Failed Attempts at Digital Journaling

My Moleskine paper journals

It is important to know what you are not good at, if for no other reason than to decide either to improve, or to stop wasting time on them. Over the years, for instance, I have made several attempts at keeping my journal in digital form, instead of in notebooks of various kinds. My reasons for doing this always seem pure. I type faster than I handwrite. It My typing is not illegible when I type faster. My hands grow less tired when I type. I think this means I’ll write more on a computer than I would in a notebook.

But it never works out. Take my most recent foray into digital journaling. I was looking for small efficiencies in my day. I thought that by being able to type my journal, I’d get it done faster, possibly write more, and also have a place where I could easily search my journal for what I was looking for. All of these were perfectly sensible. And still, things turned out much worse than if I just stuck to writing in my Moleskine notebooks.

This most recent adventure began about a month ago, and at first, it seemed to work well. Between June 29 and July 16 I banged out nearly 7,000 words in my digital journal, far more than I probably would have written on paper, although I’m not completely certain of this. So far, so good, right? Well, since July 17, I haven’t written a word–the longest stretch I’ve gone without writing in my journal since possibly 2017.

This is part of a recurring pattern. Ever since I first started keeping a journal in 1996, I’ve been repeatedly fooled by the paradox of journaling, in much the way Charlie Brown is lured by Lucy’s promises that she won’t pull the football away this time. Every now and then, some whisper in my mind tells me it will be much easier if I type it into a computer than writing in a notebook. It hints at time saved; it hints at the ability to search my journal using regular expressions. It is an alluring voice, the dark twin of the call of the wild. The problem is, I can never sustain it for very long, and ultimately give it up.

I cannot explain why this should be. When I write in my notebooks with pen and ink, I can go for years without skipping a day. It took all of two and a half weeks for me to give up my digital journal. I’ve tried to think about what causes this. The answers I have thus far are weak and uncertain, but two are worth contemplating

  1. I spend enough time on computers that I want to be done and so I don’t put in the extra time to write my journal.
  2. I somehow feel that there is more permanence to what I write in a notebook, and am therefore more committed to it as a lasting repository of my writing than digital media.

I think the latter point may be the crux of the issue for me. When I read Walter Isaacson’s fantastic biography of Leonardo da Vinci, I was impressed by a point Isaacson made the importance of which seemed all out of proportion with the rest of the book. Isaacson wrote:

[Da Vinci’s] mind, I think, is best revealed in the more than 7,200 pages of his notes and scribbles that, miraculously, survive to this day. Paper turns out to be a superb information-storage technology, still readable after five hundred years, which our own tweets likely won’t be.

Somehow, I have internalized this. Indeed, I’ve had the experience where some of my digital writing is forever lost to the ether. While I have most of the stories I’ve ever written going back to 1992 in digital form, I have nearly none of the digital journaling I’ve ever done. Instead, I have diaries and notebooks filling with my journal writing. The one exception to this strange rule is my writing here on the blog, which covers a span (as of this writing) of 16 years and is, in some respects, a kind of public-facing journal. Still, I have this suspicion that because my physical notebooks have weight and texture, they, and what they contain, are more valuable than intangible bits stored in clouds.

I suppose that if you were to search this blog, you’d find among the nearly 7,000 posts, a few where I confess this problem, only to write later on about yet another attempt to migrate my journal into the digital realm. This is me in the role of Charlie Brown, to the digital world’s Lucy, holding a virtual football, and then pulling it away at the last moment. Sometimes, even when I recognize my mistakes and failings, it is hard not to repeat them.

All of this to say: as of this morning, I am back to fountain pen and ink in my Moleskine Art Collection large sketchbooks.

In the future, if you see me eagerly writing about how I am once again going to move my journal into digital form of some kind, kindly drop a comment on that post with a gentle reminder of the inevitable results. I think a simple, “Good grief!” would do the trick.

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  1. I work in IT and I feel similar with being on a computer at home and tend to do very little.

    How are you liking the fountain pen? I got into them a few years back and really enjoy the different inks more than the pens that I have. Are you using cartridges or an ink converter and filling with different inks? I don’t have particularly attractive handwriting but I’m also a big fan of the wider stub nibs.

    1. Steve, so far I really enjoy using my fountain pen. I’m thinking about getting another one so I can have one with black and one with blue ink. Currently, I am trying to slow down my handwriting to make it more legible. Somehow, I thought that by virtue of using a fountain pen, my handwriting would magically come out looking like a master calligrapher’s. Turns out that is not the case.


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