DESIGN WAS so much easier before I had clients. I assigned myself projects with no requirements, no schedule, no budget, no constraints. By most definitions, what I did wasn’t even design—except that it ended up creating new things, some of which still exist on the web. Soon I had requirements, schedules, and constraints, but most of those were self-imposed: for instance, I designed the first A List Apart, published a fresh issue every week, and created title illustrations for every article. This was design, but self-directed. I found it easy and natural and it never felt like work at all.
But then a curious thing happened: I began to get clients. And the more clients I got, and the more complex and sophisticated the projects became, the harder design became for me. I wish I could say I approach design with fearless joy, but the truth is, the longer I do it, the harder and more unnatural it becomes. Starting new projects is easy when you have almost no clue what you’re doing—as easy as playing is for a child. With experience comes knowledge of all the depth and skill you lack. You know how great some design can sometimes be, and how unlikely you are to attain anything resembling greatness on any given project. The very idea of beginning terrifies you.
You work past that, because you’re a professional, but the ease is gone. Maybe it’s just me.
And it isn’t just design. Writing comes naturally to me when I’m expressing myself on my own site, with no outside assignment and no deadline except my own sense of urgency about an idea. It’s easy when I’m crafting a brief text message or tweet. Or a letter to a friend.
But give me a writing assignment and a deadline, and I’m stuck. Paralysis, avoidance, a dissatisfaction with myself and the assignment—all the usual hobgoblins spring immediately to life. I fulfill my assignments, because I’m a professional. Sometimes, once I’m far enough past the initial internal pleading, denial, and bargaining, and have put in the first dull miserable hours of setting one word in front of another like a soldier on a long march through waist-high, rain-drenched mud—sometimes at that dreary midpoint, everything unblocks, and I feel pleasure and clarity as flow returns. That’s what writers on assignment fight for—to reach clarity and naturalness after slogging through the hateful murk.
I also play music, and I’m good at it as long as I’m sitting in a corner at an instrument or console, making stuff up for my own pleasure. But create a commercial music product? Not so much. I once had a small recording studio. I got rid of it. Too much pressure.
You get it.
In my heart I remain an amateur. The spirit of play is where my gifts lie. After 30 years in business I can do the other thing—I can fight through the loneliness to make good product on demand. That is, after all, how I feed my family, and there are many far worse ways to earn a dollar. But it’s never easy. It’s never The Joy.
You got this.
I’M LEARNING new tech and it’s hard. Maybe you’re in the same boat.
Through the rosy lens of memory, learning HTML and Photoshop back in the day was a breeze.
It wasn’t, really. And CSS, when it came along in 1996, was even tougher to grasp—in part because it was mostly theoretical, due to poor support in some browsers and no support at all in others; in part because the design model in early CSS wasn’t conceived by designers.
But my memory of learning these tools in 1995 and 1996 is pain-free because it’s an old pain, forgotten because of time passing and even more because the pleasure of achievements gained by acquired knowledge masks the pain of acquisition. (See also: learning to read, learning to ride a bicycle.)
Beyond all that, my old learning’s pain-free in hindsight because I view it through the filter of nostalgia for a younger, simpler me in a simpler time. I was faster, sexier, ached less. Maybe you feel that way sometimes.
Most of all, I falsely remember it being easy to learn HTML, CSS, and Photoshop because I wanted to learn those things. I was doing it for me, not for a job, and certainly not to keep up.
I was a pioneer—we all were, back then. I was passionate about the possibilities of the web and eager to contribute.
Do you dream in color?
That first year of learning web design, I often, quite literally, dreamed in four-color GIFs. I got near-physical pleasure from reducing file sizes. I subscribed to every web design mailing list out there, and even started one of my own.
Remember mailing lists? I don’t mean sponsored, monetized newsletters with images and tortuous HTML. I mean stuff you read in Lynx.
When I shared what I was learning, by writing about it—when I learned what I was learning by teaching it—I felt euphoric. We were at the dawn of a new kind of information age: one that came from the people, and to which anyone could contribute merely by learning a few simple HTML elements. It was going to be great. And democratic. And empowering. Our tech would uplift the whole suffering world.
With every new discovery I made and shared, I felt a sense of mastery and control, and a tingling certainty that I was physically contributing to a better world of the near-future. A world forged in the best tech ever: simple, human-readable HTML.
Design is supposed to fix the world, not break it. Yet some of us, possibly even most of us, work on products and at companies we feel conflicted about.
Design is supposed to value simplicity. And yet here many of us are, struggling to learn new tech, and not feeling it.
But enough about the universe; let’s talk about me.
I’m learning new tech and it’s hard.
I work at a company that makes it easy to use a popular open-source publishing platform. Making things easy for customers is what design’s about. It’s also, always, hard work. And it’s supposed to be. The harder designers work behind the scenes, the easier the experience is supposed to get for the customer.
I have a confession to make: I love hard, mental, strategic design work. I love going cross-eyed envisioning customer journey options small and large. I love it like I love good typography and icons and layout, and I’m way better at it than I ever was at those things. I love it like I love color schemes, and, again—I’m better at it than I was at those.
And, stop me if you’ve heard this one, the more strategic I gets, the further from the code I feels.
Learning new code and tools
I’m not on a product team—I do client-facing design on a special projects team inside our product company—but every designer at the company should understand our products on a deep level, and every designer at the company, whether officially working on product or not, should be able to help make the products better for the customer.
For team-building and other reasons, every designer at our company who can do so is flying to a desert resort next month for a meet-up. And at that meet-up, each of us will fix at least one thing that’s wrong with one of our products. And when I say fix it, I don’t mean file a bug report as a GitHub issue. I mean fix it.
To be ready for that, I’m learning code and tools I probably should have learned a few years ago, but, as a rich man says of his servants, I always had people for that.
New to my work day, before and after internal and client meetings, I slog away trying to master command line interfaces, GitHub workflow, WordPress Calypso, Gutenberg, and React. I’ll need facility in these areas to do a live product fix at next month’s meetup.
Getting the hang of this tech will empower me to fix broken designs and create good ones. That excites me. But learning new things is hard—and GitHub, Terminal, Calypso, Gutenberg and React do not come nearly as naturally to me as HTML, CSS, and Photoshop did 25 years ago (or so I remember).
Age. It’s not just a number.
We’ve all heard that the body replaces itself every seven years. Which means I’m not just a different person mentally, emotionally, and spiritually since I first learned web design 25 years ago; I’m also physically an entirely different person, inhabiting a body that’s been rebuilt, cell by cell, more than three times. (The actual science is more granular than the seven-year meme, but go with me, here.)
At my age, change comes harder than it used to. Guess what? That means I need to change, not just to do my job; I need to change to stay young. (No, that’s not science, but yes, it works.) When it’s hard to move, you need to start exercising, even if starting is hard. When you’re trapped in a dead-end relationship, it’s time to say goodbye, even though breaking up is sad and scary and hard as hell. And if you work in tech and find yourself thinking your past learning gets you off the hook from having to learn new things, you need to think again.
Change. Try it, you’ll like it.
I’m lucky. I work in a supportive place. When I get stuck, a dozen people offer to help. (If where you work isn’t like this, consider working with us.)
Learning new things is hard, and it gets harder if you’re rusty at it, but it gets easier if you keep at it. Or so I tell myself, and my friends tell me.
Maybe you’re in the same position. Maybe you’ve even wasted time and energy on mental ju-jitsu like this: “I believe in semantic, accessible HTML. Therefore I don’t need to learn React.” If that’s you, and it was me, review your thinking. There is no therefore. You can have both things.
You can do this, because I can, and I’m more stubborn and more full of myself than you ever were.
So to my old-school sisters and brothers in HTML. If you’re struggling to learn new things today so you can do your job better tomorrow, I’m going to tell you what a friend told me this morning:
For the past two years, I’ve been publishing a daily work-and-life diary on Basecamp, sharing it with a few friends. This private writing work supplanted the daily public writing I used to do here. In an experiment, I’m publishing yesterday’s diary entry here today:
YESTERDAY, Ava and a few of her schoolmates participated in a giant, citywide Math Team competition. Hundreds of kids from public middle schools in Brooklyn, Queens, the Bronx, and Manhattan took part in the big, noisy event, which was held in The Armory in Washington Heights from 10:00 AM to 1:30 PM.
I woke at 6:30 to be ready to roll, but made the mistake of drinking my espresso and Diet Coke eye-openers in bed, where exhaustion from two weeks’ nonstop work and travel soon knocked me out again. At 9:30, Ava woke, burst into my room, and woke me by shouting, “Let’s go!”
As we live off First Avenue at the East River, we were able to quickly Uber up the beautiful FDR Drive to 177th Street, arriving on time despite our late, last-minute start. Inside the giant arena, Ava found her team, and I joined hundreds of parents, siblings, and well-wishers up in the stands.
In our last-minute rush, I’d forgotten my glasses, so I couldn’t really see much, but, after all, what was there to see? Hundreds of teens quietly solving math problems while a traditional sports announcer tried to keep the audience hyped by belting out the kind of ra-ra hype you’d hear at a ball game or wrestling event.
Each team had a poster representing their school, and of course Ava designed her school’s poster, a demented two-sided cartoon satire somewhere between R. Crumb, South Park, and tagging. It reminded me of the kind of stuff I used to draw in eighth grade to amuse my hoodlum friend Mike G_____.
(Needless to say, _I_ was no mathlete, nor was Ava’s mom. I took photos and videos during the event and shared them with Carrie, so she could participate from Chicago; she and I joked about our misspent youths, and marveled at how our kid is turning out.)
After the competition, Ava and her pals and teacher joined me up top. Judging took a long time—hey, it was math!—so the event coordinators tried to amuse us by having Middle Schoolers breakdance. Ava and I left as the winners were being announced. (Her school didn’t win, but that’s fine.)
A leisurely ride down the FDR offered breathtaking views of parks and bridges in the Bronx and Queens, and eventually brought us home by 3:00. Where I made our first meal of the day: vegan black bean burritos for Ava; scrambled eggs, cottage cheese, and a sweet potato pancake for me. After our big late breakfast, we played Episode.
Then Ava went off to paint a Mother’s Day portrait of Carrie—and discovered that Maria, who cleans our apartment once a week, had thrown out her watercolor paintbrushes. (“Not her fault, she probably thought they were dirty,” said Ava.) No brushes, no painting—what to do?
Art supply stores in New York close at 6:00 PM on Saturday; we discovered that the brushes were missing at 5:30.
So we raced out of the house and made it to the nearest art store: DaVinci, on 2nd Avenue below 23rd Street. Sadly, the place is going out of business. Fortunately, they haven’t closed yet. We grabbed what we needed and came home.
Ava spent the rest of the night (until quite late) working on her Mom’s Mother’s Day portrait and chatting with friends via speakerphone. I listened to music and did what I could with the iPhone 7 photos I’d taken during the competition and the two long drives.
On Teaching (plus Monday links)
TEACHING is a great way to find out what you know, and to connect with other human beings around a shared passion. It’s an energy exchange as well as an information one, and the energy and information flow both ways.
I’ve been a faculty member in the MFA in Interaction Design program at New York’s School of Visual Arts since my colleague Liz Danzico cofounded the program with Steven Heller in 2009. As with all programs and departments at School of Visual Arts, the MFA IXDprogram is run by a faculty of busy, working professionals who teach one three-hour class per week, one semester per year.It’s the kind of gig that doesn’t interfere with your full-time job, and even makes you better at it.
(Fun facts: In 1988, I moved back to New York, the city of my birth, specifically so my then-girlfriend could study computer graphics at SVA; the highlight of my advertising career, which preceded my ascension into web and UX design, was spent working for top SVA advertising instructor Sal DeVito; and I subsequently enjoyed a long romantic relationship with an artist who’d moved to New York to study painting at SVA. So you could say that my eventuallyteaching at the place was overdetermined. When Liz told me of her new program and invited me to teach in it, it was as if half the prior events in my life had been whispers from the future. But I digress.)
Helping students have better careers
Since the program began, I’ve taught a class called “Selling Design,” which helps students completing their Masters thesisdecide what kind of work they’d like to do when they leave with their MFA, a few months after the class begins. There are so many opportunities now for people who design experiences, digital or otherwise. What should they do? Where will they be happiest? Inside a big company or a small one? A product company or an agency/studio? Should they start their own business?
And there are so many kinds of workplaces. In some, it’s your work that matters most. In others, it’s politics. How can you tell the difference before taking a job? We illuminate the right questions to ask and the clues in a student’s own personality that can lead to a great career or a blocked one.
The main teaching method is discursive: I invite designers who’ve had interesting and varied careers to come into the studio and have a conversation in front of the class. Mainly I ask questions and the guest speaker answers; then the class asks questions. Over time the speakers’ experiences and the takeaways I synthesize from them for the class create a picture of everything from how to tell if someone’s lying to you in a job interview to the signs that you’ve come to the right place.
A blaze of glory
This Thursday, May 2nd, at 10:00 AM, I teach my last class of the year, and I’m thrilled that my guest speaker will be Alexis Lloyd, Head of Design Innovation at Automattic, and previously Chief Design Officer at Axios, and Creative Director of The New York Times R&D Lab. In my initial months at Automattic, I’ve reached out to Alexis many times for help and insight, and she’s always generous, patient, and illuminating. It will be an honor and a pleasure to end my teaching year in what will surely be a great conversation with this experienced design leader.
For more about the MFA IXD program at School of Visual Arts, follow @svaixd on Twitter and visit https://interactiondesign.sva.edu/ . And for those who don’t yet know Alexis, here are some points of reference:
Every once in a while, life gifts you with a genuine moment. “>Here’s my friend designer/author Justin Dauer and his newborn, exchanging important information during, of all things, a business conference call. (By the way, Justin is now hard at work on the second edition of his book, Cultivating a Creative Culture, which I recommend for anyone leading a team: www.the-culturebook.com/.)
For your viewing pleasure…
We’re standing at the threshold of an entirely new era in digital design—one in which, rather than hacking layouts together, we can actually describe layouts directly. The benefits will touch everything from prototyping to custom art direction to responsive design. In this visionary talk, rooted in years of practical experience, Jen Simmons shows you how to understand what’s different, learn to think through multiple stages of flexibility, and let go of pixel constraints forever.
Unintentionally hilarious Style piece on Stoicism as misunderstood and ostentatiously practiced by trend-conforming Silicon Valley billionaires. (Ooh, billionaire walks five miles a day? So does everyone with two legs in New York.)
I’m one of the lucky ones. I have a great doctor and good health insurance.
A boring generic healthcare company bought my longterm doctor’s group practice a few months ago. First thing they did was screw up the online patient portal, changing it from the poorly designed, barely usable mess I’d learned to navigate to a slightly more polished but somehow blander portal that instantly got hacked. In consequence, they seem to have hired an Internet security firm that advised them to make changes they apparently didn’t understand how to execute. Thus, sign-in was broken for two months. Doctors kept sending patient results to the site, but patients couldn’t access them, and nobody told the doctors. You’d try to explain the problem to a phone receptionist, but if it ever got to the doctor, it was likely phrased as “Another one complaining about the website.”
The site’s makers apparently weren’t informed of the problem for some time, and there was no way to find out who they were to contact them, since there was no contact information available until you signed in, which no one could. Healthcare in America, 2019.
Anyway, they seem to have fixed a couple of the nonfunctioning loops that would prompt you to create a new password and then not recognize that you had done so and prompt you to create a new password and then not recognize that you had done so and prompt you to create a new password and then not recognize that you had done so and…
So today I was able to create a password, almost get 2FA to work, and reorder medication I’d been doing without. Yay!
Designing usable websites is an undervalued art.
Browser diversity starts with us.
Developers, designers, and strategists, here’s something you can do for the health of the web:
Test all your sites in Firefox.
Yes, we should all design to web standards to the best of our ability. Yes, we should all test our work in *every* browser and device we can. Yes, yes, of course yes.
But the health of Firefox is critical now that Chromium will be the web’s de facto rendering engine.
Even if you love Chrome, adore Gmail, and live in Google Docs or Analytics, no single company, let alone a user-tracking advertising giant, should control the internet.
The development and adoption of accessible standards happens when a balance of corporate powers supports organizations like the W3C, and cross-browser-and-device testing is part of every project.
When one rendering engine rules them all, well, many of us remember when progress halted for close to ten years because developers only tested in IE6, and more than a few of us recall a similar period when Netscape was the only browser that mattered.
Don’t think the need to test in phones will save us: Chromium powers most of them, too.
And don’t write off the desktop just because many of us love our phones more.
When one company decides which ideas are worth supporting and which aren’t, which access problems matter and which don’t, it stifles innovation, crushes competition, and opens the door to excluding people from digital experiences.
So how do we fight this? We, who are not powerful? We do it by doubling down on cross-browser testing. By baking it into the requirements on every project, large or small. By making sure our colleagues, bosses, and clients know what we’re doing and why.
Maybe also we do it by always showing clients and colleagues our work in Firefox, instead of Chrome. Just as a subtle reminder that there are other browsers out there, and some of them kick ass. (As a bonus, you’ll get to use all those amazing Mozilla developer tools that are built into Firefox.)
Diversity is as good for the web as it is for society. And it starts with us.
At the end of therapy this morning, I felt like the lone Samurai at the end of a Japanese movie. His warlord has betrayed him, his fellow Samurai have fallen into dishonor, and the rice crop failed. After a last meditation, he emerges from his tent, sword flashing, to die fighting 10,000 men. I told this to my therapist and we both laughed.
A narcissist’s prayer of Thanksgiving. (My Glamorous Life)
I’m about to have Thanksgiving at home with my daughter for the first time since her mom and I split ten years ago. Ours is a gender reversal of a typical divorce situation: usually it’s the mom who does the everyday caregiving, and the dad who gets holiday time with the kid(s).
I grew up in an isolated nuclear family. No relatives came for holidays. My dad, who was always off working or away on some mysterious other business, would be physically present for holidays, but his mind was elsewhere. Instead of holiday cooking smells, the house was notable for my dad’s loudly booming classical music.
My mom, who hated “women’s work,” would announce that she had done the very minimum—for instance, quickly boiling chicken instead of slowly baking turkey. “Done, enough, finished!” she’d exclaim, as if we were all rooting for her to get out of that sexist kitchen prison. And we were.
We ate like the animals in “The Fantastic Mr Fox.”
As soon as we could decently say we were finished, my younger brother bolted out of the house to hang out with his many friends, and I retired to my room to draw comics.
…Until I was about thirteen, when I took over the dishwashing so my mom wouldn’t have to bother with it. This wasn’t, as you might think, simply cheerful pitching in. No. I was trying to rescue my mom from her deep depression, and model what I thought was feminist behavior to my dad.
That my dad worked sixty-hour weeks to support us, and was every bit as imprisoned in a thankless role as my mom, somehow didn’t enter my calculations until I was much, much older.
And that both my parents, if they were somehow made differently, could have enjoyed working and doing for their family, was also something I didn’t understand. I didn’t know that doing for those you love could be joyful until I grew up and fell in love. And even then, I didn’t totally understand until I became a father.
From my still-bewildered perspective, I had a wonderful marriage with my daughter’s mom until everything suddenly fell apart. It was like plunging into an alternate universe. And felt like falling down an endless well. My love for my daughter, and her need for me to be here—stable and strong—is all that saved me, I know.
During the next ten tumultuous years, one thing was constant: I spent most holidays alone.
Given how little most of them had meant to me growing up, this was less of a problem for me when I just hung out at home, than when I tried to do better by joining other people at their festivities. There is one exception—a gentleman in Chicago whose family makes me feel like one of them, with whom I have passed a joyful Thanksgiving, and where I am always welcome.
But other times, when kind friends and acquaintances opened their homes to me, and I took a subway into another borough, say, to spend the holiday with their friends, whom I did not know, the warm laughing flesh surrounding me actually made me feel my divorced aloneness and temporary childlessness much more profoundly. I really did better just slurping down Ramen alone at home, as sad as that surely sounds to you.
For I had spent many hours as a child alone in my room, drawing, and they were good hours. As a young adult, I spent many hours alone writing unpublished fiction and producing music with no commercial potential that went nowhere except my own headphones. The point being, I don’t mind alone. Alone is familiar. I’m happy parenting. I’ve been happy when I’ve been in love. And I’m also quite happy alone. It’s only the contrast of missing someone that makes it bad.
But this Thanksgiving, I’ll be with my daughter. A 14-year-old vegan.
So yesterday, in a low-key way, because doing things up in a big way is not our style, I showed her a dozen or so vegetarian Thanksgiving recipes I’d been saving for probably five or six years, and we picked four of them to make together on the big day. Four simple vegetarian recipes. Not much work or time required. Like momma used to make, only meatless. Things we can make together, because the kitchen belongs to everyone.
Somehow this story, which was supposed to be one sentence—Yesterday my daughter and I planned our small Thanksgiving dinner together—has turned into yet another episode of All About Me. But the day itself will be about us.
To those who celebrate, whether alone or together, at home or far from it, Happy Thanksgiving.
For Jim Coudal.
My Glamorous Life: On Returning
Landed 10:00 PM JFK, picked up baggage after Delta sent everyone to the wrong carousel and an exhausted airport worker before giving up told maybe five passengers about the correct carousel, and those passengers told nobody else because people are selfish, but I am hyper-vigilant about luggage—being anxious and having had some bad experiences—so I spider-heard the airport worker’s whisper from 10,000 feet away, made sure to tell everyone around me that the carousel had changed, and ran to get my bag.
More drama at the cab stand. A pirate in a three-piece suit tried to steer me into his air conditioned sedan, claiming he worked for Uber (but then why would he be standing around instead of cruising and waiting for a signal?). The cab drivers then called him a crook and told him to fuck himself and he directed them likewise and it looked like a hot night fistfight at JFK was going to break out like the rash I felt growing on my sweaty back, but then I made a decision and got into a hot cab with duct-tape-patched seats and the driver sat down to drive, and the dispatcher, who hated all of us, after a great show of delay and neglect, eventually reluctantly gave the cab driver permission to drive me, and we drove for 30 sweaty minutes with the windows open, blowing humid NYC air into our faces, and then before midnight I was home, sweet, home. I ♥️ NY.