The hunt for the perfect productivity app is making me unproductive

In an effort to marshall all the activities of my life hats – employee, mom, grad student, homebody (not really, but I wish), community volunteer, wife, friend, and on and on, you see? – I decided to amp up my chores/tasks/to-dos, noting them down properly and actually ACTING on them.

Easily said.

For the past couple of years, I’ve fiddled around with quite a few applications/systems. I really did start with pen and paper – I LOVE notebooks and agendas and have tons of lists, even a notebook JUST for lists. But during the past four years, coinciding, really, with the birth of le Petit, I’ve tended towards a digital lifestyle: digital writing, journalling, bills storage, document management, and it only made sense that my tasks system should be digital, and any associated task reminders be in digital format, since my iPhone and laptop are daily, essentials tools that are always on hand.

So over the past three years, as I came across task apps, I took note and tried them out. I was looking for one that fit for my, and later, for our life.

The number of apps I’ve actually tried is somewhat ridiculous:

  • Remember the milk
  • Todoist
  • Toodledo
  • Ta-da list by 37 Signals
  • Google calendar
  • Yahoo calendar
  • iCal
  • Producteev
  • Cheddar
  • Asana
  • Coolendar
  • Orchestra
  • Astrid
  • HitList
  • Google tasks
  • Wunderlist
  • Things

(And this isn’t even all of them. There are so many one-offs in the Android Play Store and iOS App Store!)

One would think that with all these choices, there would be something that would work. But nooooooo, maybe I’m just that exacting (not really), or that anal (I don’t think so); I’m still on the hunt for a perfect system. (I’ve listened to enough podcasts to know that ha! I am not the only one with this disorder. There are many many folks out there looking for an app/system that really fits their bill).

So, no, I haven’t found ONE that totally works, but I know now that there are elements that are necessary for me, for my system (which very well may be different for what you need for your system):

  • sync between desktop and mobile device, preferable multi-platform (Android & iOS)
  • time-specific reminders
  • natural language entry (once you start, you can’t go back. That’s entering “2d 1pm” or “next week” or “tomorrow noon” and having the app add the right date/time without having to type in or scroll through a calendar to get it just right)
  • entry shortcut keycombo
  • various views (by due date, by project)
  • really really preferable with Google Calendar sync (since mon mari and I put all our home events into one shared Google calendar, I detest having to enter something twice, once in my task management app, once on the calendar)
  • preferably with Contacts integration (i.e “call Esther” will auto-populate Esther’s phone number)
  • easy edit of tasks, including moving to different project or list
  • hide completed tasks but keep them for reference
  • allow image insert

I have some beefs with apps that I have tried out, some of them for over six months:

Astrid: what’s with “social sharing of lists”? I just want to share my list with maybe mon mari but not see the world’s “featured” lists on my homepage.  Wunderlist: why is it essential to show ALL completed tasks on a tasklist? The length of the completed to-do’s  (much longer than the current tasks)  totally clutters the page and strips away my delight at the brevity of my efficient, manageable to-do list.  Appigo’s To-Do: I totally don’t get the free/pro models since the free app requires an annual subscription to work, and the free model requires one to pay $14 for the app.  Omnifocus: I’m halfway convinced to jump on board but really, would it be worth $110 for the ecosystem of apps for me? iCal: why is syncing with Google so. dang. complicated on the iPhone? There is an exchange way of syncing, an iCal way of syncing, which might/might not be ideal for Google Contacts, but syncing one way won’t get your Google tasks to show up, and another way makes calendars appear twice.

So I’ve just installed Things for Mac. I am a sucker for a gorgeous UI and this one is lovely in spades, but I am daunted at how much there is to learn about how it works. It’s definitely the most complicated to-do management app I’ve ever tried. But I want to give it a go, having read that so many of my hacker/developer superstar idols just love it. (Although I was DISMAYED three days ago to discover that there is no calendar sync with the tasks. But then, it syncs with Reminders on the iPhone, WHICH I DON’T USE. And I’m watching video tutorials on managing tasks and projects in this app. That just seems wrong.)

The short of it all is that I’ve seemingly wasted a LOT of time trying to get a system of managing work tasks, and by implication, my TIME, better.

However, there is some secret pleasure in the fiddly-ness of it all, a weird, somewhat twisted pleasure that’s ok until it cuts into my ability to actually get things done.  I’ve heard people swear by their systems, and ultimately, there is some effort/learning curve in getting up to speed with a system that will ultimately help one become a task ninja. That’s what I’m aiming for: becoming a task ninja and mastering my life projects.