Working in tech means being comfortable with change and uncertainty. Successfully working in tech means not letting change and uncertainty paralyze you.
Forge ahead on the best information you have, and be prepared to change direction as needed.
Or not.
My fears melted away. And in their place came acceptance. All this vast majesty of creation. It had to mean something. And then I meant something, too. Yes, smaller than the smallest, I meant something too. To God, there is no zero. I still exist. —
The Incredible Shrinking Man (1957)
AKA:
How I feel after not updating Designing With Web Standards or writing a new book since 2013.
AND:
And also how I feel now that there’s no longer a single, agreed-upon digital town square (and, further, now that the biggest one, where I once enjoyed a hefty following for some pixel pusher, has turned into a N*zi bar, where I no longer choose to spend time).
And since Covid killed the conference I co-founded, and I cut way back on travelling and giving conference talks and focused on paying off the debts we were left with.
And since financial reality forced us to kill our publishing company, too. So many nice things, all gone.
I had the world, or at least a wee piece of it, by the eyeballs, and, not entirely by my own choice, bit by bit, I let it go.
Kinda depressing, sure. But also, and mainly, pretty liberating.
I also learned something about people and friendship, and remembered something about the passing of all things.
Just as nobody who marries spends their wedding day planning their divorce, almost nobody starts a business contemplating what rocks it will eventually splinter and break upon, and how to build a life raft for themselves.
I take that back. Some folks I know, who played pivotal roles in the evolution of the web, actually started their businesses with a clear goal of selling them to somebody bigger. Like Typekit was designed to sell to Adobe. Or Blogger was designed to sell to Google.
Such folks, several of whom are now post-economy wealthy, lived in the Bay Area in the 1990s and early 2000s, where building to flip was widely discussed and accepted.
I, on the other hand, live in New York. So I started my web businesses (like Happy Cog™ design studio) to serve clients, as NYC creatives have always done, and with no understanding that I would one day need to leave the company and should have an exit plan. Why would I exit? Why would I ever stop doing work that brought excitement and meaning to my life?
Similarly, I started my personal site with its “Ask Dr. Web” tutorials in 1995, and co-founded my web design publication, A List Apart, in 1997, for the sheer joy of sharing knowledge, with no concept of making money, let alone of one day selling the business.
Eventually, despite my naivete, and mostly thanks to Jim Coudal and Jason Fried, A List Apart began making money by running one carefully screened ad per page. I used that money, as you will expect, to pay our writers, editors, and producers. And when it came time to stop running ads, I slowed our publication schedule, paid writers out of my own pocket, and worked with a small crew of fellow volunteers, who published ALA because we believed in the mission. (Still do.)
If I had come of business age in San Francisco, I likely would have sold A List Apart to somebody like O’Reilly, but that was never my plan because I make toys to play with, not to give away.
In spite of A List Apart’s running at a loss, in the early 2010s I co-founded two businesses that spun out of it: An Event Apart design conference with Eric Meyer, and A Book Apart with Mandy Brown (later replaced by CEO Katel LeDu) and Jason Santa Maria. And during those first years, business was great.
We published HTML5 For Web Designers the day after Steve Jobs, waving an iPhone on the world’s biggest stage (okay, sitting at his desk), announced that Flash was dead because HTML5 would bring app-like dynamism to the web using open standards instead of proprietary code. It (our first book, I mean) sold brilliantly. “Gee, publishing isn’t that hard” I naively told myself. (No, I knew it was hard. My favorite publishers had been laying off my favorite editors for ten years before my partners and I took the plunge. But the early success did make me think the books we published about web design would always find a large, eager audience. In time, I would learn otherwise.)
And while we began the publishing house by relying on the best writers we knew personally to write about the topics they were most passionate about, I’m proud to say that, as we went along, we also discovered brilliant first-time book authors, helping them create perfectly polished, fluff-free manuscripts that made genuine contributions to our readers’ understanding of UX and all it entails. (And not just to our readers. The insights they brought to their work after digesting our books rubbed off on their colleagues.)
In giving these brilliant writers a platform, we not only helped them take their careers to the next level, we also helped people who create web content think and work better, which in turn helped the people who used the websites, applications, and products our readers designed and built. Of that, I am proud.
An Event Apart (RIP) was also a damned fine early success. Web designers liked our innovation of a multi-day, single-track conference, with a holistic approach to web design, code, and content, and unifying themes between the individual talks. Our freaking-amazing speakers debuted Huge Ideas including Mobile First and Responsive Web Design—ideas which, like perfect contextual menus in UX, arrived at the very moment designers needed them.
Not only that, but these humble geniuses also sat in the auditorium with our audience for all three days of each conference event: listening to each other’s presentations, and updating their own presentations to better bounce off each other’s ideas and the evolving themes of that particular show.
I could spend hours telling you how our producer Toby M. made miracles happen at every show, or how person-in-charge Marci E. brought joy to our community. How many of our speakers became authors. How some “graduated” from An Event Apart as newcomers replaced them. How the diversity of our speaking line-up, which wasn’t terrific in 2008, improved greatly each year. (Not that we ever said, “We need another black speaker” or “We need a trans speaker” or what-have-you. Just that we learned to swim outside the pool we came from, and discover great talent everywhere.) Our speakers were also almost uniformly Just Nice Good People, which doesn’t always happen when you’re collecting the greatest minds in an industry.
That’s not even to mention the incredible people who attended our shows, some of whom became lifetime friends for me.
So why, given the joy these businesses brought to everyone connected to them, including me, would my partners and I have even conceived of an exit strategy? We wanted the Good Times to roll on forever.
But of course they never do.
COVID did in An Event Apart. Some conferences survived, of course. Different priorities, different overheads, different business models. Some that survived do not pay their speakers. Others, where the conference is an adjunct to a bigger business, laid off or reassigned conference staff while the pandemic made live events impossible. Others that survived mostly rely on volunteer labor, whereas we had paid staff. They were worth their weight in platinum, and we’d have paid them more (because they were worth more) if the pandemic and six-figure hotel contracts hadn’t made continuing the show impossible. My partner and I earned nothing during the business’s last five years, and got personally stuck with a six-figure debt when the event closed. It is what it is.
Although books should be COVID-proof, multiple financial problems eventually beset our publishing house as well. For most of the run of the business, my partner and I earned nothing beyond the glow of contributing to our community’s knowledge. We paid our CEO, authors, and editors, kept nothing for ourselves, and tried, oh how we tried, to keep the business going as its revenues tanked.
Speaking only for myself, I’ve learned that I am good at starting businesses and keeping them going creatively, as long as somebody else figures out the money. I suck at that, and I’m obsessed with the notions of fairness and self-sacrifice that were drummed into me by a narcissistic family that valued me for taking on the roles they were emotionally incapable of handling—such as bringing up my baby brother in my father’s absence, which no child is equipped or should be asked to do, and yet it happens all the time. Growing up this way made me put my own self-interest last. Which is also why it never occurred to me to plan an exit. And by the time I needed to do so, the businesses were not in shape to sell.
Closing a conference is bad, but attendees can go to other conferences, and speakers can speak at other conferences; closing a conference doesn’t end a community. It sucks for the business but doesn’t strand participants.
But closing a publishing house hurts like hell, and you feel you let everybody down. I know how much our closing hurt some of our authors, and I think about that, instead of the good we achieved, when I look back.
No doubt when my partner and I write the large personal checks to cover our deceased business’s outstanding debts, we’ll be regretting the harm our closing caused, not basking in the warm glow of how many careers we changed for the better. Like the standup comedian who obsesses about the guy who’s frowning at table 3, and doesn’t hear the laughter of the rest of the crowd. We also, hopefully, won’t focus too closely on our financial wreckage. Just pay the bill, and move on.
Anyway, I hadn’t publicly addressed the endings of these businesses, so I figured it was time to do so. I’m sharing my experience only. If you ask any of the people I worked with on these projects, they might have a different story to tell. And that would be their story, and it would be every bit as valid as anything I’ve said here.
I also didn’t ask permission of my partners, speakers, or authors before sharing these thoughts. Probably I should have. But, hey. As I’ve said. I’m speaking here only for myself.
So, anyway.
Is it worth the risk of starting a web-related business that isn’t a venture-backed startup? I still think it is, and I applaud all who try. Heck, I might even do so myself someday. If you’re doubtful because of (((gestures at everything))), it might be worth noting that I started Happy Cog™ during the dot-com crash, when studios were closing all around me. And we launched A Book Apart during the world financial crisis of late 2008. Don’t let (((all this))) deter you from trying something bold. Let me know when you do. I’ll keep watching the skies.
P.S. Under swell third-party ownership and management, Happy Cog is still going strong. Check it out!
My insight into corporate legal disputes is as meaningful as my opinion on Quantum Mechanics. What I do know is that, when given the chance this week to leave my job with half a year’s salary paid in advance, I chose to stay at Automattic.
Listen, I’m struggling with medical debts and financial obligations incurred by the closing of my conference and publishing businesses. Six months’ salary in advance would have wiped the slate clean. From a fiduciary point of view, if nothing else, I had to at least consider my CEO’s offer to walk out the door with a big bag of dollars.
But even as I made myself think about what six months’ salary in a lump sum could do to help my family and calm my creditors, I knew in my soul there was no way I’d leave this company. Not by my own choice, anyway.
I respect the courage and conviction of my departed colleagues. I already miss them, and most only quit yesterday. I feel their departure as a personal loss, and my grief is real. The sadness is like a cold fog on a dark, wet night.
The next weeks will be challenging. My remaining coworkers and I will work twice as hard to cover temporary employee shortfalls and recruit new teammates, while also navigating the complex personal feelings these two weeks of sudden, surprising change have brought on. Who needs the aggravation, right? But I stayed.
I stayed because I believe in the work we do. I believe in the open web and owning your own content. I’ve devoted nearly three decades of work to this cause, and when I chose to move in-house, I knew there was only one house that would suit me. In nearly six years at Automattic, I’ve been able to do work that mattered to me and helped others, and I know that the best is yet to come.
I also know that the Maker-Taker problem is an issue in open source, just as I know that a friend you buy lunch for every day, and who earns as much money as you do, is supposed to return the favor now and then. If a friend takes advantage, you’re supposed to say or do something about it. Addressing these imbalances is rarely pretty. Doing it in public takes its own kind of courage. Now it’s for the lawyers to sort out.
On May 1, 1992, a man who’d been horribly beaten by the L.A. police called for calm in five heartfelt, memorable words: “Can’t we all get along?” We couldn’t then, and we aren’t, now, but my job at Automattic is about helping people, and that remains my focus at the conclusion of this strange and stressful week. I’m grateful that making the tough business decisions isn’t my responsibility. In that light, my decision to stay at Automattic was easy.
P.S. We’re hiring.
They say you should manage down. You’re supposed to manage the people who work for you. For many people who become leads, it’s the toughest and least satisfying part of the job. This is especially true for people who become leads primarily because they’ve been on the job longer than the people around them—not because they had a management jones to satisfy.
They also say you should manage up—subtly assert control of the people you work for. Help them stop short of a bad idea and find their way to a better one. If you can manage up without being obvious about it, you just might save your job, your boss’s job, and your team’s work.
And yet—
The pains of managing up and down are better than the pains of not being able to manage at all. Further, if you swear by managing up or down, I’m not here to discredit you, nor would I dream of doing so, nor would I have cause.
But I am here today to ask you to also try thinking a different way.
Do keep helping people, whether you work for them, work with them, or they work for you.
But don’t think of it as managing them.
Think of it as helping a colleague, just as you’d help a friend, a family member, or (when you’re at your best, and when it’s safe) a stranger.
Help to help, because we’re built to help. We feel better when we do it.
Life is not a contest. At least, it doesn’t need to be chiefly or primarily a contest. If you request feedback and I provide it, what counts is that it helps you. Same when I ask for your help. My position versus yours within this particular hierarchy doesn’t matter. The ideas matter. And the best idea can come from anyone.
Hierarchy matters at times, sure. But not most of the time. Most of the time what matters is showing up, doing your work, and helping others do theirs.
Have a better day!
Soon after we launched A List Apart Magazine, we began to notice other websites reusing our content (including illustrations) without permission, and often without so much as a credit. As that violated our author’s copyrights and ours, we’d invariably reach out to the makers of those websites with brief, politely worded takedown requests.
Not every content poacher was contactable, but those we did reach almost always quickly complied with our requests. They also nearly always claimed that an “intern” or “freelancer” had grabbed the content without their knowledge or permission. Some, perhaps fearing that we might be litigious, even went so far as to tell us that they’d “fired” the imaginary intern/freelancer the instant we informed them of the issue.
We always pretended to believe them.
Why? Because letting embarrassed people save face is kind. It also helps the whole interaction go more smoothly. Besides, the amateur pillager claiming “the intern did it” today may be your colleague or friend tomorrow.
I recalled this common awkwardness yesterday after a former US president who’s running for reelection blamed Nazi language in his social media post on a “staffer.” It would seem the buck stops anywhere but here.
ONE MONTH and 24 years ago, in “Where Have All the Designers Gone?” (my HTMHell design column for Adobe of March 20, 2000), I discussed the deepening rift between aesthetically focused web designers and those primarily concerned with creating good experiences online:
More and more web designers seem less and less interested in web design.
Over the past 18 months or so, many of the best practitioners in the industry seem to have given up on the notion that a low-bandwidth, less than cutting-edge site is worth making. Much of the stuff they’ve been making instead has been beautiful and inspiring. But if top designers wash their hands of the rest of the Web, whose hands will build it, and whose minds will guide it? The possibilities are frightening.
Why were many of the leading graphic designers and studios at the time uninterested in web design? For one thing, designers trained to strive for visual perfection found the web’s unpredictability depressing. The article provided clues to the frustrations of the time:
Good designers spend hours tweaking typography in Illustrator and Photoshop. Then visitors with slow connections turn off images.
Of course, where professionals trained in graphic design saw a distressing lack of control, others glimpsed in the infant technology a tremendous potential to help people, pixel-perfection be damned. To reduce the conflict to a cartoon, you might characterize it as David Carson versus Jakob Nielsen—though doing so would trivialize the concerns of both men. Designers already charged with creating websites found themselves somewhere in the middle—barking themselves hoarse reminding clients and managers that pixel-perfect rendering was not a thing on the web, while arguing with developers who told designers the exact same thing.
Visually inspiring websites like K10k showed that the web could, if approached carefully and joyfully, provide aesthetic delight. But many designers (along with organizations like AIGA) were unaware of those sites at the time.
Another source of tension in the medium in 2000 sprang from the discrepancy between the privileged access designers enjoyed—fast connections, up-to-date browsers and operating systems, high-res monitors (at least for the time) offering thousands of colors—versus the slow modems, aging and underpowered computers, outdated browsers, and limited-color monitors through which most people at the time experienced the web.
Which was the real design? The widescreen, multicolor, grid-based experience? Or the 216-color job with pixelated Windows type, a shallow “fold,” and pictures of headline text that took forever to be seen?
To view your masterpiece the way most users experienced it, and at the syrup-slow speed with which they experienced it, was to have an awakening or a nightmare—depending on your empathy quotient. Some designers began to take usability, accessibility, and performance seriously as part of their jobs; others fled for the predictability of more settled media (such as print).
My March, 2000 article ended on an upbeat note—and a gentle call to action:
For content sites to attain the credibility and usefulness of print magazines; for entertainment sites to truly entertain; for commerce sites and Web-based applications to function aesthetically as well as technically, the gifts of talented people are needed. We hope to see you among them.
That was my hope in 2000, and, all these years later, it remains my vision for this web of ours. For though the browsers, connections, and hardware have changed substantially over the past 24 years, and though the medium and its practitioners have, to a significant extent, grown the Hell up, beneath the surface, in 2024, many of these same attitudes and conflicts persist. We can do better.
Minus the framesets that formerly contained it, you may read the original text (complete with archaic instructions about 4.0 browsers and JavaScript that broke my heart, but which Adobe’s editors and producers insisted on posting) courtesy of the Wayback Machine.
☞ Hat tip to Andrey Taritsyn for digging up the article, which I had long forgotten.
It’s nearly twenty years ago, now, children. Facebook had only recently burst the bounds of Harvard Yard. Twitter had just slipped the bonds of the digital underground. But web geeks like me still saw “social media” as a continuation of the older digital networks, protocols, listservs, and discussion forums we’d come up using, and not as the profound disruption that, partnered with smartphones and faster cellular networks, they would soon turn out to be.
So when world-renowned CSS genius Eric Meyer and I, his plodding Dr Watson, envisioned adding a digital discussion component to our live front-end web design conference events, our first thought had been to create a bespoke one. We had already worked with a partner to adapt a framework he’d built for another client, and were considering whether to continue along that path or forge a new one.
And then, one day, I was talking to Louis Rosenfeld—the Prometheus of information architecture and founder of Rosenfeld Media. I told Lou about the quest Eric and I were on, to enhance An Event Apart with a private social network, and shared a roadblock we’d hit. And Lou said something brilliant that day. Something that would never have occurred to me. He said: “Why not use Facebook? It already exists, and that’s where the people are.”
Reader, in all my previous years as a web designer, I had always built from scratch or worked with partners who did so. Perhaps, because I ran a small design agency and my mental framework was client services, the habit of building was ingrained.
After all, a chief reason clients came to us was because they needed something we could create and they could not. I had a preference for bespoke because it was designed to solve specific problems, which was (and is) the design business model as well as the justification for the profession.
Our community web design conference had a brand that tied into the brand of our community web design magazine (and soon-to-emerge community web design book publishing house). All my assumptions and biases were primed for discovery, design, development, and endless ongoing experiments and improvements.
Use something that was already out there? And not just something, but a clunky walled garden with an embarrassing origin story as a hot-or-not variant cobbled together by an angry, virginal undergraduate? The very idea set off all my self-protective alarms.
Fortunately, on that day, I allowed a strong, simple idea to penetrate my big, beautiful wall of assumptions.
Fortunately, I listened to Lou. And brought the idea to Eric, who agreed.
The story is a bit more complicated than what I’ve just shared. More voices and inputs contributed to the thinking; some development work was done, and a prototype bespoke community was rolled out for our attendees’ pleasure. But ultimately, we followed Lou’s advice, creating a Facebook group because that’s where the people were.
We also used Twitter, during its glory days (which coincided with our conference’s). And Flickr. Because those places are where the people were.
And when you think about it, if people already know how to use one platform, and have demonstrated a preference for doing so, it can be wasteful of their time (not to mention arrogant) to expect them to learn another platform, simply because that one bears your logo.
Of course, there are valid reasons not to use corporate social networks. Just as there are valid reasons to only use open source or free software. Or to not eat animals. But those real issues are not the drivers of this particular story.
This particular story is about a smart friend slicing through a Gordian Knot (aka my convoluted mental model, constructed as a result of, and justification for, how I earned a living), and providing me with a life lesson whose wisdom I continue to hold close.
It’s a lesson that intersects with other moments of enlightenment, such as “Don’t tell people who they are or how they should feel; listen and believe when they tell you.” Meet people where they are. It’s a fundamental principle of good UX design. Like pave the cowpaths. Which is really the same thing. We take these ideas for granted, now.
But once, and not so long ago, there was a time. Not one brief shining moment that was known as Camelot. But a time when media was no longer one-to-many, and not yet many-to-many. A time when it was still possible for designers like me to think we knew best.
I’m glad a friend knew better.
I started telling this story to explain why I find myself posting, sometimes redundantly, to multiple social networks—including one that feels increasingly like Mordor.
I go to them—even the one that breaks my heart—because, in this moment, they are where the people are.
Of course, as often happens, when I begin to tell a story that I think is about one thing, I discover that it’s about something else entirely.
Designers can either become drivers of business within their organizations, or they can create the businesses they want to drive. We’re entering an era of design entrepreneurship, in which some designers are realizing that they’re not just a designer employed by a business; they’re creative business people whose skill set is design.
—The State of UX in 2024
The quotation above is from a report at trends.uxdesign.cc subtitled “Enter Late-Stage UX.” It is an important thought. And if it seems like a new one to designers in their first decade of work, it will feel quite familiar to to those of us who earned our merit badges during the 1990s and 2000s. See, for instance,
by Jim Coudal (2005),
by Kevin Potts (2003), and
by Scott Kramer (2000, one of four terrific ALA articles by Scott on that subject).
That widespread, intoxicating entrepreneurial impulse led to a cornucopia of internet content and products (and, eventually, “real-world” products, too). Some flopped. Some flowered for a magical season (or twelve), and then faded as times and the market changed. Some grew and grew, growing communities with them. A few changed the world, for better or worse. (And, occasionally, for both.)
History repeats, but it also changes. If flying from your corporate perch feels like your best response to an industry where the idealism that led you to UX feels somewhat beside the point, go for it! —But first, check your bank balance, and talk with family, friends, and a business advisor, if you have one.
Trusting my ability to use design and words to say something original enabled me to work for myself (and with partners) from 1999–2019, and it was good. Financially, running independent businesses is a perpetual rollercoaster, and it can crush your soul if your beloved creation fails to connect with a community. Some people exit rich. Others just exit. “Don’t burn any bridges” is a cliché that exists for a reason. But I digress.
“Consider entrepreneurship” is but one piece of useful advice in this year’s excellent State of UX report by Fabricio Teixeira and Caio Braga, with deeply clever illustrations by Fabio Benê and significant contributions from Emily Curtin (God bless the editors!) and Laura Vandiver.
I invite you to read and bookmark the whole thing. I plan to reread it several times myself over the next weeks. It’s that deep, and that good. Hat tip to my colleague Jill Quek for sharing it.
Read: The State of UX in 2024.
Herewith, a scene from last night’s interview with legendary web & book designer (and Dean of The Cooper Union School of Art) Mike Essl, who shared his portfolio, career highlights, early web design history, and more. Fun!
If you get a chance to meet, work with, or learn from Mike, take it. He’s brilliant, hilarious, warmly human, and one of the most creative people you’ll ever have the good fortune to know.
So ended Day 2 of An Event Apart Online Together Fall Summit 2021. Day 3 begins in less than two hours. You can still join us … or watch later On Demand.
In my earliest 20s, I wrote a novel. Make that three. The first two were garbage—a kind of literary throat clearing. I shelved the manuscripts and moved on. But my third draft novel, “Sugar and Snow,” seemed to have something.
My Uncle George connected me to his friend, a famous writer. She read my manuscript and shared it with her daughter, who also thought there was something to it.
The famous writer asked if she could share my manuscript with her publisher. I, of course, said yes. Then I phoned all my friends to tell them I would soon be a published author.
After three months of silence, the publishing company returned my manuscript, untouched. No word of explanation. Not even the courtesy of a boilerplate rejection letter.
Unless you count a few fibs on the resumes I submitted to potential employers, I never wrote another line of fiction.
I drank my way through the next decade, and did not exercise my writing ability for nearly ten years.
I should not have been so sensitive at age 20, I suppose. Older writers had told me that rejection was part of the life. John Casey, an early writing mentor, survived the Korean War, wrote a novel about his experiences, and submitted it to two dozen publishers who weren’t interested. Eventually he siphoned a short story out of one of the chapters of his rejected novel, and found a little magazine to publish it.
John Casey became an award-winning novelist, but first he slogged through years of rejection, as all writers must. He’d told me that was the game, but my heart wasn’t ready for it. At 20, I wasn’t strong enough.
Perhaps as a partial consequence of how badly a single rejection spun me out of control, when I sometimes have to deliver tough news to a creative colleague, I’ve always striven to be kind about it. Maybe I’m excessively careful about not hurting people. But is that a bad thing? After all, I don’t know which people whose work I need to criticize or even reject are strong enough to take it, and which aren’t.
And neither do you.
Being kind as well as clear becomes a moral mandate when you realize the power your feedback has to encourage another person to do their best work … or to shut them down creatively, possibly forever.
In “Wild Strawberries,” Professor Isak Borg is told in a dream, “A doctor’s first duty is to ask forgiveness.” We never know whom we may harm, or how deeply.
I told you a sad story, now here’s a happy one. I’m part of a small publishing company. Evaluating book proposals is where our process starts. Being clear compassionately is our mandate—we recognize the tremendous emotional risks folks take when they submit their ideas for review.
Last year an author approached us with a proposal that wasn’t quite right for us. We responded with detailed feedback about what would have made it the right fit for us … and we chose our words carefully to avoid inadvertently causing harm.
This year that author returned with a spectacular proposal that we’ve accepted gratefully and with real joy.
I thanked the author for having had the courage to come back—after all, I’d lacked that courage myself after my brush with rejection. The author thanked us for the feedback and the way we’d presented it, saying they would never have had the willingness to come back if not for the quality of our feedback.
As a result of an author’s determination and our compassionate clarity, our readers and this industry will benefit from an author’s brilliance.
Creators, never give up.
Gatekeepers, first be kind.
Photo by Kimberly Farmer on Unsplash
This story is a bit long, but I promise it will be worth it, because it contains the two most important principles every designer must know and take to heart if you intend to do great work anywhere, under almost any circumstances, over the long, long haul of your career.
Sticking To It – fresh from JZ in Automattic.Design
One of my first professional jobs was at a tiny startup ad agency in Washington, DC. The owner was new to the business and made the mistake of hiring a college buddy as his creative director. This guy was not up to the job. He was not the slightest bit curious about our clients’ businesses, or what mattered to their customers. His day was one long lunch hour bookended by naps. He thought we couldn’t hear him snoring through the closed door of his office.
Once a day, he would call a “creative meeting” to discuss whichever project would soon fall due. He would not bring sketches, or notes, or a creative brief to these meetings. Instead, he would “lead a creative brainstorm,” which meant we had to listen to him spout whatever shallow, idiotic idea proposed itself to his limited mind at that moment. We were then supposed to leave the room and execute his so-called “concept.” It didn’t matter if the idea was derivative of someone else’s widely known better ad, or if it was superficially cute but meaningless, or wrong in tone, or more likely to hurt than help the client’s business. He had spoken, and that was that.
Needless to say, after a few weeks—and even though they were old friends—the agency owner realized he had to fire this creative director. After all, it was widely agreed, a quarter-page newspaper ad for a local Ford dealership was far too important to entrust to the whims of an imbecile.
Posted here for posterity:
Design kickoff meetings are like first dates that prepare you for an exciting relationship with a person who doesn’t exist.
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.