January 29, 2019

The Return of “Task Manager Followup”

0/ quick recap

In November, I thought Big Changes were coming that would overwhelm my humble task management system, such as it was.

I downloaded the trial versions of Things and OmniFocus and proceeded to hammer at them. I fell for both, but found myself preferring OmniFocus somewhat.

1/ sideways

First, the Big Changes didn’t pan out, which caused me to reconsider if I even needed to take on a new task management system. Second, despite a childhood of elite, rigorous education, a lifetime of constant reading, and a career devoted to tireless research and the careful analysis of details and definitions, I apparently could not wrap my head around the byzantine mystery of what Apple means by in-app purchase.

In short, we would need to buy a whole second licence of OmniFocus for my wife. It’s a great app, but not that great. We just couldn’t justify the expense. Regretfully, I returned it for a refund. I resolved to remain for the time being with my current system.

Meanwhile, after Thing’s trial period ended, it reverted to read-only mode. But I discovered that as long as you don’t quit the app, it continues to function fully. On a whim, I kept testing it. I had been pretty deep-in with OmniFocus, so I was better prepared to see how Things would handle the same sorts of actions.

I imported everything that I’d exported from OF, dumped some other task-lists that had been hiding in Bear, and started to really stomp all over Things.

And it started to click. I had found Things to be annoyingly prescriptive, but now I started to see how I could downplay or ignore it. I could, in short, bend it to my will much more easily than I’d thought. Having “areas” distinct from “projects” meant I didn’t need the swamp of tags that had grown so necessary in OF. Tasks with a due-date didn’t result in a flurry of notifications. And all my repeating reminders are in Due, which takes that responsibility off Things. Everyone’s happy doing what they do best.

So, even though I really wasn’t sure I actually needed it, I bought Things, and I’ve come to love it.

2/ hijinx

Then something else happened.

About a week ago, I was finally ramping up to train my wife in on Things. But something was still nagging me.

The last puzzle piece left was that Things — like OmniFocus — was stubbornly and defiantly an app for individuals. No shared task lists or projects. I had deeply disliked all the other apps I’d looked at that offered shared management.

Then, a few days later, we had another big planning & process session at the dining table. After I transcribed everything into a shared note in Dropbox, the whole thing looked like… well, it looked like a project, with boards and lists and cards.

Board, list, card? Of course. Trello.

I launched Trello, and started entering stuff. Yesterday morning, my wife created an account, and joined the little team I’d set up. We spent the day clicking around, just naturally stumbling on features. Everytime she said, “Why can’t I just—” she’d cut herself off and say, “Oh, look, I can.”

I feel dumb that I hardly gave Trello a thought, particularly beause I’ve worked in it before and, after @mdhughes mentioned it, I even spent a day testing it.

I don’t know why it clicked now, when it didn’t click in November. On the other hand, in my experience, nothing ever really clicks in November.

For most of my own personal stuff, I still use Things, Due, and a growing library of Field Notes that I trash my way through each month or so. But for shared activities and projects, we’re rocking out in Trello, with maybe a half dozen boards already. It does absolutely everything I wanted OmniFocus to do for my little self-employed husband–wife team, with almost no friction, a shockingly short learning curve, and a very nice price — free.

So that’s the whole sordid tale.

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