While writing up my thoughts on what a notes app is, I had a thought about my own genesis of where and I why I developed this predilection.

My first portable device was a Handspring Visor. I did have a laptop at the time as my main machine, but wifi was anything but ubiquitous, and the notion of typing notes in class (I was in grad school) never really occurred to me. in fact, at the time, it was sort of odd to see someone using a laptop in class.

I really enjoyed using the Visor; it was small, kind of hot at the time (everyone was into Palm Pilots and Handsprings and shortly after, Compaq and Dell handheld PCs). It synced with your Mac, so your calendar events and contacts and to-dos were always with you. Assuming the sync went as expected, of course.

The issue with the Palm handheld was the alphabet you had to learn to enter input into the device. Called Graffiti, it was a modified version of English print that required you to write individual letters without lifting the stylus from the screen.

Palm’s Graffiti Character Set

This was hard for two reasons: first, you had to learn new gestures for characters you had been writing to everyone’s satisfaction since elementary school. Second, even when the letter or character was gesturally identical to the printed alphabet you knew, you sometimes had to learn a new way of transmitting it to the screen. So for example, Z was basically still Z, but A? A missed the crossbar between the legs, and you just wrote an upside-down V. Super weird. And let’s not forget the handwriting input area: you had to write letters to the left of a subset of the screen, not directly on the page where you would eventually see the notes, and numbers to the right. And never the twain shall meet: Palm’s OS didn’t recognize alphabet characters on the numerical side, and vice versa.

Palm did replace Graffiti with a previously competing product called Jot, which allowed for multiple strokes in a character, and did not object to the stylus lifting off of the screen. What’s more, you could write anywhere on the screen, obviating a third of your digitizer in favor of a more natural handwriting process.

I had actually purchased Jot, because using regular Graffiti was crazy-making. Jot was immediately better and “right” in a sense. Palm rebranded it as Graffiti 2, making it a bit simpler than Jot, but it was a marked improvement from the original.

Me, being curious about technology, started peeking around on eBay in 2002 at Apple MessagePads (aka Newtons). I was able to get a fairly worn out MessagePad 2100 as my first device of that make and model. I opened the box when it arrived and attempted to apply my Jot/Graffiti 2 skills to the screen, and initially concluded that the Newton must have been broken: the digital recognizer made odd lines and marks on the screen, and then attempted to interpret my handwriting, but my message was not getting across to this newish device.

I learned by watching the tutorials on device, though, that you just used your natural handwriting. And it got better as you used it; you could tell NewtonOS what you meant to write, helping it learn your particular version of print or cursive (yes, cursive was supported too), but it would make guesses about what you were trying to convey as well. My impression of the device went from “this is broken” to “this is amazing.” It was truly remarkable to write with, and like coding up a page and then seeing it rendered in your web browser or spit out of LaTex and into a PDF, its own brand of satisfaction seeing your handwritten words converted into digital text.

Newton OS did another cool thing: interpreted what you wrote into other kinds of data. If you wrote “Lunch with John at noon on Thursday” in the notes app, the MessagePad would offer to create a calendar event for you in the calendar application. It did the same with tasks. While these features often worked and made for a great demo, they could be fiddly and not always work the way you wanted them to.

I remember being so excited about the possibility of using this device, and the handwriting support and translation features, that I wrote up a quick note of what I thought “Newton 2.0” might look like were Apple to resurrect the idea of a handheld computer again in the new millennium. That, of course, didn’t happen, although there was a brief moment there where the “iWalk” device rumors and fake images started popping up on the internet. I was really excited about the possibility of an iWalk.

Apple’s Rumored “iWalk” Device

There has never been an iWalk, but there was an iPod, and shortly after that, of course, the iPhone. As Steve Jobs famously quipped about the iPhone’s competitors, though, “if you see a stylus, you know they blew it.” I didn’t share his dismissal of the stylus at all; I liked the idea of pen-based input, but did understand why the technology’s execution wasn’t as good as its promise.

And the size of the original iPhone didn’t lend itself very well to handwriting. But the iPad? That seemed like a no-brainer. A number of styli leapt into the void that Apple left in not supporting pen-based input on iOS, including the Studio Neat Cosmonaut. But writing on the screen with a capacitive stylus never felt like Newton OS’s implementation, and it was frustrating to know that the technology existed in Cupertino but languished on a digital shelf.

Handwriting support on the iPad has iterated slowly but steadily in the intervening years. Apple eventually supported digital conversion of inked text into typewritten text across the OS, which was a neat first step. But using handwriting that way never really jibed with my evolving preferences, and wondering if the text would be rendered correctly was (and remains) additional cognitive overhead in something that should be effortless and natural: taking handwritten notes.

Apps like Notability and GoodNotes were better than Apple’s own Notes app for a long time regarding accepting handwriting. Notability put a good inking experience at the forefront of their app, while GoodNotes focused more on conversion. I got to a point where I felt that perhaps the best way to take notes, with my first iPad Pro with a 120 Hz refresh rate, might just be Notability. That phase was short-lived, because text input was so far in the rear view for that app that I didn’t like it. I wanted to be able to print, but I also wanted to be able to type when that made the most sense. And in many cases, I wanted something that supported mixed usage: I’ll write on the go with the Apple Pencil, but when I’m seated at my desk or doing something more long form, I’ll type. If I saw a passage online that I wanted to copy, I wanted to select the text and copy/paste, not reprint.

I still really like Notability, but I don’t use it. I would still be using OneNote, were it not for Smart Script. That feature alone puts an iPad+Pencil+Apple Notes in the top spot for me now. In fact, I’d prefer a Surface Pro and OneNote were it not for Smart Script. It just makes writing more enjoyable.

There are still features that Newton OS offered that the much more powerful iPad doesn’t do. The Notes app doesn’t function as the central experience of using the iPad, where that was more the case with the Newton. And that’s not necessarily the right thing for the iPad; it’s a very serviceable laptop when that form factor is most appropriate, for example.

But that’s where so much of my hope in the potential of the iPad lies: the old technology found in the Newton. I loved using the device, but was often flummoxed by its limitations.

So, too, I suppose, with the iPad. And Notes.