Curiosity and Empathy Aren’t Bad: What Leonardo da Vinci Can Teach Us

Leonardo da Vinci is often treated as the emblem of genius, the Renaissance mind par excellence. And yet, late in life, Leonardo regarded himself as something of a failure (a point that gets picked up a good deal in mainstream articles about him these days). He believed he had not finished enough, not delivered enough, not brought his restless investigations to proper completion, as in this post I read this morning, Why Da Vinci Thought He Was a Failure, The Culturist.

Obviously, this feels almost absurd. How could someone whose work reshaped art, anatomy, engineering, and natural observation judge himself so harshly… The Mona Lisa, The Last Supper, having a Teenage Mutant Ninja Turtle named after you (also my favorite one)? But if we approach Leonardo phenomenologically, attending not to outcomes but to lived experience, his dissatisfaction begins to make a different kind of sense.

What Leonardo struggled with was not a lack of talent or discipline, but the burden of curiosity itself.

Curiosity as a Way of Being

Leonardo’s notebooks reveal a mind endlessly drawn outward. I suffer similar tendencies, and the notebooks that I’ve meticulously kept since around 2010 would probably testify to that for an outside reader. He observed water curling around obstacles, birds banking in flight, muscles tightening beneath skin, and light diffusing through air. These observations were not collected for a single project. They were acts of sustained attention to the world as it presented itself.

Curiosity, for Leonardo, was not an instrument aimed at mastery. It was an orientation toward phenomena, a continual turning of the self toward whatever appeared. In phenomenological terms, this resembles intentionality, the basic structure of consciousness as always being consciousness of something that we find in Edmund Husserl’s Ideas I (PDF here).

Maurice Merleau-Ponty later argued that perception itself is a bodily engagement with the world rather than a detached mental representation (Phenomenology of Perception… dense but one of my fav works that should be more read these days!). Leonardo seems to have intuited this centuries earlier. His curiosity was embodied, sensory, and relational. He learned by lingering, sketching, returning, and allowing phenomena to resist easy explanation.

From this perspective, curiosity is not a trait one possesses. It is a way of inhabiting the world.

Why Curiosity Can Feel Like Failure

Leonardo’s sense of failure arose precisely because this mode of being does not align well with cultures of completion. He moved slowly, followed questions wherever they led, and often abandoned works when new phenomena called for his attention. Patrons expected finished paintings. Leonardo found himself perpetually unfinished. I often feel the same!

Phenomenologically speaking, this tension reflects a clash between two temporalities. One is the linear time of production and achievement. The other is the lived time of attention, where meaning unfolds through repeated encounters and deepening perception.

Leonardo lived primarily in the second. What looks like failure from the outside can, from within, be fidelity to experience. To remain curious is to resist closure. It is to stay with the world longer than efficiency allows. It’s certainly a curse on one level and we often treat it with pharmaceutical medication these days… but it’s also a blessing or superpower, depending on your persuasion.

Empathy as Curiosity Turned Relational

Leonardo’s curiosity did not stop at nature or mechanics. It extended deeply into human expression. His drawings and paintings reveal a remarkable sensitivity to gesture, posture, and facial expression. He did not simply depict bodies. He rendered states of being.

This is where curiosity becomes empathy.

Phenomenologically, empathy is not projection or emotional contagion. Edith Stein describes it as a way of accessing another’s experience while preserving their otherness (Stein, On the Problem of Empathy PDF, which should be required reading in all colleges and universities, if not in high schools). Empathy begins with curiosity, with the willingness to attend to another without collapsing them into our own expectations.

Leonardo’s art practices this attentiveness. His figures invite us to linger with them, to sense the interiority suggested by an angle of the head or a softness around the eyes. He does not explain them. He lets them be encountered.

This pairing of curiosity and empathy is essential. Curiosity without empathy becomes extractive. Empathy without curiosity becomes sentimental. Together, they form a disciplined openness to reality as it shows itself.

Curiosity Beyond the Human

Leonardo’s curiosity was also ecological, long before the term existed. He did not treat nature as inert matter to be controlled. Water had character. Air had movement. Plants and animals exhibited their own intelligences.

This resonates strongly with phenomenological approaches to ecology, where attention is given not only to systems but to lived encounters with the more-than-human world. To observe a tree across seasons, or to watch how rain alters the texture of soil, is not merely to gather data. It is to practice a form of relational knowing grounded in care.

Curiosity, in this sense, is ethical before it is theoretical. It teaches us how to stay with what exceeds us.

Real Being as Attentive Presence

Leonardo’s evident dissatisfaction with his life’s output may say less about his achievements and more about the cost of living attentively in a world that rewards closure. His life suggests that real being does not consist in finishing everything we begin, but in remaining responsive to what continually addresses us.

Curiosity keeps us open. Empathy keeps us responsible.

Together, they shape a way of being that is not centered on control or accumulation, but on presence, participation, and care. If Leonardo indeed felt like a failure, perhaps it was because he measured himself by standards that could never capture the depth of his engagement with the world.

Phenomenology invites us to reconsider those standards. It asks not what we have produced, but how we have learned to see, to listen, and to remain with what is given.

In that light, curiosity and empathy are not distractions from real being. They are its conditions.

Rembrandt’s Dog in ‘The Night Watch’

Fascinating story…

What’s the Dog in Rembrandt’s ‘The Night Watch’? A Longtime Mystery Is Solved. – The New York Times:

“Even 400 years after the creation of one of the most known paintings, you can still discover things,” Dibbits said. “With art, you will always continue to pose questions, and in this case, it’s: Which dog is it?”

Stare at Bosch’s ‘Garden of Earthly Delights’ Today

Give yourself 10 mins today to stare at Bosch’s work and learn a little about yourself, the world, consciousness, and projection (not a bad use of just 10 mins of your day instead of doomscrolling Reels or TikTok)…

10-Minute Challenge: Bosch’s ‘Garden of Earthly Delights’ – The New York Times (Gift Article):

Today, we bring you another focus challenge, in which we invite you to spend uninterrupted time looking at one piece of art. This one is a 500-year-old, three-paneled triptych by the Dutch painter Hieronymus Bosch.

Inside a Genius Mind: Leonardo’s Notebooks

Amazing web app here (bottom link to direct Google Experiment) focused on major themes in Leonardo’s notebooks and connecting them with machine learning. I’m a huge fan of notebooks, and I use the example of Leonardo keeping his thoughts in them all the time with my own students.

If you’re like me and really into Leonardo’s “notebooking” practices and history, I highly suggest you check out the videos Adam Savage has done on his Tested YouTube channel. Wonderful and inspiring videos. May we all find something that moves us in such a way!

Leonardo da Vinci: Inside a genius mind post:

From the stages of his life to dispelling myths, and examining his masterpieces up close, everyone can delve into Leonardo’s mind as we’ve brought together for the first time 1,300 pages from his collections of volumes and notebooks. The codices, brimming sketches, ideas, and observations, offer a window into the boundless imagination of one of history’s greatest polymaths. With the aid of Machine Learning and the curatorial expertise of Professor Martin Kemp, the accompanying experiment also called “Inside a Genius Mind” unravels these intriguing and sometimes mysterious materials.

Full experiment here!

When you tell your daughters that you collect images of Jonah and they send you one from a Basilica

Pretty cool kids…

It’s always been my conjecture that the Dura Europos Baptistry had images of Jonah present as a representation of the 3-day Resurrection event in a Jewish/Chritian context. There were depictions of Adam and Eve in the Baptistry area (along with Jesus as the Good Shepherd as well as other common representations from the Old Testament/Hebrew Bible in places such as the Catacombs in Rome).

Here’s an image of the Dura Baptistry from the original printing of Dura Europos and Its Art by Prof. M. Rostovtzeff (1938, Oxford Press)… one of my favorite books and possessions:

The top register includes a depiction of Jesus telling the disabled person by the Bethesda Pool to grab their cot and get up and walk off (John 5). It’s a terrific passage.

The amazing (and frustrating thing) is that the register literally flows the pool into a depiction of Jesus walking on water on the Sea of Galilee and getting Peter to hop out of the boat to walk towards him (Mark 6, Matthew 14, and John 6)… which doesn’t turn out well for Peter. The depiction here actually shows Peter sinking in the waves!

Here are the two panels we have with the earliest depictions of Jesus that we know of …

Dura Europos Baptistry Depictions of Jesus Healing the Paralytic and Walking on Water

While a grad student at Yale, I was fortunate enough to spend a couple of years working at the incredible Yale Art Gallery with Prof. Susan Matheson and the talented staff there. One of my “jobs” (it was more like dream assignments) was working in the basement to catalog the Dura Europos collection with digital photography. I got to see this fresco on a pretty regular basis and we became good pals. If I knew then what I know now…

However, the frustrating part is that the water continues to flow to the next register… which has been lost to history after the sack of the (then) Roman Dura Europos in 256-257 CE by Sassanians and subsequent abandonment of the fort / town and eventual disappearance into history before the complete looting of the site by ISIS over the last decade. It’s a sad tale and I had always hoped to travel to Dura and participate in a dig where we’d uncover the other pieces of the top register in the Baptistry that would almost certainly have included Jonah being regurgitated from the fish and therefore seal my case about Jewish-Christianity extending well into the 3rd and 4th centuries. Alas.

Again, Jonah shows up quite often in early Christian artwork and imagery as a signifier of the Resurrection (the Catacombs especially), but I always wanted to see what those genius artists who designed the Dura Europos Baptistry did with the rest of the panels and the water theme as they perched between the edge of the desert and overlooking the Euphrates River.