On a recent episode of Back to Work, Merlin bemoaned the struggles of using Apple’s new iCloud service. In short, iCloud fails to let Merlin have everything everywhere. He contrasts this with Dropbox, which–while lacking in Apple-like integration–does just that. Merlin’s iCloud woes echo a struggle I have in my own system, which is making sure that what I want is where I am, whether I’m at my computer, or on my iPhone. This isn’t nearly as complicated as Merlin’s struggles. I have only two devices after all.[1]

A long time ago, I wrote about having a hole in my software library, and the hacked together system I had developed to work around it. I still use that system, more or less, but I’ve run into a few holes that drive me bonkers now and then–and it all has to do with my task management system. For the longest time, I’ve used Things, which is a lovely, easy-to-use application. There’s an iPhone version as well, which is pretty solid and elegantly designed. Both work well on their own, but getting them to work together is a pain. It’s one of the few multi-platform applications I use that has no cloud-based synchronization.[2] To keep all my data from Things in concert across my Mac and my iPhone, I have to launch Things on my iPhone, while connected to my home Wi-Fi network, and let it sync with the desktop application.[3]

Look, despite what the folks at Cultured Code say about it, synchronization of something like this is a solved problem. Sync is hard, yes, but that doesn’t mean you need to re-invent the wheel when you’re doing something as low entropy as this. Case in point: Wunderlist. Wunderlist is not as nice, or as Mac-like as Things, but it does do one thing very well that Things does not: cloud sync. I can add something to the Wunderlist iPhone app, and it just appears, like magic, on the desktop app. They’ve got a solid web-based infrastructure for this, and it works out of the box. Also, Wunderlist is freeware, which is a nice plus compared to the expense of the more heavy-duty task management applications out there.

Wunderlist falls down for me in that it does not support repeating tasks. When David Allen suggests having a mind like water, I don’t think he meant it in the way my mind is. Without something popping up in my view to remind me about, say, watering the basil plant on my windowsill, I would no longer have access to fresh basil. I spent a couple days trying to kludge some form of reoccuring tasks using iCal and Wunderlist’s ability to add tasks by e-mail, only to throw my hands up in frustration after needing to break out Automator and Mail.app to do it–and finding even that didn’t work properly.

Here, someone would suggest using OmniFocus. I have tried. Lord, how I have tried. I tried it for the first time when it was Kinkless GTD, consisting of a bunch of scripts and things for OmniOutliner. I tried it again when it was in Public Beta. I tried it one last time before I wrote the first draft of this essay. All I can say about OmniFocus is that while it may work for certain people whose brains function in a certain way, I simply cannot wrap my head around it. We’re talking about an application for managing tasks. This is the sort of thing that could be done with a pencil and paper. After using OmniFocus for ten minutes, I felt so overwhelmed that I was ready to go back to a pencil and paper–even going so far as to check if the 2012 Moleskine Weekly Planners were on sale yet.[4]

So, I’m back to using Things. I stick with it, though I am well aware of other options like The Hit List, Remember the Milk, and a dozen or so other pretenders to the throne. Truth is, the minor inconvience of having to launch Things on my iPhone every morning and every evening to keep my world in sync is nothing compared to the sheer pain in the keister of switching systems now.

What I would like is something that combines the ease of use and design sense of Things with the power and flexibility of OmniFocus, has an iPhone app, some form of cloud-based sync, and a price point that won’t make me feel like I’m throwing away the $60 I’ve already spent on Things for the Mac and iPhone. There’s got to be an app developer out there who can do that.