For Chloe

The first time I met Chloe, she arrived at a party wearing a very opinionated, seering yellow raincoat. I had not seen that specific hue of yellow since my freshman year in college. Funny how a color can send you back so far.


It is seven years before the raincoat.

I am enrolled in a music appreciation class. One day, we are discussing songs in terms of colors. This is particularly interesting to another student, Anna, who just happens to be blind. Anna, being courageous, raises her hand and asks us to try to explain the specific yellow we were discussing, the yellow I’d see years later in Chloe’s raincoat. Another student raises his hand to attempt an answer. He stands up, walks over to Anna, and holds her hand.

“Can I do something now?” he says. Anna nods. “This is yellow.” And he slaps the back of Anna’s hand.

Chloe liked that story. I suppose it’s the closest I’ll ever get to understanding how she experienced the world.


Imagine your experiences come through a small aperture. Everything you hear, taste, read, touch, and—more than anything—feel, passes through that tiny hole to form your experience of this waking world. Now, take that pinhole and open it just a bit wider. A little wider still. And then, if you can, imagine what that does to your life. Everything you feel becomes sensational—highs are higher, lows are lower, the light—instead of just lighting—can now also burn. The incoming streams flood in and start to cross. There are now connections where otherwise there would be none. Songs point to seasons. Words taste like food.

That was Chloe. She was exceptional. I hate that “was” is not “is.”


It is now one year after the raincoat.

Chloe, like me, is from New York and left the east coast to live in Portland. I had just moved back east after a two year stint in Oregon, and I was having trouble adapting to the particular hardships of big city living that New York City so easily offers up in droves. She was in sympatico with me: happy with Portland and aware of its Neverlandish advantages, yet high-strung like a true east coaster, and thus slightly bored with the pace of the west coast. There was a longing for home and to be surrounded by those as quintessentially neurotic as you, yet also a fear of adjusting and suffering through all the bowls of shit New York serves up each day. It was a hot topic between us—it’d come up each time we saw one another.

I tend to ruminate on my troubles, and eventually, I can figure out how to frame my feelings to have them make sense. But this anxiety, this fear, was a sensation I couldn’t imagine how to describe. Then, finally, Chloe gave it to me, clear as day:

Portland is the island on Lost. You get there, magical things happen, and you are in disbelief. You make a go of living there. Things go exceedingly well for a while, but eventually you realize time is wonky, and you must escape. You work diligently to reconnect with the rest of the world. Eventually you leave the island and get back to where you were. Then, the everydayness of your own life sinks in, and you say to yourself, “We need to go back to the island!”

I needed Chloe to figure that out for me. I couldn’t do it, because my aperture wasn’t open enough. This wasn’t just a take on two cities—it was coming to grips with how to make yourself a home and how to be a person who lives there. It was wrestling with how to feel comfortable in your own skin.


It is three years after the raincoat.

I am with Chloe and Andy, her boyfriend and my friend friend. We are sitting in the lobby of The Merchant Hotel, ensconsed in an over-stuffed, Victorian sofa. The hotel is showy: high, vaulted ceilings, rococo-framed everything, oil-painted portraiture of the bourgeoisie you’d presume lived in the place, if you didn’t already know it used to be a bank. And there we were, cracking wise in the corner about crass subjects that shall not be mentioned here for the sake of preserving a bit of honor to this recollection. Chloe, for the first time all week, had a lightness about her. Her laugh is running up the wall, and bouncing off the ceiling. We are delighted. We are drunk in more ways than one.

A lot of Chloe’s rememberances have mentioned her smile. It’s true, it was a real stunner—wide and mischevious. She was so quick to offer it up. But I’m a man of rarer game—her laugh was always what I wanted, and it was just as special. She had a 100 watt smile and a 100 decibel laugh. That laugh is what I’ll miss the most.


My friend Chloe Weil died earlier this week. I won’t make a fuss in public. She wouldn’t have wanted that. Instead, I’ll sit and try to feel as much as I can—to open myself a little wider, let a little more light in, and have the current go a bit stronger. But, I must be careful. When the current is strong, a boat can go lost.

So long, Chloe. You will be so deeply, deeply missed.

Massimo and Me

I can pinpoint the moment where my grudge against Massimo Vignelli began. About halfway through Gary Hustwit’s documentary Helvetica, Vignelli is filmed isolated against a gray background, and after some playful grousing, he says, “The life of a designer is a life of fight: fight against the ugliness.” I found this simultaneously offensive and confusing, because of a conflict of my own. I wanted the design profession to be more important than aesthetics, but not so full of itself to believe it could change the world. Of course, this is a ridiculous and self-defeating set of demands: you must fly while wearing handcuffs. Good luck, kid.

Youth brings stubbornness, and insolence is a pair of earmuffs. While coddling my immature grudge, I missed the rest of Vignelli’s statement: “The life of a designer is a life of fight: fight against the ugliness. Just like a doctor fights against disease. For us, the visual disease is what we have around, and what we try to do is to cure it somehow, with design.”

One of my perpetual mistakes is believing that insight must be dramatic. Not so. In fact, the most mundane and obvious advice is perhaps worth the most consideration. There are reasons things won’t go away. Massimo was giving that kind of advice, and my stubborn ears were missing it. Of course life devolves into confusing ugliness unless you fight against it with clear beauty. Of course it does.

My grudge left when I inverted Vignelli’s words. When you fight against something, you are also fighting for its opposite. Design isn’t just battling ugliness. It’s also an unending fight for beauty, balance, consistency, and parity, because the world devolves into an ugly, imbalanced, inconsistent, and unequal place unless we are vigilant. Beauty has a role in the good life, so designers like Massimo chip away at their corner: visuals. I’m in that corner, too, with my tiny rock hammer. We all have our place in this effort, not just designers.

A few weeks ago while Massimo’s health was waning, the Vignelli family invited the public to send him personal notes. Massimo famously worked for years using only five typefaces, and I thought it suitable to use five words in my note. I bought a stamp and said what I had been meaning to say for the longest time.

Thanks Massimo. We'll keep fighting.

Two Sentences About Getting Older and Working on the Web

It is time to come clean: Github is confusing, Git is confusinger, pretty much everything in a modern web stack no longer makes sense to me, and no one explains it well, because they assume I know some fundamental piece of information that everyone takes for granted and no one documented, almost as if it were a secret that spread around to most everyone some time in 2012, yet I some how missed, because—you know—life was happening to me, so I’ve given up on trying to understand, even the parts where I try to comprehend what everyone else is working on that warrants that kind of complexity, and now I fear that this makes me irrelevant, so I nestle close to my story that my value is my “ideas” and capability to “make sense of things,” even though I can’t make sense of any of the above—but really, maybe I’m doing okay, since it’s all too much to know. Let the kids have it.

No New Tools

Being an early adopter is exhilarating in the same way that riding a rollercoaster can feel like travel. You’re moving, but you’re not actually going anywhere, only devising ever-increasingly complex methods to make yourself feel slightly more barfy. You are in a loop de loop of productivity, changing for change’s sake. I made an agreement with myself in January: no new apps on my phone or computer. Don’t do new stuff. Just do your work.

Text editor, spreadsheet, email, pencil, paper, Photoshop. OK. That’s enough.


Let’s talk about making tools. The things we make should either reduce pain, increase pleasure, or do some mix of the two. If you’re really good at goal A, you get a bit of goal B for free. And if you don’t figure out how to do either, you’re playing dress-up. Increasingly, I feel like a lot of my tools are dressing-up as tools, because they don’t offer any savings in time or effort, just slightly different methods to mindlessly shift information from one bucket to the next. And if one bucket has a hole in it, you get another, smaller bucket to catch anything coming out of the hole in the first bucket. This goes on and on with more holes and buckets, and before you know it, you have an intricate network of buckets whose reason for existance is to catch the information you can’t manage in the first place. You are stuck in bucket recursion, adding tools to patch the shortcomings of other tools. Those patches are how you know you have dress-up tools.

Now, don’t get me wrong: no tool is perfect. And sometimes a thing dressed up as a tool can be quite profitable, but this profitability has less to do with being useful, and a lot more to do with luck, lock-in, group delusion, a bubble/echo chamber in the industry, and saaaay—a life-long disagreement between me and money about what is valuable.

There are whole breeds of technology that do the opposite of my stated goals—they increase pain and reduce pleasure. For instance, the hot topic of tech pundits is wearable technology, but pretty much every instance of wearable tech seems like a nightmare. Ignore all the privacy issues of Google Glass, look over the utilitarian hurdles in making a smartwatch seem useful to a normal person. Instead, ask yourself a question: who wants to have perpetually visible email notifications? To me, this sounds more like an anxiety bomb waiting to go off than a tool or toy. No delight, no productivity, just more anxiety medication.

My world is laden with bad tools, because my culture is simultaneously obsessed with productivity and novelty. It is a perfect vector for fixation, because the failure of a tool only feeds the desire for new tools. Meaning, I get to feel honorable in my vigilant search for productivity while scratching my itch for novelty.

Technology also has the benefit of not talking back. If I try something in an attempt to be more productive, and I move on to other options because it didn’t work, the technology can’t tell me that I failed because I lacked the will to actually do the work in the first place. Thanks for not tattling, tech. (Or, well, at least in that way.)


What’s interesting about digital tools for information work is how frequently they are born from a specific ideology: someone thought work should be done in a certain manner, they found no tools to support that method, so they set off to build their own tool that presumes their ideology is true and best. Thus, we get another to-do app, Twitter client, or project management app.

Everything that’s made has a bias, but simple implements—a hammer, a lever, a text editor—assume little and ask less. The tool doesn’t force the hand. But digital tools for information work are spookier. The tools can force the mind, since they have an ideological perspective baked into them. To best use the tool, you must think like the people who made it. This situation, at its best, is called learning. But more often than not, with my tools, it feels like the tail wagging the dog.


So, now I come to the part where I make my plea: no new tools, please. If you are interested in improving how people work, you should devise methods for work, manners of behavior, and methods of decision making. Document your ideology and apply it with existing tools, so nearly anyone can follow along. Why don’t you use our best tool? Language. Increasingly, I feel documentation beats an app if you’re trying to shepherd an idea along. This approach seems to have worked pretty well for David Allen’s Getting Things Done and Josh Clark’s Couch to 5K. Of course there are innumerable apps supporting each method, but the ideas are bigger than an app, so you don’t need to download anything. Buy a notebook or put on your running shoes. Commit to the plan. They are not leaky buckets.

Consider making a program for people, not a program for a computer. I don’t want a new app to help me do work; I want different ways to think about work so I can get more done. It’s a nuanced difference, but I think it is an important one.

A Bit of Nothing on Madness and Rowing

So, journal: I was in a tough spot this past week. The Great Discontent magazine is consuming all of my work (waking) hours, and I’m grunting my way through the center half of the process where you can’t see the end or the beginning. I’m the guy on a raft with an oar in the middle of the Atlantic Ocean. There’s water on all sides, and I’m rowing, rowing, hoping east is still east and that I am still supposed to be going east. I needed to finish something—anything—to not feel so helpless.

Books weren’t their usual escape: I was reading Dance of Dragons, the last book in the A Song of Ice and Fire (Game of Thrones) series, but that idiotic paperweight suffers the worst possible fate for a book: it is long and complicated and boring, which is much, much different than the first three books in the series. I’ve tried to finish it four times out of a stubborn commitment to closure. Could you blame me? I had already spent so much time on the first four books. But, nope—I give up. It’s not my fault. A Dance for Dragons has danced its way onto my front stoop to be picked up by someone else.

I bought a copy of Mary Ruefle’s Madness, Rack, and Honey on the recommendation of Austin Kleon and Mandy Brown, two trusted reader friends, who, once again, made an excellent recommendation. I finished Madness in four days, and it was an antidote. Oh God—what a book.

Maybe it’s a book? It labels itself as “Collected Lectures” on the cover, and almost immediately, Ruefle backtracks from calling them “lectures” in her introduction, instead saying,

I was told the students preferred informal spontaneous talks, but I am a rotten and unsteady extemporizer. I preferred to write my lectures because I am a writer and writing is my natural act.

Meaning that Madness probably isn’t a set of lectures, but a collection of Ruefle’s readings of writings. I think that’s why the book reads so fast: it was written to be read by someone who doesn’t want to be in front of people lecturing. In spite of that, it contains so much wit and charm, and so rarely gazes at its navel or twiddles its thumbs while turning over some pretty serious questions about poetry by braiding in topics like secrets, the moon, fear, reading, memory, and sentimentality. I’m with Mandy and Austin on this one: I highly recommend Madness, Rack, and Honey. For the next few months, this will be the book I buy for people.

The second lecture in the book is titled “Poetry and the Moon.” A bit about halfway through caught my attention. Ruefle writes (says?):

Really, people must think literary aficionados are all addicted to painfully heavy, slow things. Like the aircraft used for the lunar launches, good books only look heavy and slow: their speed depends on their internal engines and where they are pointed.

Now, A Dance of Dragons isn’t on the A-list of literary aficionados, but its “pulpiness” actually means it must contain even more rocket fuel than a more literary novel. The joy of pulp is the guilty pleasure of momentum, the sensation of progress, the whiplash of a joyride. That’s why chapters are so short in those terrible Dan Brown novels. You here and then you’ve finished it and now you’re there, and woah, look I’m reading! Look at all I’ve read! It’s the same thing that somehow carries you through thirty hours of Veronica Mars on a flu-addled weekend.

Ruefle’s short rocket-fueled analogy made me feel some pride about ditching Dragons. There are so many long texts that are paced much more to my liking. And the reminder that not all long things are slow, complicated, boring things gave me the courage to pick up Edith Grossman’s translation of Don Quixote. And wouldn’t you know? A couple of hours and a handful of full-on belly laughs later, I am about 150 pages in, and flirting with the idea that this may be my favorite novel.

And now, ironically (and perhaps quixoticly?), I am precisely back to where I started. I am still mired in the middle of a big project, and wedged into the center of a very long book, but the views are good, I am laughing, and I am rowing. Oh god, am I rowing…

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