
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
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 Otter.ai 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
voice to text has been around for a looooooong time. you know that as well as i do and it still hasn’t quite caught on. even my teenager (15) and my 11 year old aren’t into it… my son, nearly 4… maybe? but, i’m still thinking “no”.
the ability to form sentences from thought is something altogether different than speech. there’s an asynchronicity that is important… pausing and the like. audio requires none which, in some ways, cheapens it.
Thanks for this Om. Made me think!
I’ve been going back and forth between voice to text and keyboarding depending on the outcome I desire.
I find that if it is a presentation that I am going to give in front of an audience, then voice to text captures “how” I talk so it is more natural for me. When I write the same presentation out, then it sounds much more formal.
I find it easier to write/type content when a convincing argument is required that is backed with supporting facts.
The hardest part for me has been learning a new workflow and trusting the outcome.
Kind Regards,
Writing is personal and as the age we have just entered flourishes so will expressions that are personal and committed with willful skilled action.
Like a chick emerging from an egg – our issues facing us will either confound us into oblivion or (as I expect) we will emerge and flourish. Those solutions (our beak?) which are happening now and those sure to come will bring exponential productivity growth.
I think of the tea ceremony as an analog for what will be of import in our future. What will be of desire when all of your needs can be met and all of those you know and the ones they know?
Oooh loved this issue Om. In the last year I have fallen back in love with writing with my fountain pen (just a simple LAMY one) and I have not enjoyed the act of writing this much in many years.
Lamy… so great!!!!
Interesting read. When I was in high school way back in the last century, typing class was a requirement for graduation. I wonder if one day soon it will be equally important to teach speech-to-text maximization alongside it.
I learned typing and short hand, plus writing — I use all of those skills even today. I definitely think speech-to-text is a tidal wave and will be here as an accompaniment to whatever we do.
I just ordered a Paperlike (https://paperlike.com) screen protector that promises to transform the iPad to lower glare but specifically for people who want a “paper-like” experience. I’ll be curious to see if that changes my relationship with this device. I’m a Wacom fan on the computer but I’ve never really spent time with the pencil because it feels… un-analog.
I would like to know what you think Jason. My impressions were mixed. I hope you enjoy it.
So far so good. Definitely cuts the glare. I can tell it’s going to wear down the tips on the pencil a lot more than normal. I’m firm in my belief that the correct software for the kind of drawing I want to do might not exist yet (either that or I haven’t taken the time to go deep on one of them and commit). Will give it some more time.