Task Management Endorphin Rush

I’ve always had a hard time finding a task management system that clicks for me. I’ve tried plenty of them — OmniFocus, Things, 2Do, Todoist, good old pen-and-paper. Each of them has pros and cons.

My needs aren’t wildly complex, and I’m not a productivity nerd the way some people are. What I look for in a task manager is simple:

• Nested projects/tasks, so not everything lives on the same level.
• The ability to create a checklist without a due date, for tracking things like groceries and my reading list.
• An aesthetically-pleasing interface.

It’s the third one that’s tripped me up the most. A task manager plays such a prominent role in one’s life — I don’t want to dread opening it up.

Unfortunately, the task managers that have the features I need tend to be ugly, and the task managers that are beautiful tend to lack the features I need.

I was previously using 2Do, which had everything I needed functionally, but it was unattractive and lacking in the UX department. It was also developed by a single person (as far as I could tell), so what happens if the developer gets hit by a bus? Or stops developing new features? It made me antsy.

OmniFocus 2 was ugly as well, and my brief couple of hours with Todoist were a wildly frustrating experience — their recent redesign still looks like it was optimized for a narrower and lower-resolution screen than my MacBook Pro, and adding new projects felt like pulling teeth.

Then, last week, Things 3 was released. My first task manager was Things 2, whose lack of nesting wound up being a dealbreaker, but the trailer for Things 3 was so pretty I decided to try it anyway.

It doesn’t have all the features I need, but it’s so pleasant to use that I decided to try shoehorning my process into its constraints anyway. Then I decided I enjoyed it, so I retooled my process to match Things 3’s proficiencies.

My grocery list is now a single task with a nested checklist. I’ve flattened some of my nested projects, and ditched some things I wasn’t really working on. And, thanks to Headings, some of my lists have actually gotten more organized since losing nested projects.

My one big frustration is the fact that Things 3 doesn’t support repeating tasks inside of projects, so my weekly “Compile newsletter” task doesn’t fit inside the Random Access Newsletter project. But the developers’ very-responsive Twitter account assures me this is coming soon.

@jordankoschei We do have checklists inside to-dos now, and repeating to-dos in projects are coming.

— Things (@culturedcode) May 21, 2017

All this brings me to the larger point I’ve been thinking about lately: your task management system can’t save you.

There’s something magical about that New Management App smell. Inputting your information into a new system, deciding you’re going to get your life in order, deciding that this one will actually work, I’ll stick with it this time. Like somehow your enhanced productivity will make everything better. I always feel like Liz Lemon after her trip to the Container Store, saying “I’m going to become wonderful!”

But productivity is just a tool. Efficiency and organization are meaningless unless they serve meaningful goals, and even the goals that feel meaningful don’t guarantee true satisfaction.

It’s easy to get caught up in the endorphin rush of feeling like our lives are under control. But the bigger question remains: Under control for what?

And that’s a question we each have to wrestle with for ourselves.