Welcoming the Self-Taught Designer

Khoi Vinh has vinh vocal for some time about the lack of a true design criticism discipline, in the way that there are literary critics or the peer review process and such. He claims we’re partly to blame, because of how we horse-trade each other for jobs (and we can’t bring ourselves to bad-mouth the work of someone we might want to work for someday). Sadly, this reluctance contributes to our field’s perceived irrelevance beyond ourselves.

If it sounds shocking to consider that not everyone believes that design is so important (I mean, we’re Creatives. Like God. The Creator!) he offers some sobering data about that.

As an industry, we just don’t have the guts to say what we think about our work. We have some legendary publications out there. Design Observer, one of my favorites, will do it, but usually it’s the, “Wouldn’t it be great if they had a designer?” kind of stuff. Even A List Apart—obviously one I’m fond of—doesn’t do it.

That’s when Vinh gets our attention, I think. As a designer, I’m familiar with not having a substantive say in the work. It happens. Even as a “Senior” designer. It feels nice to know there are people whose jobs are to get Design a seat at the table. But to argue that this is a hole I’ve dug for myself—that my desire to make my discipline get the appreciation it deserves might be making me (and the rest of us) isolationists—is interesting. Almost as though we went from not wanting to be a part of this internet thing and to having a victim attitude about feeling left out.

Khoi Vinh has lived through some of what I think were very important iterations in the field of design. He worked before and after the dotcom crash, Web 2.0 (the Windows ME of our craft), the arrival of the walled gardens, to this interesting place we are now where we’re many of us are making comfortable money working in-house for large tech behemoths, but are working in a way that is making us miss agency life and the old days where “Webmasters, we did everything.”

His solution is not to go and share the Joy of Making with the outside world—just making sure they’re clear that we’re the real thing, not them—and all of this will figure itself out. Nope, his solution is more radical. He thinks we should be more like engineers. Where we like to think of ourselves as the empathetic and open-minded bunch, engineers, relatively-speaking, have an open borders policy on who they let in. And given the issues that the engineering world in the tech industry has, this is a sobering comparison.

Which brings me to my own radical belief (which shouldn’t be, in 2019). AIGA releases an annual Census and of course in the last few years it muses about how we might do better in terms of diversity and inclusion. Get more people to go to design school, help them break into the industry, get them promoted, get them into leadership roles. Get them to come, and get them to stay.

I think it’s part and parcel of Vinh’s solution to the problem (and consequence of) having no design criticism:

We need to finally welcome the self-taught designer.

I know we do this better in the web community. It’s how I got in, for example. We let people work for us at tech companies, we buy their logos on the internet. That’s not what I’m talking about and I don’t think that’s what Khoi Vinh’s referring to either. We’re referring to the Design Establishment, the same folks that quibbled twenty years ago about whether designing for the browser was real design or a schmuck’s side hustle. The same Establishment that has finally let people like Vinh (and myself) in. Through the back door, perhaps, but we’re in. We’re Real Designers. And now we’re kind of doing the same thing to people on the outside, on the valid claim that our work has grave, real (not futurist clickbait) consequences.

But as long as we let this cycle continue, not only are we being jerks, but we’re helping bring about our own irrelevance? Certainly that can make us look up from our innies and outies for a moment, can’t it?

/ Cover photo is “Tijuana Border,” by Barbara Zandoval

Letting Go of the Old Web

Last year I wrote a thing on Automattic’s design blog about something I keep noodling on, which ultimately boils down to what makes us creative. What gets us to build a website? What the hell is a website today?

I don’t mean “Us” the web community, or tech industry. I mean “Us” as Humankind.

It started off as thinking through what gets a person to Post, or Build, or Edit, or Publish something to the web. At work, we had invested in a big user research initiative, and there was a decent pattern of people feeling much more confident about the idea of making a website on a desktop/laptop versus a mobile device. Tweaking content, checking activity, sure. But not the big stuff. Not the upfront stuff. The decisions felt too big, or their idea of how that would work on a phone was too overwhelming. Tactically and strategically, as a designer, the take-away could be, “Ok, we don’t have to worry about making a 100% parity experience for mobile. Sigh of relief.”

These last few days I’ve been forcing myself to post using my phone, mostly because I need to enforce my work boundaries right now, and want to finish this 100-day project on a strong note. But I haven’t been able to shake that research. Knowing that the rest of the world is coming into the web on a phone, (not in their basements), and for reasons other than sheer Awe and Wonder—that this is something important to keep in mind. It’s not even an emerging markets product thing or a mobile-first web standards thing. Just something Important.

These things are what separate the good research from the meh research anyway, right? Things that still make you think months or years later. Sometimes bringing the giddiness that you’re on the cusp of that exciting “Aha!” moment—or the unease of that dreaded “Fuck.” moment. By then it is probably too late to choose which one.

It was fine blogging on my phone. Awkward, at first, like being abruptly asked to switch from speaking one language to another. It’s so cool how all five senses have to recalibrate to reach an equitable state from which to proceed. I think I still prefer to have my writing in a sort of sandbox. I always used client back in the day when auto-save was not a thing, and once hand-coding blog posts became a glorified thing of the past.

My client/sandbox/writing application of choice across all devices is Ulysses, and I am so excited to share more about it. I have been testing different writing applications for years now, and can now confidently say that I Have Chosen.

But I will post that one from my laptop 😆.


Regarding that nagging research, I still think there is a crucial distinction—that it matters whether people can reach a “Create” mindset versus Edit/Build, or Post (which only connects with bloggers), or Publish (the scariest one). For us, the makers of these publishing platforms, or, The Folks Formerly Known as the People Who Make Websites, we can get ourselves to put something out there easily no matter what mindset we’re in. It’s work.

But not everyone else. Yet, we implicitly still hold them to our standard, expecting them to discover the joy of the web, or come to see our esoteric tools and frameworks charming and endearing? When they really just want a place on the web to display something about themselves that reflects the actual world they live in.

Sometimes I wonder if we’re not aware of how much we’re shutting them out. We live in this interesting time in the web’s history where more and more people are making websites, but they are not coming to it with awe and wonder, like we did. They are not about to find a new hobby. They have already found their passion and it’s not this. And it’s like we’re interested in making it easy for people to make a website, or learn how to code, but so long as they’re coming to church on Sundays.

In glorifying our past, we delight in still being able to do it the hard way. We’re still making it about us. We can’t fully set our users up for success this way. Moreover, we are perpetuating the very walls that keep people from discovering the joy of the web the same way we were so fortunate to experience.

It’s taken me a while to make peace with the reality that most new homebrew websites today aren’t people’s first transformative experience on the web: that first foray into Geocities, or first post on WordPress, or saving a text editor file as .html and opening it up in a browser. More importantly, accepting that has made me understand that it’s not that people have stopped caring or don’t want to express themselves on the web. Or that we’re on our phones now, and you can’t Make a website the same way. Or that the walled gardens have hijacked our desires to create something on our own terms.

We miss the old Web and we miss Making Websites. But that time has gone and passed. The future web can only hold as much wonder, discovery—and community—as it did back then, when we let go.

Mopping the Floor in a Flooding Room

Ruined by Design is one of the most important books I’ve ever read for my career. I knew I was in for a ride when the foreword described a classic scene from the early days of psychology field.

I don’t know Mike Monteiro or Vivianne Castillo. They sound like good people. I don’t know, and I might not care. We need more people from inside the industry saying these things.

The book spends most of its time critiquing the “evil” tech companies, their leadership, and the people who idolize them. When I read it, I kept thinking, “Thank goodness I don’t work there. My company has actually made the web a better place.” But my conscience still felt a degree of unease. I didn’t feel off the hook, and I recently realized why:

Those of us lucky enough to work on an honest, valuable, and resilient product aren’t exempt from the problem. We could still be in our own slowly flooding rooms. If we take our work for granted and just keep mopping along, one day, we will inevitably drown too.

When that happens, that’ll be one more part of the free internet dead without the walled gardens even having to do anything. The best defense is a good offense. We can fight all we want, but we have to make sure we’re strong, too.


In the early 1900’s, some psychiatric hospitals gauged patients’ readiness to integrate back into society through a simple and peculiar test. The patient was ushered into a room with a sink, where the hospital staff would place a plug in the sink, turn on the faucet, and wait for the sink to overflow. As water bubbled over the ledge and splashed onto the floor below, the patient was then handed a mop and the staff would leave the room, closing the door behind them. If the patient turned off the water, unplugged the sink, and mopped up the water that had spilled onto the floor, they were deemed as ready to go home and enter back into society. But if the patient opted to frantically mop as the water gushed over the sink, failing to turn off the faucet or remove the sink’s plug, they were deemed insane and prescribed more time in the psychiatric hospital: they failed to acknowledge and address the root of the problem.

Many of you in the tech industry are frantically mopping.

Foreword by Vivianne Castillo, in Mike Monteiro‘s Ruined by Design