198: Revisiting Journaling


About 12 years ago, I ran a technology blog. Nothing major, just a personal blog, but it gained some followers and got to the point where some companies (when I approached them) would provide me with free licenses to try an app out, or to give something away to my readers.

In 2012, Day One gave me a license to use the app on my phone and on desktop, and I’ve been using it ever since. A few years back – whatever that license was – moved over to a “Plus” account. I could still sync journals to devices and such, but I was limited to 10 photos per journal entry and was not able to upload videos.

Neither of the aforementioned limitations bothered me that much. It was rare that I’d ever try to add more than 10 photos or a video.

But as I was listening to this episode and hearing David and Mike speak highly of Day One, I found myself nodding in total agreement the entire time. I got thinking about how that app has housed many of my thoughts and memories over the years and how I love looking back on old family events and things that were percolating through my brain years ago. As they said in the episode, you can look back and really see how your viewpoints change or how your feelings have shifted since you wrote something. It does give you that high level, third party view of yourself.

Then it occurred to me. For an app that I’ve used for so long and that houses such valuable information to me – how could I continue to use the free version. It’s high time I supported this app where it counts.

Just subscribed today. :grin:


Day One is such a fantastic app. I even use it to store my handwritten journal entries. Journaling is such an essential practice for me. You don’t have to be a stationery geek (like me) to love journaling. What’s most important is finding space to contemplate your thoughts and actions and figure out what you need to do to be who you are and do what you feel led to do. In my opinion we can’t get there without some form of contemplation, which is becoming harder to find in our world today.


I have wanted to journal for several years, and made some attempts ove the years, but always failed to make it stick.

I even had a subscription to Day One, followed David’s Webinar he did about journaling 2-3 years ago, but even then, i failed to really find the benefits, so eventually gave up again.

Last year, when Apple announced their journaling app, I decided I would give it another try. So I patiently waited for it’s release, and when they finally did, to my big disappointment, it was an iPhone only app, and I cannot type long texts on my phone, I need a physical keyboard.

So I went in on Day One again, paid for the year, and this time managed to really make it stick and a habit.

What made the difference this time? My mindset. In the past, I had the idea when I was before my blank page I had to add certain things, I had to answer certain questions, I had to.

This time my mindset is “I can journal about everything I want”, it doesn’t have to be pretty or stylish, and I can put anything I want in there.

And that mindset made all the difference. I have been journaling daily now since october. Sometimes my entries are short, sometimes longer, but the mental switch from “I have to” to “I can” made all the difference for me.

Now I have several journals, and adding new ones as I go!


I’m really pleased that people find and like Day One and that people are discovering the value of journalling in their own way, as I have for the last couple of decades.

In a power users’ forum, I feel the need to point out that “other journalling apps are available”. On the Apple ecosystem it’s definitely worth looking at Diarly and Everlog as viable alternatives to Day One: cheaper and with more access to and control of your data and both developing more quickly than Day One is and without the overhead of setting up a bespoke system (e.g. with Obsidian). It’s great we have a choice, but it’s sad when commentators only know about Day One, have never tried anything else and assume that digital journalling = Day One.

As someone who watched Day One with years of my journals, teeter on the cliff edge before it was rescued by Automattic, I don’t buy the security or reliability argument. Any app might disappear - just make sure you can back up and easily access your stuff.


Can Diarly or Everlog import Day One entries?

I think you identified my issue with journaling. I’m going to try your attitude as it seems to resonate a litle bit differently than other advice. Thank you!

Yes, both do and very well.

1 Like

Glad to help, good luck on jour journaling journey!

Day One’s my go-to, and has been a daily place to write since my first entry on the 22nd of November 2012. I’ve even backfilled a bit. Truly good software, and I hope it never goes anywhere I cannot follow. But yeah, just in case, I do an export annually of the whole thing in PDF and JSON. Used to be PDF was all you’d ever need, but journaling has evolved to include sound bytes and video, which makes it harder to properly make software-agnostic backups.

1 Like

I must confess; I’ve been a “jounaling app jumper” the last few years. I used Day One for a while, then used the daily note in Craft, then back to Day One, then the daily note feature in Obsidian. Beginning this month, I’m now back in Day One. I copied my Obsidian entries to Day One today.

I was drawn to Craft and Obsidian primarily because of the ease of linking to other notes. Not only can I link to other notes, but I can also see the backlinks to my daily journal notes in my notes. I understand that some linking is possible in Day One, but it’s a workaround and not simple or easy as it is in Craft and Obsidian.

What brought me back to Day One (again) is some correspondence with a friend, and the realization that while the linking function sounds wonderful in theory and works great, I was not taking advantage of it very much. If I was “all in” with Obsidian as some are, then perhaps I would have used it more. But I’m not, and I don’t.

For me, what is most attractive in Day One is the ability to easily scan entries in chronological order in the listing on the left side, including photos, and pick the ones I want to read. And speaking of photos, using multimedia in Obsidian is a mess, and too much of a hassle since I can’t directly access my photos app. In Day One I can easily add photos from my photos app. The visual recordings of my life are an important part of my journaling, and I realized I was missing them in Obsidian.

So I’m back in Day One again. I find that I really enjoy dictating my journal entries. I feel my thinking is more open and freer when I’m dictating than when I’m writing (and trying to conserve words). I used to dictate directly into Day One but now, most of the time, I dictate into the Whisper Memos app and it gives me an almost error-free (although yesterday my spoken “MacSparky” became “MacSmarty,” which while true is not what I intended). I like the way it divides itself into paragraphs and I never have to edit it.

I’m saying all this not to convince others to use Day One or not use Obsidian or Craft or anything else, but to explain what my experience and thinking have been.


My experience over the years is that for the things that are my most important use-cases, it’s better to invest in a specialty tool more than a multi-tool. If I want to journal, I go find the journaling app that works and stick with it rather than any note taking app. From experience, it really pays dividends to use the same tool for the long haul, and it has specialized capabilities based around this specific use-case. For me, that’s true of long-form novel writing and budgeting as well. The one-trick pony app has always been the best solution for me rather than a tool that tries to do too much. Of course, different strokes for different folks, YMMV.