being too ambitious is a clever form of self-sabotage

on starting, doing, being, and becoming.

There is a moment, just before creation begins, when the work exists in its most perfect form in your imagination. It lives in a crystalline space between intention and execution, where every word is precisely chosen, every brushstroke deliberate, every note inevitable, but only in your mind. In this prelapsarian state, the work is flawless because it is nothing: a ghost of pure potential that haunts the creator with its impossible beauty.

This is the moment we learn to love too much.

We become curators of imaginary museums, we craft elaborate shrines to our unrealized projects… The novel that will redefine literature. The startup that will solve human suffering. The artwork that will finally make the invisible visible.

But the moment you begin to make something real, you kill the perfect version that lives in your mind.

Creation is not birth; it is murder. The murder of the impossible in service of the possible.

the curse of vision

We are perhaps the only species that suffers from our own imagination. A bird building a nest does not first conceive of the perfect nest and then suffer from the inadequacy of twigs and mud. A spider spinning a web does not pause, paralyzed by visions of geometric perfection beyond her current capabilities. But humans? We possess the strange gift of being haunted by visions of what could be, tormented by the gap between our aspirations and our abilities.

This torment has a name in cognitive science: the "taste-skill discrepancy." Your taste (your ability to recognize quality) develops faster than your skill (your ability to produce it). This creates what Ira Glass famously called "the gap," but I think of it as the thing that separates creators from consumers.

Watch a child draw. They create fearlessly, unselfconsciously, because they have not yet developed the curse of sophisticated taste! They draw purple trees and flying elephants with the confidence of someone who has never been told that trees aren't purple, that elephants don't fly. But somewhere around age eight or nine, taste arrives like a harsh critic, and suddenly the gap opens. The child can see that their drawing doesn't match the impossible standard their developing aesthetic sense has conjured.

This is what leads most of us to stop drawing. Not because we lack talent, but because we've developed the ability to judge before we've developed the ability to execute. We become connoisseurs of our own inadequacy.

And this is where our minds, in their desperate attempt, devise an elegant escape. Faced with this unbearable gap, we develop what researchers call "productive avoidance" — staying busy with planning, researching, and dreaming while avoiding the vulnerable act of creating something concrete that might fail. It feels like work because it engages all our intellectual faculties. But it functions as avoidance because it protects us from the terrifying possibility of creating something imperfect. I see this in wannabe founders listening to podcasts on loop, wannabe TikTokkers watching hours of videos as “research,” and wannabe novelists who spend years developing character backstories for books they never begin.

The spider doesn't face this problem. It spins webs according to ancient genetic instructions, each one remarkably similar to the last. But human creativity requires us to navigate the treacherous territory between what we can imagine and what we can actually do. We are cursed with visions of perfection and blessed with the capacity to fail toward them.

my favorite anecdote… “the best is the enemy of the good”

In a photography classroom at the University of Florida, Jerry Uelsmann unknowingly designed the perfect experiment for understanding excellence. He divided his students into two groups.

The quantity group would be graded on volume: one hundred photos for an A, ninety photos for a B, eighty photos for a C, and so on.

The quality group only need to present one perfect photo.

At semester's end, all the best photos came from the quantity group.

The quantity group learned something that cannot be taught: that excellence emerges from intimacy with imperfection, that mastery is built through befriending failure, that the path to creating one perfect thing runs directly through creating many imperfect things.

Think about what those hundred attempts actually were: a hundred conversations with light. A hundred experiments in composition. A hundred opportunities to see the gap between intention and result, and to adjust. A hundred chances to discover that reality has opinions about your vision, and that those opinions are often more interesting than your original plan.

The quality group, meanwhile, spent their semester in theoretical purgatory… analyzing perfect photographs, studying ideal compositions, researching optimal techniques. They developed sophisticated knowledge about photography without developing the embodied wisdom that comes only from repeatedly pressing the shutter and living with the consequences.

They became experts in the map while the quantity group was exploring the territory. When the semester ended, the quality group could tell you why a photograph was excellent. The quantity group could make excellent photographs.

your brain, it turns out, is an exquisite liar

When you imagine achieving something, the same neural reward circuits fire as when you actually achieve it. This creates what neuroscientists call "goal substitution"—your brain begins to treat planning as accomplishing. The planning feels so satisfying because, neurologically, it is satisfying. You're getting a real high from an imaginary achievement.

But here's where it gets interesting: this neurological quirk serves us beautifully in some contexts and destroys us in others. An Olympic athlete visualizing their routine creates neural pathways that improve actual performance. They're using imagination to enhance capability they already possess. A surgeon mentally rehearsing a complex procedure is optimizing skills they've already developed through years of practice.

But when imagination becomes a substitute for practice rather than an enhancement of it, the same mechanism becomes a trap. The aspiring novelist who spends months crafting the perfect outline gets the same neurological reward as the novelist who spends months actually writing. The brain can't tell the difference between productive preparation and elaborate procrastination.

the illusion of instant excellence

The algorithmic machinery of attention has, of course, engineered simple comparison. But it has also seemingly erased the process that makes mastery possible. A time-lapse of someone creating a masterpiece gets millions of views. A real-time video of someone struggling through their hundredth mediocre attempt disappears into algorithmic obscurity.

Instagram shows you the finished painting, never the failed color experiments. TikTok shows you the perfect performance, never the thousand imperfect rehearsals. LinkedIn shows you the promotion announcement, never the years of unglamorous skill-building that made it possible.

This creates what media theorist Neil Postman would have recognized as a "technological epistemology:" the platforms don't just change what we see, they change what we think knowledge looks like. We begin to believe that learning should be immediately visible, that progress should be consistently upward, that struggle is evidence of inadequacy rather than necessity.

The truth is that every masterpiece exists within an invisible ecology of lesser works. The great painting emerges from hundreds of studies, sketches, and failed attempts. The brilliant book grows from years of mediocre writing. The breakthrough innovation builds on countless small improvements and partial failures. We see the oak tree, never the acorns. The symphony, never the scales. The masterpiece, never the apprenticeship.

Too much ambition disrupts this natural ecology; it demands that every attempt be significant, every effort be worthy of the ultimate vision. But the ecology of mastery requires something our culture has systematically devalued: the privilege of being a beginner.

Watch a four-year-old finger-paint. They don't create for Instagram likes or gallery walls or market validation. They create for the pure joy of watching colors bleed into each other, for the satisfying squish of paint between fingers, for the magic of making something exist that didn't exist before. They possess the freedom to create without the burden of expectation.

Learning anything as an adult means reclaiming this beginner's privilege. It means giving yourself permission to be bad at something, to create things that serve no purpose other than your own discovery and delight. The beginner's mind understands that mastery emerges from play, that excellence grows from experimentation, that the path to creating something great runs directly through creating many things that aren't great at all.

My alma mater, Olin College of Engineering, had a motto that rewired how I think about everything: "Do-Learn." Those two words contain a revolution. Not "learn-then-do," which implies you must earn permission to act. Not "think-then-execute," which suggests theory should precede practice. But the radical idea that doing is learning! That understanding emerges from your hands as much as your head, that wisdom lives in the conversation between intention and reality.

This philosophy saved me from my own perfectionism more times than I can count. When I wanted to learn cooking, I didn't read recipes endlessly; I burned onions and discovered how heat actually behaves. When I wanted to learn a language, I didn't memorize grammar rules; I stumbled through conversations with native speakers who corrected my mistakes in real time. When I wanted to learn how to monetize on YouTube, I didn't write elaborate content strategies; I started posting videos and let the brutal feedback teach me what actually resonated.

"Do-Learn" gave me permission to start before I was ready, fail early, fail often, to discover through making rather than thinking my way to readiness.

the quitting point

Here's what happens to those brave enough to actually begin: you discover that starting is only the first challenge. The real test comes later, at "the quitting point" —that inevitable moment when the initial excitement fades and the work reveals its true nature.

courtesy of Tomas Svitorka, at tomassvitorka.com

The quitting point arrives differently for different people, but it always arrives. For writers, maybe it’s around page 30 of their novel, when the initial burst of inspiration runs out and they realize they have no idea what happens next. For entrepreneurs, maybe it’s after the first few months, when the market doesn't respond as enthusiastically as friends and family did. For artists, it might come when they see their work objectively for the first time and realize the enormous gap between their vision and their current capability.

This is the moment that separates the quantity group from the quality group: not at the beginning, but in the middle, when the work stops being fun and starts being work.

The quantity group has an advantage here! They've already become intimate with imperfection. They've learned that each attempt is data, not judgment. They've developed what psychologists call "task orientation" rather than "ego orientation;" they're focused on improving the work rather than protecting their self-image.

But the quality group approaches this moment with a different psychology. Having spent so much time crafting perfect plans, they interpret early struggles as evidence that something is wrong! They expected the work to validate their vision, but instead it reveals the distance between intention and capability.

I think this is where most creative projects die — not from lack of talent or resources, but from misunderstanding the nature of the work itself. The quitting point feels like failure, but it's actually where the real work begins.

It's the transition from working with imaginary materials to working with real ones, from theory to practice, from planning to building.

The quitting point is the moment you discover whether you want to be someone who had a great idea or someone who made something real.

lower the stakes!

Counterintuitively, the path to creating your best work often begins with permission to create your worst.

When you lower the stakes, you enter into a conversation with reality. Reality has opinions about your work that are often more interesting than your own. Reality shows you what works and what doesn't. Reality introduces you to happy accidents and unexpected directions. Reality is the collaborator you didn't know you needed.

This is how standards are actually achieved… through process, not proclamation. The photographer who takes a hundred photos develops standards through practice. The writer who writes daily develops judgment through repetition. The entrepreneur who starts small develops wisdom through experience.

Last week, something I wrote went viral on Substack. In a matter of days, I gained over a thousand new subscribers, watched my piece get shared across platforms, and felt that intoxicating rush of work that resonates beyond your own echo chamber. I'm deeply grateful, truly. But almost immediately, a familiar pit opened in my stomach. What now? What if the next one doesn't land? How do you follow something that took on a life of its own?

I found myself opening blank pages and closing them again, paralyzed by the very success I'd worked toward for years.

When I expressed this fear, a reader named Harsh (@harshdarji) left this comment: "You are a shooter, your job is to keep shooting. Don't even think about misses. Because as soon as you start worrying about the misses, you'll start doubting your ability."

Not much of a sports gal, but the metaphor moved me. And the irony wasn't lost on me! Here I was, dispensing advice about creative consistency and the dangers of perfectionism, yet falling into the exact trap I warn others about.

I started writing on Substack in December 2022. It's now mid-2025, and I've just reached my goal of being in the top 50 Tech Substacks in the world. There was so much doing, doing, doing before this one hit. Dozens of pieces that barely made a ripple. Months of showing up to write for an audience I wasn't sure existed.

But success has a way of making you forget the very process that created it. It whispers seductive lies about repeatability, about formulas, about the possibility of controlling outcomes rather than focusing on inputs. It makes you think you need to "top" your last success instead of simply continuing the practice that made success possible in the first place.

I need to remind myself:
Your masterpiece won't emerge from your mind fully formed like Athena from Zeus's head. It will emerge from your willingness to start badly and improve steadily. It will emerge from your commitment to showing up consistently rather than brilliantly. It will emerge from your ability to see failure as information rather than indictment.

The work that will matter most to you, the work that will surprise you with its significance, is probably much smaller than you imagine and much closer than you think.

My Olin professors were right about those two words. Do. Learn. But what I didn't fully internalize until after graduation: the learning never stops requiring the doing. The doing never stops requiring learning. The work changes me. I change the work. The work changes me again.

We are still the only species cursed with visions of what could be. But perhaps that's humanity's most beautiful accident. To be haunted by possibilities we cannot yet reach, to be driven by dreams that exceed our current grasp. The curse and the gift are the same thing: we see further than we can walk, dream bigger than we can build, imagine more than we can create.

And so we make imperfect things in service of perfect visions. We write rough drafts toward masterpieces we may never achieve. We build prototypes of futures we can barely envision. We close the gap between imagination and reality one flawed attempt at a time.

The photography professor divided his class and waited. He knew what the darkroom would teach them, what the developing chemicals would reveal. Fifty rolls of film later, some students had learned to make beauty from mess. Others had learned to make theories from anxiety.

The film didn't care about their intentions. It only responded to their willingness to press the shutter.

Your hands are already dirty. The work is waiting. Lower the stakes, and begin.