iPadOS 14 is the best digital handwriting yet

I’ve written before about digital handwriting. There have been hundreds of products working on the digital handwriting experience for decades, from the Newton to reMarkable, the promise of a digital device that can truly understand your handwriting still looms large.

This is not a comprehensive review, but a written observation that the Notes app on any modern iPad with an Apple Pencil is my favorite place to handwrite with any type of stylus. The imperceptible latency (partly achieved through iOS 9’s predictive drawing), opening space anywhere in your document, data detectors, & natural selection just by moving your finger & solid OCR for sharing make it best-in-class. Their hard work seriously paid off.

The FiftyThree Pencil still beats Apple Pencil at having an eraser simply on the back of the Pencil itself, instead of the slightly convoluted & difficult-to-explain double-tapping against the Pencil itself. (FiftyThree’s Pencil also had a banging landing page that’s an obvious precursor to Apple’s recent web design; Apple Pencil’s used to be better but never came close to FiftyThree’s. And pour one out for everything FiftyThree’s Paper was 2011–2014—it pioneered a lot of what drawing & writing on the iPad is now, and Muse, GoodNotes, Procreate, even the Apple Pencil are descendants of their remarkable work.)

In addition to the Apple Pencil hardware itself, Apple’s software has its issues as well. Using a Clear-like pinch-to-open gesture to open space instead of the finnicky popup menu + slider would be even more natural & elegant. Being able to drag content like links & photos inline (like Muse) would be even better as well. It’s difficult to read notes handwritten on iPad on iPhone since they’re so scaled down.

Beyond the scope of the iPad itself, we still have no good way of representing handwiting in an accessible, responsive way on the web. This post’s first draft was scribbled in iPadOS 14 Notes, converted to text, then edited & hyperlinked with Markdown/MDX because standard HTML is so drastically easier to publish & read on the web. Unfortunately, the text conversion process takes a hot second for a full document, even on recent A-series chips, & the process of cleaning up the mistakes made by the conversion is almost more frustrating than typing out the whole document fresh.

Combined with iPadOS 14 Scribble, there’s no question we’re making big strides toward having computers that can more naturally understand our chaotic monkey body inputs. But like voice assistants, it sometimes feels like the closer they get & the higher our expectations become, the more continually disappointing they are that we just aren’t there with fluidly understanding human inputs like handwriting. That said, I sometimes have trouble deciphering my own handwriting, so maybe I’m just expecting too much.