iPhone and iPad Mac

Should You Upgrade to Day One 2?

Bryan Wolfe 22-03-2016

In recent years, folks with a story to tell have turned to Day One, the incredibly popular journaling app for OS X and iOS. Earlier this year, developers Bloom Built introduced Day One 2, which isn’t an upgrade, but rather a completely new application. The previous version now becomes Day One Classic.


So is Day One 2 worth buying all over again? Let’s find out.

Change Is in the Air

There are two big changes in Day One 2: the ability to add multiple journals (up to 10), and the addition of multiple photos per entry (again, as many as 10). To keep things organised, users can now pick from an array of colors to uniquely identify one journal from the other. In another change, users now have the ability to toggle between List, Photo, Map, and Calendar views. You can also sort and find entries quickly through the use of a star, tagging, years, and other filters.


Behind the scenes, Bloom Built has changed how journal entries are backed up and synced. Previously, Day One users had the choice of syncing data through Dropbox, iCloud, or the company’s proprietary service, Day One Sync.

In Day One 2, Day One Sync is the only supported sync service. Bloom Built cites “reliability and security” as the main reasons for discontinuing support for Dropbox and iCloud, stating that the other services “had too many cases of data loss and duplication.”


Day One 2 also includes some minor feature upgrades, including 3D Touch support, custom reminders, and timezone support.

Multiple Journals

As a long-time Day One user, I never thought I needed multiple journals. The application’s tagging system was all I thought was necessary to organize my daily thoughts. I was wrong.


Having multiple journals, in different colors, has changed how I write. In Day One 2, I organize my thoughts primarily between two journals, Personal, and Work-Related. A third journal, Vacation, is helping me with planning a trip. The application uses this division throughout. For example, one can filter journals via the map or photo viewer.


Map View

Visualization is important when telling a story, and the new map screen takes that concept to a new level. Now you can see where you were when making a journal entry. This information proves useful over time as one adds entries.

For example, I tend to journal more when I’m working from Starbucks, rather than from my home office. As a writer, knowing this information is of great importance. It could be that I’m less distracted at Starbucks, which is great to know on days when I’m struggling to find the right words for a story.


Day One 2 on iOS also features a nice little feature called “View Visible Region in Timeline,” which gives you a summary of all entries written within the area on the map. A minor feature, of course, but a good one nonetheless.


All Those Images

In Day One Classic, you’re limited to one image per entry. Imagine being on a family vacation and only allowed to choose one image to represent the experience on any given day. In Day One 2, you can add up to 10 photos for each entry. That family vacation will look so much better now, dont you think?


Easy Syncing

One of the things that annoyed me most about Day One Classic was the intermittent appearance of duplicate entries, which occurred with both Dropbox and iCloud as my backup solution. It happened most when using Day One on a new device for the first time.

Duplication is no longer a problem in Day One 2, courtesy of Day One Sync. I’d like to note that my duplicate entries had already disappeared in 2015 when the service first arrived on Day One Classic.


What Hasn’t Changed?

Simplicity was one of the reasons Day One Classic found success. The application received nearly 40 free updates over the course of its product life cycle. Each of these updates enhanced the writing experience but did not change the way to add journal entries.

As we once noted Keep a Digital Diary with Day One for Mac OS X and iOS Everyone has a story to tell. It's not always a story in need of an audience, sometimes a story just needs to be told. You may want to continue the journal you started when you... Read More  about Day One, “Simple lines and simple fonts, yet great typography make Day One a pleasure on the eye.”


In Day One 2, this simplicity remains. Setting up Day One 2 is effortless, and beginning that first entry couldn’t be more intuitive.

Mac Versus iOS

When Day One 2 launched, I first purchased the iOS version. I waited for a few days before buying the Mac version. The reason for this hesitation was the price disparity between each version.


The iOS version of Day One 2 is $9.99. For a limited time, it’s selling for $4.99. The Mac version, by comparison, is $39.99 regularly, but $19.99 for a limited time.

This price difference is a bit confusing. Other than some minor design differences, both versions are pretty much the same. And while I recognize that Mac applications are usually more expensive than those for iOS, $39.99 is a lot to spend for a new journal program.

Is It Worth It?

Day One 2 is a powerful application that’s pleasant to use. For me, the new features are enough to justify paying for the product again. However, the average user might not feel the same way, especially when the Mac version is $39.99. Fortunately, you can have your cake and eat it too.


You can purchase Day One 2 for iOS and still use Day One Classic on your Mac. Sure, the new features won’t show up on your computer. Your actual journal entries, however, won’t be affected. Just be sure to use Day One Sync for backup purchases, not Dropbox or iCloud. If you favour writing on your iPad or iPhone and simply need occasional access to your journal on a Mac, this is ideal.

Don’t want to upgrade? For now, Day One Classic is still being supported and it’s still available for purchase from the iOS App Store [No Longer Available]. New Mac users, however, must buy Day One 2 on the Mac App Store.

Will you be upgrading to the new Day One?

Related topics: Buying Tips, Writing Tips.

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  1. Janneke
    October 30, 2016 at 7:45 pm

    I would love to upgrade To Day One 2 and use the great new features. I'm a 'fanatic' Day One Classic-user. Just the sync service makes me hesitate. Already using Dropbox and iCloud for several sync-functions I don't like to add another sync-option. And what would happen if this company stops alltogether? The Day One Classic app would still work and sync with Dropbox but what would happen to Day One 2? I have now almost 4000 entries (and counting) that I would not want to loose!

  2. Brent
    March 29, 2016 at 2:34 pm

    to answer the question, will I upgrade? no. The features are not worth the extra cost, and I do not want to switch from Dropbox synching to their servers.

  3. Deja
    March 28, 2016 at 12:35 am

    Why not mention that sync isn't available at all outside of their servers. You write to be sure to "use Day One Sync" as if it's an option, when it's the only option. You are forced to create an account and use their servers to get the same kind of basic functionality that you had in the original DayOne app. It's one of the biggest complaints people have and yet this article doesn't even mention it.

    • Deja
      March 28, 2016 at 12:39 am

      Never mind, in my rush I missed the mention in the "Change is in the Air" section while expecting it to be in the "Easy Syncing" section. Seems like something that should be reiterated in a section dedicated to talking about syncing options.