September 28, 2015

Obstacles in my current plaintext productivity

I have used plain text productivity for quite some time via Taskpaper format and associated apps. I like the low-level format for longevity and portability. I also enjoy the blank canvas of a plain text document rather than trying to bend to the vision of an app developer (I favor a GTD hybrid).

I’m running into trouble with my productivity lately in some key areas:

  • Difficulty bringing inboxes to the Taskpaper list.
  • Difficulty with repeating tasks.
  • Desire for calendar and tasks to be unified in some sort of view.
  • Low utilization of Notification Center and Watch which are compelling developments.

I’ve long thought the app model on iOS had a weakness of creating app buckets” which fragmented some information. In the instance of productivity, habits, tasks, and calendar are difficult to unify. Some apps try but none have done it well. Notification Center and watch are a sort of unification of these separate app buckets. Using these, one can select the best available app for each theme and bring them together.

What to do?

Taskpaper format

Scripts are available that add emails to a Taskpaper list and that allow repeats. Taskmator can send a timed alert to Apple Watch and to Notification Center. Alerts are not possible on Mac (although Taskpaper 3 is in progress - could it bring such functionality?). I have used Geek Tool to put the next few days of appointments on my desktop using iCalbuddy along with tasks from Taskpaper. I tried putting a list of the day’s tasks on Notification Center and Apple Watch via TextFlight but this required too much upkeep and items cannot be checked off. I’ve considered using a modified script (one method) to append the day’s appointments to my Taskpaper list. A remaining obstacle is putting the Taskpaper list on Notification Center and the Apple Watch such that it can be manipulated - I’m not aware that this is possible.


An obvious inclusion here, Omnifocus is a high-end app from a quality dev house. I’ve never jumped in fully but have monitored it closely and bought updates from time to time to foster good development in the community. Omnifocus brings together disparate buckets such as tasks in email, has repeats, has a Calendar view, and utilizes Notification Center and Apple Watch well. I’ve always thought Omnifocus needs to have deferred items in the Forecast View counts (could be simply implemented as a fraction such as 2/2, 1/5, deferred/due). Also, my personal GTD hybrid philosophy favors multiple tags (contexts) per task to allow high-end filtering and searching. This is not consistent with the Omni view. When I’ve used Omnifocus in the past I tend to hate not being able to see the full list of tasks easily; I start to dislike having to tap endlessly into and out of screens or pickers to add metadata to tasks (a strentgh of Taskpaper paired with TextExpander); and I go down the rabbit-hole of frequent tinkering with a powerful app. I’m curious at the frequency with which I see Omnifocus users also using Due for reminders which suggests disatisfaction with internal reminders. A weakness of Omnifocus that I don’t care about is a lack of collaboration.


A popular app at present with syncing across multiple platforms as well as strong collaboration options. Since I care about neither, Todoist looks to me like a mediocre task app. Really it reminds me of Things or Omnifocus circa 2011. Not interested in paying money for that. It does have Notification Center and Apple Watch presence as well as repeats.


I invested in all versions of Things years ago and used for quite some time with wifi sync. The wedge that dislodged me from it was lack of search on more than one tag. There used to be many scripts for Things (such as to insert emails as tasks) but the dev shut down the repository. Well-known is CulturedCode’s exquisitely slow pace of development. Things does not incorporate the calendar. Interestingly, present in the app is a calendar to defer tasks to the future but one cannot see tasks on any date in the future to better select a date for deferral (might as well have a random date generator). Things dose repeats well.

Reminders ecosystem

Siri can now be asked, in iOS 9, to remind of an email. However, this is simply a task with the subject line as the task name and no link back to the original email. Reminders can do repeats fairly well. Some apps, such as Fantastical, Busycal, Calendars 5 bring tasks and apps together. GoodTask and 2Do allow higher level manipulation of the list. I don’t really like the UI of either, though. The Reminders app itself is not a joy to use. Reminders can appear on Apple Watch and Notification Center. Sharing is possible via iCloud. This is a consideration for me since my wife does use Reminders extensively.


I know there are other apps/systems out there such as Wunderlist, Asana (insert endless list). I’m stopping here for now arbitrarily becuase I don’t currently see any other serious contenders that I personally like. Never fear, though, since I’m the kind of person, often to my detriment, that keeps scanning the possiblilties.

So, what to do? I’m not sure. I really want to continue with Taskpaper format but the lack of presence in Notification Center and Apple Watch is a growing concern. If anyone has any ideas, feel free to contact me. Maybe I’ll engage in full-dives into different possibilities of 30 days each. Perhaps I’ll post again later regarding my solution.

Additional reading

Makeuseof: Tips for maximizing the Reminders system

Sweet Setup: Omnifocus 2 review

Macstories: Why I left iCloud Reminders for Todoist

Conrad O’Connell: What GTD looks like in 2015

Churchmag: The best task management tools for 2015

Macdrifter: The Taskpaper R&D Notebook

Ruminatr: Still love plain text; Omnifocus still tempts

Ruminatr: Taskmator and Omnifocus

Ruminatr: iCloud Calendar + Taskpaper app concept

  • productivity
  • apps
  • iphone
  • mac
  • plaintext

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