As you know, I am a big advocate of writing on paper with a pen. Many studies have shown that we learn and retain more information when we write with our hands. Sure typing can let us capture more information, but writing gives more cognitive context. Today, we mostly type on our keyboards. Some of us have started to use Apple iPad and the Apple Pencil. Jon Callaghan, my partner at True Ventures, is an unabashed fan of Remarkable.

The challenge with these digital writing devices is that they are a “one size fits all” solution. In the analog world, writing instruments are highly personal, and each one fits our unique writing styles, and where we fall in the demographic spectrum — age, gender, and geographic locations define what we use to write. Writing surfaces, aka the paper we like, too are highly personal.

I personally prefer fountain pens and good Japanese paper — and despite using the iPad for pretty much everything, I don’t much care for writing with the Apple Pencil. I like my pens, big and thick, like Sailor King of Pen and a vintage Montblanc 149. The Pencil is too thin and too slippery, and as a result, it is nothing more than an appendage used for photo editing. Navigation with touch and gestures is better on iPad, which was built for touch, not for pencils.

“You have to get ’em, put ’em away, you lose ’em. Yuck! Nobody wants a stylus. So let’s not use a stylus.”

Steve Jobs, co-founder, Apple.

It is not just Apple’s Pencil — I have never linked any of the digital handwriting devices, including the not-so-great digital writing devices made by luxury pen brand, Montblanc. Personal distaste aside, there is something else that ails the digital writing domain. Ben Brooks’ in his member newsletter, explains this problem with digital devices.

Digital note taking tools all lack universality of pen and paper. It doesn’t matter where in the world you go with pen and paper, you can write on many surfaces, and you can pass off the paper to anyone no matter what tech access they have. It’s truly universal. And this is what bothers me about digital notes: they are proprietary. The Apple Pencil only works with Apple iPads, and other Styli only work with their gear. And none of them work with paper. But they are all needed to make those tools work well.

The Brooks Review
white pen on white table

Beyond that lack of interoperability, another elephant in the room is the very future of the Apple Pencil and the keyboard as an input device. Lately, I have been using as a transcription service. I dictate my ideas, notes, and what I believe could be longer pieces to the service using its app. I get a transcript. I cobble together many such transcripts into a longer piece and eventually go to the “keyboard” to give it a final spit-and-polish.

Admittedly, I have struggled with these voice interfaces for many years — I have an accent and don’t have perfect diction. As a result, I experience frustration when using Apple’s Siri, Amazon’s Alexa, and other services. However, it would be unfair of me to say that they are standing still. For instance, I use Otter for my transcriptions, and it does a decent enough job of transcribing my notes. The interview audio files get better results.

I am inreasingly bullish about the voice-to-computer interface, mostly because of the rapid increase in the capabilities of chips focused on machine learning. Both, desktop and mobile devices are seeing a sharp increase in the capabilities of graphic processing units and neural engines. The chips are only one part of the equation. Software too is getting better.

But more importantly, we have a whole generation of kids growing up talking to their machines — and I wonder if in the future keyboards will become relegated into the background. If you saw the movie, Her1 , then you know it is not outside the realm of possiblity.

August 9, 2021, San Francisco

  1. KK Barrett interview[]