I’ve had dinner with friends starting new projects every night this week. They always arrive with a bit of a glazed look in their eyes, limp from exhaustion. Their pace of conversation is slow. My pal T, while we were carbo-loading on German beer and pretzels as if for a marathon, said that the most exhausting part of the process was that all of the work was conceptually difficult. They were caught in an endless cycle of racking their brain for insights, making something based on those insights, and then desperately awaiting some wave of resonance to occur amidst silence. The waiting for the resonance coupled with the pressure to generate new insights was demoralizing, they said.
My friend A describes that search for insight as the “squiggle.” A is just like T — they’re bounding off in various directions in pursuit of creative inspiration and real-world confirmation. For A, each day crawls. Each week has a 45 degree pivot (or two.) Each moment is spent thinking about their work. During dinners or hangouts, I can see that they are unable to escape that crushing sense of urgency, that they’re thinking about ways to find insight. They secretly pull up their phone and send a few more cold emails while I’m refilling the water glasses.
Of course, nobody said doing something novel would be easy. It doesn’t matter if it’s a startup or an art project or a book — the search for inspiration and affirmation is grueling. Many of my friends have been at this for months, if not years. Some of them are on the verge of giving up on finding insight, going back to big companies in order to feel a more direct relationship between effort and results.
Is earning insight meant to be such a struggle? I started doing some research. After looking at the founding stories of so many of our favorite businesses, reading Rick Rubin’s book of Zen koans, and even starting to trawl through JSTOR for theories of creativity, my favorite theory is one that a friend mentioned to me around 10 years ago, that of UChicago economic historian David Galenson.
Galenson believes there are two patterns of creativity in art: experimental creativity, and conceptual creativity. Experimental creators have imprecise goals and take an incremental approach to discovering insights through immersion in a particular discipline. They often revisit subjects multiple times in order to distill insights through trial and error.
In contrast, conceptual innovators have intended to communicate specific ideas or emotions. Their goals for a particular work can be stated precisely in advance. They often make detailed preparatory plans for their paintings, and execute their final works systematically. The execution means less to them than the idea itself, and the execution is rarely a medium for discovery.
Galenson arrived at his theory by asking a somewhat naive question: what’s the relationship between price of painting and age in famous painters? After taking a sample of 400 painters and looking at the prices of their work and age, he found two clusters, best exemplified by Paul Cezanne and Pablo Picasso. Galenson called the artists in the Picasso cluster the “Young Geniuses” and the Cezanne cluster the “Old Masters.” Young Geniuses make their best artwork very early in their careers, while the Old Masters have steadily increasing prices till they hit a peak in their old age.
When Young Geniuses describe their work, they describe starting with an idea. They have radical motivations. Their first action upon entering a new field is often to discard rules of the field in order to enact their own principles. Picasso fundamentally believed that art should not be about literal vision, but about what he “saw in his head” instead. All of his artwork is underpinned by that specific concept. Picasso describes his work as a way to make statements that he already knows to be true:
The several manners I have used in my art must not be considered as an evolution or as steps toward an unknown ideal... I have never made trials or experiments. Whenever I have had something to say, I have said it in the manner in which I have felt it ought to be said. [citation]
In contrast, Old Masters must immerse themselves in a field over years in order to develop insight. They learn its rules and over time learn to break them. Jackson Pollock dripped paint on a canvas from all four sides before he came upon his preferred approach, and Georgia O’Keefe started every painting with a realistic portrait before repeatedly removing elements with each version. Old Masters use their work as a tool for experimentation, rather than conceptual statement. In the year before he died, Cezane said the following in a letter to a friend:
Now it seems to me that I see better and that I think more correctly about the direction of my studies. Will I ever attain the end for which I have striven so much and so long? I hope so, but as long as it is not attained a vague state of uneasiness persists which will not disappear until I have reached port, that is until I have realized something which develops better than in the past... So I continue to study... I am always studying after nature, and it seems to me that I make slow progress.citation
Cezanne was a huge squiggler! The critic Roger Fry on Cezanne:
For him as I understand his work, the ultimate synthesis of a design was never revealed in a flash; rather he approached it with infinite precautions ... For him the synthesis was an asymptote toward which he was forever approaching without ever quite reaching it. [citation]
Technology loves the conceptual innovator
In mathematics, the best contributors to the field are conceptual innovators. Fields Medalists are famously under 30 years old. We like to imagine the same is true of technology. The most famous stories about technologists tend to be those of the young genius, the special insightful conceptual innovator who gets it right on the first try. Steve Jobs and Bill Gates are both examples of the approach of conceptually innovating and then applying those thoughts to various products and ideas throughout their lives. Jack Dorsey seems to base his product development insights on a fundamental understanding of people at the conceptual level, and his repeated success comes from the accuracy of those assessments. But in reality, technology is more like art than mathematics: there’s innovators of both types.
In the case of Jobs, Woz was his trusty experimental innovation sidekick who studied computer science in the details, experimented, and came up with the set of small insights that added up into the big personal computer. Jensen Huang, the founder of Nvidia, started the company with the same hypothesis that approximately 80 other companies at the time shared. Nvidia became successful due to a series of experiments: they first learned what wouldn’t work, they copied Microsoft to learn what would, they attempted to make chips faster than anyone, they finally learned how to innovate on the concept of the GPU, and finally made enough of an inroad to experiment with new ideas. He famously bet the company on three big pivots that required scrapping their approach, laying off workers, and trying something new. Nvidia was the ultimate deductive reasoning company. They experimented their way to their current dominance.
We undertell the stories of experimental innovators because they’re less neat. They look like sitting in a lab for years, or taking winding paths to greatness that involve what looks like failure along the way. They often are still happening (they require becoming wiser with age, and the industry is still quite young!) But both approaches can lead to success.
It also goes without saying that both approaches can lead to failure. Some conceptual innovators have bad ideas, and are therefore unable to come up with anything better throughout their lives. Some experimental innovators never experiment enough in order to reach their zenith.
Who is the real radical?
Conceptual innovators are often radical because they discard the rules of the past. Experimental innovators can often do something simply incremental because they’re steeped in the past’s scholarship. Nevertheless, you can iterate your way into something great.
Experimental innovators are often innovators of methods in addition to ideas. Cezanne, famous experimenter, was Picasso’s inspiration. Picasso regarded Cézanne as a "mother hovering over," Henri Matisse as "father to us all." (I guess great artists don’t see gender?) As said by the Picasso Foundation:
In Cézanne's work Picasso found a model of how to distill the essential from nature in order to achieve a cohesive surface that expressed the artist's singular vision. Beginning in 1907, Picasso began to experiment with Cézanne's techniques alongside fellow artist Georges Braque. Cézanne was a constant touchstone…which eventually resulted in the invention of Cubism by 1909. Throughout Picasso's stylistic evolution over the next seven decades, he continued to borrow from and reinterpret Cézanne's art.
Experimental innovators are often innovators of methods in addition to ideas. Their mingling of idea and method can lead to even more transformative outcomes. In technology, the “Google way” of running a company (very Eric Schmidt inflected!) combines the concepts and execution strategies very tightly.
Stopping the squiggle
I recently heard a story about one of the most famous and successful Thiel Fellows giving advice to someone in a squiggling state. The Thiel Fellow’s advice question to the squiggler was, “What’s the thing you would do if you could do anything in the world, if nothing was holding you back?” For a conceptual innovator, this question might have served as a reminder to believe in themselves. For an experimental innovator, the only product of that question is confusion and self blame.
It is true that everyone squiggles. Picasso squiggled after he made his initial groundbreaking work, Les Demoiselles d'Avignon.
Cezanne squiggled until his 40s, but started to squiggle less at 67. He was revisiting past work again and again till he got it right. He kept painting the mountain I featured as the cover image, the Mont St. Victoire, repetitively till his ideas began to clarify, and the amplitude of the squiggles went down.
Conceptual innovators might squiggle on the execution of their concepts and ideas — it can be hard to translate a closely held belief into action. Experimental innovators can often struggle in hypothesis generation — they don’t have a high conviction view of the world. As a result, most of us commit type errors while trying to absorb advice on how to stop the squiggle. The Thiel Fellow’s advice was perfect for a conceptual innovator who was overemphasizing the obstacles blocking their dream. But the person receiving the advice might have been questioning whether they have a specific dream at all.
Is flipping your approach a valid strategy during a squiggle period? Maybe Picasso could have taken a careful iterative approach and painted the same women over and over. Of course, David Galenson believes that you can’t turn into one or the other. Like all inventors of frameworks, he thinks the framework’s strict application is helpful.
In reality, the conceptual versus experimental framework is a tactic. Maybe if a nice economist sat Picasso down, he could have been convinced to try something different. It’s often incredibly difficult to realize how to unstick yourself in the moment of a big squiggle. Maybe changing tactics can help.
The only good advice I can think of for squigglers isto regularly deposit into the bank of emotional assets to extend your runway. You can only last as long as you think you can. As Dee Hock, famous Visa founder says, “The greatest challenge is the management of the self,” after all.