A Journey of To-Do Lists

A while back, I made a comment on Twitter about how I just never "got" to-do lists. I understood that they worked for some people, but I just didn't see the point for myself. A couple of people agreed with me, a few disagreed, and I didn't think much of it.

It kind of nagged at me, though, and shortly thereafter, I decided to try and give using a to-do list another try again, and finally it clicked. I had to go through a few different apps before I found something I liked, and I'm still not running my life from an OmniFocus list like some people I have heard of, but I have finally figured out a system that works for me. So I thought that I'd a bit of a write up of what I tried, what stuck, and the part that I've found the most important), what I had to change to make lists work for me.

The Apps

When I decided to give to-do lists a shot again, I had a plethora of apps available to me, which was great, but it did make picking the right app for me a challenge. I ended up cycling through quite a few before I found one that finally stuck with me, and even then, it's not quite perfect for me.

I had a few key requirements; first, whatever app I chose had to sync between all my devices. I switch between my phone and my iPad pretty much constantly. So I had to have my lists in both places. Second, I wanted the ability to break things up. The ability to split my work to-dos and my personal to-dos was really appealing to me. And finally, I had to have time-based reminders. The ability to remind myself to do a thing at a specific time was pretty crucial for me.

Here are the apps that I tried:

Apple Reminders

The first one I tried was the built in Apple Reminders app. I rather liked the fact that it integrated nicely with Siri, and Reminders.app was great for time and location based reminders. Also, the syncing between my iOS devices was definitely the best out of all of the apps that I tried. The only problem that I had was that it kind of dumps everything into a single list, and there's not a lot of customization to be had. So while it was a good start, it wasn't quite what I was looking for.


The next app that I switched over to was Things. Things is an interesting app that just never quite gelled with my particular workflow.


Things had the very nice ability to separate out tasks in to different projects, different schedules, and different categories. The ability to tag entries was particularly nice, and the way that it color coded tasks was a neat little touch.

I used Things for a pretty long time, but two things finally killed it for me. First, I could set date-based reminders, but couldn't set time-reminders. Second, it always felt a little cumbersome to add tasks. I had to decide what list they went in, when I wanted them in which list, and if I wanted a reminder every time I added a new to-do. I'm sure that level of verbosity is useful to a lot of people, but for quick things like reminding myself to take out the trash later, it was needlessly cumbersome to me. Also, I never had the best luck keeping my tasks in sync between my devices, even though Things has their own cloud service.


The app that finally won me over was Clear. Clear managed to hit all of my requirements in a kind of fun, minimalist manner. The drag-to-manage interface is really nice, and well suited to the fast paced way that I like to add my to-dos.


I can create and remove items and lists quickly for things that I need or complete, and time-based reminders are just one or two more taps to add to any task. The themes are nice, and you can actually unlock more, which adds a fun little "gamification" of lists. And it uses iCloud to sync, which works fine most of the time, so it meets that requirement, too.

It's not perfect. The iPad app is, in my opinion, a little nicer than the iPhone app, mostly because the extra screen real estate makes the interface slightly more intuitive, but I got used to the quirks of the iPhone app after a while. Also, occasionally I run into issues with getting iCloud to sync up properly, but a quick force quit usually resolves that. Overall, I'm pretty happy with it.

So, what made it stick?

Honestly, finding the app that works with your particular workflow makes all the difference. Being able to add and complete to-dos easily helped make Clear stick better than anything else I tried, but I also had to adjust my personal workflows to accommodate using a list at all.

I had to train myself that if my wife asked me to do something, I added it straight to the "Personal" list. If it occurred to me that I needed to do something to the car, it needed an entry. I still haven't fully gotten my tasks integrated into my work workflow, I still kind of use email as my tasks manager there, but I'm getting better, and I can see what the process looks like elsewhere in my life, which helps.

I also added a little time into my morning and evenings where I sit down and check over the list and think of things that I might need to add or complete for the day. It provides a nice few minutes where I can kind of take stock of my day, organize my thoughts, and help prepare for the next day.

My process isn't perfect, things still kind of slip through the cracks where either things don't get added to the list and I still get them done, or I forget to add them and they never get done. But it is just that, a process, and I keep improving over time. Overall, I feel like it help me keep things a little better organized, which is obviously the ultimate goal. There may be other apps that I'll try here and there (I'd love for OmniFocus to go on sale so that I could feel a little better if it doesn't work out), but, overall, I'm pleased with where I am.