That might be pointless

When adopting a new productivity system the second way of procrastinating – after coming up with any required names – is, of course, choosing what software to use.

I’ve been using Things on Mac and iOS as the holder of all my to dos for many years. When I started it seemed the best choices were that or OmniFocus and my life has, thankfully, never been complicated enough to require OmniFocus.

In fact, over recent years I’ve been seriously under-using Things: its Anytime and Someday lists go un-looked-at for months, and I’ve stopped using Areas, Projects, and Tags entirely. It’s mainly been a single Today view (where tasks often sit for weeks) plus some tasks dated for the future, or recurring every so often.

Given this under-use I was wondering if now would be a good time to switch to something else, to make a fresh start. However, whenever I’ve dabbled with this decision in the past I hit the problem that two features I do actually rely on in Things are rarely available elsewhere:

• A task can have both a When date (when it should appear in the Today list) and a Deadline date (when it needs to be finished by). Tasks with future When dates live in the Upcoming list. This is invaluable for tasks like paying a tax bill: I don’t need to see it until, say, 2nd January but it has to be done by 31st January.
• Like most apps Things has repeating tasks. But a task in Things can, instead of repeating on a set schedule, repeat a set period after the task has been completed. So if there’s a chore you need reminding to do once a month or so, it might pop up on the 15th but you might not do it for another week. So the task will next appear in the Today list on the 22nd of the following month, not the 15th. It’s so nice for need-to-be-done-regularly-ish-but-not-like-clockwork tasks.

In thinking about potential new tools I immediately thought of Kanban boards. I’ve always liked the ability to see several lists at a time, the ease of re-ordering and placing tasks, and the sense of progress in moving a task across the board to “Done”. I thought it might work well with my plan to think in terms of quarters. Perhaps I’d have columns like:

• Someday
• Summer 2025
• Spring 2025
• This week
• In progress
• Done

I haven’t used the Kanban-style app Trello for years but always liked it. Easy to use, friendly-looking, free. Unfortunately, since I last used it it’s been taken over by Atlassian, so any sense it might have had of being “Not just for work!” is undone by the little Atlassian logo casting its Enterprise spell over your boards.

Apple’s Reminders app recently added a “columns” view which is like a Kanban board. Every so often I give Reminders a try because it’d be nice to use an in-built app, and it being a bit more tied-in to other Apple apps and OSs gives some nice positives (and lock-in, but still).

However, when I tried it recently I realised it still doesn’t have those two essential features I rely on Things, so it’s a non-starter for me. You could manually hack your way around this, like adding a Deadline date in the task’s title, but why make life more difficult? Annoyingly, I think Reminders did, once upon a time, have separate When and Deadline dates but one of them was removed in some past simplification.

I use Obsidian to store notes, although as with Things I use very few of its features. I remembered that some people use it with plug-ins to manage calendars etc. Maybe I could combine tasks and notes into one app?

There are various plugins that often interact, such as the possibly neglected Kanban, Tasks, CardBoard, and the feature-rich but only-documented-in-YouTube-videos-by-content-creators Projects. Ultimately I decided that any Obsidian plug-in was going to look a bit too complicated, fiddly, and un-fun compared to the simplicity of Things, however useful it might be:

CardBoard, with Tasks, seems the most promising combination though, and I might try that again at some point if Things doesn’t work out for me.

Because, yes, I’ve decided to stick with Things for now. Nothing else has those two features I need plus the nice, simple design of Things.

But I’m not quite sure how best to organise it for my use. For now I’ve created two Projects: Winter 2025 and Spring 2025, and created Headings within those to organise the tasks I hope to get done in those quarters (only populating Winter for now). Each Project has an overall deadline of the end of its quarter. Here’s some of what’s there, to give an idea:

I’ve sorted through my Anytime and Someday lists and deleted or given a date to most of them.

I’ve used Tags to categorise every Task, although I’m not actually using them for anything so that might be pointless.

I’ve only used Areas to group those Projects and Tasks so far. Maybe Areas will be more use at some point.

At the start of each week I’ll review how things are, and give When dates over the following few days to a handful of Tasks from the current quarter. And check through everything else to make sure it’s not urgent or deletable. In theory.

It’s OK. But I do miss the visibility that a Kanban board provides. Each Things view is a one-dimensional list of Tasks but I value the 2D-ness of a board’s columns, giving a better at-a-glance overview of much more. I feel like I need to frequently flip between views of lists – or keep multiple Things windows open – to know what needs doing. I fear I’ll miss tasks, no matter how carefully I review and date them.

I’ll see how it goes. If you have a suggestion for something I’ve overlooked, let me know. So long as it has those two essential features Things has.

When I last looked at Todoist it lacked one or both of them. TickTick might have them but it was so fiddly I gave up trying to work it out.

While writing this I came across the Godspeed app (via The Hiro Report) which I hadn’t heard of. It has both essential features, a nice simple design, and a few more useful features than Things. It’s still a single-list-at-a-time view though so, given its subscription, I won’t jump ship yet, but it looks worth a try.