frozen octopus

Tag files with keyboard on Mac OS

1. Select file with arrow keys
2. Click command-I
3. Click Tab twice
4. Type the Tag

Tagging is how magic happens on my laptop. I have the Hazel app watching my Downloads and other folders, like a hawk. When I tag a file with a context (e.g. work), Hazel moves it to a Work folder. That folder also has a bunch of rules that automatically organize the file where it needs to go.

So if I tag a file in Downloads with the "work" tag plus a client tag, Hazel moves the file to the work folder, then moves it to the correct client folder in a folder with the date as a name.

I had a keyboard shortcut set up to make the tagging so easy. I would select the files, hit my keyboard shortcut, tag the files, and Hazel kicks in. It is truly magical when you tag a bunch of files and folders in Downloads and they start flying around to the spots they need to be in.

That keyboard shortcut stopped working in Tahoe though. I have tried everything to get that shortcut working, but no dice. Nothing fixed the issue. When I relaunch Finder, the shortcut works for a bit and then just quits working. Even tagging in the Finder preview window isn't working 100% for me.

Then I remembered you can click Command-I and tag a file there too. Those tags are working 100% like before the Tahoe update. Then I started noticing that it is actually just as fast tagging this way as my old shortcut was. I hit Command-I, tab, and type the tag.

Why was I so hung up on getting my shortcut working for so long? This route is the same level smooth for me. Files get tagged without touching the trackpad. It also reminds me to quit being so hardheaded trying to use this laptop. 

Every morning I respect my brain/mind by making an Americano, putting on a jazz record, and writing 200 words of free writing. It is a really nice way to fade into a day instead of reading some dire news or sitting down and laboring right away on tasks.

So morning is pleasant. But evening not so much. I really need to get a night version of that happening. Some sort of fade out to match the morning fade in.

Reading seems like a good evening bookend for morning writing. Music writing also seems like a good thing to schedule. Like making the equivalent of 200 words in sound somehow.

Don't know yet but this is a thing that is brewing. It took a bit to become muscle memory but the 200-word morning writing took for me. Seems reproducible at other times of the day for sure.

I got a shortcut setup that I run daily that I am really into right now. It is for a daily review that I run first thing when I wake up. It sets me up a little better for the day, which I always need a little helping nudge with. When I get to the end of the shortcut, I have a rough list of where I am at and kind of where I need to be heading. The list is saved in Drafts but could go anywhere though.

The shortcut starts by getting the upcoming weather.

Next is a list of prompts that asks me various questions like these. There are more and I don't need to answer them if I don't want to:

• What was the very last thing you were working on yesterday?
• Do you need to "nudge" anyone on anything?
• Is there anything you noticed yesterday that you haven't logged as a task yet?
• Are you missing any content needed to finish a milestone today?
• Are there any messages or emails from anyone that you read but didn't actually "capture"?

Then the shortcut grabs all upcoming events in Calendar for the next seven days.

After that, the shortcut grabs all upcoming things for the next seven days in my to-do app.

The shortcut then uses the Apple Intelligence "Use model" action set to on-device. There is a prompt telling it to tidy up all this info into a plan for the day. Also, have it set up to add a next action for tasks where possible.

What I get back is a nice overview of what I need to do for the day. It isn't perfect, but it is really fun.

I finally finished moving 800+ album listens from my old blog to this one. While it feels great to have everything under one roof, the process was a serious slog.

The technical side was a mixed bag:

• Setup: It took several hours of spreadsheet slog to get the data ready for the merge.
• Import: Once the data was clean, the actual import was a breeze.

The "Water Torture" Workflow

The biggest takeaway wasn't about the tech, but about my habits. I have a tendency to take giant projects and drip-feed them over months. I’ll set a repeating task like "Add all albums from today’s date" to make the work feel manageable.

I used to think "five minutes a day" was the best way to keep moving pieces forward. I've realized now that there's a mental toll to keeping a project in "active" status for that long.

Lessons Learned

I got my head around a couple categories my tasks can get sorted into:

• Slow Burn: Things like drum rehearsal. Five minutes a day is perfect here; consistency builds muscle memory.
• Burn Through: Data migrations and administrative overhauls. These are better handled in one focused "sprint" rather than being dragged out.

Dragging out a "Deep Dive" task is just mental water torture. I’m keeping that in mind when I look at my task list. Are there any other lingering projects I can kill or complete once and for all?

When I want to open an app on the MacBook, I have a keyboard shortcut setup to open the app launcher. The key combination I chose is preventing me from using a different shortcut to open the downloads folder. Since I live in the downloads folder, I had to decide on a different plan.

I decided to go all in with Spotlight. It is weird, I know, that I don't use Spotlight or the Documents folder. So I started in on doing everything with Spotlight. My life is now command-space, a right arrow push, and type the first couple of letters of the app name. It is one extra click, but it is very smooth.

The only issue is my muscle memory keeps trying to use the old shortcut. It has been days now, and my fingers keep hitting opt-command-L. It has gotten to the point where I am noting each day I keep hitting the old shortcut. How long is it going to take to unlearn a keyboard shortcut I have used for at least 10 years? Probably more like 15-20 years, maybe.

On the topic of keyboard shortcuts, a shortcut I use religiously has stopped working. I had shift-command-T set up to let me tag a file or folder. It was amazing because I have the Hazel app set up on my downloads folder to perform magic when a file is tagged. Ever since Tahoe was released, that has stopped working.

I thought it was a conflict with the Better Touch Tools app. That is not the case after some troubleshooting. If I relaunch Finder, my tagging keyboard shortcut works. After a while, it just stops working. It is very odd. Shrug level odd.

Also, when I try to tag a bunch of files at the same time, none of them get the tag. Again, odd.