Journaling Dilemna

Stuck between two worlds

Call it the perils of being forty (at this point in history,) but more often than not, I find myself slamming back and forth between digital and analog. I just can’t seem stay on one side of the issue. And lately, I’ve been measuring the two against each other when it comes to journaling.


The argument for digital

This isn’t really anything new; anybody alive right now knows the advantages of digital.

  • It’s searchable

  • It’s far less likely to be lost or destroyed

  • It’s neater and easier to read

  • It’s taggable and sortable

And to get even more specific, when talk about the incredible Day One journaling app, there’s:

  • The activity feed — which remembers where I go so that I can add those places to my journal later. (For someone, like me, who gets caught up in what they are doing, this is huge. I don’t always have time in the midst of living to journal, so those little placemakers are crucial.)

  • The ability to add old scribblings and still get full featured entries. The entries I put in today will map my location and save the weather. Well, if I put in an old paper notebook entry from 1992 and I know where I was on what day, like magic it’s on the map with the weather from that day.

  • End-to-end encryption. This is about as secure as a journal can get.


The side for analog

If you’re like me, you’re pretty much sold on the features I listed above. But (of course there’s a but,) there are just some things about pen and paper that I can’t let go of:

  • The feel — yes, most of us are sick of hearing it, but it’s true. I can’t let go of the way that a pen feels going across a piece of paper. There’s no inherent advantage to it. There’s no difference between catching words in ink, or on an iPad, or typing at your Mac. But after 40 years, the feeling of paper is natural; it’s security of another form. I’m still tied to tangibility as reality. If I can hold it, it exists.

  • You learn better when writing rather than typing. I’m not gonna pull up research to prove it, maybe it’s not even true for everyone, but it’s true for me. And journaling is about growth, thinking and learning.

  • It’s distraction free. No pop-ups or badges.

  • My eyes don’t burn after an hour.

  • I don’t have worry about charge levels or signal.

  • It has also been said that cursive handwriting stimulates both sides of the brain simultaneously in ways that few activities do.

The Current Situation

I’m literally living in both worlds.

  • I carry a pocket notebook and pen with me everywhere. (I hate typing notes into my phone.)

  • I log my daily activities like where I go, what I do, what I eat and any other brief event-related thoughts into Day One every night. I like using the On This Day feature to see what I was doing in previous years.

  • I put my commonplace notes (what I read, and watch and listen to) in Day One as well, because it’s searchable and I like seeing what I was into years later and what I was thinking about them.


I’m pretty happy with those three things. They work for me. But it’s the questions of what to so with my long personal journals that I’m worries about. I love the feeling of grabbing a notebook and scribbling out some stream of consciousness pages. It’s not the same with a keyboard. But of all the different things that I journal, these entries are the ones that I worry most about losing — because they’re as personal as personal can get.

Now, I considered for a bit the possibility of taking photos of my paper journals and dropping them into Day One, but that lasted about three minutes. I’m not gonna do that. I’m not gonna make something simple into something complex just because I can’t choose.

The Solution

One of the biggest problems for me when it comes to technology is that I get caught up. I get fascinated about the possibilty of something — which isn’t a bad thing. It just happens a lot because I don’t sit and actually think enough about my actual use and my actual needs. I spend hours debating features I won’t even use.

So, the reality here is, my long personal journals are morning pages. They’re about self-discovery. They don’t serve a purpose beyond the experience of actually writing them. I won’t ever be looking at them again. That’s not what they’re for. So, they don’t need to live anywhere digitally. In fact, I don’t wnat them to. When I get to the end of a notebook, I’m gonna shred it and move on to the next one. And everything else, all my other journals, they’ll live happily and securely in Day One.