Some personal news: after four years of working on design systems at Stripe, I’m leaving to join Era as a design engineer.
This change is going to be pretty big for me in a few ways. I’ll be going from a large, enterprise company to a tiny, consumer startup. It will also be the first time in ~9 years that I won’t be focusing on design systems.
Why the change? One of the reasons is a desire to sharpen my hard skills. Running a design system involves lots of glue work, and while I really love that type of work, I could feel my core design and engineering skills atrophying.
Design systems work can also be very repetitive. I should feel as though I have 9 years of experience building and operating design systems, but instead I feel like I have 3 years of experience repeated 3 times.
Rather than jumping into another design systems role where I will ultimately repeat a lot of the work I’ve already done for other companies, I’ve decided to move to a role where I can practice my core skills daily on new and exciting problems, and ship software directly to end users.
And then there’s the burnout. Working on systems is hard, especially when you’re working in an organization doesn’t understand or value that kind of work.
The constant need to explain why what we’re doing is valuable is exhausting, and really feeds into that feeling of futility - that nothing we do is ever enough.
What I didn’t understand then, but I’m painfully aware of now, is that a lot of folks in management don’t get this kind of work. They can’t sell the work to leadership because folks in management often don’t use the product they work on. And they can’t see progress made because they’re not building the same thing that you are. They’re not building software, they’re building a giant spreadsheet of numbers.
Our industry will have to reckon with the tension between building quality software at scale and failing to understand and value platform teams. But I will not sit around and wait for that reckoning to happen.
I wanted my next gig to be as far on the opposite end of the spectrum as possible, focusing directly on designing and building a product with a small team of passionate builders. That’s why I’m so excited to join Era, a startup focused on building a consumer finance app to help anyone and everyone make the most of their money.
Like so many others, I grew up in a middle class family with parents who worked hard just to make ends meet and provide for my future. Investing was a foreign concept to me until later in life when I became more financially literate.
There are so many folks out there who make good money but don’t know what to do with it or how to manage it. Era wants to put a financial assistant in their pockets, and I’m excited to help with that mission.
Will I work on design systems again in the future? Maybe, if it feels right. In the meantime I’m going to enjoy shipping some hand-crafted software.
When I’m writing, I’m trying to be an architect. I’m trying to get the reader to feel the way I do; even when I don’t intend to convince them of something, and most of the time I don’t, writing is a subtly coercive act. The coercion is cooperative, like any performance. More precisely, I want a reader to arrive at my thought and feel close to the way I felt when I thought it. This may be authorial fantasy, delusions of grandeur, impossible dream, but it is what I want. I’m making the place where the thought is possible. I’m building a house to showcase the tree.
Just by beginning to think about an essay as such—by forming the intention to write on an idea or theme—I’m opening a portal, I’m creating a site, a realm. It’s a place where all my best thinking can go for a period of time, a place where the thoughts can be collected and arranged for more density of meaning. This place necessarily has structure, if it feels like a place.
Another experiment showed people judge houses with greater degrees of transition between inside and outside to be more “houselike.” If there is a courtyard or a partially hidden garden or a curving pathway to the front entrance, the house exhibits more “houseness.” The transitional space makes room for a shift in mood, for what Alexander calls “ambiguous territories” and “intimacy gradients”—increasing degrees of closeness, as you reach the inner realm. The vogue for conversation pits exploited this phenomenon. The act of descending, getting closer to the earth, is metaphysical; it changes how you speak and think. It is literally profound.
From A Year With Swollen Appendices by Brian Eno:
Are humans communicating more than they ever did in the past? Is this process of community forming now in hyperdrive because our old ways of making communities (i.e., by growing up and living and working with other people, or by engaging with them in common causes) are no longer working? Or do we just need more forms of community? And from whence arises this insatiable appetite for constant conversation? Is it a case of, in Eric Hoffer's words, you can never get enough of what you don't really want?
I have a wonderful life. I do pretty much what I want, and the only real problem I ever have is wondering what that is.
If you interact with things in your life, everything is constantly changing. And if nothing changes, you're an idiot.
I really enjoyed Kyle Chayka’s latest piece for The New Yorker about using the Process Zero feature of the Halide camera app for iPhone, which forgoes the AI-powered image processing that iOS applies by default.
My phone camera roll looks different now. There are fewer repeats or slight variations on the same image, taken in a burst. The compositions are less static or symmetrical, and the colors are funkier. I have a Halide snapshot of some leaves casting shadows on a tree’s trunk, which occupies most of the frame. Whereas the Apple phone app tends to turn every color warm, this one is very blue and cool, and the background behind the tree is dim rather than eye-burningly brightened. But I prefer the photo that way: the visual qualities of the specific scene are still there to be appreciated. It doesn’t, and shouldn’t, look like everything else.
I’ve been using Process Zero the past few weeks as my main shooting mode, and I couldn’t agree more. I don’t see myself going back to the iPhone’s default image processing.
It occurs to me that Process Zero is popular for the same reason as Instagram’s original filters—imperfections imbue a kind of personality that feels more human. AI-perfected pixels feel cold and lifeless because they optimize and average away the details, leaving photos without any distinct “vibe.”
The images that an iPhone produces by default are a form of advertising for Apple. Buy an iPhone, snap a photo, and it will always look great. The uniformity of the experience ensures the results are always good, but it has the side effect of preventing them from feeling great.
Apple has a history of sherlocking great features introduced first in third party apps, and I would be very pleased if they decided to bake this into the native camera app.
A good day on the web is one where you stumble across a website that makes you go “woah??” and then “huh…?” followed by a wide grin. I have one of those websites to show you!
Digital Divinity is a really neat project documenting the ways in which new technologies are being incorporated into religious practices. Each entry is accompanied by a lovely illustration from an artist named Glenn Harvey.
Those illustrations are hiding a secret though, one that is only revealed on specific devices under specific conditions.
You might be aware of a visual effect related to HDR videos if you’ve ever scrolled Instagram on your iPhone—the pixels displaying the HDR content display in full brightness, while the rest of the screen is slightly dimmed.
The effect can be disorienting and strange, especially for content that is pure white, which appears as some kind of ultrawhite. It makes other white areas of the screen look pale and pallid.
The illustrations for Digital Divinity make use of this effect in a brilliant (literally) way by masking a pure white, HDR video such that parts of the illustration glow with an ethereal brightness. For devices that support displaying HDR content brighter than the rest of the screen, the effect is stunning.
It’s quite difficult to get an image of the effect that captures the striking glow, so I definitely recommend checking out the site on your own device.
This is the kind of creative touch that makes designing for screens so special: our work gets better when we give ourselves over to the unpredictability of the medium. Many users will never see this effect because their device doesn’t support it, but rather than flattening the experience for consistency the designers behind this project decided to embrace the chaos.
Every device and screen is different, and one of the biggest mistakes we can make in web design is pretending as if we’re creating a singular experience to be experienced uniformly by each user. There are opportunities for delight in the gaps created by our medium’s flexibility.
Kudos to all of the designers who had a hand in this wonderful project.
Who’s out there making new plans and trying new things based on hard-earned experience of life and work in the debris of the internet dream? Can their approaches and countermoves jostle us out of lazy assumptions?
The networks we use to communicate across fields and distances, to find our friends and learn from people unlike ourselves—and to organize ourselves to respond to acute crises and long, grinding institutional failures—are the same networks that are making so many of us miserable and/or deranged.
Traditional media makes lists because platforms don’t, and we need some semblance of cultural map by which to navigate. There are too many lists, but at the same time not enough. I’m afraid that we consume too many of other people’s lists and don’t keep enough of our own.
Because here’s what I’ve learned: if you give your fucks to the unliving—if you plant those fucks in institutions or systems or platforms or, gods forbid, interest rates—you will run out of fucks. One day you will reach into that bag and your hand will meet nothing but air and you will be bereft. You will realize the loss of something you did not know you ever had. But if you give a fuck about the living, about all your living kin in all the kingdoms, they will give a fuck right back.
And yet: as much as the Fediverse is different (the governing structures, the incentives, the moderation, the absence of ads and engagement tricks), so much of it is also unsettlingly familiar—the same small boxes, the same few buttons, the same mechanics of following and being followed. The same babbling, tumbling, rushing stream of thoughts. I can’t tell if we’re stuck with this design because it’s familiar, or if it’s familiar because we’re stuck. Very likely it’s me that’s stuck, fixed in place while everything rushes around me, hoping for a gap, a break, a warm rock to rest awhile on. Longing for a mode of communication that lifts me up instead of wiping me out.
What is the experience of asking for something to appear and then instantly receiving it? What changes between the thought and the manifestation? I fear that nothing changes, that nothing is changed in such a making, least of all ourselves. But then, what does it mean to be unchanged, for your feet to pass so lightly over the ground they don’t so much as disturb the sand? Even the dead make change in the world, as their bodies decay and and are transformed into food for beasts and bugs and trees. But in eliminating the effort, in refusing the temporality of making, the outcome of an “AI”-driven creative process is a phantasm, an unsubstantiality, something that passes through the world without leaving any trace. A root that twists back upon itself and tries to suck the water from its own desiccated veins.
A website is, among other things, a container. The shape of that container both constrains and makes possible what goes within it. This is, I think, one of the primary justifications for having your own website. Not just so you can own your stuff (for some meaning of “ownership,” in a culture in which any billionaire can scrape your work without permission and copyright only protects the rich). Not just so you have a home base among the shifting winds of the various platforms, which rise and fall like brush before the fire. Not just so you can avoid setting up camp in a Nazi bar. But also so that you can shape the work—so that you can give shape to it, and in that shaping make possible work that couldn’t arise elsewhere.
To step into the stream of any social network, to become immersed in the news, reactions, rage and hopes, the marketing and psyops, the funny jokes and clever memes, the earnest requests for mutual aid, for sign ups, for jobs, the clap backs and the call outs, the warnings and invitations—it can feel like a kind of madness. It’s unsettling, in the way that sediment is unsettled by water, lifted up and tossed around, scattered about. A pebble goes wherever the river sends it, worn down and smoothed day after day until all that’s left is sand.
Riley Walz hid a solar powered Android phone in the Mission and set it to run Shazan all day, every day. The result is Bop Spotter, a site listing all of the songs that have been detected.
This is culture surveillance. No one notices, no one consents. But it’s not about catching criminals. It’s about catching vibes. A constant feed of what’s popping off in real-time.
Culture Surveillance is a newsletter to which I would happily subscribe.
Throughout my career as a designer, I’ve experienced a recurring struggle with the concept of process.
I used to look at process as something sacred: a holy calculus through which I could find the right answer to a problem every time. All I needed to do was remember the steps and apply them in just the right way. Wash, rinse, repeat.
Maybe this idea stems from my background in programming, or maybe it’s just an attempt to comfort my own fears and insecurities, but I wanted my work to follow a clearly defined algorithm.
The way I’ve seen great work made isn’t using any sort of design process. It’s skipping steps when we deem them unnecessary. It’s doing them out of order just for the heck of it. It’s backtracking when we’re unsatisfied. It’s changing things after we’ve handed off the design. It’s starting from the solution first. It’s operating on vibes and intuition. It’s making something just for the sake of making people smile. It’s a feeling that we nailed it.
For me, overly relying on process might also have been borne out of a distaste for what I perceive to be the opposite of process: vision. Blue sky design visions, if not done with care, can turn into uninformed expressions of ego and hubris.
If you’ve worked within a large design organization, you’ve probably seen this play out. A designer, usually one with lots of tenure or clout, goes heads down to produce a north star for the design direction of a product that is usually impressive but disconnected from both the needs of users and the realities of building real software.
Visions too often fall out of a coconut tree, not existing within the context of the current product or what came before it. (Sorry, I had to.)
Of course, vision work can be useful as an instigating factor: to excite stakeholders, secure funding, or drive alignment by raising key questions. But too often these visions are taken more seriously than they should, and they get handed down to other teams in place of an actual roadmap.
I think that the act of designing and shipping real solutions happens somewhere in between process and vision. It’s not a carefully defined algorithm, and it’s not a moonshot.
If you want to find a good design—be that the design of a house or an essay, a career or a marriage—what you want is some process that allows you to extract information from the context, and bake it into the form. That is what unfolding is.
Click through for a more details explanation of how unfolding works.
Henrik goes on to say that unfolding is the opposite of vision, but I like to think of vision and rigidly defined process as two ends of a spectrum, with unfolding sitting somewhere in the middle.
The opposite of an unfolding is a vision. A vision springs, not from a careful understanding of a context, but from a fantasy: if you could just make it into another context your problems will go away.
None of this is to say that there is no place for more formal processes. When unfolding a problem we need to establish feedback loops and respond to those in a way that resembles improv, but the act of responding may itself leverage repeatable processes.
We might choose to think about these recurring patterns in our work as frameworks, which are applied to solve specific problems or answer certain questions.
For example: unfolding a problem might present a difficult decision that needs to be made, and that’s when leveraging a decision making framework might be useful.
Should every decision that needs to be made have that framework applied to it? Absolutely not! And it’s our job as designers to know what parts of our work should be scripted and what parts should be improvised.
I’m trying to let go of my conditioning to attack every problem with process, and these ideas are helping me frame my work in a way that invites spontaneity and is less concerned with artifacts of the work that aren’t actual software. Because at the end of the day, any artifact that isn’t the product itself should be in service of the product, not any one person’s process.
I stumbled upon a great site which acts as an explainer for vanilla web development techniques called, well, Plain Vanilla.
When I was starting out as a developer I had a hard time learning the basics of the web platform because so many resources and examples used a framework. It was mostly jQuery at the time, and today I’d assume React and Tailwind are the most common starting points for new developers.
But the web has come a long way! A framework might not be necessary for lots of projects, and going as far as you can with the grain of the web comes with lots of benefits. I’m happy to see a high quality resource like this that can help folks avoid complexity and start simple.
If you don’t tell the story of your life, someone else will do it for you. Google, Instagram, and the sketchy recollections of strangers can offer fragments of a mirrored self. You can dress up in the identities that others draw; you can outsource your memory and legacy to the highest corporate bidder. You can look back through your Oura ring, your credit score, your likes. From Charlie Squire again: “There is museum upon museum dedicated to myself within the geography of my phone, and like all museums they are fallible to misrepresentation and selective curation, and like most museum-goers I choose to believe they are peddling me an objective truth.”
I’m fascinated by the way that CSS, as it becomes more powerful, can be used as a visual language for representing the physical world. Combined with the longevity of the web, which strives to never break backwards compatibility, it’s a powerful tool for sending information into the future.
I grew up dreaming about the esoteric user interfaces seen in science fiction films, many of which featured circular screens, control panels, and UIs. Now we can achieve those with CSS!
I also love the whimsical nature of Orbit’s API, which requires a single “big bang” element on the page, and uses a “gravity-spot” class for creating an area with a radial layout. The library comes with support for adding orbits, slices, satellites, capsules, and more around user-defined gravity spots.
Most importantly, a mountain’s currency is physical labor. I need to hike a lot to get to the vast part. Social media’s currency is time. I don’t need to do much to get there.
My hope is that this is a move to my forever domain, but if someone at JPMorgan Chase wants to chat about donating a better domain, they can find me (and so can you) at [email protected]
I recently showed a few friends around Chicago, and as we passed by the Art Institute and the two lions guarding the entrance, I wondered if they had names like the lion sculptures outside the New York Public Library.
New York’s lions have had several nicknames throughout their lives, but received their current names from Mayor LaGuardia in the 1930s based on the qualities he thought New Yorkers would need to have to survive the depression.
So what about the lions in the second city? Strangely enough, they were also created by a sculptor named Edward.
Edward Kemeys didn’t names to these lions, which took their places in 1894, but did assign them unofficial designations based on their poses. The lion on the north pedestal is “on the prowl,” while the one to the south is “in an attitude of defiance.”
We don’t seem to assign names to the objects around us as much as we used to, but I think it’s an important part of creating meaning and connecting to our environment and our history.
Next time you’re in downtown Chicago, don’t forget to say hi to Prowl and Defiance.
This is how we restore the old internet — not in its original form, but in its glorious, fragmented essence. People call Twitter an indispensable public space because it’s the “town square”, but in the real world there isn’t just one town square, because there isn’t just one town. There are many.
Listeners become alienated from their own tastes; when you never encounter things you don’t like, it’s harder to know what you really do.
Rather than optimizing for the user’s experience, it optimizes for the extraction of profit. If Spotify succeeds at turning us all into passive listeners, then it doesn’t really matter which content the platform licenses. As Fuller put it, “It’s about ‘How do you get through as much music as you can so you keep paying for it?’ ”
Life is not something you perform for the benefit of other people. When you perform for other people, you rob yourself of the chance to relate to them in a real way. Everything collapses inwards, becomes solipsistic: you and the camera, you and the mirror, you and the void. But we need the Other in order to feel real. People are doorways out of solipsism.
The way I’ve seen great work made isn’t using any sort of design process. It’s skipping steps when we deem them unnecessary. It’s doing them out of order just for the heck of it. It’s backtracking when we’re unsatisfied. It’s changing things after we’ve handed off the design. It’s starting from the solution first. It’s operating on vibes and intuition. It’s making something just for the sake of making people smile. It’s a feeling that we nailed it.
Figma announced a host of new AI-powered features this week at their annual conference, and they have been received by designers with both cheer and dismay.
Tools like the ones that were announced are showing up across the industry, but as the most popular tool for modern product design, Figma will make them commonplace, and we’ll soon be taking them for granted just like any other advancement in design tools over the past several decades.
Some folks are panicked, some are excited, and some are indifferent. I’m somewhere in the middle, but I do have concerns that are exacerbated by these new tools and capabilities.
To explain those concerns, I’ll draw a distinction between two types of AI-powered features that Figma announced this week:
Using AI to eliminate or reduce the time spent on constructing designs and prototypes in Figma.
Generating UI designs from scratch, based on a text prompt, using models trained on common product interfaces (and, in the future, the work created by Figma users, unless they opt out).
I’m excited for and have very few concerns about type #1, because the job of product designers is not to create Figma mockups—it’s to solve problems and ship software.
To the degree that new features allow us to spend less time creating ephemeral artifacts that are merely a stop on the way to a final destination, I’m sold.
Those features involve things like automatically wiring up prototypes, filling in a mockup with fake data, translating strings into other languages, automatic layer naming, generating placeholder images, etc. These are all good and helpful, and are geared towards saving designers time to spend on things that they are uniquely positioned poised to do.
But what about type #2, the feature that Figma labels in its UI as “Make designs”? This allows anyone to enter a prompt and have Figma create a mockup from scratch. In the future, the company plans to train their models on designs created by users.
Some are concerned that this type of feature might take jobs away from product designers, and some see it as simply another way to automate away the tedious parts of a designer’s job in order to give them more time to do what they do best.
I think it’s both, and/but I don’t think it’s because of AI.
There are many companies, and the number seems to be increasing, that are more than happy to turn the jobs of designers over to folks who are able to wield tools to produce a facsimile of what a designer is actually capable of.
For those that see the primary value of designers as producing interface mockups, the advent of new AI tools in the vein of Figma’s “make designs” button will absolutely seem like a viable replacement for the work of a designer. And this isn’t limited to AI—as design tools become more accessible and approachable to everyone (which I consider a net positive on the whole), the barrier to creating something that looks, on the surface, like the work of a designer is lowered.
Canva is an excellent example of how this is not strictly because of AI, but might certainly be accelerated by it. The commodification of design as a practice began long before the widespread availability of generative AI.
Product managers, engineers, and others are now able to produce designerly artifacts easier than ever before, and too many companies are willing to accept the sub-par solutions that result in order to cut costs and move faster.
Machines will not make our jobs obsolete, but corporations will, and they’ll use smarter and smarter machines as an excuse to do so.
It would take a lot of thought to detail my research techniques but they include the following imperatives: write early in the morning, cultivate memory, reread core books, take detailed reading notes, work on several projects at once, maintain a thick archive, rotate crops, take a weekly Sabbath, go to bed at the same time, exercise so hard you can’t think during it, talk to different kinds of people including the very young and very old, take words and their histories seriously (i.e., read dictionaries), step outside of the empire of the English language regularly, look for vocabulary from other fields, love the basic, keep your antennae tuned, and seek out contexts of understanding quickly (i.e., use guides, encyclopedias, and Wikipedia without guilt).
Many applications (including Chrome and Firefox) use a font rendering engine called HarfBuzz, and HarfBuzz recently added support for running arbitrary WebAssemply code in order to “shape” the pixels that are drawn onscreen when rendering a font.
You can see the font, llama.ttf, in action in this video.
I wonder if, in the years to come, it might be LLMs that get embedded into all the things.
A smart refrigerator that can reason about what’s inside and maintain a grocery list for you? A font that completes your sentences? A doorbell that answers in your voice and tone when you’re not at home? In-flight entertainment that generate content based on your preferences?
Just so it’s said: creating a design system’s assets has never been the end game, but rather an important foundational layer for other important work to stand on. What you do with the design system is where the excitement and focus should be. Whether it’s the ability to blast out higher-quality work faster than ever, explore new technologies, or spend more time building relationships, the opportunities are many.
One of my favorite forms of online content is when someone finds an interesting, obscure story from the past and manages to extract a lesson that’s widely applicable today.
I like to think of it as something like fan fiction: we, as individuals, retcon and re-tell stories from the past to help us make sense of the present.
It features the story of a king in 18th century Spain who ordered a geographer to create a map. The geographer attempted to delegate this work by asking the priests of towns across the country to create maps of their own provinces.
The idea was to put all of the maps together in the end, but because there was no standardization, all of the maps were created in entirely different forms. Those forms are beautiful! But ultimately not useful as an actual map.
Rather than seeing this as a failure, Elan asks us to consider the things we might be losing when we impose structure, standardization, and process. We might have gained a useful map, but we would have lost the creative perspective that each of the pieces represents.
I’m obsessed with this story because it gets at a dynamic embedded within everything designed that we rarely think about. Once you notice it, it is present in almost every conversation, at every aperture and zoom level: modularity is inversely correlated to expressiveness.
This hit me like a rock, in no small part because of my career focus of choice: design systems.
Fortunately, Elan goes on to reassure me:
I am someone that preaches expressiveness to a fault, but the truth is that I make decisions to scale all the time. I don’t necessarily see this as a compromise of values. There is beauty in trying to express something specific; there is beauty too in finding compromises to create something epic and collective.
In order to succeed in a hypercapitalist society, we must focus. And to focus usually means to specialize: acquiring a skill, becoming a special version of ourselves—a person with a “bit” that distinguishes us from the cross section of people who otherwise share our Google AdSense data metrics. It can be hard work to become this particular, outward-facing self.
To get the AI to do unique things, you need to understand parts of culture more deeply than everyone else using the same AI systems. So now, in many ways, humanities majors can produce some of the most interesting “code.”
When you let people inside your head, they come away smarter. When you work in public, you create an emissary (media cyborg style) that then walks the earth, teaching others to do your kind of work as well. And that is transcendently cool.
Teaching a company to value something it doesn’t care about is considerably the hardest sort of work you can do, and it often fails, so you should do as little of it as you can, but no less.
