Disappointment in My Favorite App: The New Day One 2.0

What happened to the award-winning UI design?

Donny Reynolds
Feb 6, 2016 · 6 min read

This email was originally written in my draft box to be delivered to Bloom Built’s Day One support email. I realized that some people might resonate with me, or have differing opinions to offer, so I decided to muster up my courage and press the Publish button on my first ever Medium post.

Hello Day One Design Team:

Thank you for the new Day One! Having been a diehard fan of your product since 5 years ago, I’ve been excitedly waiting for the new release like a little kid anticipating a big gift for Christmas. Yesterday, I bought the new version for both Mac and iPhone in a heartbeat. Heck, I didn’t even realize it was 50% off. The abilities to upload multiple photos and keep multiple journals (which I view as a great organizational foundation for the future Publish 2.0) are much welcomed!

I’m notorious for being slightly obsessive when it comes to design. I couldn’t help but notice some things that could use improvements in the new app. That being said, while the iron is still hot, I hope you don’t mind some UI feedback coming from a part-time UI designer:

Redundancy Brings Confusion

I personally believe in this design philosophy I learned from The Humane Interface by Jef Raskin: too many choices can overwhelm a user, increase learning curve, and make overall user experience more confusing. The award-winning to-do app was a great example that offers a sensible UI layout with minimal redundancy.

Image courtesy of Cultured Code Press Kit.

Day One 2.0 for Mac, on the other hand, has a total of 6 ways of creating a new journal, 5 ways of creating a new entry, two places of viewing the same stats for one entry, and many other redundant UI elements. Allow me to demonstrate a few of these.

6 Ways of Creating a New Journal

For most users, writing a notebook/journal is quite a committed task. I wouldn’t think that “New Journal” option is a frequently used action by many people. Having six different entry points to this action seems a bit overkill.

Actually, that gear to the left of the bottom “Plus” also gives a “New Journal” option. So including the boxed ones, that’s a total of 6 ways to create a new journal.

5 Ways to Create a New Entry

Day One comes with reminders and prominent “New Entry” button right at the top, which helps nudge me to write more entries. However, it really strikes me as an overdone design when a “New Entry” is tucked into unnecessary places whenever possible. You might argue that these forms of choices are necessary because the new Day One app has customizable views so that users have access to this action in all modes (i.e. dual-panel vs single panel, etc.), but I beg to differ. Although that’s another whole conversation on modeless design and minimalism.

I have an explorer’s mindset, wanting to explore every bit of a product as soon as I get my hands on it. Perhaps that’s why things like this bother me more than it should.

The Pile of Filtering Options (and Other Stuff)

The filtering options come in two forms, icons and menu items, which sit right next to each other in the exact order. The search button, which would normally be functionally grouped with filtering options, is placed far apart from the filters. The “Print”, “Export”, and “Open PDF” items are redundant as well (and can be accessed from two other menus). I suddenly had this thought: are you guys designing this in preparation for a Windows release? That would make a little more sense, since Windows provides no universal menu bar.

Don’t even try to guess my apartment address. Not even the mailman could find me. Now where’s my delayed package?

My biggest pet peeve, if not considered a general design taboo, is to put read-only content (i.e. the journal stats) in a menu bar, especially when doing so serves no additional value.

I was hoping these menu stats might at least serve some sort of purpose, but was only disappointed to find out, after trying several possible view configurations, they are never necessary. You can always see the iconic stats at all times. To my dismay, as I adjusted this vertical sidebar to accommodate more filter icons, the menu items didn’t trim the repeats. One would normally expect the triple-dot to contain additional actions that don’t fit, not simply the same lineup offered in menu form.

The same problem happens here. Please make up your mind.

Switching Journals

While having multiple journals is a fantastic new addition, UI-wise I’m not completely sure why the Journal Sidebar is necessary, when the dropdown takes care of switching just as well, albeit with one more clicking. Therefore my question becomes: is decreasing the action cost of switching journals really worth the additional complication of a third collapsable column in the app? Uncomfortably, this design pattern evokes the bitter-taste of Evernote for Mac (yikes!).

On top of my examples, I’m afraid to say that I have noticed more UI inconsistencies and parts with ambiguous hierarchy. I can’t help but feel that my initial experience with this app can be described in three stages: “wow” for the much needed feature addition and overall UI refresh; “hmmm” for some thinking and reflection on the UI decisions; “arghh” for thinking that it’s a shame the app turned out this way. Although, since this is only an initial public release, I’m rather confident that your team will fix up these design bugs quickly.

What Happened?

I thought about the reasons behind these design decisions, so here are just some of my guesses. Day One 2.0 was supposed to take one year of development but spanned two years unexpectedly. For a team of a dozen developers, this is a huge project. As an engineer myself, just seeing you guys pull off a cloud syncing platform, a universal iOS application (iPhone + iPad), a watchOS app, and a Mac application all with full-fledged functionality leaves me no doubt that this is an excellent team equipped with amazing weapons of productivity.

Meanwhile, when a team is so crammed for time, it’s inevitable that some design flaws slip through the cracks. It’s more than likely that my conjectures are wrong though.


I’m not a design veteran by any means, so I’m just going to jot down some of my suggestions that may or may not be useful.

  • Reduce the number of menus, and the number of items in each menu. Consolidate these options into the OS X menu bar. If you’re designing for a possible Windows version, please reconsider the extent at which you want to unify both designs.
  • Combine search and filter options into one width-adaptive adjustable bar below the view options (Timeline, Photos, etc.). The iOS version is doing pretty well at this.
  • Get rid of the journal sidebar. Just do it. Please.

Thank You

It pains me to be the party-pooper in this release hype, especially amid the launch party of one of my consistantly favorite apps. Writing this mail feels almost too harsh, because your design is still far better than many other rivals out there. Nonetheless, I think that’s exactly why I want to send you my unsolicited feedback and opinions, which may or may not be redundant (no pun intended). I hope you find some of my perspectives helpful in some way.

Lastly, thank you for your hard work on building (in my opinion) the best journaling app. I look forward to every future update from you guys!

Your Big Fan
Donny Reynolds

Donny Reynolds

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APM @Google, designer at heart. Our publication Fwd: Thoughts left Medium, new home at https://fwdthoughts.com. https://donny.io