When my Great Uncle Howard passed away, they found a shoebox in his closet that was full of journals. They were those thick, index-card-sized, 5-year diaries that allot just a few lines of space per day. He had 8 of them, and they were all filled with what the weather had been that day. 40 years worth of Uncle Howard’s daily local weather report.

I’m not as regimented or peculiar as my Great Uncle Howard was, but I have been keeping a personal journal for the past 20 years.

My journals have always been logged with pen and paper. I very much enjoy the time when I leave my standard-issue Apple nerd gadgets in the other room and sit down with the analog to write about what’s currently on my mind.

In a way, perhaps I am more regimented than my Great Uncle Howard was. Through Twitter, Instagram, Path, Stamped, email, and other such apps, my days are meticulously logged with over-filtered pictures of the sandwich I ordered for lunch and tweets about the friends I’m out to coffee with. But how many of my tweets or Instagram photos are worth revisiting 40 years from now? Some of them, but surely not all of them.

And this is where I see the difference between the deeply personal issues that I write about in my Moleskine and the memories that I log on my iPhone and iPad. The former have great value to me now as it’s a way to help me process the current season in life, and the latter have great value to me in the future as they are a way to look back on memories and significant events.

For a few months I tried to use Path as a way to capture the little memories. Path is a beautiful and fun app that makes it easy to check in at places, snap photos, shoot videos, and write notes. But as a “journal” Path has a few shortcomings. For one, what gets logged in Path stays in Path (Is this an app that will be around in 20 years? I doubt it. How then will I get my data?). Secondly, the app is iPhone-only. And lastly, Path is a social network and not a personal journal — something that in and of itself causes hesitation when considering posting a personal memory.

Regarding Day One

Then there is Day One: a Mac and iOS journaling app. Day One shipped in March 2011 as a Mac and iPhone dynamic duo, and a few months later the iPad version was added to the line up.

I bought the iPhone and Mac apps when Day One first shipped. In part because I’m a sucker for a good looking app. And, to be sure, Day One is extremely well-designed. The color scheme, typography, and the overall design are all clean. No detail is left wanting, no pixel out of place.

Additionally, Day One supports Markdown, it works with TextExpander on iOS, it syncs via Dropbox or iCloud, it has a passcode lock, and it will export all your entries as plain text.

For a classy journalling app that works on all your devices, I don’t think you can do better than Day One.

But despite its ubiquity and style, Day One never stuck for me because it only allowed text entries.

A text-only digital journal is too much like a replacement to my Moleskine. And I don’t want to replace my analog journal, I want a compliment to it. And if it’s going to be digital, I want all the benefits that digital provides. And so the text-only limitation was something that kept me from using Day One on a regular basis.

That is, until about two months ago when I was fortunate enough to get early access to the current version of Day One.

Day One’s Big Update

Day One now supports adding images to entries. Also your current location and the current weather (Uncle Howard would be proud) are automatically added to your entry’s metadata. These seemingly small changes make Day One an order of magnitude more appealing to me.

Over the past few months I have been using Day One regularly and enjoying it. Many of my entries have been nothing more than a photo and perhaps a quick descriptive sentence. That, combined with the automatic location and weather logging, and I’m creating worthwhile journal entries with very little effort on my part.

Day One has nearly all the advantages that Path had for me, but with none of the disadvantages. I can use my Mac, iPhone, or iPad to log pictures, notes, and locations. I can know what the weather was like that day, I can know where I was when I wrote that entry, I can export my entire journal as a Plain Text file that will be readable 20 years from now, and I don’t have any friend requests to wade through.1

As a long-time Mac nerd, something I appreciate about Day One is that it’s both simple and geeky. It’s easy and fun to use, it sports a clean design, and yet it has a lot of under-the-hood horsepower that you can use to do a lot of nerdy stuff with.

For example:

• There is a command line interface so you can write scripts that interface with the Mac app. Helpful for importing into Day One from other apps, logging via Alfred, and more.
• Day One on iOS supports URLs, and it has a pretty robust library that plays well with Launch Center Pro.
• Day One on iOS works with TextExpander for iOS.
• Markdown, of course.

In a day and age where an app like this could have easily justified a heavy-handed skeuomorphic design, Day One keeps it clean. Normally I would say here that Day One is very Mac-like, but Mac design has been getting more and more skeuomorphic these days. (Sigh.)

Though Day One has been updated across the Mac, iPhone, and iPad, it’s the iOS version that I think shines the brightest. In part because of the iOS app’s ability to include location and weather data to your entries (more on that in a bit). And also because I find the iPhone version to be the best version of the 3-device suite. (Similar to how I find OmniFocus on iPad to be the best version of its 3-device suite.)

Photos, Location, and Weather

When you open up the new Day One on your iPhone, its main menu screen (or the sidebar on the iPad) which used to feature just a “+” icon, now features a camera icon as well.

This encourages you to consider that creating a new journal entry using a photo is just as legitimate as a text entry. And, as I mentioned above, it is this feature that turned Day One around for me and I’ve been using it ever since.

But it’s not just that you can slap a photo into a journal entry. Day One is very smart when it comes to adding photos. Say you snapped a picture yesterday when you were out to lunch with some friends. If you use that picture to create a new journal entry then Day One will ask you if you want to use the date and geolocation data from the photo (even the past weather for that time and place is added to the entry). Thanks to this cleverness, it’s as if you created the journal entry when you were out to lunch rather than the next day.

Moreover, If you have Camera+ installed on your iPhone, then Day One takes advantage of its API so you can edit your photo and add cool effects and stuff.

If being able to add photos is Day One’s killer new feature, the icing on the cake is the automatic adding of location and weather data to your journal entries. For example, in a previous version of Day One, if I wanted to make a note about how Macworld throws a classy WWDC get together, it would have been text only, and I probably would have just skipped it.

But now, that same entry can include a snapshot of the party, a quick caption, a map showing where the party was, and the info about what the weather was like.

All this is added with little or no effort, and it makes the entry far more valuable. (Note that when creating a new journal entry on the Mac version, automatic location and weather data are not yet supported.)

Typography

Previous versions of Day One offered broad-stroke typography options — you could chose between Serif, Sans, or Monospaced. The new version gives a more granular choice of typefaces (though it still doesn’t open up the whole font library that you have on your Mac).

And on the Mac Day One now includes Avenir, a typeface that ships with Mountain Lion and will ship with iOS 6.

Markdown

Speaking of typography, Day One has long supported Markdown. In the latest update to the iOS app there is now a Markdown formatting bar that rests at the bottom of the text entry box.

Adding a custom row to the on-screen keyboard isn’t new, and many fine apps have their own take on it. Compare and contrast to the custom keyboards of Byword, iA Writer, Scratch, and Writing Kit.

But the Markdown formatting bar in Day One isn’t just for quick access to common Markdown syntax. Swipe the bar left or right (a feature which several of the aforementioned apps also support) and you’ll get options for adjusting the metadata of your entry: You can change the date and time, add a photo, share the entry via Email or Twitter, delete the entry, open a new entry altogether, launch into “full screen writing mode,” and more.

Basically everything you need for that journal entry is a swipe and a tap away.

Reminders

If you want to be regimented about your Day One entries (as opposed to writing whenever the mood strikes you), Day One can remind you to punch in.

These reminders can be as often as every 15 minutes or as infrequently as once per week. If, like my pal Chris Bowler, you use Day One as your daily work log or the place for your end-of-day brain dump then setting a daily reminder just a few minutes before the work day is done could prove helpful.

And hey, if you’re not ready (or if you’re still not in the mood to type something), then you can snooze the entry or just skip it altogether.

Full-Screen Writing

The iPhone and the Mac versions both have a nice Full-screen mode. (For whatever reason, the iPad does not.)

The iPhone version removes the system status bar, the top navigation bar, and the Markdown formatting buttons. Presenting you with as much screen real estate for your words as possible.

The Mac version doesn’t need to take up the entire screen (especially if you’ve got a large external monitor), so its custom full-screen view sports a dark textured background with subdued controls on the left-side and a focus on the writing space.

* * *

As a writer, I believe journaling on a regular basis is critical. It’s writing that will never be judged. It’s writing that doesn’t require an editor. It’s the only place where I am completely free to write for my truly ideal reader: a future me. I have my own inside jokes, my own running story arc, my own shorthand. I love the freedom to write whatever I want, however I want, with no need to make it tidy or clear or concise. And I have no doubt that it makes me a better professional writer.

As a new dad, my latest hobby is the incessant documentation of every cute thing Noah does.

Over the years, most of the major, monumental milestones of life were documented in my Moleskine. But not all. And that’s why I’m glad to have an app that let’s me easily and joyfully add a snapshot or a quick note about an important or memorable event. These are the things my family and I will look back on 20 and 30 years from now with great fondness.

You can get Day One for $10 on the Mac App Store and $5 on the iTunes App Store.