Seems obvious, but so many places fail at some, and sometimes all of these.
I love looking at origins of obvious things, because of two things:
I’ve been emulating the Apple Lisa recently, and I was struck by how many of its UI strings were slightly or wholly different than what we’re used to.
It makes sense. Lisa came out in 1983 as Mac’s predecessor and really the first GUI that is directly linked to what we’re using today. Even though it borrowed things from work done at Xerox, tons of conventions were not established yet.
So, I thought it would be fun to actually take a closer look.
For context, Lisa was as slow as it was expensive, and generally considered a failure. It was basically abandoned by 1985. Not much third-party software has ever been written, but Lisa shipped with 7 impressive office apps with fantastic names: LisaWrite, LisaCalc, LisaDraw, LisaGraph, LisaList, LisaProject, and LisaTerminal.
The screenshots below come from an emulator and from manuals (this links to the 1984 version, but each manual also includes a link to the original 1983 edition). The emulator is pretty harrowing; please upvote the idea of Lisa in Infinite Mac if you would want to see it!
As Lisa powers up, we see the appearance of the “wait” dialog box. We’ll encounter more symbols like this triangle, inspired by traditional flowcharts.
Let’s start with menus, as these really were the treasure map to the whole system.
The Desk menu is basically the equivalent of the dock today.
The File menu has Print appended to it, indicating how important printing was still then; a truly “paperless office” won’t really be possible for two more decades (and seemingly still hasn’t fully arrived).
There is no Window menu yet, so the menu also contains some of that burgeoning functionality. Set Aside is what we would call Minimize today. Save & Continue is basically a contemporary Save, and Save & Put Away a hypothetical Save & Close. Revert to Previous Version is the same as today’s Revert. By the way, in the Revert dialog I appreciated the nice gesture of telling the user how much time passed since the last save, and a warning about undo (we’ll get back to this):
Print Current Selection would today be just Print Selection. Print As Is is basically Print… but skipping the setup dialog with number of copies, etc. It was added later in Lisa’s life, and today, we’d probably call it Print Again?
If you’re noticing a pattern already, it is more wordiness compared to what we see these days. It makes sense. Our growing familiarity with these concepts is what will allow these strings to become tighter over time.
This is that Print… dialog, by the way, with beautiful “while you wait” and “while you work” verbiage (although usually I do not condone strings getting so close to each other). The manual explains: “You can have the Lisa use most of its attention to print your document while you wait. A document will print more quickly if you choose While You Wait, but you won’t be able to use the Lisa for any other tasks.”
The other strings feel less typical. Format For Printer… is Page Setup, but with a lot of quirks. Printers were not usually yet WYSIWYG, able to mirror stuff exactly on the screen. They often came with their own fonts, so some matching was necessary:
The manual had an entire section called “When Settings Don’t Match a Printer,” and there were I imagine god knows how many error cases that had to be covered, including:
And Monitor The Printer… is today’s Print Center: a way to see the real-time printing status. Note a lot of writing here elaborates further on the “while you wait/while you work” dichotomy:
Monitor The Printer was important, by the way, since the manual warned you your printer might occasionally become haunted:
But, let’s go back to the File/Print menu. I actually found a version of this menu that comes from a 1982 pre-release Lisa, never launched to the public. Let me show them side by side:
It’s fun to see designers figuring it all out. You will notice the lack of dividers and ellipses actually touching the work-in-progress strings. 1983’s Set Aside is 1982’s very modern Close. Save & Put Away is Put Back. And, at the bottom, it seems the team didn’t yet figure out that the menu options need to consistently use verbs for commands, and adjectives or nouns for toggles – so we see Intended for Printer… (rather than Format For Printer…) and Printing in Progress… (rather than Monitor The Printer…).
Lastly, in a released version of LisaList, this menu would come bearing a harrowing Fix Damaged Document command. Not only it doesn’t even have an ellipsis, but the manual also says “there is always the chance that the recovery process will make things worse instead of better.” Vaya con dios, I suppose.
Let’s move on to the Edit menu.
Today’s Select All is a verbose Select All Of Document, and since this is the first public appearance of undo, that feature is also more descriptive, appearing as Undo Last Change. But otherwise the menu feels surprisingly modern, shortcuts and all.
Unsurprisingly, the first undo wasn’t as developed. We saw earlier in this post “Once you click OK, you will not be able to change your mind, even with Undo,” which today would probably say “This is not undoable.” You could also see a frightening error message arriving without any further clarification, like above.
Sometimes, the app would warn you undo doesn’t have your back. We’ve seen this before, and here’s another example.
Since undo only had one step, LisaCalc and LisaList also had Restore Previous Entry for when you changed your mind after editing a cell in the spreadsheet. You had to employ this strategically, as you did the already-mentioned Revert to Previous Version.
“You can even undo Undo!” bragged the manual, and I imagine there must have been interfaces where undo came without a matching redo. But the eventual solution, of course, was bidirectional undo/redo with many steps. This basically only needed more memory, still very expensive in 1983.
Above we also see Clear Entries that would just be called Clear today.
Elsewhere in Edit menu, Clear Lines Off Top would appear in LisaTerminal only, and was a charming (and I would argue better) way of saying Clear Scrollback.
The next menu, Type Style, would be called Font today. “Type” is typewriter nomenclature – Lisa was meant to be a typewriter replacement. The point/pitch convention for font sizes and letter spacing also comes from typewriters, and in an older version of that menu even font names arrive from that universe (PS = Proportionally Spaced!):
Otherwise, notable is the deterministic Plain Text reset with a P shortcut that would in time lose to printing. I miss this sometimes, this “reset” idea, as I think it would nicely compliment Paste And Match Style.
(By the way, Lisa was the last computer to use Apple logo as a modifier key.)
While Type Style is for selection, Format ¶ is all about paragraphs – HTML people know this distinction as “inline vs. block.” (The pilcrow symbol means “paragraph,” although I did not expect it to be common use even then.) The flyout menus with their convoluted mechanics weren’t invented yet, but in some sense there was no need for them as the options were very limited.
It is interesting to see Margin/Tab Ruler as two options with deterministic shortcuts ([ and ]). But the most unbelievable shortcut must be Same As On Clipboard. It reformats the current selection to match what you have in the clipboard – an early salvo in an endless battle that later brought us Paste Special, Paste And Match Style, Paste And Retain Style, Copy/Paste Properties, Paint Format and so on, and so on. And it was given S, rather than spending it on Save (& Continue).
Otherwise Left Flush and Right Flush would be called aligning today, and the ¶ pilcrow symbol would be replaced by a simple Paragraph Spacing.
In LisaCalc, Format is missing the ¶ because, well, there are no paragraphs in spreadsheets! I love Words Left/Nos. Right, and empathize with trying to align the digits. But it wasn’t even close, was it.
Page Layout shows that we’ve had UI boolean problems from day one. Show Page Ruler and Hide Page Ruler do it deterministically, with one always disabled, and without checkmarks. Preview Pages and Don’t Preview Pages do the checkmark, but introduce a dreaded double negative. (These last options, by the way, is the “pages/pageless format” showing page margins and dividers, that bother us so much about Google Docs.) Today, these would all be in the View menu that doesn’t exist yet.
And speaking of boolean challenges, here are some top-level menus from LisaList with even more conventions:
But, back to the Page Layout Menu. Insert Page Mark would be Insert Page Break today. I really love Allow To Cross Pages as the opposite of Keep On Same Page, and the incredible O and Q shortcuts.
In LisaCalc, this particular menu comes with a beautifully named For Your Information (sentence capped, for some reason)…
…throwing up a sheet-like window showing basic stats. Today, that window would have a more boring name and probably land in the File menu:
The Search menu is fascinating – why wasn’t it called Find like its items are? I am particularly enjoying W keyed off of Find What (today: Find), while F is taken by Find Next Occurrence (today: Find Again). There is some mnemonic sense to it all, but I like today’s proximity of ⌘F/G better.
What we know as Replace is Change here, and I am particularly loving Cases Must Agree and Cases Need Not Agree (today usually called “case sensitivity.”)
Hide Dialog Box is a string with surprising to me amount of UI jargon. The H shortcut was added later in Lisa’s life, presumably at users’ behest. It’s strange today to see a shortcut like this to hide one specific floating dialog box.
Similarly, Insert Wild Card with a confusing ellipsis allows you to insert a symbol in your find dialog that stands for “match anything here” – top-level menu options reaching inside specific dialog boxes were not uncommon in early years of GUIs, but I think fell out of favor over time as the idea can be conceptually confusing.
The menu below is from LisaWrite, and I like how comparing it with other apps makes us see the team trying to settle on a convention. In LisaList there are no ellipsis, but question marks!
And in LisaCalc, there are… both:
You can notice that it wasn’t clear where one would put Find-related commands and their today’s presence in Edit menu doesn’t really make a lot of sense, either. We just got used to it. (Also note the “occurence” typo.)
Spelling menu has a bunch of fun options and conventions, and an extremely generous use of keyboard shortcuts:
LisaDraw sports the Arrangement menu, which will look very familiar to anyone using Illustrator, Sketch, Figma, and so on. This is where Bring To Front and Send To Back started! With a tiny bit of editing (Arrangement is now Arrange, and some of the Objects nouns would be omitted), this would feel pretty modern.
I love these visual menus, and I think we lost that kind of stuff along the way:
Okay, let’s move on from menus. The system also relied a lot of dialogs. Let’s look at some of them:
This wordy dialog would become a small loading state today. The verbose “To terminate the operation, hold down the Apple key while you type a period” probably felt necessary because other than Shift on a typewriter, people were not familiar with modifier keys. Lisa doesn’t have the Esc key, and Mac still respects the ⌘. convention in many places in 2026.
(By the way, why would you want to stop saving? Presumably because it could take quite a while.)
In this similar dialog, you can see a reference to a “micro diskette.” Even though Lisa’s “Twiggy” disks seem gargantuan today, they were smaller compared to the original, 8″ floppy disk. (In a similar way, Lisa and other machines of the era were called “microcomputers.”)
Lisa had some proprioception: In this dialog, the disk put in the first drive is called an “upper diskette.” (Also note: more undo education.)
Disks were not large, so sometimes you had to deal with this kind of horror. It’s interesting how the dialog plain sends you to the manual – an early equivalent to eventual Learn More links.
This is another example of a rather verbose set of instructions. On one hand, this is better than “Error 456” and nothing else. On the other hand, it feels like a lot of stuff to memorize.
Also of note, the beautiful Housekeeping menu. I actually forgot about the Finder (or, in Lisa’s parlance, Desktop), so here’s a screenshot of it also:
Housekeeping was basically the junk drawer – on the Mac a year later, this will be named Special. It also has some stuff that today would be in the View menu. (This later version of Lisa calls Trash the same as the Mac. Earlier on, you would see it named a Wastebasket instead.)
Of note elsewhere in Desktop is the use of the term Stationery, roughly meaning “template,” but with extra sprinkling of desktop-metaphor skeuomorphism. Also, Attributes Of is an early version of Get Info.
Another verbose dialog (compare with Abort/Retry/Ignore from around the same time). This is before we invented hint text that we’d just put under the buttons themselves.
In case you haven’t noticed by now, Lisa’s strings all have two spaces after a full stop!
There was lot of “you cannot” dialogs, walking you through some recovery steps.
Plug and play didn’t yet exist (this would all happen in the 1990s), so that had to be explained also.
I also love the anthropomorphic phrasing “Preferences has been told,” which I don’t believe you see anywhere today.
And I think we can round up this post with a few small delightful language details like this one.
As a huge fan of the slightly pretentious “presently” over “currently,” I smiled seeing this next to the printing status.
“Just a moment, please…” feels so old-fashioned, somehow.
And I want to end on a pre-release version of the Edit menu we’ve already seen. You can spot here Select Entire Document (instead of eventual Select All Of Document), but of course the best thing is the Copy, Cut, & Paste with an ampersand! I find it so, so charming.
I hope you enjoyed this tour. It was interesting to me to see how many of these became the standard back there and then, how many were tweaked a little bit, and which ones had to be redone more thoroughly.
Now, excuse me as I have to go deal with my whistling printer.
I like sharing, thinking about, and revisiting basic rules and principles because they really do ladder up to help you with more complex things down the road.
I wrote before how a simple rule to give some breathing room to your length-limited edit fields can be upleveled to a more general “let me color outside the lines when I’m editing” principle. This is another example of a similar situation.
I am in Buttondown, which is a mailing list software. I created a quick test draft just to check something out in the editor, I didn’t do anything else, and then I proceeded to delete it. Then, I was greeted with this:
This is nothing more than a larger version of the “You have 1 email(s)” problem. There might be a situation when I’m deleting something that has been published and linked to. In that case, it’d be good to know about how any links to that thing will cease working.
But this is not that kind of a situation, and the software has all the info to know that. In this moment, it could show me a simpler, much less alarming message more appropriate to my situation. This is not the end of a radio pharma ad where you have to rattle out all the legal disclaimers just in case something could happen.
One tiny counterexample from my neck of the woods: in Figma, when you start writing a comment and then exit without posting it, you get a little warning. But you don’t get that warning when you type something that’s <= 8 characters. In this case, the assumption is that retyping a few characters elsewhere (assuming you haven’t just changed your mind altogether) is much easier and faster than cognitively processing and dismissing the warning.
The challenge with Buttondown’s dialog is that this is more than just extra cognitive processing and “cheapness.“ Here, the stakes are higher, as we’re talking about something adjacent to data loss; the dialog really does feel a bit scary and makes me think I can do some real damage in a situation no real damage is possible.
I recently installed a screenshotting utility CleanShot, and I was enamored with its settings:
There’s much to like here – thoughtful grouping and layout, good explanations, more details than expected.
There are some nice interaction moments, for example the hints swapping to reflect the current status:
The fact that the tool allows you to override its single-key shortcuts, which are the hardest to change using third-party keyboard customization apps:
Or, when you want to customize the key visualization, Settings shows a nice preview:
There was even this lil molly guard:
But also just the settings themselves gave me a sort of competence contact high. A few clicks in, and I thought “oh, they do know what they’re talking about.” So many things here were for me, to solve specific problems I encountered.
It all gave me confidence this is the right tool for the job. (Also, perhaps a corollary: has there even been a bad tool with well-designed settings?)
Compare with also-new-to-me settings from Affinity, which I was much less impressed with:
It uses the troubled right-aligned style originating in iOS, the capitalization is clumsy, and the navigation muddy (it feels like in-page links on the web, which are always confusing).
Is this a fair comparison? Not at all. I don’t actually want to say that CleanShot is better and Affinity is worse. This is so very much east coast apples and west coast oranges.
I don’t even want to say settings are always worth designing well in the traditional sense; sometimes the only thing between you and 20 unnecessary options in your app is simply having no surface that could host them. A limited (but never unpleasant!) settings UI might be an intentional design decision.
But there was a nice quote in the Shadow of the Colossus book: “I often find myself exploring simply because it’s beautiful.” I too became a tourist in all of CleanShot’s settings because they were put together so well, and I was so curious what’s behind the next corner. Its creators understood that the best way to get to know what the tool is capable of is to take a stroll through the settings. I think it’s a good case study at how a proper welcome mat doesn’t always have to be a few onboarding tooltips flying spastically around the screen. Sometimes it won’t look like a welcome mat at all.
If there was one go-to example of an impenetrable error message in the 1980s, it must have been this – popping up, for example, if your disk drive was dirty:
On some technical level, the options made sense: “Abort” would stop whatever you were doing, “Retry” would try to repeat the action, and “Ignore” would proceed as if there was no error. But in the heat of a moment, or seeing it for the first time, this was a puzzling choice to be asked to make. Not only were the words weighted improperly (the seemingly most innocuous action here, “Ignore,” was actually the only one that could do actual lasting damage), but it also wasn’t entirely clear what’s the safe thing to do to get out of the situation.
(The redesign of “Abort, Retry, Ignore” was “Abort, Retry, Fail,” and it wasn’t really a huge improvement.)
Last night, I installed Google Photos on my iPhone, and the first message that greeted me was this:
This is really a matryoshka doll of bad dialog presentation.
First: any buttons in a dialog should be labeled with enough information to keep me going. Here, both have generic labels, so now I need to pay attention.
Second: Even after reading, I have no idea what is the choice I’m making. I see the pathway marked “yes, keep it the way I had it” and, sure – this would be generally what I want from any given computer on any given Sunday. But what’s the actual alternative?
But the third, and most important one, is this: this dialog has no safe escape hatch. By now, in UX design, we established quite a few canonical escape hatches:
But you can’t × this dialog out. The main button seems positive, but it also feels like I’m taking an action with consequences, and I don’t want to deal with that. There is a “No, thanks,” but it doesn’t feel like the other “No, thankses” I have seen – it’s juxtaposed with copy that makes it seem… a dangerous thing to choose.
And this last bit makes it a pretty serious design offense, because you are now messing with foundational stuff. You need to protect those escape hatches for the future; the moment you introduce hesitation into the mix and taint “No, thanks” as a concept, really bad things will start happening all across your product.
In real life, fire doors have to open outwards when pushed with body weight, aircraft stick shakers are impossible to ignore, and anti-lock braking systems do smart things even after your brain turns off its smart parts.
I know seeing a dialog like this would never happen in a moment of true panic, but sometimes I think of the user in their most absent-minded moment: trying to get their kids to hurry up for school, on hold with an annoying cable provider, with a cat looking like it’s about to jump up directly into a running toaster. A dialog on their phone pops up. If that dialog absolutely has to happen, what is the escape hatch it can offer so they can dismiss it safely if they cannot think about it at all?
This Google Photos screen needs a lot more rethinking and rewriting, but in its current incarnation, it desperately needs a clear and trustworthy escape hatch I can tap absentmindedly, just so I can get to my photos.
I moved Keyboard Maestro app to a different folder as it was running. I gather there must be some technical reason for the app to have to be power cycled, so I appreciated this warning, and the thoughtful bit of copywriting: “Continue” is caveated with “not recommended” so that you feel more comfortable choosing “Quit,” usually the less safe choice. I thought it was a good attempt to add the right scent to the strange options at a strange moment.
(This tradition has reportedly been started by a software company Rogue Amoeba, which wrote about it in 2019.)
I have been at times frustrated by cute placeholder text in places, most notably Dropbox Paper, which still puts them in a just-created doc…
…and in new to-do items:
This bothered me for two reasons.
First was a potential tone mismatch. What if you are writing a layoffs announcement, a project cancellation doc, or something personal and heartfelt? At Medium back in the day, at some point we added a fun celebratory dialog after publishing that said something like “Now, shout it out from the rooftops!” We took it down very quickly as people made us realize Medium is used to write many kinds of things we didn’t anticipate, and in those situations the cutesy message really failed to read the room.
But the other half of my frustration with Paper was that it felt like the app was making itself too comfortable in my space, in effect shouting all over my inner voice and distracting me. I felt like any app giving you a creative canvas should back off of that canvas unless it’s explicitly invited to participate.
Turns out, I can now attach something tangible to that discomfort. From Scientific American earlier this week (emphasis mine):
The researchers asked participants to fill in an online survey with questions about hot-button social and political issues. Some were prompted with an AI autocomplete answer that was deliberately biased toward one side of the issue. For example, participants who were asked whether they agreed that the death penalty should be legal might receive an AI suggestion that disagreed.
Across all the different topics in the survey, participants who saw the AI autocomplete prompts reported attitudes that were more in line with the AI’s position—including people who didn’t use the AI’s suggested text at all. Overall, the study participants who saw the biased AI text shifted their positions toward those espoused by the AI.
Interestingly, the people in the study didn’t tend to think the AI autocomplete suggestions were biased or to notice that they had changed their own thinking on an issue in the course of the study.
The quoted study shows an example…
…and elaborates on how adding warnings didn’t really help:
The Warning and Debrief messages failed to significantly reduce the attitude shift, which is concerning because they were also inspired by those used in real AI applications. AI tools such as ChatGPT show brief and general statements about AI’s propensity to hallucinate false information (e.g., “ChatGPT is AI and can make mistakes. Check important info.”), similar to the messages used in our interventions.
I know on this blog I often focus on the mechanics of interactions, but the job of every designer is to think of more than that. I keep coming back to both pull-to-refresh and infinite scroll mechanics. Both can be put to good use and feel “delightful,” but both started being abused so much that it led to their respective creators disowning them.
Nice, clear, simple copy in ClarisWorks from 1997:
No “Maybe later.” No “Not now.” Thirteen characters. Now, Later, Never.
(Can’t help but notice that Esc and ⌘. – the classic Mac’s equivalent of Esc – still map to Later, however. Also, this breaks the rule of button copy being fully comprehensible without having to read the surrounding strings first, perhaps most well-known as the “avoid «click here»” rule. Never Register/Register Later/Register Now would solve that problem, but wouldn’t look so neat.)
In my head, some bugs belong to categories that feel important, and yet remain hard to define and quantify: embarrassing bugs, dumb bugs, flow killers.
Somewhere in the hard-to-explain space is another tricky category: UI decisions that feel cheap.
The examples of cheapness that come to my mind readily will, I bet, be different for each one of you reading this:
But my absolute #1 go-to example is definitely this:
Computers could pluralize nouns basically for free already in the 1970s, and sure, there are objective arguments of why this is bad, but there’s also this: I wince so hard every time I see something like this.
I think it’s important for every designer to notice when they wince, and teach others how to wince and notice, too.
(I stole the brilliant title from this short post by Joe Leech in 2018, in which Leech uses the word “lazy” rather than “cheap” – they’re related!)
When you start a new game in SimCity 2000 (you can try it in the browser yourself), as the city is generated, you see a few messages fly by: Creating Hills, Tracing Rivers, Smoothing. Among them, for a bit, one can see “Reticulating Splines”:
If it was not obvious from seeing Smoothing followed by More Smoothing and then Yet More Smoothing, the phrase is a joke. From The Official SimCity 2000 Planning Commission Handbook:
“Reticulating splines” is a giant pulling of our legs. Will and some others made up the phrase because they thought it looks and sounds as if it means something. It might: the word “reticulate” means to divide something so that it looks like, or appears to be, a net or a network generating, perhaps, from a single point; a “spline” can be an irregular curve or the approximation of a curve. Individually the terms have meaning. Together – in the case of SimCity 2000 – they don’t. It’s just a prank and a joke.
In some versions of the game, there was also a seductive woman’s voice saying the phrase out loud, which presumably made it even more memorable.
The phrase moved to other Maxis games, notably The Sims…
…and subsequently Minecraft…
…and then tons of other places.
I’ve heard the argument that it wasn’t just Reticulating Splines – that Will Wright’s joke was the beginning of the habit of putting “cute” loading messages in apps, including actual not-game and definitely-not-cute applications. I am 100% sure there are some earlier examples of “funny” loading or error states, but I also see how this one attained a certain critical mass and influence.
I hate these cute loading strings with passion. I think I’m in the minority. It’s a topic for a future time, but it was fun at least to trace some part of its history, sifting through hundreds of pages earnestly explaining the concept of “reticulating splines” to people. Whether they’re in on the joke, I am not sure.
Also, okay. Fair enough. I chuckled just now when I saw this:
This is inside my Sony Alpha camera: a teensy too technical, or maybe slightly-lost-in-translation-from-Japanese message. I love it. It has personality without trying to be cute.
But here’s what modern UI design looks like: There’s always a confusing title; it doesn’t quickly tell me what to do or what it wants me to understand; beneath that there’s a subtitle, explaining the title again; beneath that there’s several sentences that restates the title and subtitle but simply jumbles all the words around to make it justify its existence; then the button—there is always a button—and it asks me to “Confirm” or “Apply” but as to what I’m confirming or applying I have absolutely no idea unless I go back to the text and fight my way through it all again.
Kept nodding through this whole essay. I don’t love nervous user interfaces that share their own problems and insecurities with their users. I love confident interfaces that know exactly what to say, and don’t outstay their welcome.