Posts about Design

The other night, I was having a couple drinks with some friends who came over to visit. I had only three drinks in the course of an evening, but I guess I was pretty tipsy — apparently your tolerance drops off a cliff in the early days of fatherhood — and I might have ranted a bit about Microsoft (and other things) on Mastodon:

While I’m drinking (in company), does anybody else think about the ribbon UI in Office and how it is a travesty of UI design? Just the worst ideas [sic] ever, and they’ve kept them for decades.

Look, when Apple f’s up, you’re stuck with it for 5 years or so. When Microsoft messes up, contraptions [editor’s note: I don’t even know what I meant here, but it’s definitely an autocorrect error that I didn’t notice at the time], live with it, it must be supported in enterprise until the cockroaches die.

The friggin ribbon bar thing sucks. Kill it already. It’s a usability disaster.

My daughter is 8 weeks old and she’ll grow up with the ribbon.

Going to pretend that Microsoft’s business tanked after Windows 95, and yes, it is very weird they never made a sequel.

My internet friend Declan Chidlow took umbrage with my slightly drunken rant and wrote a rebuttal sharing that the ribbon is good, actually. (I’ll just add that I’m very disappointed that the coolest people I know all live thousands of kilometres away.)

I disagree strongly with Declan, but I want to credit his writing and how thoughtfully he argues his point:

The grouping of related items together in labelled sections helps with association and understanding of function, even when just an icon is shown. The ribbon also at least displays some textual labels, which is nice for usability over everything being an icon.

Being a bit taller, the ribbon also has room to significantly flatten the hierarchy by exposing items users had to go digging for in the menu bar, so feature discoverability is much improved. Contextual tabs that only appear while performing an action that necessitates them also reduce the clutter of appearing toolbars.

He has many more additional points, but I want to do him the credit of encouraging you to read his thoughts in full, rather than reading my abridged version. He also has a number of screenshots of different versions of the ribbon which aid him in sharing his point.

Once you’re done reading that, let me share why the ribbon is a complete travesty.

Since Declan is sharing screenshots, I figure I better share a few of my own. 

When I think about Word, I tend to think about the versions I wrote a lot of school papers in. I was using Windows until high school, so my memories of Word span from Word 95 to around Word 2007 (which is around the time I stopped using Windows and got a Mac).

Declan shared a number of screenshots of just the ribbon, but I think it’s better to show the ribbon in context of the full window. The following screenshots are all sourced from Version Museum’s history of Word (this site is an invaluable resource, holy smokes).

I spent a lot of time as a young child using Word 95 on our Windows 95 machine at the house. (I wrote books in it! When I was eight, I wrote a 600-page fantasy novel. I don’t think it was very good.) Here’s the UI, pre-ribbon:

I will not pretend this is some bastion of glorious design, but at the time, this felt pretty remarkable. The GUI was easy to use, Windows 95 supported real multitasking, and Microsoft was smart enough to ​“borrow” a lot of good ideas from classic Mac OS (or System 5, at the time, since Apple didn’t call it Mac OS until 1996).

Granted, I was four when Windows 95 came out and six when I started using it, so I didn’t have all that context.

As an adult though, it’s obvious to the naked eye. This UI is half baked, and worse than anything Apple would ship under Steve Jobs’ supervision, but I’ll give it a pass for its time. (I don’t love what I call double-decker navigation. More on that later, but this is the early days of the GUI, and everybody was figuring this stuff out in real time, so let’s not rush to judgement just yet.)

A few quick notes, since I can’t resist:

1. There are two separate window controls, stacked on top of each other (see the top right), and that is inexcusably confusing.
2. There are two navigation layers of icons/​buttons, and then above a Mac-style menu control. The menu-control was always excellent (I remember using it!), but two layers of proportionally different controls below was confusing.
3. If you include the menu bar and the page margins, it looks like the control area is about four rows tall, which is a lot of vertical space. This has always been the problem with Microsoft’s Office UI.

I also spent a lot of time with Word 2002, which looks like this:

(Word 2000 looks quite similar, but not quite as nice, and my family never got Word 2000, so I have less experience with it.) 

I think this is a nice improvement. The controls are all in one row, so to speak. Icons are grouped together nicely — bold, italics, and underline controls are right beside font selection, and the new document, save, paste, and undo buttons are all grouped, which makes some sort of sense.

I think Word 2002 is probably peak Word design. I don’t think it gets better than that. The only Word UI that looks better, I think, is Word 1.0 for Mac (in 1985):

Obviously, display and rendering technology had advanced well beyond Word 1.0 by 1995, but this version of Word was ahead of its time and looked fantastic. The simple controls mean that it’s obvious where to go if you want to make changes (the menu bar). Today, an entire cottage industry of Mac text editors (like iA Writer, Ulysses, and Byword) all imitate this minimalist aesthetic.

Word 2003 would carry along the tradition of Word 2002, but with more style and less taste (the blue is a lot and I’m certain it influenced the colours people used in their documents during this period, because blue doesn’t look good with everything).

So let’s say that Word 2002’s design is better. But this isn’t awful. I wrote more than half of my high school essays in Word 2003. It’s nice to see some colour in our user interfaces, so long as that colour is used to differentiate either the app, window, or actions. In the case of Windows, it was just blue. Blue everywhere!

There have been worse sins.

Speaking of, it’s time to talk about the ribbon. The ribbon UI debuted in 2007. Declan has great screenshots. Here’s his screenshot of the ribbon UI. From top to bottom: 2007 on Windows 7, 2010 on Windows 7, 2013 on Windows 10, and Microsoft 365 on Windows 11.

I think it’s important to share the context of the ribbon in the context of the window, so here it is in 2010 (the cleanest screenshot I could find of a non-beta version):

On a widescreen display, vertical space is at a premium. (This is the primary reason I’m a left-dock Mac user on my laptop). This is especially true on Windows, where most displays are 16:9 instead of the taller 16:10 aspect ratio used by Macs.

The ribbon is far too large, eliminating a lot of space that should be used for working on your document.

The UI is also exceptionally strange, and I don’t think it’s user friendly. I think that the more adept the average person becomes at interacting with Office, the less adept they are at navigating the rest of their machine, because the UI is so alien compared to the rest of the operating system.

Declan says the following about the ribbon:

Being a bit taller, the ribbon also has room to significantly flatten the hierarchy by exposing items users had to go digging for in the menu bar, so feature discoverability is much improved. Contextual tabs that only appear while performing an action that necessitates them also reduce the clutter of appearing toolbars.

I disagree with this so strongly. The hierarchy has not been flattened. It’s been rearranged. Clicking Insert doesn’t reveal a menu; it completely changes your navigation. Home has nothing to do with a home; it’s really for text editing. 

So clicking Insert, Page Layout, Mailings, Review, View — that all changes the UI out from under you. I think it messes with your sense of place and space the same way that the ever-changing UI in Adobe’s creative suite makes it difficult to learn. 

But the two rows of buttons is, I think, the greater sin. Particularly over time, as Microsoft removed borders to clearly indicate the boundaries of these buttons. Their groupings largely don’t make sense — bullet points are above left alignment, and text alignment is nowhere near font size like it used to be, for example. 

And some of the buttons are two rows high, indicating their prominence. These buttons are used for Style previews, but they only display six style previews at a time.

I’m not a Word connoisseur (ick), but if you know people who use Word, you know there are two kinds of people:

1. The people who don’t use Styles.
2. The people who use Styles religiously, and have far more than five in a document. (These are the same people who make the presentations that line up perfectly with corporate branding, so I appreciate them as a designer.)

These two groups do not understand one another, and the UI serves neither of them. Styles get in the way of and confuse the first group (“why did my text formatting just change?”), and the people in the second group are frustrated they can only see a few at a time.

Right around this time was when people began to get very frustrated with Word. John Gruber invented Markdown just a few years later. There was a palpable sense that you would buy a Mac if you wanted a good word processing program (Pages), or you might use LibreOffice if you wanted a sane alternative for Windows (I knew many people and corporate environments who were doing this by 2010).

There was this feeling that Word had become too bloated. Nerds complained about the actual bloat in the file sizes, but normal people felt the program itself had become bloated and harder to use. I think the new features in 2007 and beyond were actually fairly narrow, but their arrangement in the ribbon meant that the UI encroached on your work, thus creating a feeling that it was harder to get things done and the program was more bloated than before.

(If this sounds familiar, Apple is experiencing similar complaints with Liquid Glass. If somebody says iOS just feels bloated or harder to use, they are reacting to the same problem — UI interfering with content — but they understandably lack the design vocabulary to voice their concerns with clarity.)

You can see that Microsoft struggled with the information hierarchy in Office 2013.

Note the ALL-CAPS TAB HEADINGS in the screenshot. My experience designing software is that, if you resort to all-caps in your UI, your hierarchy is messed up and you’re struggling to communicate how to use your app. (All-caps is useful in marketing, but not in UI.)

You’ll also note that, as of 2010, FILE came before HOME in the navigation. (What is Home if it’s not the first tab? So strange.)

And if you were to click Review, you would see the deck chairs rearrange and the UI slip out from under you.

There aren’t a lot of screenshots of ribbon menus outside of the Home tab, which is arguably its best conceived tab. The Review menu is a bit of an abomination. Each grouping has its label below the other labels, instead of above. (They can’t be above the others, because the main menu bar is already above the others, so there’s another hierarchy problem.) 

Some of the labels are two lines long, some are one line long. While it’s nice that there are labels, this is unsightly. There’s a three-line menu item for Tracking, which is entirely inscrutable to me.

The labels, the shifting UI, and the hierarchical issues all exist so that these labels and icons can be as large as possible. Clearly somebody at Microsoft thought people couldn’t use computers because the previous layouts, which required you to hover over each icon for a tooltip, were inscrutable. So they went to tremendous lengths to make the labels visible all the time.

But despite all those efforts, the UI is still unknowable and inscrutable. So we have gained nothing, and lost a good deal of the clarity that might exist if the toolbar just followed normal system conventions.

I am not the world’s best designer by any stretch of the imagination, but I feel comfortable saying I would not design this.

The Mac version of Word didn’t get the ribbon bar until 2011. In 2008, while Windows users were adjusting to the new ribbon UI, Word for Mac was much more elegant:

I don’t know about you, but if I need to prepare a document, I can tell you which of these UIs I would vastly prefer. 

This version of Word follows OS X’s general design philosophy. When you look at it, it almost feels inevitable: how else would this be designed? But we have seen how else it could be designed: it could have a ribbon bar.

In 2006, I got my first Mac. I think it was this Core Duo model, in white plastic. (It was before the plastic unibody design, which came a couple years later.) So while I used Word throughout the rest of high school, I didn’t get the ribbon bar on my Mac until 2011. In 2011, I was already using Pages for schoolwork, and Markdown for all my professional writing, so I was happy to let the ribbon pass me by.

Unfortunately, the ribbon bar can’t be viewed in isolation.

In my opinion, the ribbon bar reflects Microsoft’s carelessness. It’s one thing to have bad taste; it’s another to be careless. The visual presentation and organization of the ribbon bar is careless, and it exists so Microsoft can avoid solving the hard problems that come with good interface design.

Millions upon millions of people use Microsoft’s products every day. When the tools you use are carelessly made, and they are the tools your organization wants you to use, the organization conveys the level of expected care and polish for their work too.

If you were a contractor, and you used crummy tools, you would do crummy work. If you worked in an office, and the tools you were asked to use for email, word processing, and presentations were crummy, I believe that would affect your work too.

We talk a lot about how you don’t need great tools to do great work. But the tools we use influence the quality of work we do, and the better the tool, the more likely the work will be good too. This is why so many of us care about the design regressions of Liquid Glass: they will have untold effects on a generation of new designers who have never learned the fundamentals.

UI design isn’t like other areas of graphic design, like illustration, poster design, or other marketing applications. It is testable and knowable. A great amount of care went into prior Mac UIs, and a lot of user testing was done to make the classic Mac and early OS X as good as they were.

I am not aware of Microsoft doing similar work, because they are careless. I believe that attitude has made millions of other people careless. (In Windows 11, the Start Menu includes ads. On my Xbox Series X, half my home screen is filled with ads for Game Pass. At one point, I saw a McDonald’s ad in there. Microsoft wants to show you ads between boss fights. Obviously, this is all in poor taste, but it’s all so careless. Nobody hates their end users more than Microsoft.)

To the degree that the world is getting worse, is it partly because of the billionaires. But it is also because carelessness and apathy have made much of our work redundant and easily replaced with automation. This has affected what we make, how we value each other and our collective humanity, and how we vote and live out our civilian lives in society. 

To blame all of society’s woes on the ribbon bar is obviously dramatic, and I’m not trying to suggest causation. But be aware that the tools you make and use will either better humanity or worsen it. A lack of care in our tools reflects a lack of care for one another.

Nothing is neutral.

The brilliant designer Louie Mantia, writing about a dearth of good design amidst third-party App Store apps, but expressing a sentiment that I think is true about the internet as well:

… software engineers have taken over more of the responsibility of designing apps. That would be great if that meant the overall design of apps has improved, but I think we can see that it has not.

…

Apps should be beautiful. They should be much more beautiful than they are now. Don’t you think so? Years ago, when I worked at Apple, my official role was Visual Designer. Think about that for a minute. I think about it a lot. My job was primarily to make things look good. I would get a wireframe from a UI designer and turn that into something that users want to look at and interact with. (It was a cool job.)

…

Virtually every app is owned and directed by an engineer. (Before you jump in, I know there are exceptions. And I know some are marketing or business-driven.) But designers generally don’t own or direct the apps they work on. At best, they’re still ranked below the engineer who owns the product. It’s been this way for nearly 15 – 20 years. Before that, I think there were a lot more designer-and-engineer partnerships.

…

I don’t know how you feel, but so far the collective output from this experiment has me convinced that this approach is neither financially viable nor a mechanism for making good products. It’s just a lot of people pumping out apps that — generally speaking — no one but them wants to use, because the entire direction of each of these vibe-coded apps only ever seem to satisfy one person, the person who ​“made” it.

The entire post is excellent and well worth your time. I’ve been thinking about it a lot since I read it, and I think he’s right: my experience working with startups and larger firms is that engineers rule the roost, generally. They dictate everything from the frameworks to the UI kits they want to use, and sometimes your job is to assemble a whole from somebody else’s junk bin.

But the rise of LLM-enabled programming has dramatically reduced the UX role. Engineers don’t think they need a designer anymore, because speed is a more important metric for capitalism than usability, which is harder to measure and reaps fewer immediate rewards. 

Earlier this year, I fired a client when they asked me to start designing everything in Claude Code and other similar AI-based design tools. They were hoping designs would be made faster, and that the code would come almost pre-ready after I was done designing.

My mantra was that Claude is about 7x slower than I am (or was; I don’t know if it’s gotten faster), and the output is much worse. I don’t mean to imply that Claude’s output was ​“not bad.” It was awful. At one point while I was trialling it, I asked it to design a new feature for a music venue, and it designed a dating app. When I asked what I did to make it misinterpret my instructions, it told me it executed my instructions perfectly. I am not making this up!

Despite all this, the client told me they wanted me to use AI tools instead, and that they hoped my role would shift to PM.

So I fired them from my client list. 

I was grateful I was in a position to take the financial hit. I felt my business couldn’t succeed, long-term, if I was doing this sort of work.

But in that position, it was obvious that many of these startups and firms don’t care about design. They care about whatever’s hot. For years, the Cool Thing To Do was have a great designer on your team, even if you stonewalled them at every step of the way, because then you could say you were doing the Cool Thing.

Now, the Cool Thing is making everything with AI. And since these companies don’t need to pretend they care about design anymore, their true colours are much more obvious.

Chris Butler’s Design Fiction mood board, largely from sci-fi movies and television, is really fantastic. It’s amazing how far ahead of their time Blade Runner and Alien looked, at least aesthetically. I’m suddenly tempted to make my own mood boards public (but I should not).

Really appreciated Matthias Ott’s take on the new Affinity suite. I love the marketing overall, and Affinity is a great tool for those who don’t want to rely on Adobe, but the now-free price point makes me uncomfortable. 

Edit to add: Jessica Hische, who serves on the Canva Design Advisory Board, posted an encouraging thread about Canva’s intent and goals.

I really enjoyed Nick Heer’s review of iOS and macOS 26. I wish I wrote something as thoughtful; after my summer spent fighting Safari’s new design, I had a lot to say, but I never wrote it down.

The whole thing is worth reading, but I’ll highlight one section I particularly enjoyed. Nick writes about macOS here, but there are many apps in iOS and iPadOS where this same critique could be levied, including Safari. (The emphasis below is mine.)

The way toolbars and their buttons are displayed on MacOS is, at best, something to get used to, though I have tried and failed. Where there was once a solid area for tools has, in many apps, become a gradient with floating buttons. The gradient is both a fill and a progressive blur, which I think is unattractive.

This area is not very tall, which means a significant amount of the document encroaches into its lower half. In light mode, the background of a toolbar is white. The backgrounds of toolbar buttons are also white. Buttons are differentiated by nothing more than a diffuse shadow… the sum of this design language is the continued reduction of contrast in user interface elements to, I think, its detriment.

Apple justifies these decisions by saying its redesigned interfaces are ​“bringing greater focus to content”. I do not accept that explanation. Instead of placing tools in a distinct and separated area, they bleed into your document, thus gaining a similar level of importance as the document itself. … in my experience, the more the interface blends with what I am looking at, the less capable I am of ignoring it. Clarity and structure are sacrificed for the illusion of simplicity offered by a monochromatic haze of an interface.

Even if I bought that argument, I do not understand why it makes sense to make an application’s tools visually recede. While I am sometimes merely viewing a document, I am very often trying to do something to it. I want the most common actions I can take to be immediately obvious.

The passage I emphasized is the very same problem I have with the design, particularly as a designer. When the tools of the OS bleed into my document, particularly when designing a website, my design has to accommodate Apple’s UI, and that deeply frustrates me. 

But Nick also writes about something else vexing. Tools are now hidden in junk drawers, and often more difficult to find. Apple’s software is great graphic design, but it is becoming frustrating interface design. These are different practices, with different goals. Graphic design is intended to draw attention, often for the sake of branding or advertising. Interface design is not unlike designing a hammer: it is the practice of making a tool useful and usable. For Apple’s software to be a great piece of graphic design, but not a great interface design, is a dramatic failure of purpose.

Nick also asks why Apple feels the need to do this now:

Why is this the first time all of the operating systems are marketed with the same version number? And why did Apple decide this was the right time to make a dedicated ​“operating system” section on its website to show how it delivers a ​“more consistent experience” between devices? I have no evidence Apple would want to unify under some kind of ​“Apple OS” branding, but if Apple did want to make such a change, this feels like a very Apple‑y way to soft-launch it. After all, your devices already run specific versions of Safari and Siri without them needing to be called ​“Mac Safari” and ​“Watch Siri”. Just throwing that thought into the wind.

Stop giving them ideas, Nick.

Apple has worked to unify their designs for years, despite the cries from the design community that this is a fruitless idea. Large, multi-window operating systems like the Mac (and now the iPad) naturally demand different interfaces than a modal OS running in a device you hold in your hand. I don’t know why they did this now. I like Craig Hockenberry’s thoughts on this, where he posits that this all might be in preparation for a foldable phone, but I question anybody who thinks Apple plans that far ahead. I think Apple looks 12 – 24 months out at a time, like most organizations I’ve worked with. 

What I’ve pieced together from years of rumours is that Apple started this redesign process shortly after Ive departed. There was a rumour years ago that Apple was working on a design that embraced ​“neumorphism,” which is a word I never hoped to have to spell. 

What Apple ended up with isn’t exactly — look, don’t ask me to spell it again. But it’s not far off. Listen to the criticism of neumorphism, directly quoted from the Wikipedia page:

Neumorphism has received criticism from UI designers, notably for its lack of accessibility, difficulty in implementation, low contrast, and incompatibility with certain brands.

That sounds about like where we’re at to me. From Wikipedia’s Liquid Glass entry:

However, other users noted that certain elements were too transparent, making text difficult to read in low-contrast environments, such as direct sunlight. Designers interviewed by Wired felt that the visual effects distracted from app content. One designer said developers with smaller teams might struggle to meet the high visual standards set by the new interface.

Neumorphism and Liquid Glass are by no means identical, but one could argue they share the same etymology. Based on when neumorphism was trending (2022 and 2023), I’d wager they’ve been working on Liquid Glass for two years. I’d also wager they might have waited another year to ship this redesign, if it weren’t for the disaster that Apple Intelligence was for the company last year. They needed a win.

If Apple was working on this for at least two years, and it involved redesigning everything (including macOS), I’m not convinced it was for a foldable phone. I’m also unconvinced their plan is to make one unified operating system. If I worked at Apple, the major selling point of a cohesive design is a manageable component library. Every large platform I’ve worked on is obsessed with minimizing components across all their apps. Apple makes a lot of operating systems and need to avoid both design and engineering complexity. It is easiest to share parts where they can. 

I don’t think they have a plan. While a unified design library makes sense to me as a design practitioner, I am not certain it works in practice (particularly on macOS). As far as asthetics, I think Apple thinks design is partially fashion, and that they need to be a forward-thinking fashion house. They are not wrong. But is OS 26 forward-thinking or merely a façade? I suspect the latter, but only time will tell.

I read something today that perfectly captures how I feel about artificial intelligence.

According to reporting from The Verge, Monotype (a company I do not like) is really pushing the idea that AI is ​“coming for our fonts.” Which is a gross way to say that AI is coming for type designers, which is a gross thing to publicly get excited about.

Apart from the fact that we continue to discuss AI taking our jobs and our humanity from us (as though it’s desirable), the other problem here is that this future isn’t real. At least, not now:

AI, the report suggests, will make type accessible through ​“intelligent agents and chatbots” and let anyone generate typography regardless of training or design proficiency. How that will be deployed isn’t certain, possibly as part of proprietarily trained apps. Indeed, how any of this will work remains nebulous.

Why Monotype would want to push any of this is beyond me. The Verge mostly attempts to draw similarities between today’s AI proclamations and the effects of industrialization on typography in the early 20^th century. The metaphor is completely broken, because unlike these AI proclamations, the effects of industrialization were actually real.

And then, the money quote. This is in reference to Zeynep Akay, director at typeface design studio Dalton Maag:

“It’s almost as if we are being gaslighted into believing our lives, or our professions, or our creative skills are ephemeral.”

It is exactly this! In a rush to get investor dollars, every company in the world is trying to tell professionals in every space (but particularly in white collar information work) that their jobs, livelihoods, and skill sets are irrelevant in the coming tide.

The current chatbots are useful tools, but any company claiming they’re ​“replacing” workers with AI is attempting to paint a narrative about layoffs with a different colour. The tool just isn’t there. It’s especially not there for any work that requires creative thought, and because the entire AI chain is more or less word prediction based on prior knowledge, there isn’t much chance AI in its current incarnation could design anything actually new.

To put it bluntly, I don’t think there’s a snowball’s chance in hell that AI is designing typefaces for us any time soon.

Adobe announced last week that many popular typefaces from Monotype are now in Adobe Fonts. This is a huge deal to me. 

In their press release, Adobe calls out Helvetica, Gotham, Avenir, Times New Roman, and Arial (I am not sure who would be excited about Times and Arial, but okay). I thought it would be worth sharing a few of the other standouts:

• Akzidenz-Grotesk Next (one of Monotype’s crown jewels, along with Gotham and Helvetica)
• Benton Modern
• Century Gothic
• Hoefler Text
• Neue Frutiger World, which is Frutiger (more or less) with support for additional script languages
• Neue Haas Unica and Neue Haas Grotesk, which (if I recall correctly) were previously part of Adobe Fonts
• Sentinel (another great Hoefler typeface)
• Univers Next (!!!)

This is a great list of typefaces. I was hoping I’d see Frutiger and Univers, but didn’t honestly expect them in the list.

I wish that Adobe would be clearer about their licensing arrangements, though: how long will these typefaces be a part of Adobe Fonts? Will they perpetually be a part of the service, or does Monotype plan on making changes down the line?

I ask because I am increasingly wary of subscription services offering content via license deals. I am immediately tempted to start using Univers for my studio’s brand — because I am a thirsty designer and my use of Graphik is starting to feel stale — but if Monotype pulls Univers Next from the lineup in two years, that would defeat the purpose. Branding should evolve around the needs of a company, not the whims of a type foundry.

I’ve become more familiar with this issue because of services like Xbox Game Pass. I like Game Pass well enough, but every time a third-party game was licensed for the service, I knew there was a secret timer attached to it. I knew I’d be halfway through Lies of P when it was removed from the service — and indeed I was. I never finished it.

I don’t begrudge third-party offerings for leaving a service. I merely want the terms of use and their expiration date to be clear — especially because we’re talking about typefaces used in corporate settings. 

This conversation is even more true because we’re talking about Monotype, a company owned by flea-ridden dirtbag corporate executives and banker types who believe the fastest way to buy a new Lambo is to become litigious about typefaces. (They’re monopolistic buttholes is what I’m saying.)¹

As summer finally breaks and gives way to fall here in Canada, I’ve spent a lot of time at work. The fall is always a busy season for me. It feels like we’re all bracing to huddle up, buckle down, and close up shop for winter mentally.

In the mornings, I catch up on a little reading. I thought I’d share what stood out to me over the past couple weeks below:

1. Cabel Sasser’s talk at the last XOXO was incredibly inspiring. If you haven’t seen it, and you’re interested in art and what we leave behind, I implore you to watch it all the way through to the end.
2. Canada has a long heritage of good design. I’m not joking! There is great stuff everywhere. We have cool brand identities dominating our grocery store aisles. But there is almost nothing more Canadian than the CBC logo. Richard Baird’s retrospective on the history of the logo was illuminating and itself well designed. 
3. Dan Mall, one of the most pioneering digital designers working today, goes on a fall photography trip every year and shares his photos. His photos this year are stunning.
4. “I installed a box high up on a pole somewhere in the Mission of San Francisco. Inside is a crappy Android phone, set to Shazam constantly, 24 hours a day, 7 days a week. It’s solar powered, and the mic is pointed down at the street below.” The Bob Spotter is cultural surveillance designed to capture the music that makes us bob our heads, without anyone’s consent, in an effort to graph our taste culturally rather than individually. I love this experiment; it reminds me of the internet of old. As Alex Cranz recently wrote for The Verge, the internet used to be for horny weirdos and college students, and Bob Spotter feels like it’s reminiscent of that time.
5. David Sparks noticed something at the British Museum in London: the ancient craftsmen were uninterested in perfection. They’re making art that is good enough, but even that art we call timeless. (There is hope for us yet.)
6. Stephen Robles, a YouTuber whose content I don’t watch, recently hit one hundred thousand subscribers. He made a video about getting started on making something with a key message: it’s never too late.
7. In what has clearly been a theme for me over the past two weeks, It’s Nice That published a feature about perfectionism and the way it helps and hurts us, seemingly simultaneously.
8. Nintendo has a music app now, in case you want to listen to any of their absolute bangers from a collection of classic games and franchises while you work.
9. On the topic of music, Apple published a press release this week about how it developed the new hearing aid feature for its AirPods Pro. Granted, this is just a press release, but it’s an inspiring story that reminds me some technology, even in our current age of AI consuming and subsuming all of humanity, is still worth being optimistic about.
10. I recently discovered Hyperessays, the home of Michel de Montaigne’s translated essays on the internet. They’re all very good, but so is the website’s design, which achieves the rarified status of feeling like you’re reading a book.
11. Tim Kreider’s 2012 essay ​“The Busy Trap” is a great read about separating ourselves from our work and our incomes. The entire thing is immensely quotable, the sort of thing you might read aloud to your spouse (if they were into that). My favourite quote is this: ​“The Puritans turned work into a virtue, evidently forgetting that God invented it as a punishment.” This essay is as strong an argument for Universal Basic Income as any could be.

Until next time: stay relentless.

The Verge reports that Adobe and Figma no longer plan to merge, largely thanks to legal pressure from the EU.

First off, this is great news. Adobe acquiring Figma was obviously bad for the industry, at least from the perspective of the designers who work in it. Adobe has a history of buying and subsequently squashing beloved industry tools.

Figma is also the only player keeping Adobe from a total market stranglehold. Bohemian Code’s Sketch would be a player if they offered a Windows app, but they’ve chosen not to pursue that market (and I think missed a big opportunity in the past decade as a result).

For the most part, life now goes on: Figma gets to do their own thing, Adobe does their thing, and all the smaller players (of whom Sketch is probably the biggest) keep doing their things too.

That being said, it’s not all sunshine and roses here. Adobe sunsetted XD, their design tool competitor, shortly after announcing the Figma acquisition. That tool has been dead in the water for a year, with little to no updates in that time. 

I have colleagues who use and like XD who will now have to migrate elsewhere. And let’s not forget the XD team: the folks Adobe had working on XD over the years were all top notch and had great ideas (Khoi Vinh is one of my heroes). I don’t know if those folks are still at Adobe. While life goes on for most of us, this sideshow has caused some actual destruction for a few.

In classic Adobe tradition, nothing meaningful has been accomplished, and a lot of people got hurt along the way.

Dan Mall’s recent post struck a chord with me when I read it. The whole post is worth reading, but in an effort to avoid quoting the entire thing, I’ll simply share his opening statement:

This past week, I finished making a small website for a family member’s business. I had an idea I liked for a subtle header animation. As I sat down to do it, I couldn’t justify how that animation would make the site any better at its job — attracting potential clients — than the static, non-animated version would.

It got me thinking: could I justify an animation for any website’s header? Can anyone justify an animation for a website’s header? A quick glance at the latest Awwwards Site of the Day nominees shows that lots of modern sites have animations in the header. But it is worth the effort to make?

This is something I’ve been thinking about a lot in the past few weeks. Dan acknowledges in his post that, of course, web design has changed a lot. These days, as he says, ​“we live in a world where a Kardashian or a Youtuber can launch a product or even an industry with a tweet or an Instagram post, a role previously dominated by The Website.”

I think there’s another change that happened: websites got a whole heckuva lot easier to make. If a designer’s primary job was to live at the intersection of art and commerce, that job has been eradicated at the low end by shrinking budgets and easy-to-use website builders like Wix and Squarespace.

The remaining websites are either vanity projects for large organizations (designed to attract attention and brand cachet), or they are designed as business tools for whom conversion is their primary purpose. If conversion is the primary purpose, there is less space for design. As Conversion Rate Experts says:

Some people ask why they shouldn’t optimize for function and aesthetics. Even if their visitors are perfectly happy with the current appearance of the website, what’s the harm in being beautiful regardless?

It’s like asking ​“What’s the harm in giving Usain Bolt an egg and spoon to carry while he runs?” They don’t realize that beauty, like an egg and spoon, tends to slow progress to a crawl.

If I’m being very cynical about my own work, I think Amazon has proved that web design is more important than ever, but beauty is less important than it’s ever been.

That doesn’t mean making something beautiful is irrelevant. I’m working on a highly-polished website for a non-profit right now. Their design has a lot of attention-catching elements (several are mentioned on this list), and even relies on a motif. That being said, the non-profit sector is a space where cohesive design goes a long way to generating goodwill from potential donors.

I don’t entirely know where I’m going with this, but I do know that web design is still a young field. I think the jury is out on whether or not good design can have a negative impact on conversion, which is really what people pay for. (If you spend a bunch of money on a site, but get no return on that investment, you are probably not getting what you pay for.)

That all being said, I think the days of being in this for the art — like a modern-day Andy Warhol — are mostly behind us. All that matters is the conversion rate. Usually, we aren’t hired to make art. I too hunt for those jobs, but I increasingly feel like a hungry lion in the jungle craving a penguin.

I am in love with Name Sans, ArrowType’s metro-inspired typeface. Not only is the typeface really good, but the web page is nice too. A lot of type foundries have websites that are borderline unusable, but this is simple and demonstrates what makes the face unique, all without making me feel like I’m entered a funhouse.

When I lived in Toronto, I was fascinated by the typography in the subway system. A lot of the type was rendered in Helvetica or Univers, but some of the walls used ​“Toronto Subway,” a bespoke typeface originally designed in the 1950s, but redesigned in 2004 by David Verschagin because the original design was missing characters, and nobody knew who the original designer was.

Here’s a quote from Wikipedia’s article on the topic:

The font was recreated by David Vereschagin in 2004. Because the original designer of the font is unknown, and no documentation of the font had been kept, Vereschagin digitized the font by visiting stations and making rubbings of the letters on the original Vitrolite glass tiles as well as taking photographs. This is now used by the TTC as their font for station names. Vereschagin designed a matching lowercase, inspired by Futura and other similar designs. As one of the few typeface designs to have originated in Canada, it was used in a number of zines as a mark of local pride.

You can purchase Toronto Subway from Fontspring.

Joe Clark has also written a great paper on the topic (in fact, it might be one of my favourite research papers I’ve ever read on the internet). According to him, Toronto’s subway typography involves the aforementioned typeface of unknown origin, subways lined with washroom tiles, a billion-dollar New York subway design system clone, a new design system from a wayfinding expert that was installed, tested, and ignored, and ​“a billion-dollar corporation that uses as its main font a Helvetica clone that came free with Corel- Draw.” 

The most wild thing about Joe’s well-researched story is how all the half-finished design systems lurk across the city after decades. I lived there from 2015 – 2021, and I can confirm all these systems were never replaced or updated. It is not cohesive, and it makes the subway very confusing for people who are new to the city. In fact, people who are new to the city often can’t explain why they’re so confused by the subway system, the same way most of us can’t explain why inconsistent branding throws us off. But the inconsistent designs have left Torontonians confused for decades.

This one story is a perfect metaphor for Canadian politics: indecisiveness, a lack of vision, a lack of clarity, and occasional deceptive appearances of forward progress and momentum.

Ever since learning all this, I’ve paid a lot of attention to subway type. Name Sans is one of the better ones I’ve come across. It’s playful enough that you could use it for branding, but I think it’d make for good signage too.

I really loved Dan Mall’s latest post about answers to common design questions. Exactly the sort of thing I wish I came up with.

I’ve always found the work of design to be difficult. 

When I started working as a designer, it was difficult because I didn’t know what I was doing. I was tripping and stumbling in the dark, messing around in Photoshop and InDesign, trying to lay out magazine ads and technical manuals proficiently. I don’t think the work was particularly good; I may have had good taste, but I lacked the required skills to get there. 

Now that I’ve been working as a designer for over nine years — ten in October! — the primary challenges are different. As I get older, the blank page becomes more daunting, probably because I don’t want to repeat myself. I’d rather be like George Carlin and come up with new material for every project. But even once we get passed the blank page (try pen and paper first), the middle — the process — is hard. Design is not a straight line.

Good design resources about the process are scarce. I assume every designer struggles with this (especially post-COVID, when so many work alone from home with less immediate feedback), but none of us share the struggle in the messy middle. We just share the beautiful end results in our portfolio. 

In that respect, design is an odd creative field. Authors love to write books about their writing process. Filmmakers make documentaries exploring their craft. Musicians release demos as bonus tracks. But designers don’t share the process. We hide it like it’s some trade secret. Even Dribbble, ostensibly a platform where we can share ​“what we’re working on,” is mostly used to share work we’ve finished.

The process is ignored.

My favourite video on the internet is Aaron Draplin taking on a logo challenge from Lynda (now LinkedIn Learning). I watch the video every time I get stuck, so I’ve seen it a few times: Draplin makes jokes, draws freely, zips around Adobe Illustrator and, most importantly, talks about all the cool stuff he has lying around his workspace.

The first several times I watched the video, I was amazed by the amount of junk Draplin collects (and worried that a key part of success as a great designer would involve becoming a pack rat). But I eventually realized that Draplin isn’t collecting these knickknacks; he’s noticing them. That act of noticing – of focused observation – is his process.

I think we as an industry could do a better job sharing how we work. A few years ago, I audibly groaned when a friend who was new to the design industry asked if I preferred Sketch or Figma. (I was kind of a jerk, I know. Dear friend, if you’re reading this, I’m sorry.) That question isn’t particularly interesting to me, although I think the evolution of our tools and the impact they have on us is worth watching and considering.

The questions that I think are most important: how do we do the work? How do we create focus? Where do we get our inspiration from? How do we survive the middle?

For years now, we’ve heard new conventional wisdom from all the creative gurus: ​“the tools don’t matter. You have everything you need to make what you want to make.”

It probably won’t be surprising to long-time readers of this site that I feel the opposite is true. The tools reveal the process, or at least imply our process. There is no right or wrong tool, so much as there are right or wrong tools for us.

No tool makes you better at your job, but the good ones make your job better. If you do high-end work with computers, a fast computer will always be a good tool. The right kitchen tools make cooking easier, or at least more fun. A good desk chair literally saves your body. Any tool that motivates you to do more of the thing you love has value.

George R.R. Martin does all his writing (very slowly) with a DOS word processor. Specifically, he uses WordStar 4. That looks something like this. One could make an argument it’s not the best tool for the job. But it’s his process. The tool merely reveals his priorities.

On the other hand, tools that get in the way have no value at all. I recently auditioned Sketch for the first time in years. Since 2019, I’ve used Figma with all my clients. In 2019, these apps were quite similar, but since then, Figma has completely leapfrogged Sketch. Things that used to take me ten minutes to do in Sketch take ten seconds in Figma. This audition was incredibly revealing of how the tools have changed, how my process has changed, and how my work has changed.

But it got me thinking: does the tool change me? Does it change my output? Are all my designs just huge Auto Layout demos?

Constraints breed creativity. What do the tools breed in us?

Copywriters have something they call a swipe file — a place they store bits of marketing and writing material they want to refer to later for inspiration. Austin Kleon’s Steal Like An Artist Journal includes its own swipe file.

Commonplace books have a similar idea: it’s a place to store your favourite stuff other people make. H.P. Lovecraft kept one. Ryan Holiday called his ​“a project for a lifetime.”

You have to make your own wells of inspiration.

For many years, when I saw designs I liked and wanted to save for later reference, I would use Pinterest to save it, or simply take a screenshot and stick a copy of it in my Mac’s hard drive somewhere. (The latter is a much better solution than the former.)

Of course, a screenshot isn’t really enough. A good swipe file tells you where your inspiration comes from. It should include notes. Maybe even a full taxonomy. At that point, your basic file browser ain’t going to cut it. There’s no way to serendipitously discover things in the Finder.

These days, I like using Eagle, a macOS app that does a great job organizing all the visual media it saves. With support for everything from pictures to videos to full webpages, I think the app is a godsend. I was suspicious of it at first, mostly because it seemed to good be true, but it has survived three computers and a silicon transition without losing a single image, so I’m pretty confident in it these days.

It’s unfortunately Mac only, but it’s a darn good Mac app (if you like Mac-assed Mac apps). If you’re a Windows person or love your iPad for this sort of thing, I can’t help you. But I’d love to hear what you use.