What Do We Think About Journaling with an App?

Can a digital diary ever replace the magic of pen and paper? I'm about to find out.

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At “Into Many Things” I write about the kind of life where the rules are optional. My two biggest joys are traveling (or even more so, living abroad) and asking big questions about life—because, honestly, why not? Expect personal essays, travel guides from the many places I’ve been to, and a few thoughts on the little things that make life worth living.

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Okay, hear me out: even typing that title felt wrong.

I’ve been a pen-and-paper journaler for more than two decades. Since I was eleven, sitting cross-legged on the floor of my childhood bedroom, scribbling song lyrics in the margins of a glittery diary, journaling has been the way I make sense of life. I’d glue in movie stubs, copy entire text conversations, and catalog my crushes like a part-time archivist of my own coming-of-age.

That analog ritual has followed me ever since, through cities, apartments, phases of life, and all kinds of pens. I’ve always preferred the tactile experience: the scratch of ink on the page, the gentle resistance of paper. Writing by hand slows my thoughts just enough to catch them. It feels more mine.

So believe me when I say: the idea of journaling with an app? It’s messing with my entire identity.

The Shift

Here’s why I’m even considering it. A baby is arriving soon. And along with all the joy and anticipation comes... stuff. So much stuff. A stroller, high chair, car seat. A crib now occupies the corner of our bedroom. My “minimalist expat” era, living out of two suitcases for years, is officially over for now.

As someone who craves clear surfaces and lightness, this influx has made me pause. A few weeks ago, I did a small decluttering sweep. There wasn’t much to toss as we already live pretty intentionally but I did linger over one bulky category: journals and daily planners. A whole box of them, spanning years of my life. I couldn’t part with a single one. They’re sacred to me. But I found myself asking: if I keep journaling like this for another 45 or 50 years, how many more boxes will there be?

Just for fun, I did the math. If I jot down a short gratitude entry every day and occasionally add a longer free-write (like Julia Cameron’s Morning Pages), I might fill four or five notebooks a year. Multiply that by 50 years, and you’ve got upwards of 250 journals. A personal library, yes, but also a logistical puzzle. Where will they all live? What happens to a life documented on that scale?

Reality Check

Right now, I’m on the last page of my current journal. And for the first time in forever... I’m not rushing to buy a new one.

Partly, I’m avoiding adding more things to the apartment. But also, I’m bracing myself for a season where time and solitude will become rare commodities. I can’t bear the thought of a beautiful, half-empty notebook sitting by the bed, quietly judging me while I try to navigate newborn life.

And anyway, there is no nightstand anymore. That’s where the crib lives now.

The App Question

So that brings us here: to the Apple Journaling app (or any app, really). I’ve been playing with the idea. If I’m already picking up my phone a hundred times a day, why not redirect a few of those moments toward reflection?

The iOS Journaling app lets you add photos, videos, even audio clips to your entries. You can tag locations, note weather, and use prompts to jog your memory. It’s not a blank page, exactly. It’s more like a scrapbook-meets-diary, woven into the rhythms of your digital life.

I’ll admit, it doesn’t feel like journaling. Not yet. I still bristle at typing intimate thoughts into a screen. If I had an iPad and Apple Pencil, maybe it would feel closer to the real thing. But I am a sucker for experimenting. And part of growing is being willing to question even your most cherished habits.

Also, full confession: I already obsessively use Timehop to relive memories from past years. What if this app becomes a new kind of time machine? One that reduces physical clutter and offers a more dynamic way to look back?

I’m not saying I’ll never return to pen and paper. I probably will. But right now, I’m giving myself permission to try something different. To make room, literally and emotionally, for a new chapter.

I’m Curious...

What’s your take on digital journaling? I know Substack is home to many pen-and-paper purists, and I get it. But have any of you tried switching it up or balancing both?

I’d love to hear your thoughts, your practices, or your own dilemmas around keeping memories in a world that’s constantly shifting.

Maybe the point isn’t the medium, but that we keep showing up for ourselves, in whatever way we can.