The First Step and Its Infinite Predecessors

The First Step and Its Infinite Predecessors
Photo by Ian / Unsplash

The first place I ever lived alone was a third-floor walkup with walls the color of depression and windows that looked onto a brick wall approximately eighteen inches away.1 I was twenty-three and determined to make it feel less temporary, less provisional, more mine. Which meant shelves. Three of them, for books I'd been hauling around since college, books I'd never read but couldn't abandon because abandoning them felt equivalent to abandoning possible future versions of myself.2

So I went to the hardware store, and I stood there, holding two different drill bits, unable to move forward because what if I chose wrong? What if the shelves fell? What if I drilled into a water pipe I didn't know existed and flooded the apartment and lost my security deposit and proved to everyone (but mostly to myself) that I couldn't handle the basic infrastructure of independent adult life?3

The guy working the aisle, maybe thirty, with the kind of practiced indifference that comes from watching people overthink simple decisions all day, walked past, saw my face, and said, “Either one works. Just grab one.” Then he disappeared into the lighting section, leaving me with what felt uncomfortably close to a koan.

Nobody tells you this about planning: it becomes a narcotic. Not the planning itself, really, but the feeling of planning, the sensation of being perpetually on the verge of doing something important.4 William James, writing in 1890, observed what he called “the explosive will”: the moment when intention converts to action. He noted how rare and almost violent that conversion feels. Most of us, he suggested, live in a state of perpetual intention, mistaking the mental rehearsal of action for the action itself. We're method actors who never make it to opening night, spending our lives in rehearsal rooms, perfecting gestures for plays that will never be performed.

The French psychologist Bluma Zeigarnik discovered something strange in the 1920s: we remember interrupted tasks better than completed ones.5 The waiter remembers your order perfectly until you've paid, then forgets it instantly. The mind holds onto the unfinished with a kind of desperate intensity, which means that planning, always on the edge of beginning, creates this awful cognitive itch, this feeling of productive discomfort that mimics actual progress.

But what if that discomfort is the point? What if planning becomes the thing we do instead of the thing we planned?6


I bought both drill bits. Obviously. Went home to that apartment with its depressing walls and insufficient natural light. Drilled pilot holes with the wrong bit first, realized my mistake, switched bits, finished the job.7 The shelves went up. They were slightly crooked, maybe two degrees off level, and I saw it every time I looked at them for the three years I lived there, but they held books just fine.8 The crooked shelves taught me more about my relationship with imperfection than any amount of planning ever could.

Søren Kierkegaard wrote about people who live “aesthetically,” perpetually sampling life, perpetually keeping their options open, perpetually preparing for the moment when they'll finally commit to something real.9 The aesthetic life, he argued, is ultimately one of despair because it mistakes possibility for actuality, potential for achievement. These people plan to start the business once they've saved enough money, taken enough courses, read enough books. They plan to write once they have the right desk, the right software, the right uninterrupted time. They plan to repair relationships once they've figured out exactly what to say, how to say it, what emotional register will produce the desired effect.

The aesthetic life is comfortable because it's hypothetical. In hypothesis, everything works. The business succeeds because you've imagined away all the variables. The novel is brilliant because you haven't written the second chapter yet. The conversation goes perfectly because you're playing both parts.

But here's the geometry of it: clarity doesn't arrive before movement; it arrives through movement. You cannot figure out how to ride a bicycle by thinking about riding a bicycle. You cannot learn to dance by reading about dancing. You cannot discover what you're capable of by imagining what you might be capable of.10

Does this mean you shouldn't plan at all? Of course not. Plans are useful. They're maps. But a map is not the territory.11 A map is always a simplification, a reduction, a guess about what matters. The actual territory reveals itself only when you're moving through it, when your body is in the space, when you're making decisions with incomplete information and discovering what you need to know in real time.


I have a friend who spent two years researching which programming language to learn. Two years. He read comparison articles, debated on forums, made spreadsheets comparing job market demand for Python versus JavaScript versus Ruby. Meanwhile, his neighbor's kid, who was fourteen, taught himself Python in six weeks by trying to build a terrible video game. The game crashed constantly. It looked awful. But the kid learned to code, actually learned, while my friend accumulated theoretical knowledge about learning.

The German philosopher Martin Heidegger had this idea about “ready-to-hand” versus “present-at-hand.” When you're using a hammer, you don't think about the hammer; you think about the nail, the board, what you're building. The hammer disappears into the action. It's ready-to-hand. But when the hammer breaks, suddenly you're looking at it as an object, analyzing it, thinking about its properties. It becomes present-at-hand. It's no longer part of your doing; it's something you're thinking about.12

Planning does this to our lives. It takes the thing we want to do and makes it an object of analysis rather than a tool for doing.

You can see it everywhere now. Apps that gamify productivity, dashboards that let you color-code your hesitation. People spend whole evenings rearranging digital to-do lists instead of touching the work itself. The software flatters us with metrics for imaginary momentum. We call it “workflow,” but it's really choreography: movement designed never to arrive anywhere.

We study the hammer instead of hammering. We become experts in the theory of hammering while the nails remain undriven.

What would happen if you gave yourself permission to be bad at something? Not forever, just at first, just while you're learning, just while you're moving from standing still to moving forward? What if the goal wasn't to do it perfectly but to do it at all?

But there's another trap: mistaking motion for progress. I've done this too; starting five projects to avoid finishing one, equating momentum with meaning. Doing can become its own anesthetic, a way to avoid the quiet reckoning that follows completion. Sometimes the fear of stopping feels just like the fear of starting, only better disguised.


The paralysis, when you really examine it, isn't about lacking information. You know enough. The guy in the hardware store was right: your gut knows which drill bit to grab. The paralysis is about wanting certainty in a world that offers none. It's about wanting to make a decision so perfect, so optimized, that you never have to face the possibility of being wrong, of failing, of doing something badly.13

But that certainty costs you the chance to do anything at all.

John Dewey spent decades arguing that we learn by doing, not by contemplating doing. His whole educational philosophy rested on the idea that knowledge separated from experience is not really knowledge at all; it's just information, floating around, disconnected from the reality it's supposed to describe. A child doesn't learn what “hot” means by hearing the word; the child learns by touching the stove.14 The learning happens in the encounter, in the friction between expectation and reality, in the adjustment that follows the mistake.

This isn't an argument for recklessness or for ignoring obvious dangers. It's an observation about how learning actually works, how capability actually develops. You don't get good at making decisions by avoiding decisions until you're sure you'll make the right one. You get good at making decisions by making decisions, observing what happens, adjusting, and deciding again.

What's that thing you've been planning to start? Close your eyes. What just appeared? That's the thing. You know the thing. You've been researching it, thinking about it, telling yourself you'll start once you've figured out X or Y or Z.

What if you just started?

What if, instead of reading another article about writing, you wrote a bad paragraph? What if, instead of researching the perfect workout routine, you went for a walk right now? What if, instead of planning the perfect way to reconnect with that person, you sent a messy, imperfect text saying you'd been thinking about them?

The thirteenth-century mystic Meister Eckhart wrote, “Whatever is received is received according to the mode of the receiver.” You can read a thousand books about swimming, but until you're in the water, choking on chlorine, figuring out how to breathe, the knowledge remains abstract.15 The water teaches you differently than the book does. The water is unforgiving and immediate and real.


Those shelves I hung in my first apartment, crooked, imperfect, evidence of action over paralysis, stayed up for three years. When I finally moved out, I left them for the next tenant because removing them would have left holes, and I'd caused enough imperfection already. But I'm glad they were crooked because their crookedness proved I did something instead of planning something. They were evidence of action, of choosing motion over stasis, of accepting that done is better than perfect.

Aristotle wrote about potentiality and actuality. The acorn potentially is an oak tree, but it becomes an actual oak tree only through the process of growing, pushing through soil, reaching toward light. The acorn cannot become an oak tree by planning to become an oak tree. It becomes an oak tree by starting to become an oak tree.

You already know what you need to do next. It's probably small. It's probably undramatic. It's probably something you could do in the next hour if you decided to stop planning and start doing.

The staircase doesn't need to be visible all the way to the top. You just need to see the next step. Once you take it, the next one appears, then the next, then the next. This is how people build careers, write novels, learn languages, repair relationships, change their lives; not through brilliant master plans but through the accumulation of imperfect action, through choosing motion over stasis, through accepting that you'll figure it out as you go.

The car only steers when it's moving. You already know this. Somewhere in your body, you know this.

  1. The brick wall belonged to another building. I never figured out what was inside that other building. In three years of living there, I never saw anyone enter or exit it. It was just brick, forever, eighteen inches from my window. This is not a metaphor for anything, though it probably should be. ↩︎

  2. Most of these books were philosophy and literary theory I'd been assigned in college and never read, just carried from apartment to apartment as if their physical presence would somehow transmit their contents into my brain through proximity. Spoiler: it did not work. ↩︎

  3. There probably wasn't a water pipe there. But the mind, when it wants to avoid action, becomes marvelously creative at generating catastrophic scenarios. This is the same cognitive machinery that produces horror movies and insurance policies, the imagination of worst-case outcomes as a form of psychological self-protection that ultimately protects you from nothing except the possibility of doing something. Also, I was twenty-three and convinced that adulthood was a series of traps waiting to catch me being incompetent. ↩︎

  4. I once knew someone who had an entire shelf of notebooks, beautiful leather-bound ones, that she'd bought for “when I start writing.” She never wrote in them because she was waiting to have something worthy of such beautiful notebooks. The notebooks remained pristine and empty, and she remained a person who planned to write rather than a person who wrote. ↩︎

  5. The Zeigarnik Effect explains why TV shows end on cliffhangers and why you can't stop thinking about that argument you didn't finish. The brain wants closure. Planning, being always incomplete, always on the verge, creates this permanent state of unclosure. You're the waiter who never finishes taking the order. ↩︎

  6. There's a certain type of person who will spend six hours researching the optimal way to do a thirty-minute task. I know because I am this person. Was this person. Am trying not to be this person. The trying is, itself, probably taking too much time. ↩︎

  7. I want to tell you I learned this lesson permanently, that drilling those holes transformed me into someone who just acts without overthinking. But that would be a lie. I still overthink. I just now have evidence that overthinking is optional, that I've survived doing things badly, that the consequences of imperfect action are usually much smaller than the consequences of no action. ↩︎

  8. I know they were two degrees off because I measured them afterward, which is exactly backward, measurement-wise. You're supposed to measure before drilling, but I measured after because I couldn't stand not knowing how wrong I'd been. This tells you something about me, probably nothing good. Though maybe it tells you something about the difference between precision and accuracy, between knowing the exact magnitude of your error and having built something that works despite it. ↩︎

  9. Kierkegaard's “aesthetic” person isn't really an aesthete in the sense of someone who appreciates art. It's someone who treats their own life as something to be appreciated from a distance rather than lived from the inside. The aesthetic person is always the audience to their own life, never the performer. ↩︎

  10. Though people try. There's probably someone right now reading a book about discipline while not being disciplined, a book about productivity while procrastinating, a book about courage while avoiding the thing that scares them. The book is not the doing. The book is often the thing we do instead of the doing. ↩︎

  11. Alfred Korzybski's famous line. The map is useful precisely because it's not the territory, it's simpler, more manageable, portable. But we get in trouble when we forget this, when we think thorough planning is equivalent to having done the thing we're planning. ↩︎

  12. Heidegger is notoriously difficult to read, and his personal history is deeply troubling, but this particular insight about how tools work, about how we experience the world through engagement rather than detached observation, captures something true about the difference between planning and doing. When you're actually doing the thing, you stop thinking about doing the thing. The self-consciousness dissolves. You're just there, in the action. ↩︎

  13. Here's something nobody ever seems to remember: being wrong is how you learn. You don't learn by being right; you already knew the thing. You learn by being wrong, adjusting, trying again, discovering what you didn't know you didn't know. Which means avoiding being wrong is choosing not to learn. It's choosing to stay exactly who you are, knowing exactly what you know, forever. ↩︎

  14. Dewey wasn't advocating letting children burn themselves. He was pointing out that genuine understanding comes from experience, from the connection between action and consequence, from doing and observing what happens. This is why you can read about riding a bike but can't actually learn it without getting on the bike and falling a few times. ↩︎

  15. This is also why lifeguards exist and why you shouldn't learn to swim alone in the ocean. There's a difference between embracing imperfect action and being reckless. The distinction, annoyingly, is not always clear in advance. Sometimes you figure it out by doing it and discovering you should have planned more. Sometimes you figure it out by planning forever and discovering you should have just started. The trick is surviving your mistakes long enough to learn from them. ↩︎