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PTPL 108 · Workflowy’s Plain Text Calendar Beats Obsidian’s

Drag and drop into the side bar was the clincher

This week: The text-based calendar and task management system that’s got me looking at a proprietary app, all thanks to one beautifully detailed Workflowy video. I’ve recreated it in Obsidian, but Workflowy is looking like the best option for this particular use case.


The No-Plugin Plain Text Calendar Experiment

It’s been a while since I was bitten by the oh-my-that-is-so-cool-I-must-try-it-at-once bug, but it’s happened again! All because of this video. It’s a 36-minute presentation by Frank Denegaar, showing in detail how he uses Workflowy as a completely manual, text-based calendar and task management system.

I’ve been aware of Workflowy for a few years now, but never gave it serious thought — until now. Believe it or not, I’ve cracked open a proprietary app to see what’s under the hood. More on that shocking news later.

Screenshot from Frank Denegaar’s Workflowy manual calendar video

It’s a great system, so naturally I thought, can I do something like this with a file-based app and wiki links?

Obsidian window showing a list of days and activities, calendar style. There’s an outline in the right hand pane showing all the months and weeks of 2024.

The answer is both yes, and no. And yes. (And no.)

In the screenshot above I’m using Markdown headers rather than a classic outline, so that sections will show up in the outline pane. This is the kind of navigation power I’m looking for in a text-based calendar.

Workflowy has some built-in outliner superpowers I haven’t been able to emulate in Obsidian, such as dragging and dropping of tasks to a list of dates and times in the side bar. Copy/paste between parallel panes really doesn’t cut it. Not even the Outliner plugin can solve this one to my satisfaction.

Lesson: Obsidian can be made to do all kinds of magical things, but it can’t do everything well.

Gems from the video

After watching the video, I am all-in on replacing the word backlog with forward log. A backlog feels like you’re behind, trying to catch up, whereas a forward log is something that flows towards you.

Here are some points of interest in the video (there are plenty of others):

  • 12:00 — Why not use a digital calendar, especially for repeating tasks?
  • 15:00 — With a Forward Log everything streams towards you, one day at a time
  • 20:00 — I don’t have an inbox
  • 21:45 — When is the next logical, opportune, or reasonable time to push this item to?
  • 23:00 — My timeline is my inbox

Why I’m mirroring the same system in both Obsidian and Workflowy

One Big Text File(OBTF) is a massively helpful tool that I use daily, but I still want the ability to write flexible, transportable plans and notes to myself on future days. Neither the OBTF nor paper easily allow for this.

I used to do forward planning in Obsidian, but even with interlinked navigation, having each day as a separate file felt fragmented. And complicated.

One aspect of the fragmentation problem was solved with a system that transcluded days and weeks onto one monthly page, compiled from individual files. It worked, but had its downsides, too. Perhaps that’s why, even though I still think it’s a perfect system for some people, I abandoned it as soon as the last kink was worked out.

And so I’m trying out my own version of the workflow demonstrated in the video mentioned above, in both Obsidian and Workflowy.

Why both?

Because getting my feet thoroughly wet in each of them is the only way to learn which suits me best.

Pick a set of drawbacks you can live with

So far I am strongly inclined towards Workflowy for my calendar. Just my calendar. It’s nice having a dedicated space for it, and it’s wonderful to be able to drag a task from one hour/day to the next with no scrolling!

I’m comfortable with Workflowy for this specific use case because a 5-second process has a complete backup safely stored with my other plain text notes in immediately usable, nested Markdown.

The one thing I miss by having a calendar that’s removed from my Obsidian vault is the ability to easily insert links to project pages and other related notes. This drawback is easier than I thought to live with, however, and it seems to be helping to keep my focus on the top-level planning process rather than being distracted by details.

If you’re inclined to try out Workflowy, this referral link will give us both extra features on the free plan.

This Medium story by Rubén García Pérez first introduced me to Frank Denegaar’s system. Thanks, Rubén!

Learning the Command Line — week 2

Johnny Decimal is teaching me the command line. He welcomes input from those already familiar with it on the way he’s demystifying this baffling super power, so feel free to join in the conversation on the Fediverse!

One of the things I learned this week is why word spaces in file names can cause a problem, and what to do about that.

Comment from Constantin, an IT guy who’s following along:

Hi both, just wanted to say thank you for this open and transparent communication about this learning experience! I work in IT for some time and its not only a great reminder on how things work but also how many things are logical and others are ambiguous and sometimes confusing.


A beige page with stylised white lines sits at an angle on the left on a white background, with black text overlaying it that reads Plain text. Paper, less PRODUCTIVITY DIGEST

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