If you have ever not walked in on someone using an airplane bathroom, you are familiar with the work of David Kelley who, in his first job at Boeing, created the Lavatory Occupied sign—and then went on to be a pioneer in the field of design thinking. Design thinking is a flexible and iterative, almost scientific methodology that adapts the stages of product design—observation, analysis, planning, and testing—into a framework for solving problems in any field, ensuring that things are usable, and bathrooms stay private.
We all know about design thinking and its value in software. But there’s another kind of thinking no one talks about—artistic thinking. If design thinking asks, "how can we do it better?" art thinking asks something fundamental: What is possible? Design thinking values empathy with users—it’s how a company like Boeing rapid-prototypes better planes. Art thinking comes first—it’s right there with the Wright brothers as they crash-land, figuring out whether flight is even possible.
Designers usually begin with a problem to be solved. As Tim Brown, one of Kelley’s cofounders in the design firm Ideo, wrote in the Harvard Business Review in 2008, design thinking is "a creative human-centered discovery process… followed by iterative cycles of prototyping, testing, and refinement." In the same way that entrepreneurs are asked what pain point their product addresses, designers are asked what solutions they can find.
Although the design process can be full of "eureka!" moments and true contributions to how we all live, what it misses from art thinking is a comfort with the possibility of failure. In design thinking, you implicitly believe a solution is possible. In art thinking, you are leading from questions—trying to ask the biggest, messiest, most important questions, even if you are not sure you can answer them. Accepting that you might fail actually frees you to fumble inelegantly, to learn, even to waste time. Even if you move forward unpredictably in fits and starts, you stand a greater chance of the brilliant breakthroughs that create rather than meet demand. Art thinking created the first iPhone; design thinking made it a manufacturable, cultural phenomenon.
Art and design thinking can go hand in hand, offering rigor in a Q&A form. But leading from questions shifts the perspective—from an external brief to an internal compass. It allows people to bring their whole selves to work, to contribute from a place of authenticity and self-knowledge. Art thinking embraces the possibility that any of us might reinvent the world, not just make it incrementally better. For software builders who can effect change at massive scales, this way of thinking is especially powerful.
The German philosopher Martin Heidegger published a 1947 essay called "The Origin of the Work of Art" in which he grappled with defining art as a category. To give a sense of how hard that is to do, Heidegger worked on the essay from 1935 until 1960, and only stopped because he died. The definition that I would borrow from Heidegger’s essay is this:
A work of art is something new in the world that changes the world to allow itself to exist.
What that means is that if you’re at point A, you’re not going to point B. You’re instantiating point B. Focusing on solutions finds the best outcome in the Point A world. Focusing on questions creates a new world, in a large or small way.
Watching people invent point B worlds can create tricks in perception where—because they have created a new world—we forget how uncertain the work was when they started at point A. It is easy to think other people’s creative work was always there, a foregone conclusion. Of course the Beatles wrote those songs and the Wright brothers invented flight. The outcomes seem almost predetermined.
In 1967, Edward Jones and Victor Harris published a paper called "The Attribution of Attitudes" in The Journal of Experimental Social Psychology. In it they described a bias in perception so acute they dubbed it a fundamental attribution error. We have a tendency to look at other people’s behavior as fixed and our own as situational. We think, that guy’s a jerk, but I’m having a bad day. When looking at other people’s creativity, it is very easy to think, that guy is a creative genius, and I am stuck.
When you are inside your own creative process, you are really in the weeds. Everything is subjective and changeable. But if you’re looking at other people’s creativity, it is a fixed external reality. You have a view of their work from 30,000 feet, after the fact of its creation.
Forgetting that their process was difficult and uncertain can discourage you from embracing that process yourself. Imagining that other people are also in the weeds humanizes them.
As Ralph Waldo Emerson wrote:
We do not know today whether we are busy or idle. In times we thought ourselves indolent, we have afterward discovered, that much was accomplished and much was begun in us. All our days are so unprofitable while they pass, that 'tis wonderful where or when we ever got anything of this which we call wisdom, poetry, virtue. We never got it on any dated calendar day.
It is easy to forget the delicacy of creative breakthroughs. It is easy to imagine that they happen only for the hardest working person hunched over the chemist’s bench, or for the most creative person having a Don Draper three-martini lunch. Working life and leisure are not as separate. And discovery of the new world is not as mappable. The stories of Whitfield Diffie and Thomas Fogarty illustrate this point.
Whitfield Diffie is the mathematician and computer scientist who invented public-private key encryption—which is to say Whitfield Diffie enables secure transactions and some modicum of privacy on the Internet. This idea of splitting the key, of combining your private password with a public key to unlock access, came to him not while he was in a Silicon Valley research lab but while he was house-sitting for his mentor. He had the idea while he was walking into the kitchen to get a Coke.
He was prepared for the insight—by his self-taught tour driving cross-country in a Datsun 510 scouring libraries for books on encryption and taking a job in the Artificial Intelligence Lab at Stanford. But in the moment, he was neither slaving away nor praying for insight. In fact, he had nearly given up hope that he would do anything of value.
Diffie’s wife, Mary Fischer, said that the night before his breakthrough, "He was telling me that he should do something else, that he was a broken-down researcher." The insight would still take a longer process to refine, over many months working with his collaborator Martin Hellman. But the insight came to the original and prepared mind of a man whose friends joked he had had "an alternative lifestyle since the age of 5."
As Steven Levy wrote, "at one time, it looked like Diffie might slip into obscurity as an eccentric hacker who never made much of his genius for math and his laser-focus mind." But then Diffie came up with "the most revolutionary concept in encryption since the Renaissance."
Another example is Thomas Fogarty, who is credited with pioneering non-invasive surgery. In the 1960s, Thomas Fogarty invented the balloon catheter. It is a device that enables a simple cardiovascular surgery. It is still used over 300,000 times each year and has saved an estimated 20 million lives. Fogarty invented it when he was in high school. He was a self-professed juvenile delinquent who had to be either "busy or supervised." At the age of 13, he was given a part-time job in a hospital solely because hospitals were exempt from child labor laws. He saw a problem: At the time, if a patient had a blood clot, the surgeon would open up the length of the artery to remove it. Many patients died. Many others had to come back for amputations. So he went home and tried to figure out a better way. It wasn’t just that he invented a better device; it was that he changed the surgical paradigm. People thought back then that "the bigger the incision, the better the surgeon."
To make the device, Fogarty had to attach a vinyl catheter to the finger of a latex glove. But no glue existed then that would make them adhere. So he tied them together with knots instead. The only reason Fogarty knew how to tie knots was that he used to cut school by jumping out the window to go fly fishing. The skills and experiences from his leisure life made his medical breakthrough possible. The engine was not his expertise but his curiosity.
Art thinking represents this kind of whole-life approach, despite the pressures toward efficiency or the psychological desire to know something will succeed.
The main, paradoxical gift of art thinking is its freedom from productivity. Wasted time might be exactly the lateral move that opens up the field of play. Roger Bannister, the runner who famously broke the four-minute barrier in the mile, actually nearly gave up and went away on a hiking trip with friends just before his times improved.
Art thinking is not a world of quick wins and assured success. You may not come up with the best solution right off the bat. You may have to wean yourself off of the constant need for external validation, which can be terrifying in cultures—corporate, academic, or otherwise—where advancing or keeping your job is based on exactly that sense of meeting outside goals and expectations.
At its worst, art thinking provides a cover for mediocrity and laziness because no outcome is required. But at its best, it can create the openness and stability from which true, and often unexpected, breakthroughs can occur.
Artistic process requires leaning in to an almost existential uncertainty. And restlessness in the face of uncertainty is a human problem. Everyday life offers a master class in how to maintain attention and intention in the midst of flashing message lights, constant breaking news news, expectations of instant feedback, and crippling administrative process or days of meetings. It is hard to stay open to broad questions, not just quick wins.
As Tim Brown writes, "We believe that great ideas pop fully formed out of brilliant minds, in feats of imagination well beyond the abilities of mere mortals." We are seeing that work from the outside, without the messy failures and weedy false starts. The myth of artistic genius is a hardy category, but usually a fictional one.
- Schedule Studio Time. If outcomes are uncertain, the discipline is in the process. The goal is simply to cordon off protected time. Google 20% time is a process goal, out of which came AdSense and Gmail.
- Coordinate. In some small companies, teams of computer programmers often report out to each other at day’s end, just to share what they are working on and to hold themselves accountable. Often, work is lessened. One person has already written a portion of code and can share it. For art thinking, managers could think of monthly meetups as the equivalent of an art-school pin-up.
- Prove the Rule by Disproving it. If art thinking has the risk of failure, then embrace failure as a brainstorming tool. What are the biggest, most important, most relevant questions that you believe certainly that you cannot answer? How can this list help you arrive at the big question you do want to work on? Art thinking and game theory converge.
- Go Off the Grid. In one of his workshops, the stress-reduction guru and doctor Jon Kabat-Zinn draws nine dots on a blackboard—a 3x3 square. He then invites anyone in the room to connect the dots using only four straight lines. The way to solve the puzzle is to go outside the confines of the original question, to draw broad sweeping lines that extend far outside the corners of the square. In any meeting or work, when you are most driven to conclusion, ask yourself the question you are trying to answer. You may have articulated the question with assumed limitations, like trying to draw lines inside the space of a box. The pause lets you realize the actual question is bigger.
- Designate producers. Hugh Musick, longtime associate dean at the Institute of Design in Chicago, makes a case for the category of the "producer." A producer is a person who midwifes the creative idea into the practical world. Designating one team member as the producer frees the rest of the team to explore the unworkable big risk, big reward space. A department can have a producer role, or in a strategic review planning session, team members can take turns acting as the producer or go-between in blue-sky and budget-planning modes.
- Cultivate a whole-person culture. A fraction of now-famous artists—and a handful of now-famous CEOs—were nearly kicked out of art school, or fired from early jobs. Creating space and acceptance for others to bring their full creative potential to work—navigating shame and resilience, as in the work of Brené Brown—makes it easier to keep the Whitfeld Diffies and the Thomas Fogartys engaged in the team instead of making balloon catheters at home after work.