Leonardo’s Code
A Blueprint for Timeless Work
***This piece was previously published at leadingsapiens.com ***
Modern organizations worship at the altar of efficiency, focus, and relentless execution. We follow suit at the personal level as well by trying to optimize everything to the hilt.
While mostly helpful, this often misses the point.
The same organizations that tout “innovation” also create environments that stifle it. Productivity systems won’t help you discern what’s worth producing to begin with.
While reading Walter Isaacson’s biography of Leonardo da Vinci, what I found most compelling was that the quintessential Renaissance man broke every one of so-called “best practices”.
He left masterpieces unfinished, filled notebooks with "useless" observations and let his mind wander down endless paths of inquiry.
In fact in a moment of self-doubt he wrote:
"Tell me if anything was ever done,"
"Tell me. Tell me. Tell me if ever I did a thing. . . . Tell me if anything was ever made."
Yet this seemingly scattered approach produced history's greatest polymath and an equally prolific body of work often centuries ahead of its time.
Isaacson summarized Leonardo’s approach that’s a useful counter to many modern day orthodoxies. His methods fundamentally challenge what we often take for granted as common sense.
Let’s examine a few.
Pursuing useless knowledge
Seek knowledge for its own sake. Not all knowledge needs to be useful. Sometimes it should be pursued for pure pleasure. Leonardo did not need to know how heart valves work to paint the Mona Lisa, nor did he need to figure out how fossils got to the top of mountains to produce Virgin of the Rocks. By allowing himself to be driven by pure curiosity, he got to explore more horizons and see more connections than anyone else of his era.
He studied things for which there was no immediate application. These were not distractions but more like deposits. Over time, they created a mental topography capable of generating ideas on multiple levels, across frames.
The interconnected nature of complexity means we don’t always know what ultimately leads to what. Except we always operate as if it's otherwise, carefully choosing and deciding.
Some of the best outcomes in our lives, and companies, happen despite of, not because of, planning. We don’t plan for enough obliquity. Steve Jobs once dismissed the iPhone as a dumb idea.
Willingness to stay naive
Retain a childlike sense of wonder. At a certain point in life, most of us quit puzzling over everyday phenomena. We might savor the beauty of a blue sky, but we no longer bother to wonder why it is that color. Leonardo did…. We should be careful to never outgrow our wonder years, or to let our children do so.
Societal norms equate maturity with narrowed focus. But Leonardo shows how maintaining childlike wonder can sustain professional longevity.
This is especially relevant in later stages of careers. We turn into cynics who know all the ways something won’t work. Sophistication is overrated, even stifling. Cultivated naiveté on the other hand is an advantage.
However, it takes conscious effort to resist the promise of cynical practicality. Real professionals work hard to remain deliberate amateurs.
Fallacy of the big picture
Start with the details. In his notebook, Leonardo shared a trick for observing something carefully: Do it in steps, starting with each detail. A page of a book, he noted, cannot be absorbed in one stare; you need to go word by word.
“If you wish to have a sound knowledge of the forms of objects, begin with the details of them, and do not go on to the second step until you have the first well fixed in memory.”
Leaders commonly advocate “big picture thinking,” overlooking the fact that often the so-called big picture is built on a bedrock of neglected details. Leonardo’s emphasis on granular details exposes this fallacy.
Genuine strategic acumen is derived from an intense, even obsessive, familiarity with minutiae. Clarity actually increases when attention to detail deepens, challenging the conventional glorification of abstract, simplified visions.
Related: How leaders botch strategy.
Foolish ambitions
See things unseen. Leonardo’s primary activity in many of his formative years was conjuring up pageants, performances, and plays. He mixed theatrical ingenuity with fantasy. This gave him a combinatory creativity. He could see birds in flight and also angels, lions roaring and also dragons.
Most of us use our imaginations to ruminate rather than create the future we want. The former comes naturally. The latter has to be developed intentionally.
Seeing angels in birds and monsters in lions isn’t fantasy. It’s imposing structure on potential. Most things worth building start as fragile intuitions. You either learn to hold them long enough for them to take shape, or you default to what’s already well-trodden.
Unfortunately, the default is neither noteworthy nor novel. If we only pursue ideas that are already clear and proven we'll always be following the herd, not leading.
Inefficient obsessions
Go down rabbit holes. He filled the opening pages of one of his notebooks with 169 attempts to square a circle. In eight pages of his Codex Leicester, he recorded 730 findings about the flow of water; in another notebook, he listed sixty-seven words that describe different types of moving water. … He drilled down for the pure joy of geeking out.
He didn’t skim the surface of a topic. He exhausted it. Not because he needed all the data, but because fluency comes from depth. This kind of obsessive recursion isn’t excess. It’s a cognitive infrastructure that allows for fast, intuitive action later. But only if you’ve gone deep enough.
Given enough structure, inefficiency can help competence, not undermine it.
Distracted wandering
The greatest rap on Leonardo was that these passionate pursuits caused him to wander off on tangents, literally in the case of his math inquiries. It “has left posterity the poorer,” Kenneth Clark lamented. But in fact, Leonardo’s willingness to pursue whatever shiny subject caught his eye made his mind richer and filled with more connections.
What might be labeled today as attention deficit was Leonardo’s strength. Modernity prizes focus, but it can also turn into fixation.
Meaningful creativity requires the intentional disruption of conventional focus. Intellectual drift is often when dissimilar ideas collide and reconfigure, creating unexpected juxtapositions
Skilful procrastination
While painting The Last Supper, Leonardo would sometimes stare at the work for an hour, finally make one small stroke, and then leave. He told Duke Ludovico that creativity requires time for ideas to marinate and intuitions to gel. “Men of lofty genius sometimes accomplish the most when they work least,” he explained, “for their minds are occupied with their ideas and the perfection of their conceptions, to which they afterwards give form.”
Most of us don’t need advice to procrastinate; we do it naturally. But procrastinating like Leonardo requires work: it involves gathering all the possible facts and ideas, and only after that allowing the collection to simmer.
“Slack” and “waste” are not the same thing, and you’d be surprised how many managers don’t get this even at the highest levels.
Leaders fear indecision. But structured delay is a sophisticated decision-making mechanism rather than a flaw. Patience in decision-making allows ideas to mature and reveals deeper insights.
You are not avoiding; you’re incubating.
Defending perfectionism
Let the perfect be the enemy of the good. When Leonardo could not make the perspective in the Battle of Anghiari or the interaction in the Adoration of the Magi work perfectly, he abandoned them rather than produce a work that was merely good enough. He carried around masterpieces such as his Saint Anne and the Mona Lisa to the end, knowing there would always be a new stroke he could add.
Likewise, Steve Jobs was such a perfectionist that he held up shipping the original Macintosh until his team could make the circuit boards inside look beautiful, even though no one would ever see them. Both he and Leonardo knew that real artists care about the beauty even of the parts unseen.
Eventually, Jobs embraced a countermaxim, “Real artists ship,” which means that sometimes you ought to deliver a product even when there are still improvements that could be made. That is a good rule for daily life. But there are times when it’s nice to be like Leonardo and not let go of something until it’s perfect.
“Perfect is the enemy of good” simplifies complex decision-making. Leonardo shows a relentless fidelity to personal standards and aspirations. His refusal to compromise his vision highlights the fact that sometimes perfectionism is precisely what differentiates true mastery from mere competence.
The skill lies in recognizing when compromising for expediency undermines what you stand for.
Dumb goals
Let your reach exceed your grasp. Imagine, as he did, how you would build a human-powered flying machine or divert a river. Even try to devise a perpetual-motion machine or square a circle using only a ruler and a compass. There are some problems we will never solve. Learn why.
The “realistic” in the R of SMART goals while practical is also restrictive, even dumb, when used without discretion. When you try something just out of reach, you reveal the limits of your current model. That tension creates movement, even when the project itself doesn’t ship.
The value of fantasy
Indulge fantasy. His giant crossbow? The turtle-like tanks? His plan for an ideal city? The man-powered mechanisms to flap a flying machine? Just as Leonardo blurred the lines between science and art, he did so between reality and fantasy. It may not have produced flying machines, but it allowed his imagination to soar.
Fantasy is dismissed as frivolous in serious business contexts. But thinking absurdly sharpens what's possible. It detaches the present from its default constraints and exposes previously hidden assumptions.
Customers aren’t always right
Create for yourself, not just patrons. No matter how hard the rich and powerful marchesa Isabella d’Este begged, Leonardo would not paint her portrait. But he did begin one of a silk-merchant’s wife named Lisa. He did it because he wanted to, and he kept working on it for the rest of his life, never delivering it to the silk merchant.
Too much customer-centricity sometimes misses the point. Lasting impact often arises from deeply personal investment in work, not solely from external demands. Sometimes your internal compass has to take precedence over market demands.
Solitary geniuses collaborate
Genius is often considered the purview of loners who retreat to their garrets and are struck by creative lightning. Like many myths, that of the lone genius has some truth to it. But there’s usually more to the story.
The Madonnas and drapery studies produced in Verrocchio’s studio, and the versions of Virgin of the Rocksand Madonna of the Yarnwinder and other paintings from Leonardo’s studio, were created in such a collaborative manner that it is hard to tell whose hand made which strokes. Vitruvian Man was produced after sharing ideas and sketches with friends. …
Genius starts with individual brilliance. It requires singular vision. But executing it often entails working with others. Innovation is a team sport. Creativity is a collaborative endeavor.
Leadership mythology, and especially the myths around creativity, often glorifies solitary genius. But Leonardo reveals collaboration as intellectual humility.
Great leadership hinges less on individual brilliance and more on orchestrating collective genius. Great teams aren’t unified by agreement but through mutual fascination.
The real value of lists
Make lists. And be sure to put odd things on them. Leonardo’s to-do lists may have been the greatest testaments to pure curiosity the world has ever seen.
His lists weren’t for managing time but for cataloguing curiosity. They weren’t about productivity, but discovery. Naming what you don’t understand changes how you see. It rearranges your mental inventory.
Rather than mere tasks, lists can be a deliberate shaping and curating of your mental landscapes and possibilities. If your lists don’t inspire, perhaps that’a signal.
Unanswered questions
Be curious, relentlessly curious. … his distinguishing and most inspiring trait was his intense curiosity. He wanted to know what causes people to yawn, how they walk on ice in Flanders, methods for squaring a circle, what makes the aortic valve close, how light is processed in the eye and what that means for the perspective in a painting. …
Leo didn’t ask questions to close them. Instead, he asked them to stay in tension with what he didn’t yet understand. That kind of questioning doesn’t lead to clean answers. It leads to better pattern recognition, more unexpected angles, and a resistance to premature answers.
Fast closure doesn’t build the muscle for real insight.
Observation as a practice
Observe. Leonardo’s greatest skill was his acute ability to observe things. It was the talent that empowered his curiosity, and vice versa. It was not some magical gift but a product of his own effort. When he visited the moats surrounding Sforza Castle, he looked at the four-wing dragonflies and noticed how the wing pairs alternate in motion. When he walked around town, he observed how the facial expressions of people relate to their emotions, and he discerned how light bounces off differing surfaces. …
He treated perception like a craft. Not something you’re born with, but something you work on.
The byproduct of this kind of trained observation is not mere data, but judgement and discernment.
Hyper promiscuity
Avoid silos. At the end of many of his product presentations, Jobs displayed a slide of a sign that showed the intersection of “Liberal Arts” and “Technology” streets. He knew that at such crossroads lay creativity.
Leonardo had a free-range mind that merrily wandered across all the disciplines of the arts, sciences, engineering, and humanities. His knowledge of how light strikes the retina helped inform the perspective in The Last Supper, and on a page of anatomical drawings depicting the dissection of lips he drew the smile that would reappear in the Mona Lisa.
He knew that art was a science and that science was an art….
Reality doesn’t respect categories. Siloed thinking cripples creativity. As another great Vincent van Gogh advised, knowing only one thing is stultifying.
Leonardo’s expansive cross-disciplinary explorations show that innovation happens at the intersection of varied fields and interests. In our modern hyper-specialized professional environments, cross-domain fluency is underutilized as a competitive advantage, both in organizations and careers.
Issacson closes his section with the following:
Be open to mystery. Not everything needs sharp lines.
We crave clarity but Leonardo’s embrace of mystery shows tolerance of ambiguity as an essential skill of mastery.
It’s a deliberate resistance to over-simplification. Rather than eliminate uncertainty, we have to learn to dance with it and see what emerges.
Seek knowledge for its own sake. Not all knowledge needs to be useful. Sometimes it should be pursued for pure pleasure.
Such an important idea!