Generative Loops

Reading Walter Isaacson’s biography of Leonardo da Vinci, I was captivated—by his story, his creations, and his singular artistry. Beyond admiration, I wanted to understand his genius because I felt a deep affinity for his process.

While Leonardo da Vinci is most commonly known for his paintings—the Mona Lisa, The Last Supper, Virgin of the Rocks, and other works—he was also a voracious learner who studied anatomy, engineering, and mechanics. He marveled at nature and reflected nature’s systems in his work. His studies of water informed his mastery of movement, echoed in his paintings of hair, drapery, and clouds. His curiosity bridged disciplines and ignored boundaries.

He was an integrative thinker.

Leonardo put theory into practice through regular experimentation. He iterated relentlessly to toil in the details, and used his finely tuned intuition to know when the work was ready. He also abandoned ideas. Some viewed this as a negative trait, but I think it was a beautiful feature of his artistic spirit.

Creating high-quality work, no matter the domain, requires oscillation between slow depth and rapid execution. Artistry operates on its own timetable, much to the frustration of societal and workplace expectations. While creating The Last Supper, some days Leonardo would paint from the beginning of the day to the end of the day without break; other days he’d just stare at it for hours; and other days he’d rush in to paint a few strokes and leave.

Ideas are volatile. You must tend to them like a garden. You can’t rush the will of nature. Obey inspiration and push through perspiration.

Early in my career, I valued speed and efficiency above all else. Now I’m more interested in the balance of deep exploration and focused creation. As a knowledge worker, your value is more than just cranking widgets. And with the rise of AI, critical thinking and human intuition are more important than ever.

Leonardo lived beyond his time. He saw a future that didn’t yet exist, devising technologies that came into existence centuries later.

While he lived and flourished in the late fourteenth and early fifteenth centuries, he has much to teach us today.

His method was a Generative Loop. It was the penultimate Generative Loop.

When Leonardo wanted to learn something, he had to either:

1. Know someone he could talk to.
2. Know of a book with the information.
3. Figure it out himself through experience.

We have information at our fingertips. While this is wonderful, it introduces the downside of taking shortcuts. Why spend time acquiring knowledge when you can just look it up?

Because you can’t prompt insights.

Clarity, knowledge, and wisdom are outputs of deep work—from putting in the time, thinking critically, and drawing your own conclusions.

1. Observe

It begins with observation.

Leonardo studied the mechanics of flight by watching birds and recording how different species flapped their wings. He studied anatomy, dissecting cadavers to understand the skeleton, nerves, and muscles. He carefully studied the movement of water. He observed shadows and light. He noticed everything.

The process of observation is the first stage in a Generative Loop, in which each successive step generates movement and compounds into the final output.

There are many types of Generative Loops, but we’ll call this The Leonardo Loop, a tip-of-the-hat to the master.

Observation generates awareness, which creates a detailed version of reality. You notice more and, in turn, understand more about the world.

You just have to look.

On my daily walk, I follow the same path. I see the same things. But I don’t really observe them—the mass of acorns strewn about the ground; the unique birdsong symphony; the mushrooms sprouting from the ground. We live in a world of beauty masked by distraction. Without observation, we miss it.

To practice observation, you can:

• Pay close attention to nature. Really look at the life surrounding you. Sometimes I’ll stop working to look out my office window and observe brown anoles (common Florida lizards) going about their business.
• Sketch or visually journal. Leonardo, like me, was a visual thinker and sketched regularly. You don’t have be an artist to sketch your ideas or journal.
• Write descriptive notes. Use words to describe your observations in rich detail. Really understand what you’re looking at. 

2. Question

An observation without a line of inquiry is just a thought that dissolves. You need to follow observations with questions.

Leonardo often structured his notebooks by pairing questions directly with their associated observation. The awareness generated by the observation stimulates curiosity, which is the force generated in the second step of the Generative Loop.

Describe the tongue of a woodpecker.

This is one of Leonardo’s most-famous to-dos in his notebooks. The origin of this task stemmed, most likely, from his observation of how woodpeckers extract insects from the deep crevices in tree bark. His observation (awareness) stimulated questioning (curiosity) to find deeper meaning.

This is true of all great thinkers.

Isaac Newton famously observed apples falling from a tree and asked a question. Charles Darwin noticed variations in the beaks of finches while in the Galápagos Islands and asked another question. Marie Curie observed phenomena surrounding uranium salts and sparked yet another line of inquiry.

As David Cooperrider said, “We live in a world our questions create.” Questions, like observations, are generative. And curiosity is the output—another step in the Generative Loop.

To practice questioning, you can:

• Keep asking “why” and “how”. My kids ask these questions all the time. It’s the best way to learn more.
• Generate lists of questions and hypotheses. Make it a routine to note questions and ideas as they come up.
• Follow the threads; the tangents; the rabbit holes. Learning is never unproductive time. Always go deeper.

3. Experiment

Leonardo da Vinci practiced the scientific method centuries before it was formalized. His notebooks were full of observations derived from extensive experimentation. His fascination with water led him to make models of rivers, channels, and dams. His studies of birds in flight generated prototype machines with flapping wings. His obsession with optics and vision resulted in experiments to understand how light reflects and refracts.

All of this was in service of his curiosity, generating fuel that would set his art apart from everyone else. His mastery of light, shadows, and the reflection of nature in the human form is no accident. He was exploring possibilities. And that’s just what experimentation generates: possibility; possibility rooted in action. Leonardo was never stuck in theory or practice. He balanced them with a beautiful interplay, creating a dynamic that shaped his work.

The lesson is simple: Try things. That’s it. Don’t overthink it. Be observant, ask questions, and then do something to test your theories.

To practice experimenting, you can:

• Build a prototype or sketch. Even a simple representation of your idea will spark new thinking.
• Mix tools, disciplines, or inputs. Knowledge has no lanes. Explore wide, explore deep.
• Create small tests or thought experiments. I wonder if is a great way to start a test. Start small and try it.

4. Iterate

Iteration is the connective tissue that drives quality, increasing fidelity with each step. Leonardo treated experiments as living questions to repeatedly test, fail, and adjust. Failure is guidance. It provides a sense of direction.

As Leonardo said:

Experience does not ever err. It is only your judgment that errs in promising itself results which are not caused by your experiments.

Failures and unexpected outcomes are the raw materials of learning. They are signals for improvement. Iteration surfaces underlying patterns, principles, and general rules.

As Leonardo puts it:

We must consult experiment, varying the circumstances, until we have deduced general rules, for experiment alone can furnish reliable rules.

By “varying the circumstances”, you can identify general rules to formalize larger learnings. Doing so allows you to dig deeper into the right details and refine relentlessly. The subtleties and nuances begin to emerge, which are where the deepest insights lurk.

The process of iteration generates understanding. The more you iterate, the higher the fidelity of understanding. Leonardo’s process directly maps to modern iterative methods in design, engineering, and AI.

It’s no coincidence. This process is timeless.

To practice iterating, you can:

• Revisit or redraw work from new angles. Sketching is great because it’s easy to throw away. Changing your perspective stimulates new thinking.
• Revise your ideas based on friction or failure. Tension guides you in the direction of revision.
• Zoom into fine details (e.g. shadows, proportion, rhythm). Leonardo wrote 15,000 words on shadows. What is your version of this to indulge the details?

5. Synthesize

Leonardo viewed synthesis as the combination of skill (arte), knowledge (scientia), and imagination (fantasia). Following this Generative Loop, he transcended boundaries between art, engineering, and science. He believed that true understanding emerged from drawing connections between fields. He was a master painter because he ignored boundaries. To him, they weren’t boundaries. They were channels of knowledge to understand the nature of things.

And, in that understanding, he constructed mental models that served as precursors to later discoveries well after his time.

He was the first to accurately depict the heart as having four chambers. He documented arteriosclerosis (narrowing of the coronary vessels) and cirrhosis of the liver, describing their effects before these became part of mainstream medical understanding. His fascination with understanding water flow generated insights that underpin modern hydrodynamics. He even proposed an early version of the law of gravity, which wasn’t formalized until Isaac Newton’s work two centuries later.

Leonardo’s uncanny ability to reason by analogy sparked invention, innovation, and unification. By comparing the movement of water currents to the movement of human hair, he illustrated turbulence in both painting and engineering research. By observing the ripples formed from a stone thrown in water and relating them to the sound of a bell, he inferred sound travels in waves, centuries before modern wave theory described the phenomena.

Invisible patterns weave a rich tapestry of commonality between universal forces. If you hold a myopic focus on a singular discipline, you lose sight of the larger patterns at play.

Leonardo da Vinci saw a different world. But we can apply this lens, too.

When you can synthesize information through observation, questioning, experimentation, and iteration, you generate the power of discernment (or intuition)—the ability to know what feels complete or true. This is a skill in critical thinking, and it’s real, tangible, and highly valuable.

To practice synthesizing, you can:

• Learn to sense when the work is “done” or whole. It’s one of the hardest things to do, but iteration is the guide.
• Step back to look for harmony, alignment, elegance. Sometimes the best thing you can do is create space.
• Let intuition signal completion or readiness. Following your gut is a powerful way to move forward intentionally.

Generating Clarity

Leonardo saw and imagined things others couldn’t. He was a genius; an innovator; an artist. We have much to learn from him, and my newfound obsession with his artistry has been an eye-opening experience as I reflect on my own craft, process, and the future of work alongside artificial intelligence.

This Generative Loop (The Leonardo Loop) generates tangible skills at each step, culminating in the compound output of resonant clarity—that feeling when all the pieces finally connect in your mind, and you uncover the force driving seemingly disparate parts into a coherent whole. When you move through all five steps with intention, you explore a new world with new eyes.

In the spirit of the master, we can reason by analogy, using Mother Nature as our teacher. Photosynthesis—how plants turn light energy into chemical energy for food—is like its own Generative Loop. During the process of photosynthesis, plants take light energy, absorb it, convert it, refine it, and release the end product. Plants literally transform light into life.

In the same way, this Generative Loop transforms observations into insights, a beautiful and refined clarity.

This kind of clarity lands, lasts, and leads to what’s next.

It starts with noticing. It ends with seeing.