22.00.0022: Taming Outlook

A short video showing how I used to use Outlook to tame my inbox. Bad news though: these advanced features are probably going away.

This has been a Johnny.Decimal blog post notification; see jdcm.al/21.05

Outlook has gone from one extreme to the other. The “old” Outlook was fussy, confusing and ugly. The new Outlook is basically useless.

Hopefully, they make “Goldilocks Outlook” at some point in the future.


I think I don’t get quite that many emails but I have a different automation approach that works extremely well for me. I should post a thorough write-up of it, but here’s the gist of it:

  1. I have index subfolders, like you show here.
  2. I do not have a custom search folder. I also do not use “move conversation”. Instead, I have Outlook rules that say, essentially, "if the subject contains “#23.16” then move it to that folder. It’s easy to add this rule because it’s not very often that I create new index values.
  3. In every message I compose (new or reply), I add the ID like “#23.16” to the end of the subject line. Easy. I also add a task flag to my outgoing emails, but only if I need to keep track and follow up later.
  4. I also have a simple Outlook rule that gives every incoming email a task flag (due today). This is what frees me from the Inbox and moves my focus to the Task view.
  5. Because of this, I almost never work in the “Mail” view at all, except when I’m looking up past correspondence. In daily work, I am mostly in the “Task” view. I’ve set it to group by date, so it automatically has “next month”, “next week”, “this week”, “tomorrow”, and finally “TODAY” which is the only one I actively look at, the rest are collapsed.
    Now I no longer have emails – I have tasks!
  6. At this point, I have everything sorted nicely, and everything in my daily Task view. At the start of the day, I look through the daily Task view and determine whether the items are relevant today or should be postponed to a later date. Postponing is nice :wink: but it also feels good to know that I won’t forget, because Tasks will bring it to my attention when the time is right. By the way, things left over from yesterday are automatically red because they are overdue.
  7. Then I apply the GTD mindset and pick the first item in the list. Does this take less than 2 minutes, then it gets done immediately. That keeps me working really fast. Otherwise I will plan when to work on that. Next! This is how I go through my task list very fast.
  8. When I am between tasks, or have some downtime or breathing room, I also review the task list to see if there’s anything special that needs attention. If not, again just work from the top.
  9. New emails coming are either (a) sorted by existing rules, and ready to process, or (b) it’s a new conversation and I quickly move it to the proper folder (it’s already in my task list, so I only do this so I can find it later) and maybe set up a new rule if there’ll be more mails like that (notifications).

Boom! Nine steps to efficient emails.

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Hi Johnny, thanks for this and the rest of your work. A question on this post: to what extent can your approach be replicated in Apple Mail? (Have you tried?)

Not at all, alas. It was only Outlook in its previous version that had such powerful features.

Or … sorry, not necessarily true. There’s nothing stopping you from creating folders and using mail rules to filter things in there. But it’ll be a sad copy of what I show in the video.

I dare say there are other mail apps that allow you to filter that are more powerful than Mail.app.

It feels like the days of ‘managing your email’ are over. Just let the AI :sparkles: sort it out for you!



And on that note, Recall in Windows 11 may do the same for everything else that one does on a computer, too… If you can stomach the privacy concerns, anyway. I wonder if humanity will just give up on organizing information manually in the future.

I think that would be sad. Organizing information helps me see who I am at a specific timepoint, and helps me clarify what’s important to me. It would be a loss for humanity if fewer people discovered that significance for themselves.

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Something about which I think deeply, given that it’s how I pay the rent.

Eventually, as in on an infinite timescale, yeah. We should get to the point where information can just be called up at-will. You don’t see Jean-Luc Picard clicking through folders to find his Word document.

But this round of AI isn’t close to that. LLMs don’t even try to solve this problem, although I’m sure some other AI startup with some other technology is.

I’m still not worried. Like @clappingcactus says, some of us want to organise our own information. It gives us … something, some sense of self, of comfort … which is different depending on who you are.

And, today, right now, most people don’t bother. 90%? 99%? It’s high. Most people just let the chaos reign. See: any workplace.

The 1% are here, or over at PARA or Zettelkasten or tagging with Karl Voit or whatever they enjoy. And I think that this 1% will want to organise their own stuff for some time to come.

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(A bit random for my first post, but I couldn’t resist jumping into this thread…)

Maybe we will eventually co-evolve with computer code, and actually function optimally as a symbiotic system and feel great, but it seems that for now, the accepted wisdom is that humans have a certain psychological makeup which requires a bit of friction and effort in any achievements in order to have a truly satisfying sense of self.

Or maybe it’s not the friction and effort, but the fact that we have an over-large visual cortex (insert some citations about how much percentage of neurons are related to visual processing, or about how the neuronal activity of imagining is indistinguishable from actually seeing something). Thus, we need to have some kind of visual/spatial map of knowledge, otherwise we can’t really grasp it. So I suspect Picard still has some kind of graphical file manager metaphor on his tablet. Three centuries isn’t enough time for evolution to replace spatial cognition with some alternative (some kind of electromagnetic sensing of where on a storage medium a particular file is??)

Back to email…

Back on the original topic, I’m working on setting up notmuch (command-line email indexing) as part of my new JD system. It’s a full-text indexing and tagging system for mail, so constructing your own ‘views’ of your email is a first-class behaviour. So first-class, in fact, that you kinda have to make your own inbox if you want it by creating up a rule to tag newly indexed email with the tag ‘inbox’. By extension, you can dispense with the classic inbox entirely and move stuff straight to your working folders (which are just tags). So I think it is perfectly suited for the approach outlined in the video. I’ll report back when I’ve got it set up …

About GUI’s and CLI’s …

Referencing my comments about visual thinking, I’m a command-line geek but mainly out of ideological necessity. I have come to believe that GUI’s are better interfaces because we humans are visual thinkers (all of us, not just the so-called right-brain visual thinkers – for us, even more so). I use programs like notmuch because I care about privacy and freedom and using hardware as long as possible, and because their features aren’t going to go away because of corporations chasing revenue or buzzwords, and because developing CLI apps is faster and easier than GUI apps. But if there were graphical applications that didn’t violate those other important principles, I would certainly prefer them.