> no one really complained

They were happy that someone finally made a decision, and freed them from the burden of fruitless repeated deliberation.

Possibly the half year of annoyance helped inform the weeks of opinionated inspiration.

I’d be interested in seeing those if you’re open to sharing.

can you share the icons? curious to see the finished product

I think this spectrum shows the issues with that though. Take the last one, the pen pot. You truly have to _learn_ what that means. Pen pots aren't a thing that most people are familiar with (I've never used one, I don't think my parents generation did mostly either), and there's little explanation of what it is.

Move up just one previous, and you've got a good looking illustration still, the pen and paper, but now a) everyone knows what a pen and paper look like, b) it literally says the name of the app, and c) the yellow colour scheme distinguishes it well when scanning many icons. It's clearly more accessible to new users, existing users, young and old users, and in terms of illustration quality, seems pretty subjective as to whether it's better or worse than the last one.

I am basically icon blind thanks to a couple decades of icon churn

Boring and same. Harder to use. It is for people who organize their books by the color of covers.

icons should prioritize usability first,and design, intersting afterwards.

if your users need billboards, then your job is to make great bill boards

One of my favorite series is Nathan Lowell's Solar Clipper... in In Ashes Born, there's an bit about creating a logo for the company...

    He pointed to the far end of his studio. Two tiny patches of white—which were probably actually gray—lay in a single pool of light. One was a smudge of red and the other was a spiral of red. “Which one of those is your logo?” he asked. 
    “Neither,” Pip said.
    “The smudge,” I said understanding where the kid was taking us.
    “Right,” he said. “The smudge.”
    “What?” Pip asked.
    The kid held up the paper from the workbench. “Look, this is nice and all, but it’s too fussy. If you look at anybody else’s logo, it’s not fussy. It’s iconic. A crown with wings. A C in a circle. That’s yours,” he said to Pip. “All of them are simple shapes combined to form an unmistakable pattern.”

The goal of an icon is to be able to identify it quickly without having to read the associated text.

The inkwell and the two with the paper are artistic - but they aren't things that stand out quickly when you're trying to find them in the launchpad or on the sidebar.

Pages is orange. Numbers is green. iTunes is red. Keynote is blue.

For Microsoft, Word is blue, Excel is green, and Powerpoint is orange (and Outlook has an envelope like shape). The letter reinforces the choice, but that's more of a hint and reinforcement.

The shape and color is the important thing for quickly finding what you're looking for.

Document, pen, orange, and name "Pages" is pretty excellent all round for recognisability in my opinion.

Over the years Word/Powerpoint/Excel have done similar things, they have their own colour, their own name/letter, and usually have had a descriptive graphic in the icon too, indicating a document, grid, or slide.

The office icons are rather subtle but do sorta illustrate what they do if you look carefully - the word icon is a list, the excel icon is a spreadsheet, and the powerpoint icon is a pie chart.

That you have to look closely is kinda crap lol. Whoever designed the icons was more obsessed with consistent branding instead of making icons that make sense.

Looking at the start menu, some MS icons are great. Paint, Notepad, Calculator are all fantastic.

I use macOS and have done so for several years. But I had to look up this app icon to know what app it was. It’s the Pages app, which I don’t use and don’t keep in my dock. Looking at only the leftmost icon, I was thinking it might be the Notes app or the Freeform app, both of which might conceivably also be represented by what to me looks like an Apple Pencil for iPad.

Looking at the reminder of the icons, I recognize that it’s not the Notes app because although I no longer use that one I have in the past so I remember that it has looked like a notepad with some lines and some yellow on it. But the leftmost one might as well have been a newer version of Notes than the one I last used.

The quill and ink at least communicates that it's about writing. The new one is so abstract that when I first looked at it I had no idea what I was even looking at, it certainly doesn't communicate "this is like word" to me. Without comparison to the previous icon, how many people do you think would understand that the bottom line is intended to be a stroke drawn by the pen?