art as a process is that once you invent a point B world, the greatest change agent of all, normality, takes over. If you look back at the last 50 years — or even the last 10— you will see how much has changed, how many things we start to take for granted — gay marriage, scientific or medical standards like in vitrofertilization, or everyday technology like smartphones — were acts of inventing a point B world first.

Art is so important in that development because art is a proxy for independent thinking, which is both the cornerstone of a thriving democracy and the very essence of what it is to be human. Our ability to make art — by which I mean to exercise agency and autonomy and to make a unique contribution that grows out of our personal authenticity — is basic to our humanness. It is like the opposable thumbs of our intellect and character, metaphorically speaking. Sections of the book also apply concepts from psychology, whether Carol Dweck’s growth mindset, aspects of dialectical behavioral therapy, the actor-observer bias, or Winnicott’s idea of the holding environment.

Can you give me some examples of business leaders who successfully applied principles of Art Thinking? And, conversely, which artists would you point to as case studies?

There are so many examples I could include here. I think the Warby Parker team are exemplars of artistic approaches to both product design and business modeling — and social enterprise, to boot. Todd Richardson and Christopher Miner, an art historian and an artist, have revitalized a 1.5 million square foot building in Memphis, Tennessee, starting with the question of “Wouldn’t it be cool if?” and undertaking a business and civic task of monumental scale and funding sophistication to get there. (I know you asked for business leaders, but I think it’s interesting that artists are acting as business leaders, the same way that I believe that business leaders are artists.)

Other business leaders in the book illustrate key parts of art thinking, whether Mark Bertolini’s focus on mindfulness at Aetna, the Pixar team’s ability to give candid and bracing feedback, or Andreas von Bechtolsheim’s, the Sun Microsystems founder’s, history of be paid a royalty in an early job developing an Intel 8008 chip, in lieu of a salary, which later became a generative foundation for his career, and for his ability to serve as a legendary early investor in Google (the person who wrote a check to “Google, Inc.” causing them to incorporate).

Without wanting to co-opt their stories to the cause of art thinking, I do think that the iconic great business leaders, whether Warren Buffett or the late Donald Keough of Coca-Cola, are inarguably independent thinkers, able to chart a course before other people, to hold firm to the values that pull them forward — what are in the book called “lighthouse questions” — while experimenting and treating management decisions as the live theater that they are.

In Mr. Keough’s book, The Ten Commandments of Business Failure, he tells a story from when he was running Coca-Cola’s foods division in 1971. In order to remind executives of the value of money, he tried to undertake an experiment in which all purchases would be made in cash for a week — cash for plane tickets, cash for newspaper subscriptions, cash for office supplies. It turned out there was not enough cash in all of the banks in Houston, Texas, to carry out the experiment, which itself is an illuminating result.

With 50 percent of the human workforce expected to be replaced by software and robots in the next 20 years, is Art Thinking the last hurrah before automation — and with it, the regime of efficiency — will have dehumanized the workplace? In other words, is Art Thinking inherently human, or do you think Art Thinking can also become a quality of machines, a feature of algorithmic organizations?

Thanks for asking a softball question, Tim. Actually, I take heart in how bad we are, generally, at predicting the future. In Art Thinking, I make a point about how fallible our judgment of success or failure is — which is heartening both for creative work and for dystopian robot futures. Our ability to imagine not just the primary and secondary effects of AI but the networked, systemic, tertiary ones — is limited. Don’t get me wrong: I’d prefer not to live in a future in which my boss is a villainous robot as much as the next person. And I’m glad philosophers, programmers, neuroscientists, and business leaders are thinking about these eventualities more than we know.

What actually concerns me most is that we are becoming the robots. Higher education has become expensive enough that people think about whether they are getting their money’s worth. That calculus shuts down many forms of open-ended exploration and risk-taking within education itself. Instead of going to college and forming your own point B as a person, you get adept at solving perfectly for what’s in front of you. To borrow a term from Bill Deresiewicz, we become “excellent sheep,” people who can answer questions perfectly but not ask them. My focus is on getting people to be able to ask the questions that really matter, and then to be able to follow up on them meaningfully, whether you know they are possible to answer or not.

Being able to ask questions of that sort often asks us to be clear about what our values are. Therefore, I might favor a values-based kind of programming of robots, for us to shift from teaching them to do tasks or to learn responsively and algorithmically from pattern recognition, and to be able to operate from first principle.

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