Happy 2010 everyone!

3 years back on the Mac fulltime and I'm still trying to find task nirvana. I need more than a simple to-do list or just starring my email, less than a full blown GTD system of complex contexts and next actions. My mantra: if it takes longer to keep my tasks organized than it takes to do the tasks, then it's the wrong solution.

Last year I bounced back and forth between Remember the Milk and Google's built-in task management. RTM is great. But it's very browser-dependent. It wasn't in my face enough outside of the browser. And I was tired of how often the integration with Gmail stopped working (not RTM's fault that Google keeps their code a moving target, but still). This eliminates other cloud-based task managers in my mind, such as Toodledo. Google Tasks doesn't have recurring tasks, and with more than a handful of tasks I was losing focus on what was most important to do. Simple sorting isn't enough. Context does matter.

So for 2010 I think it's time to move back to a desktop solution. But which one? As a Mac user, I've narrowed it down to 3 main contenders: OmniFocus (which I already have a license key buried somewhere), Things and The Hit List.

My priorities:

• Each morning, I look at all my tasks and decide which ones have to be done today, while allowing wiggle room for the fires that I know will pop up. For the most part, I try and end my day with a clear "today" task list. I want software that works that way too without my having to fight it. If I complete that list, I want to see what I need to do next without being distracted by someday or "can't do this until…" tasks.
• I want to be sure I can get email messages in it easily. I'd say 80-90% of my tasks come from email messages.
• I have a MacBook, an iMac and an iPhone. I want to get at my tasks no matter where I am.

I took a second look at OmniFocus and once again, dismissed it. Too complex and fussy. I typically have no more than 3 or 4 projects on my plate, the rest of my tasks are broader. I can look at OmniFocus with 40 open tasks and have absolutely no idea what I should be doing next. I do have to say I like that it does Bonjour syncing which would make keeping things aligned between computers a lot easier.

So for me it's between Things and The Hit List and I can't decide between them. They're both around the same price. Both written by single developers or very small teams who have real lives and have taken hits for not working as fast as their user base wishes. The Hit List is still in a so-called public beta/preview release, with the iPhone version coming soon.

Comparison points:

I like the quick entry box in Things. If you hold down control-option-space it will look at what you have in the active application or selected and include detail in the task notes. If I'm on a Gmail message, a link to the message is automatically included. That works for linking my task application to my email. I could also drag any file or URL to the Things dock icon to create a task.

The Hit List works in a similar way, but the quick entry box doesn't read the context of where you are, requiring an extra step to get the URL. A better way of dealing with URLs is to drag the icon from the address bar to The Hit List dock icon, and then you get a task that automatically is "Look at…"

In both applications, the inbox is the place where items are captured unfiltered. On a regular basis, you are expected to go through the inbox and decide what to do with each task. Is it something to be done immediately? Part of a project? Scheduled? Repeating? The idea is to deal with it once on collection, then not think about it until it's time to actually do it.

Things and THL handle the inbox differently. And it's this difference that is giving the edge to Things for me. In Things, as soon as you make any kind of decision about a task it's out of the inbox. You can give the task no tags, no projects, nothing special and just drag it to Today and it's out of the inbox. Or, if it's something that you know you can't deal with for at least a week, you can drag it to "Scheduled," decide when you'll be ready to look at it again and it's gone. With THL, a task is only out of the inbox when it's assigned/filed. You can set it as a "today" task, but it still sits in the inbox with a blazing "deal with me" badge until you assign it to a list of some sort. I like a very clean inbox, but don't necessarily want to categorize every single thing into a bucket. If I've decided I'm going to do the task today, it shouldn't be in the inbox.

Overall, The Hit List's interface is a little cleaner and uses simple Start/Due dates. Things can get a little confusing between scheduled and due dates. Both have repeating tasks and handle them nicely.

Both handle multi-Mac sync in the same way. Both have a library/database file that was easy enough to place in DropBox so I can get the same view of tasks on both my iMac and MacBook. Both have the same limitation in that the applications must only be open on one machine at a time. I'm going to try and remember to quit my task manager on whichever machine I'm on before I walk away, but that's not my habit and may be a challenge. I much prefer how 1Password does it…the shared keychain file is updated when it's updated, so I can have it running all the time on both machines without a problem. Things and THL only update their database when the application quits, which could mean lost work if the application crashes.

Things has an iPhone application which syncs with the desktop version over wifi, similar to 1Password's solution. I can't test that until I've committed to the desktop version as I don't want to spend $10 on an iPhone app I may not keep. THL has been promising an iPhone app for a while and the developer seems to be actively working on delivering on that promise.

Longer term, it's harder to figure out which is the safer bet. Both applications are by very tiny companies. Things seems to have a bit of a small team behind it, while THL seems to be a single-person shop. The guy goes on vacation or stays quiet for a while, and the users wonder if the app is still actively developed/supported. Things is further along, but it seems to be more about being out of the gate sooner than a fair comparison of commitment to the project.

It's going to be a bother, but I think I'm going to try and use both applications equally for the next week, then decide which one gets my $50.