In this corner, costing $39.99 and wearing purple trunks, please welcome the 800-pound gorilla of task management, the titan of to-do lists, the giant of GTD, OmniFocus!

And in this corner, costing $49.95 and wearing blue trunks, please welcome the little app that could, the tortoise to the hare, fresh from a four-year nap and ready to sync, Things 2.0!

Alright. I want a good, clean fight. No hitting below the belt, and no violating Apple’s sandboxing rules.

*ding, ding*

Quite literally a couple of months ago, I switched from Things to OmniFocus. This was not done lightly, as I’ve tried OmniFocus in the past, and couldn’t make heads or tails of it. With this latest attempt to make OmniFocus work for me, I at least managed to keep my head above water for a time. This was probably by virtue of using the iPhone app first rather than diving into the deep end of the Mac app’s absolutely confounding and endlessly fiddly interface. Instead of staring down a blank, intimidating void, I was able to acclimate to OmniFocus though the gentler, more obvious iPhone interface. I even managed to recover from a database sync disaster early on with no outside help. Once I started using the Mac app heavily, however, I began to feel overwhelmed.

One thing I’ve learned about myself in my brief time on this planet: if you give me something to fiddle with, fiddle I will, often to the detriment of getting anything else done. OmniFocus has endless ways to fiddle. I can add start and due dates set down to the minute, tweak contexts to be super-granular and location-aware, hook it up with Siri, set up perspectives to get a different view of things that need to be done, script it and use templates, customize the theme… There’s so much that can be done to get stuff into OmniFocus and have OmniFocus nudge you to do stuff. It’s the Swiss Army Knife of task management applications. Sure, you can use it to whittle, but even as you whittle, the corkscrew, fish-scaler, tweezers, magnifying glass, bottle opener and other geegaws are there to tempt you.

Things is much, much simpler. It’s not as simple as some apps, but compared to OmniFocus, it’s a breath of fresh air. It may be that I lived in Things for so long, but opening it up again and seeing the soft, slightly textured blue-gray window felt like coming home after a long journey. Well, coming home to a house where I had forgotten have the mail and newspaper delivery held, as a bunch of my repeating tasks—bills and errands, mostly—had piled up. First thing I did was clean up. I’ve opted to start over from scratch this time, and hopefully get my system right and avoid the pitfalls that made me want to switch away in the first place.

One of the problems I’ve had with Things and OmniFocus is figuring out what goes in there. Is my list of artists and albums to check out for future Crush On Radio picks a project? Books to read? Post ideas for Sanspoint? Does any of these belong in my task manager? If so, how do I organize it? These are fundamental problems of any GTD system, and I’m going to be wracking my brain to figure out a solution for a while. For the time being, endless lists like this will end up going into my system in some form, once I can establish a method for doing so. In fact, this is one of the areas where OmniFocus does beat out Things—there’s the option to set a project as merely a list of unconnected Single Actions [1] with no “completion” state, which served as good buckets for lists like that. Things is a bit less structured, but the “Areas of Responsibility” feature might make for a good substitute.

Things is also a little more nebulous with regards to GTD’s Contexts. [2] OmniFocus is built around a canonical GTD view of Projects and Contexts. Actions are part of a Project, and assigned to a Context. All actions can be viewed in relation to either Contexts for the actual implementation phase, or Projects for review. Things doesn’t have any specific implementation of Contexts. Instead, there’s the “Areas of Responsibility” which can house projects and actions, though an action housed in an “Area of Responsibility” cannot also exist as part of a project. This is mildly infuriating. I’ve taken, this go around, to using the application’s tagging feature to add contexts to actions, which feels like a serious kludge.

What I have to figure out, when it comes to these potential trusted systems, is which allows me the least friction not only in getting my stuff in there, but processing it and doing the work. It’s easy to get stuff into OmniFocus, but it’s hard to process and organize that stuff due to both the friction inherent in the interface and my own endless desire to fiddle and futz to get my tasks organized just right. Things is slightly less flexible in terms of getting stuff in, but so much easier to take what’s already in the app and process it. The final part, the actually getting things done part of GTD, is something that can’t be fixed by software. My hope is that if I can reduce the friction of getting stuff where it needs to be, I can reduce the friction of actually doing what needs to be done.