San Francisco, California

A Rocket-Powered Jumbo Jet

I was about to get my ass kicked. The design critique had barely started and yet I knew that my designs weren’t good enough; I watched as my mentor’s eyes narrowed and then focused into a point the same way that a hawk scans a field from three miles away.

My work was the rabbit and I had made a terrible mistake.

As the feedback unrolled and intensified, each part of my design was torn to pieces and it dawned on me just how much I had half-assed this project. I melted in my chair and whilst I was slumping towards the ground, my pal John took a screenshot as my spirit left my body.

In my defense, I’m not making this expression because I hate criticism. I’m becoming a goo monster here because I could see all the holes in my logic and it was thoroughly embarrassing. Anyone having their work trashed in a public space will be made uncomfortable by it but half my job as a designer should be to think clearly, to step through a problem with unwavering logic and attention. Designers ought to be able to see problems, eloquently give the necessary context, form simple solutions, and to make a damn fine argument about why this is the best way forward.

And, well, my argument was extremely bad.

As the Great Slumping began I realized I had made the rookiest of mistakes by spending too much time moving pixels about in Figma. Things sure looked pretty, but they didn’t make sense. And I could now see from the hawk’s perspective: I had to admit in a room full of people that I hadn’t understood the problem correctly, that the UI was weak because my thoughts weren’t clear enough.

“None of this makes sense,” my mentor sighed.

Now usually when giving feedback to other people, my mentor is somewhat reserved and nice but with me she lets it fly because we trust each other. It can hurt an awful lot disappointing her, yes. But it’s important for me to grasp what she sees and this form of bluntness is the fastest way for us to get there. This feedback is probably what most people would consider to be hell itself—the absolute opposite of nice—but strangely enough I find it to be overwhelmingly kind. To be this blunt with someone and know that it won’t hurt their ego, this kind of feedback is a blessing.

A form of respect.

The misstep I had made is a common one, and a lesson I must learn over and over again. I had forgotten that there are two modes of design, just as there is in writing.

The first mode is understanding the problem, getting a ten-thousand foot view of the land. It’s getting people to acknowledge that this really is the problem we need to agree upon. This work needs to happen in a sketchbook in the form of messy, back-of-the-napkin drawings or in writing. All this helps you to form a proper argument and focus your thoughts.

The second mode of design is taking that ten-thousand foot view and zooming all the way in to the hairs on the back of the rabbit; figuring out the precise UI and components, the copywriting, the animations, the everything else. This should be done in a design tool like Figma or Sketch. And this is when we should be talking about color palettes, icons, design systems, and consistency.

The problem with almost all design work is that first phase never really happens. People don’t take that ten thousand foot view of the problem and are focusing instead on the pixels; they’re trapped by the system they know too well.

Junior designers (like me) tend to forget that when you’re thinking about UX you should ignore the design tools. Figma and Sketch are useless in the first mode of design because you can spend hours in those pixel-perfect design tools aligning tables and futzing with icons, worrying about the leading and spacing and margins between things, without understanding the actual problem.

But the pixels do not matter. Not yet.

Instead we must learn to sketch, we must draft and draft and draft again until it hurts. We must then show engineers and product managers those ugly drafts, too. We must think about the problem from every angle, and we must avoid being precious with our work.

I think people get stuck in that second mode because productivity in design is often tied to “how many pages or frames did I design today?” when productivity should instead be thought of as “how did my understanding of the problem change?” Does your brain hurt from thinking and being confused and talking about the problem, or asking endless questions about it?

That’s the sign of true progress, as much as it might hurt.

So this is the pickle I found myself in the other day. I suddenly realized that the tools I had been using were forming my thoughts, trapping me in a certain mode of thinking. The physical keyboard, and Figma, and knowing too much about the code, everything had been pushing me down a certain path that I couldn’t avoid.

So the tools had to go.

Sketching was the solution and showing people those nasty little drawings. I needed folks to review them first, before I head into production-level mockups where I tend to get distracted by the UI. This way I expected to save tons of time moving borders and boxes around and hopefully people would give more honest feedback because they can see that all of this is temporary. At any moment we can change things with a sketch.

How do you go about sketching like this though? Well, after looking around at the tools out there I went ahead and did the most boring thing imaginable; I ordered the big iPad Pro, the Apple Pencil, and the Magic Keyboard.

I exhaled aloud as I bought the thing. How excruciatingly boring.

I’m not an artist and cannot draw to save my life but perhaps this would help though. I would get this thing and it’d just be another iPad, another big dumb expensive tool that could support my work and help me escape that second mode of design. It’d be fine, but I knew for a fact that it wouldn’t be anything special.

But shortly after it arrived, I found myself...lost.

I was entirely, thoroughly, exponentially woo’d. After a few hours using this device—switching from sketching to typing to tapping on the screen—I realized that this is the most exciting computer I’ve used in more than decade. Perhaps since the Kindle? After two short days of using this thing full time, all my opinions flipped upside down and inside out. And I know this is turning into a clickbait post about How X is the Future of Y but I truly do believe now that this is how design should be done. Laptops are simply the wrong tool for the job. They help with production but they do not help with understanding problems.

Let me explain.

First off I downloaded Paper, a sketching app that I had used years ago. It’s formed around the idea of Journals and within each of them I realized I could treat them like a sketchbook. I could brainstorm first and write notes. I could combine it with Safari to take screenshots from the Sentry app, throw them into a Journal, and then make messy designs on top of them.

The reason why Paper is so damn good is because it’s not a sketching app though. It’s secretly another kind of app altogether...

I realized that half my problem when it comes to design is that I’m terrible at giving context. In design crits I can’t seem to find the right words—why did I do this, why does it help? But I avoided making formal presentations because those absolutely suck and exporting things from Figma into Google Slides is exhausting and a lot of dumb, stupid work.

But—then it struck me—what if I treated Paper like an essay or, better yet, like a keynote?

After braintstorming ideas, I would slowly morph each idea into a slide with a single bit of information that I could then share with folks during design crit. After organizing things in this way I found that Paper is the best slidedeck app I’ve ever used. I could share the screen of my iPad and flip forward between the pages of the Journal as I go, jotting down feedback or notes on the slide itself. Each slidedeck is a sketchbook, every journal contains the problem, the context, and eventually the very rough solution that I want us all to talk about. And at no point in this process have I touched a laptop.

This reminds me that at the beginning of the quarantine I was playing a DnD-like game with Jez and he was the Dungeon Master. He shared his screen to show our crew a map that he had drawn and with each new development in the fight or the story he would show where each of us stood and where the enemies were, and it suddenly made the world so much more real.

I wanted to do the same for my designs. To share the screen on the iPad you can plug it into your Mac and open up Quicktime > Create a New Movie. From here you can select the iPad as the source and then share your screen with any video app like Google Meet or Zoom. It is absolutely remarkable and I’m upset I didn’t think of this sooner. Flipping through a notebook in a design crit is the way this should work.

Also, side note, the tools in the Paper app are perfect for making quick wireframes for things, too. There’s one tool which fills in color and it is magic and genuinely ingenious.

Also also: being able to draw well with Paper is not really the point. You don’t need to be able to draw to be a designer, you just need to be willing to think about problems intensely. Look, I will prove it. Examine this absolute crap design I made earlier:

A bad drawing in the Paper app for the iPad Pro

Is it beautiful? No. Can I draw a straight line to save my life? Also no. Does this look like a sketch you’d find on the back of a toilet stall? Absolutely yes.

But that’s not the point! In search of great design we must forego being pretty for being understood. And this setup—the pencil, the iPad Pro, the Paper app, and the Magic Keyboard—becomes the perfect way for me to lock myself into the first mode of design until the time is right to zoom in.

After my first experiment with this stuff this morning I had a ton of feedback and it was unanimous: this way of making designs and presenting them helps me focus, helps me communicate, guiding my hand as I walk through the problems and the potential solutions to them.

But wait, where does the Magic Keyboard come into this though? Well.

When I first heard of the Magic Keyboard I scoffed aloud because it’s horribly overpriced and is made of that same nasty plastic material they use for their old iPad covers. Nah, I’m good mate, I thought rather obnoxiously.

But! The Magic Keyboard changes everything. And I feel like a terrible-tech-daddy-shill for saying this, but it’s true. The Magic Keyboard feels like a Kindle in the same way that you’re not precious about it. It is designed to get a job done and it feels like a keyboard from those old plastic laptops made for kids back in the 90s. It is familiar and warm and somehow...better than a laptop keyboard (?) because it’s so much closer to the table that your wrists don’t have to arch up slightly to type.

Sketching an idea, then snapping the iPad back onto the keyboard to record a longer paragraph of text, is’s not just how design should work. It’s what we ought to expect of computers in general.

The Magic Keyboard by itself is nothing more than an expensive keyboard. The Apple Pencil by itself is nothing more than a fancy and expensive stylus. The iPad Pro by itself is nothing more than an expensive, bigger tablet.

But together, this fabulous system emerges. I can hop into a text file, edit things on my site, and then I can pop the iPad out and sit on my couch and sketch out UI ideas without having to be precious about them. I can share my screen with distant colleagues and scratch notes and improvements that need to be made. With the Files app and iPhoto, sharing bits of data back and forth between people is almost perfect.

It is serious bicycle-of-the-mind type stuff.

This reminds me of seeing the iPhone for the first time; I genuinely didn’t care. Eh. It has a touch screen, sure, but it’s expensive. There’s so few apps, it has a broken web browser where I have to zoom in all the time. The things are cool and interesting but the system is bad. Not bicycle-of-the-mind at least.

And then the second generation iPod Touch came out. By that time the App Store had released, the device wasn’t tethered to a network but you could use WiFi, responsive design had swept the world, and a million iterative improvements had suddenly made the device this glorious, perfect machine. All the constituent parts made sense and improved all the other parts in the system. Absolutely perfect, bicycle-of-the-mind.

The Apple Watch right now is just before that stage, I think. It‘s mostly useless except for the calorie counting stuff. Notifications are a bad and a stressful idea. Phone calls on it don’t really make sense (yet?). Other apps don’t make sense for it either, to me at least. But maybe in a few years all these disparate, clunky, half-finished parts will click satisfyingly together and then—boom!

This is the space where the iPad Pro, the Apple Pencil, and the Magic Keyboard, occupies today. They’re not just another way to do laptop-things-on-the-go. It lets me perform entirely non-laptop actions.

It’s not even a bicycle-for-the-mind, it’s a rocket powered jumbo jet; this little machine is what every computer should aspire to be.