Task management: Taking care of things (or Things)

I’ll confess this right up-front: I am not, by nature, the very most organized person on the planet. My mother used to call me the absent-minded professor (she was from the Jerry Lewis era*), and indeed, I tend to forget anything that’s not on my most immediate radar.

Over the years, I’ve tried quite literally every task management approach under the sun (or it feels that way), and I’ve had trouble sticking with anything very long, either because I forget to use it (that’s a joke), or more often because the task management system simply doesn’t work the way my brain does.

For me (and I suspect actually for most people), tasks blend several attributes in unpredictable and variable ways:

  • A description of the task (the headline);
  • Applicable notes or details;
  • Some indication of when you want to do it, or expect to do it;
  • Some indication of when it has to be done (the deadline);
  • A bucket (is it work, home, personal, or some other thing);
  • Some indication of relative, subjective importance to me;
  • Perhaps some list of tags or other sorting mechanisms (but usually not);

and, perhaps most important of all,

  • A visual way to indicate that I did the task when I have done so.

Technology seems like it should be a perfect solution to the task management problem. I want an application to tell me, based on all the inputs above, what I should be doing right now. If the computer knows what, and when, and how important it is, and when the deadline is, etc., etc., then cough-up a list of the stuff I need to do, with the most important thing sorted to the top, the second most important thing sorted under it, and so on, and let me focus on getting stuff done.

Alas, any software I have previously tried for this omits one (or usually far more) of the items above, and leaves me covering the shortcomings with manual effort, which in the end, completely defeats the purpose of trying to manage tasks with a piece of software to start with. I might as well go back to a simple list of things, store it in OneNote, and cop to being an absent-minded professor who’s going to drop balls constantly, and disppoint all the important people in my life. (Like me spouse. And my boss.)

Never one to (completely) give-up, I’d seen references to a software ecosystem called Things from German company Cultured Code, particularly when Things 3 was released awhile back. In fact, I’d even tried Things 2 at one point when it was either free, or deeply discounted, for a short time (maybe it was Apple’s App of the Week or something). I wasn’t impressed, and didn’t use it for more than a week.

But Things 3’s feature list and teaser videos piqued my imagination, and boy, was I tempted. But I didn’t buy it (literally, or figuratively). It seemed too good to be true, and my mix of Post-it notes on my monitor, stuff in OneNote notes, and pieces of scrap paper with handwritten stuff on them was working just fine, thankyouverymuch. (OK, it wasn’t, but let’s overlook that for now.)

Months go by. I change jobs. Suddenly I have a lot to do, and a lot of keep track of. I knew my current approach wasn’t up to the task (bad pun), and it was time to reconsider. I watched the Things 3 videos again. It seemed to tick most of the boxes. I got Things 3 for iPad.

This is a good point to take a detour; Cultured Code, much to its credit in my view, takes a classic approach to app release and pricing. There’s none of this ad-supported, freemium, download-for-free-and-we’ll-gouge-you-with-in-app-purchases crap. Instead, you pay up-front, and no, it’s not 99 cents. The iPad version is $20, and the iPhone version is an extra $10. If you want it for your Mac, you’ll be dropping a whopping $50 more, although for the desktop, there is a trial available. I guess if you want to organized, it’s going to cost you.

So, what do you get for the spend?

Things checks all the boxes I listed above, with two exceptions:

  • There’s no indicator of relative importance; and,
  • There’s no auto-sorting as a result.

Everything else, every other dimension by which I think of my stuff to-do, Things does. And it’s easy. And it’s intuitive. And it’s cloud-synced.

One of specific challenges I have with tasks is just getting them documented in the moment, when they occur to me. Things makes that easy, and it provides an Inbox for that. You can send e-mail to add a task. You can turn-on Siri integration and speak them into the app. Or you can go old-skool and type them in. Regardless, an ability to quickly and easily get items recorded feels like half the battle.

The other half, of course, is organizing stuff once you’ve gotten it captured. Everything else on the bullet list provided earlier is supported. Buckets are called Areas in Things. In terms of when, you decide when you’re doing something — or leave it in Someday and deal with it… someday. You can set deadlines. You can tag things. You can add notes. You can put a list of things in a task. You can break a task down into smaller parts by converting the task to a project and putting tasks in it (which addresses a common challenge for me and many other people: being overwhelmed by the scope of a task, and then never starting it).

I’m roughly two weeks into my Things 3 experience, and so far, I have to say it’s been a godsend. At home or work, I have my iPad handy. And I have my iPhone with me anywhere else — so one of the devices is ready at any time, either for task addition, or task completion, or task sorting. And I seem to be getting stuff done. And I seem to be less stressed-out about it.

The primary challenge with Things 3 has nothing to do with Things 3 — it’s simply forming three basic habits about task management:

  1. Starting each day by reviewing your tasks, bucketing them, deciding when to do them, seeing what’s coming due, sorting them if you want. For me, one critical part is getting stuff out of the Today view when it’s not going to happen (or doesn’t need to happen) today; that’s what keeps me from being overwhelmed by the amount of crap that’s in there. The app is there; use it.
  2. Getting new tasks added; those fleeting moments when something occurs to you is exactly the moment you need to write it down. The app is there; use it.
  3. Reviewing the tasks throughout the day, checking stuff off (critical for a sense of accomplishment) and making adjustments. Interruptions happen. Urgent things come-up. Your day gets derailed. Use the app in these moments. Task management needs to be an active process; it’s fluid. The app is there; use it.

You’ll see a couple of things in those three items that are super-critical for me:

  1. Not getting overwhelmed.
  2. Having a sense of accomplishment.

Face it: We all have a crap ton to do. You’re never going to do all of it; certainly not today. Take the time to use the tool to sort things appropriately, and you won’t get overwhelmed and then freeze (as I tend to do in such situations). Equally critical is feeling like I’ve done stuff, that I didn’t waste my day. Things, of course, let’s you check stuff off, but you can adjust its behavior; you can immediately move completed tasks to the Logbook, and off your task list, or you can leave them in-place and it’ll move them to the Logbook at the end of each day, or you can leave them there until you manually move them out. I picked the middle option; I love ending my day by seeing what I managed to get done, and basking in the accomplishments. I can start each new day with a cleaner view, and the Logbook is always right there so I can always look at it, and think to myself, “Holy crap, look at how productive I am these days!” It’s a great feeling.

If you’ve surmised that I’m quite happy with my $30 investment in the Things 3 app ecosystem, you’d be correct. It has a stunning, clean, and modern UI, and the design of the UX is well constructed and conducive to adding every one of my key challenges in task management. Consider me a convert.


* The Jerry Lewis reference was actually a movie titled The Nutty Professor, but the two references seem to get crossed quite often.