Learning to See

When I was little my grandfather wrote a novel for me.

Or, rather, I started a novel and he finished it for me.


It started with short stories. 

As a kid, I wrote a lot of them —  keeping folders and folders of ruffled lined paper filled with scribbles, or pecking them out on my AlphaSmart. (For those who don’t remember, an AlphaSmart is basically a calculator with a full-sized keyboard attached to it. Ahh the memories.)

But I didn’t want to just write short stories. I wanted to write a novel, and my dream was to write a really long one — something with heft. 

I wanted to make it at least 100 pages in length. That was my goal. It seemed impossibly long — even writing a one page story as a 9 year old is a pretty taxing thing to do. But real authors write long books, and I wanted to be a real author so I was going to write a long book too.

I devised a solution. 

A hack.

One I believed would help write a book without having to worry about coming up with compelling characters, plot twists, or dialog: on page 1 of my story, I had my character begin counting. 

What he was counting is unfortunately lost to time. But I started him counting something in some way or another. It looked something like this:

“He said, ‘1, 2, 3, 4, 5, 6, 7, 8, 9, 10….

The idea was to keep the character counting until the book reached 100 pages in length. Then he would stop counting, I would wrap up my story, and WHAM! I would have a novel. 

I would be able to print it at Kinkos, and get it bound in leather or fabric like a real book, and then I would be a real author and maybe I could even sneak it into the library and someone would pick it up to read it.   

I started writing this book some time shortly before winter vacation. I would sit at my family iMac and diligently write out each successive number one digit at a time:

“100,025, 100,026, 100,027, 100,028…”

Nowadays I would just write a little script to generate this string of numbers, but as I said, I hadn’t learned to program yet. So I had to do things the old fashioned way.

It was hard work, but I had a goal, and I was determined. When winter vacation rolled around, I had plans to spend most of my time working on my novel. 

It turns out, though, that the powers that be don’t view typing out strings of numbers into your computer as a proper way to spend winter break, and so, to my chagrin, my plans were interrupted by a ski vacation. 

I went away to a mountain with my dad, my sister, and my grandparents — Pop and Gram. We ended up spending all day on the mountain, which meant that I wasn’t making much progress on my book.

But Pop and Gram didn’t ski — they spent most of the time back at the hotel room, or walking around the town, waiting to see us at mealtimes. 

I remember telling Pop about my project, and I remember him being very amused by my 8 year old solution to the problem of novel writing. So he decided to write my novel for me. 

Every morning we would leave to ski, and he would sit down at the computer in a sweater and neatly pressed khakis and begin typing: 

“1,000,243, 1,000,244, 1,000,245, 1,000,246...”

I remember this very particular swell in my throat — this feeling of fascination, and wonder, and adrenaline-fueled excitement that this was happening. 

I remember being so caught up in it that I found it hard to concentrate on skiing. I was so excited to get home and see how much progress he had made that day.

I knew that soon my very first novel would be completed, and it would be a whopping one hundred pages long. 

And then I would be a real author, and then, who knows?

It was so real, I could almost see it in my mind. All I had to do was wait.


When I’m having trouble seeing I usually pull out Annie Dillard. Pilgrim at Tinker Creek, Chapter 2, to be exact.

It’s a nature book, written about her time living in Tinker Creek in Virginia’s Blue Ridge Mountains. She spends most of the book looking at nature, and describing what’s around her.

“It is still the first week of January, and I’ve got great plans. I’ve been thinking about seeing,” says Annie. 

But the seeing she’s talking about isn’t just normal looking. The type of seeing we’re referring to here is less ocular and more oracular. The object of this kind of sight isn’t letters and numbers on a chart, but living itself. 

Annie opens the book by telling us about her habit of hiding pennies in the woods. 

“When I was six or seven years old, growing up in Pittsburgh, I used to take a precious penny of my own and hide it for someone else to find.

“I would cradle [a penny] at the roots of the sycamore, say, or in a hole left by a chipped-off piece of sidewalk. Then I would take a piece of chalk, and starting at either end of the block, draw huge arrows leading up to the penny from both directions…

“I labeled the arrows: SURPRISE AHEAD or MONEY THIS WAY. 

“I was greatly excited, during all this arrow-drawing, at the thought of the first lucky passer-by who would receive in this way, regardless of merit, a free gift from the universe.” 

This passage always hits me.

One cent, of course, isn’t much of a gift from the universe. But the reason these pennies have value—the reason they were so important to Annie and are so important to me—is because they are symbolic of something much larger and more important: there are invisible surprises and sources of delight even in the most mundane places.

There are hidden pennies everywhere. Our job is to see them.


Annie says: “There are lots of things to see, unwrapped gifts and free surprises. The world is fairly studded and strewn with pennies cast broadside from a generous hand. But — and this is the point — who gets excited by a mere penny?” 

Who gets excited by a mere penny? It’s a good question. I certainly don’t a fair percentage of the time. 

I’m ambitious. 

I want to do big things. And in order to do that, you need to cultivate a healthy grasping, a sense of striving. You’re constantly going over in your mind, What will happen if I do X? If I do Y will I achieve Z?

I’ve noticed this pattern of thought creeping in again as I’ve started to spend more time writing and building this newsletter. It’s exciting. This is growing. Sometimes, I can’t sleep at night because I’m so excited to get to work in the morning. It’s the same feeling I had when I was starting my last company. 

But it also blocks off other forms of thinking that I think are just as important.

Ambition often makes it hard to see pennies. 

So the question becomes, how do you maintain a healthy sense of ambition, while also stooping to pick the pennies? These things seem to be in conflict. It’s very hard to do.

Well, it turns out that seeing the pennies happens the same way you get to Carnegie Hall:

You need to practice. 


One way to practice seeing pennies is to use words. 

Our brains are excellent at filtering out the ordinary. Things we’ve seen before become invisible.

We can name the things in front of us in order to make them visible again. Naming things is one of the most basic of human tasks, and in order to name something you have to notice it.

This is the kind of seeing I’ve long been familiar with because this is the task of a writer: noticing little things, identifying the key elements, and rendering them cleanly on a page. 

You can train your mind to see by writing. And of course, Annie is a master at that: 

“Seeing is of course very much a matter of verbalization. Unless I call my attention to what passes before my eyes, I simply won’t see it...

When I see this way I analyze and pry. I hurl over logs and roll away stones; I study the bank a square foot at a time, probing and tilting my head…” 

I think this way of seeing is familiar to anyone who makes things. 

In order to make things you need to understand them. In order to understand them, you need to first learn to notice them. You need to see the little details of the stitch on the handbag, or the almost imperceptible swipe animation on the app’s login screen.

You can’t be wrapped up in yourself to see these things. If you are you’ll hide from them, afraid that someone else will have gotten there first, or that it will somehow ruin your creativity.

You have to break out of the smallness of what you’re trying to achieve, sit up, and pay attention to what’s in front of your eyes.

But the problem with verbalization is that it’s often a way to see by looking through a tape measure. Seeing verbally is to compare and contrast, to measure and manipulate. 

And often, as when we’re doing that, the hidden pennies in our experience are harder to appreciate.

When you’re thinking about what could be, or how what is relates to what you expect, it makes it hard to appreciate your reality. 

But there’s another kind of seeing too. 


About a year and a half ago I was going through a very rough time. 

My ex-girlfriend had begun a serious relationship with someone else. I was suffering from an undiagnosed stomach ulcer that made me feel anxious and terrible all the time. And I was still very much in search of what I wanted to do next. 

It all made me feel listless and ungrounded and basically terrible. 

I’m not sure how it happened, but my good friend Alex Godin dragged me to a Zen center in Flatiron. I was a fairly experienced meditator before this, but Zen was a completely alien and terrifying experience. 

I didn’t like it. 

There’s lots of bowing, and chanting. It seems very rigid from the outside. It’s all stuff that a highly individualistic, independent American would totally hate. 

But for some reason I went back. And I’ve been going back every Sunday that I can since then.

Zen teaches a specific type of meditation called zazen. Here’s how it works:

You sit on a cushion with your eyes half closed, looking at the floor. You pay attention to the spot 3 inches below your belly button as it rises and falls. You count the rising and falling:

1, 2, 3, 4, 5….

If you get distracted in the middle you start over:

1, 2, 3


1, 2, 3, 4, 5, 6….

That’s it.

It’s kind of the meditation version of sitting and typing numbers into a computer. The only difference is that number-typing is goal driven, and Zen is not.

I don’t really understand Zen enough to say more than that, but I can tell you something interesting about it:

When I’m practicing regularly I notice that the moments in my life where I can see the pennies increase in frequency.

When I walk around New York, shadows are beautiful. There are hidden delights in the way taxi headlights reflect in a rainbow on rainy asphalt, or the silent hulking grandiosity of the skyscrapers above my head.

I feel like I’m in my life, rather than constantly wishing for what comes next. It’s beautiful, and complicated, and important.

And as usual, Annie was there first.

“There is another kind of seeing that involves a letting go. When I see this way I sway transfixed and emptied. The difference between the two ways of seeing is the difference between walking with and without a camera...When I see this second way I am above all an unscrupulous observer.”


After I sold my company, I took a year off, and then spent the next 2 years working on a novel. Old habits die hard, I guess.

This time there’s no character that starts counting on page 1. Instead it’s got scenes, and dialogue, and plot twists — I’m trying for lots of action, and little quiet moments.

But I still started it with the same desire for length, and heft. I wanted to write something important, something that I felt like expresses a few important things I’ve been turning over in my mind for the last few years.

I hadn’t written much fiction since my first attempt at novel writing 20 years ago, but I figured I’d get it done in 6 months and then start another company.

So, I sat down and started writing 1,000 words a day in a Google Doc.

It’s now been 2 years, and I’m on my 4th draft. I don’t know when it’s going to be done, but I can feel that same impatience creeping in on me.

I’m doing so many things every day it’s hard to keep up. I’m writing the book, and I feel like I’m closer to writing the thing I imagined than I ever have been before. I’m writing this newsletter, and working on turning it into a startup. I’m advising founders, and helping out at prehype.

It’s really hard to see pennies working 12 hour days.

And it’s especially hard to write the book. There’s nothing less urgent than the task of eeking out your daily word count for a novel. Watering your plants is usually 10 spots higher on the todo list.

It’s especially hard because this time Pop isn’t there to write it for me.


Pop died last month. He was 88, but it was still unexpected. 

He was this legendary patriarch grandfather figure who absorbed all the hits and kept getting up. You just assume a person like that never dies.

But Gram, his wife of over 68 years, died after a long battle with Alzheimer’s, and 30 days later — right at the end of the mourning period prescribed by the rabbis — he followed her.

It turns out the novel I’m writing is about him. It’s also about Gram, and my other grandmother, Omi who died this fall too.

I never told them I was writing about them. I wanted them to read the full thing, not hear about it in snippets. 

Of course, now, they’ll never read any of it. 


It can be hard to see the pennies when people you love are dying, and you’re drowning in work and emails you haven’t responded to. 

But even as Pop was dying, I tried as much as I could. I held his hand and told him I loved him. Those little moments are enough to take a painful experience, and turn it into something more.

And what’s interesting is that, when you’re trying your best to see, every once in a while, something bigger happens: you are seen. 


It was a few weeks into the constellation of problems that would eventually kill him. He was on his 3rd hospital visit that month.

It was 11 at night. I was just arriving at a friend’s apartment when the Facetime came in.

“Dan,” said Pop through the oxygen masks and tubes surrounding his face. “I want you to invent something.”

“Okay, I said. “What do you want me to invent Pop?”

He gave an exasperated laugh, like I had asked him a ridiculous question.

“I don’t know,” he said. “I want you to invent something unique, something that will change the world. You’re smart, you can do it.”

I stood there for a minute, not really sure what to say. So I said the only thing that you can say in a moment like this:

“Okay, Pop. I will.”

Rendering this in words, it seems like an almost cinematic moment: boy gets pushed to follow his dreams by his dying grandfather.

And it has a few of those elements. But at the time it was a mix; a swirl of strong emotions, too strong to render clearly. A feeling of sadness, because I knew he wouldn’t say that unless he thought he was close to the end. And a feeling of being loved, and of care.

A feeling of being seen.

These moments come in different flavors, for different people, at different times. For some, it’s getting down to a deep level of unfiltered experience. Stripping away the facts, and the preferences, and the verbalizations of reality. 

For me, it was a feeling of being connected in a moment with someone else. 

Here’s Annie again:

“It was less like seeing than like being for the first time seen, knocked breathless by a powerful glance…

I was still ringing. I had been my whole life a bell, and never knew it until at that moment I was lifted and struck.”


We spend a lot of time on this website talking about productivity. 

I hate that word, but we use words because other people do. So, what can you do?

There’s a tendency in ambitious people to set goals, and then try to hack our way to achieving them. We’re looking for shortcuts. We’re looking to get there now, not tomorrow or next week.

We want to write a 100 page novel, so we start the character counting on page 1.

Time is money, and money is burning a hole in my pocket.

And something I catch myself doing a lot. I want to finish the novel now. I want to grow Superorganizers into something big, and important — something that touches a lot of people, and makes a lasting impact.

Sometimes I do this so much it interferes with my ability to enjoy my life. And when that happens I sometimes fall into self-reproach: I feel like I shouldn’t be grasping so much to be somewhere else, because I know that when you arrive, you tend to wake up and find that not much has changed.

I feel like I should be paying attention to the pennies.

But what I think is interesting is that all those years ago when Pop saw his grandson grasping to write a novel, he didn’t reproach me. He sat down every day, and wrote it for me. With love.

Breathe in.


Breathe out.


I think there’s room to do that for ourselves. To create space to be in whatever moment, and brain space we’re in — even if it’s coming up with a new hack to write a 100 page novel.

There’s room to balance both ambition to do big things, and the simple practice of finding pennies.

You don’t have to be a crazy monk sitting in silence all day to enjoy your life. You should be able to enjoy it right now, with what’s around you.

Balancing seeing with being seen. Balancing striving with finding pennies. 

Applying love and understanding to ourselves and the people around us.

In short, seeing clearly.


I hope this year you become a bell, and that you are lifted and struck.

What’s more, I hope you learn to find the hidden pennies in your own life. The pennies in a co-worker’s smile, or in the way a tulip droops as it slowly ages in a vase, or in the way light prisms and blooms into shadows cast on the sidewalk at your feet.

Because in the end, after all of your goals are over and through (achieved or not), when the final tally is counted, these are the only pennies you can keep.

Happy New Year.

Thank you to Sam Koppelman and Nathan Baschez for reading and providing feedback on this piece.

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