Journaling On Day One

The best time to start journaling is a day far in the past; the second best time is today. Whether you have a paper diary or a digital journal, writing your thoughts in it regularly is vital. Over the years, I’ve used different tools to journal, tending to switch them up for various reasons. So, surprising nobody, I’ve moved from Apple Notes back to Day One.

Apple Notes is a general purpose note-taking app and Day One is a dedicated app for journaling. That difference alone should suggest how or why Day One is worth using for a daily habit as important as journaling. Being focused and equipped to the task, Day One shines with many journaling-friendly features, like a built-in calendar view for entries and the ability to efficiently import photos or events into those entries.

There’s much more to like about Day One (owned by WordPress parent Automattic), such as the Streaks widget on Mac and iPhone: it shows a daily checkbox of your recent consecutive entries. This one feature, in fact, was key in helping me finally make a habit of journaling daily, a goal I’d had for long time. And my current streak is now well over a year!

The thing is, I started this on October 2021…then switched from Day One to Apple Notes…and am now switching back. So what happened?

As you might imagine, using Apple Notes for all my notes plus all my journals added up to a lot of stuff, and journal entries didn’t fit well among my notes. I use Notes like a dumping ground for all sorts of things: links, checklists, random thoughts, receipt scans… Journal entries are simple but feel out of place in my mind-space inside Notes. And since I kept them locked, I couldn’t tag them, yet I’m not sure I would because the tags would be mixed with general notes tags. Things felt messy and limiting.

What really drove me to uproot my journals from within Notes was my ongoing process of re-organizing my thousands of notes since Apple introduced tagging capabilities in the last few updates. Upending my folder system to augment it with tags has been quite the productivity exercise; removing my journals would help simplify and declutter things.

So I felt the need to move my journals out of Apple Notes, but why go back to Day One? Sure, it’s great, but I already used it before and left it, so what was the deal?

At the time, I had journaled in Day One exclusively in the Mac app and thought that it would be enough, but I very much needed and wanted to also journal via the iPhone app. To do so required an upgrade from the free version to premium, which cost $35 per year. I wasn’t willing to pay for it.

I think that’s kind of sad. Day One is a great app. Developing and maintaining it requires much work; it shouldn’t be free. It costs people their time and energy to make Day One and make it excellent. The Day One team deserves income to compensate, and their app earns revenue. Storing, syncing, and encrypting everyone’s journaling data is no small feat, for example. And the app simply needs good coding and designing. It’s certainly worth more than $0.99.

So I decided to not be a cheapskate and just subscribe. After my 30-day free trial ends, I’ll be auto-billed for a whole year. Now I’m using Day One with all features unlocked, and it’s syncing across my Mac and iPhone apps beautifully.

Your take-away here is simply to start reaping the benefits of journaling yourself if you haven’t yet made it a daily habit. There are many other journaling apps besides Day One on both iOS and Android. I can recommend Journey, for example, as I’ve enjoyed it before too. Or if you prefer a traditional paper notebook like a Moleskine, go for it.

Do you journal daily? How do you like to journal?