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Day one

“As designers, we see the world as it could be. This can be a blessing, or a curse.”


“As designers, we see the world as it could be.
This can be a blessing, or a curse.”
— Jerry Takigawa

True story: I once returned an iPod to the Apple Store because it had a shitty user interface. It was during the dark final days of the senile Model Classic, and I remember feeling vaguely ashamed about it — if Apple’s UI is not good enough for you, did you consider it’s you who might be the problem? — but I just couldn’t stand the slowness and unresponsiveness, opting to stick to my old gray Mini with its dying battery and storage constrained enough to make it a glorified Shuffle Before Shuffle.

(Fortunately, just a few months later the iPhone raised the bar with its smooth, genre-creating interface.)

I guess I’m the kind of person who judges a book not only by its cover, but also the typography inside it. Disappointed with PowerPoint and Keynote, I wrote many bespoke presentation engines for my talks. I know not only that ellipsis is something different than three dots side by side, but also the keyboard shortcut to invoke it. (It’s a great pick up line for the parties I am no longer invited to.)

So, yes, you might call me “picky” although, I suppose, a kinder way to put it would be “hypercritical.”


In the lobby of the offices of Medium in downtown San Francisco, next to a few dozen books, one can find a vintage rotary phone. It’d be cute to assume that this black, massive artifact from the times when Bakelite was The Future is there to send some grand message about the changing nature of the communication technology. A disciple of Mr. Ockham, I bet its presence is something much more accidental. Either way, I’m drawn to this phone, and the reasons I keep playing with it every time I visit are much more basic — it’s simply an uncomplicated thing made very, very well.

Last year, Ian Bogost bemoaned how smartphones made it possible no more simply to hang up on someone in anger — the last of flip phones took away the satisfying physicality of a conversation’s end, and these days the connection drops off so often you can be never sure any hangup was truly intentional.

Yes, so perhaps playing with the phone in the Medium lobby, I did pretend to call my number and then hung up furiously when no one was looking. (There really is no way of knowing.) There’s so much more than that to like about that obsolete artifact anyway: the pleasant heft of the handset, the ticking of the perfectly-balanced rotary dial as it unwinds back, the delay with which the polished, spring-loaded hook sticks back up after you grab the receiver. None of those things seem accidental; whoever designed it, and whoever manufactured it, must have put a lot of thought into the minutiae of their product.


I’ve been thinking about craft a lot over the last few years, and recognizing that the things I worked on that I was the most proud of were the ones where I could, likewise, spend my time deliberating the details. The Pac-Man doodle needed to behave like the original, even if no one asked for it. The doodle celebrating my favourite writer had at least nine easter eggs, and so did many others. At Streetmix — one of my projects at Code for America last year — I had as much fun thinking of the biggest, longest-term questions, as when debating… our URL scheme. Somewhere next to me right now is a booklet I designed for Computer History Museum a few years ago, whose colophon states Revision 159.

(I felt bad for it not reaching 200.)

Over time, however, I’ve learned that attention to detail and finding pleasure in work is a double-edged sword:

“The craftman’s desire for quality poses a motivational danger: the obsession with getting things perfectly right may deform the work itself. We are more likely to fail as craftsmen, I argue, due to our inability to organize obsession than because of our lack of ability.”
— Richard Sennett

There are more accessible versions of that sentiment, floating around as “Real artists ship,” and “Great is the enemy of good.” Because as a maker, it is easy to find yourself in a spiral of the pursuit of perfection; easy to give yourself just one more day to finish your work; easy to lose the sight of forest while designing a tree, or a tree even when you spend days meticulously shaping one of the leaves. (One of Isaac Stern’s rules claims “The better your technique, the more impossible your standards.”)

But then, one of my friends quipped once that, of course, “Good is the enemy of great” as well. Giving up, compromising, making the least possible effort, shipping before it is time are the even more likely avenues, especially in situations where no one else appreciates the effort put into the microinteractions, the 99% invisible, the little big details.

I want to find good answers to all of these questions: How do you find a good balance between those two extremes? How do you allocate time and collaborate with people whose priorities are different than yours? How do you measure the impact of your craft? How do you give back? (These mere 50 words I rank among the most thought-provoking things I’ve read in 2013.) How do you justify spending time on things no one but you might ever notice? How do you know when you’re done? How do you even define what you do?

“Nobody, however, is prepared to say where craftsmanship ends and ordinary manufacture begins. It is impossible to find a generally satisfactory definition for it in face of all the strange shibboleths and prejudices about it which are acrimoniously maintained. It is a word to start an argument with.”
— David Pye

Medium impressed me since the first, limited release. It too was an uncomplicated thing made very, very well. Before I had a chance to talk to any of the insiders, I recognized how its functional and visual simplicity were all hard-earned, results not of running out of time or energy, but of deliberation, self-imposed restrictions, and tough discussions. (You could make an argument the most interesting parts of Medium are the things that aren’t in it.)

A year later, I sometimes liken Medium’s appearance to that iPhone premiere in 2007 that saved my sanity — a great benefit to anyone who bought an iPhone, but also to anyone who bought any phone since then. Medium, likewise, elevated the baseline, the most obvious examples being the slew of sites “like Medium” and slowly raising expectations towards publishing on the web.

I have also been thinking a lot about passion being the best catalyst — how doing things you personally care about can bring the highest satisfaction and productivity multipliers, impossible to achieve otherwise. And I find myself passionate about so many of the things that Medium tackles: typography, written word, sharing, story-telling, photography, the solitary and social acts of both creation and consumption.


Today is my first day at Medium. I will grab a couple of books about typography and typesetting that so often inspire me, and put them on my new work desk. I will talk to as many people as I can — hearing their ideas, getting feedback on mine, and slowly figuring out what Medium is. (I don’t know that yet. I’m perfectly fine with that.) I’ll open my new computer and eagerly sink into the codebase. And I bet, once in awhile, I will stop by the old phone in the lobby and make one more fake dramatic call ending in one more fake hangup.

I’m looking forward to all that follows, in no particular order: working on something that is ɪ. a beautiful set of high-quality pens set against an empty sheet of carefully selected paper, ɪɪ. a magazine meticulously typeset and laid out, and ɪɪɪ. so, so much more; debating the smallest of details and thinking about the big picture; being surrounded by smart, enthusiastic people in a place that’s not afraid to experiment with itself. And I can think of no better environment where I could try to find answers to my bigger questions above — about craftsmanship, design, passion, and many other things.

And, seeing how someone at Medium already made sure that the two hyphens I just typed turned into a beautifully crafted combination of an em-dash flanked by hair spaces… I think I’ll feel right at home.


To all the people I had a chance to talk to in 2013 that informed a lot of my thinking about all this: Thank you. You know who you are.