Essays on Technology and Culture

Moving for the Sake of Improving

There’s a debate brewing around Michael Lopp’s (aka Rands) reasons for ditching his task manager. [1]

The issue that pushed me over the edge had nothing to do with functionality or stability, but stagnation. I was performing my morning scrub on Things when I realized that nothing much had changed in Things UI in, well, years.

R.I.P. Things – Rands in Repose:

Of course, if the app works, there’s little reason to ditch it just because it hasn’t seen a major update. Law offices used WordPerfect 5.4 for DOS for years until Microsoft Word finally superseded it in the 90s.

And yet, having switched from Things to OmniFocus—twice—I can see why Rands jumped ship. Things is a very simple application, for good and for ill. If your task management needs run into the limits of what you can do with the app, you can quickly get frustrated. OmniFocus, though it has not so much of a learning curve as a learning right-angle, is much more open and flexible as to how you can use it. It can open up a lot of new ways to get things done.

Rands’s new tool of choice, Asana seems to be doing the same thing:

It’s added a little more friction and a little more religion to my task tracking process, but it’s also done something Things hasn’t done in years – it’s new bevy of functionality has me asking one of my favorite engineering questions, “How can I do this better?”

Which leads me to Daniel Jalkut’s rebuttal, and one section in particular:

[W]hat really frustrates me in this case is the software has served him perfectly, and he thanks it with a slap to the face. It’s one thing to denigrate a product for failing to meet your expectations, or for exhibiting a clear lack of craftsmanship, but Lopp admits that those problems do not apply…

Has the software been serving him perfectly? I’d say not. I remember the absolute frustration while Cultured Code took two years to figure out how to sync tasks across devices. The first iPad hadn’t even been released when they started working on the problem. I’ve said that “right trumps fast”, but OmniFocus beat them to the punch. This was why I jumped to OmniFocus the first time, once the dance of syncing my tasks with Things on my iPhone every day grew frustrating. I don’t see it as a slap in the face. I paid $70 for all three versions of the App. I think that’s compensation enough.

This is why I sympathize with Rands’s complaint that Things has “stagnated.” He’s wondering if there are ways that he could improve how he’s working, and that involves new tools. As long as it doesn’t keep you from doing the work, what harm is there in trying other tools? Especially if you feel limited by what you’re using. Enter Ben Brooks who has been inspired by the discussion to do the same thing.

My goal isn’t to try and leave OmniFocus, but to make sure OF still is the best solution for me. OF has gotten so ugly on the Mac and iPad I almost refuse to use it in those places. Which means I am essentially using the iPhone app, and even the new iPhone app isn’t the best looking app

Moving for the Sake of Moving — The Brooks Review

I disagree about the iPhone app, though doing my reviews on the iPad often makes me frown when I see the old iOS 6-style UI. I’ve also tried the OmniFocus 2 betas and I like the direction the Mac interface is taking, though I switched back to OmniFocus 1 because I actually needed to get work done. Still, it’s Ben’s opinion, and he’s entitled to both it, and to try and find ways to optimize his workflow.

Which leads to Patrick Rhone’s series of posts on App.Net on simple systems and the concept of the no-grade. There’s no question that any digital task manager adds a lot of complexity to something that should be simple. I can only speak for myself, but having a complicated system I understand and can manipulate to a great degree really helps me a lot. I’ve tried simple systems, including pen and paper, and have gotten lost.

However, I have (re-)introduced pen and paper to augment how I get stuff done, via Bullet Journal. I see it as a way to supplement the digital system I’ve built. I’ll provide a full report on how well it’s been working once I’ve spent more than a few days with it. So far it’s been helpful, but I wouldn’t have tried it unless I’d noticed a dissatisfaction with OmniFocus and my existing system. Switching for the sake of switching can be a waste of time. Switching for the sake of trying to improve something can have huge benefits. It never hurts to at least dip in your toe.