The Problem with Calendar Apps

I’ve used and tested many apps over the last 10 years and the first app category that comes to mind when thinking of lack of enhancement is (1) email, the second that comes to mind is, of course, the (2) calendar.

Why has the calendar not been improved over the last 10 years? Who is to blame? Who is the leader? Were there any hopeful apps that failed? Is there a need for a better calendar?

These are important questions to ask when thinking about, not only calendar software, but also any type of software in general. Google Calendar launched on April 13, 2006 and has remained as the leader when it comes to a web-based calendar app. Other popular contenders: Apple Calendar, which is strangely now online and Microsoft’s Outlook Calendar.

Google Calendar is convenient because as someone who uses several other Google apps, like Gmail, having my calendar linked to my other commonly used apps allows me to (1) keep my data under one roof, (2) sync my contacts across multiple apps, allowing Google to auto-complete people’s emails in form fields (forwarding emails, event invites, sharing docs), and (3) making sharing and collaboration easy. But as the years went on, the UI barely changed, obnoxious errors quietly appeared, and no new features were added. I found myself dreaming up new ideas that Google could implement but alas nothing happened. I decided to start searching for the ultimate calendar app and kept an open mind.

The first that I discovered was not really a calendar app but a simple task app called TeuxDeux which mimics the “week view” of Google & Apple’s calendars but limited this view to 5 days instead of 7. The beauty of TeuxDeux is that each item you create is a task rather than an actual “calendar event” which means you don’t need to think about dates, times, or locations; you just type what you want the task to look like and hit enter. The tradeoff with this approach is that you lose calendar functionality, like auto sorting by date & time, and gain better control over the visual aspect of your plans. For example, you can format the time however you want without the format getting in the way of auto sorting. TeuxDeux was nice and I did use it for a few years alongside Google but items in TeuxDeux aren’t really calendar events or even tasks, they’re more like one line notes.

A few years later, I stumbled across Monday, a calendar app that proposes one concept: to combine calendar events and tasks together in one view, and also displays events from Facebook “but does it in a way that informs and not distracts.” I was obviously hooked after reading this tagline on their landing page and was hoping their solution would be my solution. Monday features an infinitely scrolling “month view” and a “week view.” And much like TeuxDeux, you can add tasks to any day and a checkbox is generated to let you know that what you created was a task. If you add a time to the beginning of the task, the task will convert into an event and the checkbox will disappear. There is no quick enter box like on Google Calendar so you must create the task or event on the correct day. Birthdays and Facebook events appear at the bottom of each day to prevent unwanted noise. Monday lacks the “day view” and “agenda view.” The main issue I had with Monday was the way it displayed my connected Google Calendar events; they were shown at the bottom along with Facebook events, even if the Google events had times. So I either had to still use Google Calendar on its own, meaning I would be using 2 apps if I wanted to take advantage of Monday’s tasks, or I would have to stop using Google and start using Monday’s native events. I already disliked Monday’s UI on top of all this so I ditched and went back to using Google Calendar exclusively.

Then in 2013 arose probably the most overrated yet potential ridden calendar app of all time… Sunrise! When I first discovered Sunrise, I was at a point where I was itching for something better than Google Calendar. It had been at least 6 years since I started using Google Calendar after finally switching to Gmail and Docs. Google did a theme reboot for all of their popular apps sometime around 2011 but for Calendar, this just meant we got a nicer create button and view buttons, other than that Google Calendar looked the same. The same old outdated UI. The same old clunky feeling. Sunrise was better. It had a fresh, clean UI and made it super easier to start manipulating events from Google inside Sunrise. The differences between Google and Sunrise were small but they were enough to feel like I was actually using a calendar app from the current era and the Android app was miles better than Google’s. I assumed the Sunrise team would keep adding features that would extend the current state of calendar apps into the future but that never happened. On February 11, 2015, Sunrise was acquired by Microsoft, the app shut down on September 13, 2016. There was so much hope and many people felt crushed by the news.

On Aug 31, 2016, the Kin calendar app was featured on Product Hunt as a proposed replacement for users with Sunrise loss. Although Kin does look nicer than Google Calendar, it doesn’t offer enough for me to make the switch and recently started charging a monthly fee to use it.

On the same day, featured next to Kin, was Sunsama, a calendar app focused on team productivity, clearly inspired by Slack. Much like Monday, Sunsama brings together calendar events and tasks into one simple interface. Unfortunately, some essential things were left out, such as linking events and tasks together. I was able to create a task, which did not appear in the calendar, but then when I dragged the task onto a calendar spot, it generated a separate event with the same title instead of just assigning that time slot to the task. I was able to drag the same task onto multiple calendar spots to create multiple events that had no relation to each other, which is great for cloning events but since the original task was not cloned on the task bar, this made no sense. I could see teams getting confused by these simple quirks as tasks and events increased over time. Overall, it’s clear that the calendar and tasks are more separate than unified.

I scoured the internet some more but nothing peaked my interest so I decided to try out some native Mac apps. BusyCal was one that I have seen mentioned quite a few times, including Issue 13 of The Journal, an email newsletter by Kevin Rose. At first glance, the UI is setup similar to Google. You have your calendar feeds on the left along with the mini calendar, which can be made hidden. The colors of my events are altered and muted which is disappointing and there doesn’t appear to be a way to turn this off. The day and week views look a little nicer. The list view is compacted nicely but I wish there were division lines separating each week. The only feature that stood out for me was the 10-day weather forecast seen on individual days of the current week, though useful, but not enough to get me to make the switch.

I then checked out Fantastical 2 which has received high praise and was named Editor’s Choice on the Apple App Store. This was definitely one of the better-looking interfaces though I wish they didn’t alter/mute my calendar colors like BusyCal also did. The mini calendar on the left sidebar was useful as it highlights the current week/day very nicely. And instead of showing the list of calendar feeds, the left sidebar also displays the list or agenda view, which I thought was a nice change. The year view is simple and elegant and displays a heat map based on the number events per day. The only feature that stood out was the ability to group calendar feeds together as sets to turn on/off which is very useful but once again not enough for me to make the switch.

Why was I unable to find a calendar app that could replace my current calendar? Why have so few (successful) calendar apps launched within the last 10 years? What is missing? I sat down and brainstormed; this is a list of features I’d like to see in a better calendar app:

• Refreshed UI — The day and week views feel outdated and somewhat useless. Is there really a need to see every single hour of time in a time stretched from top to bottom? Am I really going to schedule events or activities at 3:00 AM? Why so many lines? These views look like confused, empty spreadsheets files.
• Repeat View — If you’re like me, you have several events scattered across the next month, some are stand alone events while others are from repeating rules set up months or even years ago.
• Categories Not Calendars — Having separate “calendars” is convenient when it comes to work vs. personal vs. family vs. public but what if I wanted to separate different types of events within just my personal calendar? If we strip this problem down, we arrive at the nested folder rule: If I can put docs and emails inside folders (inside folders) then I should be able to do the same for events. In this example, categories within calendars.
• Inbox & Drafts — I find myself constantly creating events that are either TBD or are just reminders to schedule an event. Having an inbox would be a simple way to hold on to pending events (similar to drafts in email) and to easily respond to invites from others.
• Accidental Deletion Prevention — It’s too easy to delete or edit an event on accident and that undo pop-up sometimes just doesn’t cut it, especially when you didn’t realize you made a mistake until days later. Having an event lock itself after creation would add a nice layer of safety by asking you to double confirm changes or deletion.
• RSVP Manager — Despite Facebook and Eventbrite being the leaders of social events, there are situations where I want to keep track of RSVPs without creating a Facebook event, usually for small parties.
• Saved Locations — Events like doctor or dentist appointments happen every year but not enough to set a recurring event since they will most likely have different times. I should be able to select the location from a dropdown of commonly used locations or the app could suggestion the location based on the event title.
• File Attachments — Being able to attach PDFs and images to events would be helpful for things like hotel reservation check-in’s, business meetings, concerts, etc.
• Time Recognition — I normally like the default time blocks set to 1 hour when creating new events but for things like doctor and therapy appointments, having the app know that these types of events would always be the same 45 minute time would be helpful.
• Tasks — And of course, I would LOVE to see my daily tasks next to my events, this is a must. Support for outside task apps would be ideal here.

I realized that out of all the apps I tried, they either had nice, modern interfaces (like Sunrise and Kin) or had new features that I just wouldn’t find myself using often (like BusyCal’s travel time estimator or Fantastical’s geofence alerts or floating time zones). I was in search of a new take on calendar interfaces and new, clever features that I would actually use. The search must continue!

Agree or disagree? Feel free to comment below or send me a message on Twitter. If you currently use an awesome calendar app that I missed, let me know! Thanks for reading :)