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.
At Automattic, we know our time is finite and precious. Here are the questions we ask ourselves before agreeing to any meeting:
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!
It was late winter when my sabbatical began, and it’s late spring as it comes to an end. Next week I return to my post after three months’ paid leave, courtesy of Automattic’s sabbatical benefit. Three months. A season. With full pay, and zero work responsibilities. In a job full of rewards, this is perhaps the greatest perk. Here’s why:
You work for so much of your life that your time passes in a blur. You don’t even notice it hastening by until someone or something calls your attention to a past milestone.
And then suddenly, into this rushing blur, comes an uncanny gift: back-to-back days that are yours, to do with as you choose. For a long enough period of time that your work brain quiets. For the first time in years, you have a chance to reflect on who you are, and where you are right now. To see where you’re going, and consider whether it’s still the right destination for the person you’re becoming. To think about who’s traveling with you.
During my sabbatical, I was able to renovate my apartment and rid it of books, furniture, and clothing I no longer need. Without three months to call my own, I would never have had the insight to seek these changes, let alone the time and energy to implement them correctly.
And because I had time, loads of it, three big swollen months of it, I was able to make these moves calmly and judiciously, instead of rushing anxiously, bungling things because I had to make snap decisions, and regretting the mistakes for years.
The gift of time also let me and the people I care most about look at ourselves, rejoice in all the good, and sand down a few rough edges.
Thanks to the sabbatical, I also tripled my daily steps. Admittedly, I started from a low step count because I am still recovering from Long COVID, and because I am slightly arthritic (age, old injuries), and because I tend to sit in my chair for huge swaths of physically inert hours, speed typing and mousing and forgetting to get up and get out. My father was always working, and so have I been. And I’ve let my anxiety (always a problem, but worse after COVID) turn me into a chair-bound workaholic, even though I know better.
I do not blame my job for the way I’d let myself run down. The job encourages us to have balance in our lives. I ignored that advice. But when I return to work, I will follow it. Because of this time in which I have luxuriated as if it were a warm bath, I have built new health habits that I will carry forward into my return to work.
I’ve even made some mature (and long overdue) decisions about what and how much I share online. Again, it’s all thanks to the amazing gift of this sabbatical. (Forgive me if following some of the older links here or on my disparate social feeds leads you to dead ends.)
I plan to use my next sabbatical for traveling, but I’m thrilled with how I spent this one, and I will always be grateful for this wonderful gift of time.
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.
“Led” is the past tense of “lead.”
L.E.D. Not L.E.A.D.
Example: “Fran, who leads the group, led the meeting.”
When professional publications get the small stuff wrong, it makes us less trusting about the big stuff. Trust in media is already at an all-time low. Don’t alienate liberal arts majors and obsessive compulsives. We may be the last readers standing.
I was a teenage telemarketer. Reading from a script, I attempted to raise money for St. Jude’s Hospital for Leukemia-Stricken Children. I was fired after three days for departing from the script.
We were supposed to hard-sell, no matter what the person on the other end of the line said. But when the people I cold-called talked about their financial hardships, I sympathized, asked questions, and didn’t try to force a donation.
Our boss listened in on the calls. My empathy toward the people I called was not appreciated.
My boss failed to see any irony in the job’s requiring psychopathically cold-hearted behavior toward some needy people in order to raise money for others.
Probably he could not allow himself to see it.
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
2006 DOESN’T seem forever ago until I remember that we were tracking IE7 bugs, worrying about the RSS feed validator, and viewing Drupal as an accessibility-and-web-standards-positive platform, at the time. Pundits were claiming bad design was good for the web (just as some still do). Joe Clark was critiquing WCAG 2. “An Inconvenient Truth” was playing in theaters, and many folks were surprised to learn that climate change was a thing.
I was writing the second edition of Designing With Web Standards. My daughter, who is about to turn twelve, was about to turn two. My dad suffered a heart attack. (Relax! Ten years later, he is still around and healthy.) A List Apart had just added a job board. “The revolution will be salaried,” we trumpeted.
Preparing for An Event Apart Atlanta, An Event Apart NYC, and An Event Apart Chicago (sponsored by Jewelboxing! RIP) consumed much of my time and energy. Attendees told us these were good shows, and they were, but you would not recognize them as AEA events today—they were much more homespun. “Hey, kids, let’s put on a show!” we used to joke. “My mom will sew the costumes and my dad will build the sets.” (It’s a quotation from a 1940s Andy Hardy movie, not a reflection of our personal views about gender roles.)
Jim Coudal, Jason Fried and I had just launched The Deck, an experiment in unobtrusive, discreet web advertising. Over the next ten years, the ad industry pointedly ignored our experiment, in favor of user tracking, popups, and other anti-patterns. Not entirely coincidentally, my studio had just redesigned the website of Advertising Age, the leading journal of the advertising profession.
Other sites we designed that year included Dictionary.com and Gnu Foods. We also worked on Ma.gnolia, a social bookmarking tool with well-thought-out features like Saved Copies (so you never lost a web page, even if it moved or went offline), Bookmark Ratings, Bookmark Privacy, and Groups. We designed the product for our client and developed many of its features. Rest in peace.
I was reading Adam Greenfield’s Everyware: The Dawning Age of Ubiquitous Computing, a delightfully written text that anticipated and suggested design rules and thinking for our present Internet of Things. It’s a fine book, and one I helped Adam bring to a good publisher. (Clearly, I was itching to break into publishing myself, which I would do with two partners a year or two afterwards.)
In short, it was a year like any other on this wonderful web of ours—full of sound and fury, true, but also rife with innovation and delight.
As part of An Event Apart’s A Decade Apart celebration—commemorating our first ten years as a design and development conference—we asked people we know and love what they were doing professionally ten years ago, in 2006. If you missed parts one, two, three, or four, have a look back.
MY DAUGHTER cries and begs me not to leave on my business trip. I hold her and tell her I will return soon.
My grandfather died in a plane crash between New York and California. My mother, who was eleven, had begged him not to leave. He lied and told her he would cancel the trip. I never lie to my daughter.
I always thought my grandfather died on a business trip. Two years ago I finally learned he was actually flying to California to divorce my grandmother. My mother never told me.
My grandmother never told her children their father was dead. They figured it out gradually.
When my mother was a young adult, her fiancée died in a plane crash.
My mother was never able to be happy, to feel safe, to trust the world.
One of my jobs is to help my daughter learn to be happy, to feel safe, to trust the world.
It is hard for any parent. Harder when you are divorced. My daughter is sensitive, creative, and has a learning disability. She feels different from other kids. Family is everything to her.
My daughter is everything to me. To support her, I do several jobs. Jobs I love, working with people I love and trust. One of my jobs requires me to travel frequently, staying away for up to a week at a time.
My father worked twelve hours a day to support his family. We grew up in his absence and long shadow.
I am grateful for my daughter’s life and my ability to spend so much time with her. She knows her parents love her and will always be there for her.
But when I leave, she cries, and I cry inside.
I CHAT with internet radio pioneer, design author, and brand maven Debbie Millman about broadcasting, writing, teaching, publishing, learning to be happy in your own skin, and the importance of early failure to long-term success and happiness. Enjoy Debbie Millman on The Big Web Show.
(Want more Debbie? Check Observer Media–Debbie’s legendary audio interviews with the likes of Jessica Walsh, Milton Glaser, Massimo Vignelli, Maria Popova, Stefan Sagmeister, Dave Eggers, Jen Bekman, Gary Hustwit, Tina Roth Eisenberg, Erik Spierkermann, Jessica Hische, and many more.)
AN EVENT APART Chicago—a photo set on Flickr. Pictures of the city and the conference for people who make websites.
Notes from An Event Apart Chicago 2013—Luke Wroblewski’s note-taking is legendary. Here are his notes on seven of the ten presentations at this year’s An Event Apart Chicago.
#aeachi—conference comments on Twitter.
Chicago (Foursquare)—some of my favorite places in the city.
An Event Apart Chicago—sessions, schedule, and speaker bios for the conference that just ended.
AEA Chicago 2013 on Lanyrd—three days of design, code, and content on the social sharing platform for conferences.
THE NEXT AEA event takes place in Austin and is already sold out (although a few spaces are still available for the full-day workshop on multi-device design).
A handful of seats are available for the final event of the year, An Event Apart San Francisco at the Palace Hotel, December 9–11, 2013. Be there or be square.
YOU FIND ME ENSCONCED in the fabulous Buckhead, Atlanta Intercontinental Hotel, preparing to unleash An Event Apart Atlanta 2011, three days of design, code, and content strategy for people who make websites. Eric Meyer and I co-founded our traveling web conference in December, 2005; in 2006 we chose Atlanta for our second event, and it was the worst show we’ve ever done. We hosted at Turner Field, not realizing that half the audience would be forced to crane their necks around pillars if they wanted to see our speakers or the screen on which slides were projected.
Also not realizing that Turner Field’s promised contractual ability to deliver Wi-Fi was more theoretical than factual: the venue’s A/V guy spent the entire show trying to get an internet connection going. You could watch audience members twitchily check their laptops for email every fourteen seconds, then make the “no internet” face that is not unlike the face addicts make when the crack dealer is late, then check their laptops again.
The food was good, our speakers (including local hero Todd Dominey) had wise lessons to impart, and most attendees had a pretty good time, but Eric and I still shudder to remember everything that went wrong with that gig.
Not to jinx anything, but times have changed. We are now a major three-day event, thanks to a kick-ass staff and the wonderful community that has made this show its home. We thank you from the bottoms of our big grateful hearts.
I will see several hundred of you for the next three days. Those not attending may follow along: