✱ Dr. Tasklove — Or How I Learned to Stop Worrying and Love the Work

Ok, so weirdest title ever? Probably. Why? Because I’ve switched task management apps more times than I can count. For years I’ve looked for the perfect option for my nit-picky ways. I’ve moved back and forth between apps, often relying on hack-ish scripts to import/export from one app to another. I want to give a glimpse into why I’ve been having so many issues settling on one system, and what I finally decided to do to stop this madness (for now at least). By now you’re probably wondering how many apps I’ve tried. To be honest, I’ve lost count but here are a few that I’ve tried extensively on both iOS and Mac (endorsements and criticisms included):

  • Appigo Todo - This was the first task app I ever tried on iOS way back in 2008. In short, I hated it.
  • Things - We’ll get back to this later.
  • 2Do - Not bad, but very very confusing (Could just be that I’m an idiot).
  • The Hit List - Beautiful, but comes with paid sync and infrequent updates. Not for me.
  • OmniFocus - We’ll get back to this one as well. I adore this app, but I’ll explain why I’ve stopped using it.
  • Clear - Another great app I couldn’t stick with for some unknown reason.
  • Wunderlist - A resounding “meh”.
  • Firetask - This one has a ‘cartoonish’ UI, and call me crazy but I felt like it diminished my work. Odd I know, but I just didn’t work out.

There are a bunch of others that I’ve given a shot, but won’t go into them mainly because I didn’t stick with them long enough to give an accurate assessment.

Nate, what is wrong with you?

I really don’t know. Those who know me well know that I have a problematic addiction to apps. It’s quite possible that this has gotten in the way of my productivity. In fact I know it has. But one thing is clear to me; once I find an app I love, I stick with it. So why can’t I seem to figure out the GTD/task problem? I think partly because there are so many good options out there. Let’s first talk about the two most well known apps on the market; Things and OmniFocus. Comparing these two is nothing new. In fact, it’s been done countless times. What I haven’t seen, is folks having as much trouble settling as I have. Usually an app is picked, and the user sticks with it. Not so much for me.

You down with GTD?

Things was the first app I was able to make a home in for more than a few days. I loved it. It’s simple and beautiful. But after a few months I felt like I wasn’t getting any bang for my buck and turned to Omnifocus since it seemed that everyone raved about it (and with good reason). Most task management apps try to in some way incorporate the GTD method1, which can be good for some. My main problem was that I read books, and watched videos about the GTD methodology, and it got me excited to try it. Why is that a problem? Well for most it wouldn’t be, but for ADD Nate it is 2. I started to obsess about the app instead of the work to be done. Contexts, Projects, Start Dates, Due Dates, Perspectives, Areas… Those became my tasks. Something wasn’t right. I turned to the Internet for help.

I tried learning from the pros, often watching videos and screencasts of how the masters of GTD set up their workflow. As you’ve probably guessed, this was my new project. Again, work was getting ignored. This was my main issue while using the incredible OmniFocus. I say incredible because I have an enormous amount of respect for both the app and its creators at The Omni Group. It’s a powerhouse. Problem is I got too wrapped up in tweaking it. Shawn Blanc explains my problem perfectly in his review:

Everyone in the GTD fraternity knows how easy it is to incessantly fiddle with our systems yet never actually work. And that is the trap door with an app such as OmniFocus. It is so powerful, so robust, and so tweakable that it’s easy to spend more time fiddling with our action items than it is to actually do them.

Most power users are able to rise above those barriers and use OmniFocus effectively. I unfortunately was not. It was such a great app with so many options that it overwhelmed me without me even knowing it. I thought I found the perfect tool to organize my thoughts and get things done. Sadly I hadn’t, so I turned back to where I started.

Back to the drawing board

I’m not going to review Things, as that’s been done to death. If you’ve been under a rock for.. Say.. 5 years or so, you can read Macworld’s review here, or Shawn Blanc’s excellent review here. Far and away what drew me into Things was the incredible UI. But what has always intrigued me about Things is its powerful simplicity. In fact after switching back to Things, I was actually completing my tasks. Imagine that! Will I ever switch apps again? Well this past weekend, I did…

Onto the next

Enter Cheddar. I took a quick look at Cheddar here on the site, and I love it so far. So much so, that I’ve almost completely switched over. The only thing holding me back is repeating tasks, which I continue to use Things for. I’ve cut ties with all the cruft that my old apps provided mostly because I’ve finally realized that I need to enter tasks -> do the work -> mark complete. That’s it. The huge feature sets were keeping me from doing what I was supposed to do. I think I’ve finally found an app that I can stick with. Doesn’t hurt that it has the fastest sync I’ve ever seen. Cheddar helped me come to the realization that I needed to stop trying to conform to an app, and instead find one that actually fits my needs.

In Closing

Here’s the deal; use what works for you. This article wasn’t meant to strong-arm you into taking sides or picking certain developers to buy apps from, it was intended to share my experience with task management apps and where I ended up. Task apps are aplenty both on Mac and iOS. My advice is read up on the systems behind them and choose what’s best for you. Otherwise you’ll end up on a strange ride like I did.

Update: I’m back to Things again…

  1. Which is not easy to do or understand at first. I highly recommend reading about it first. 

  2. Yes I really have ADD and it can be a serious hinderance even though I’ve got it mostly under control hooray for ADD-ish run-on sentences.