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Working in educational IT since the 90s. Dedicated Mac user trapped in a PC world. Obsidian fanboy. Blogger.
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Crucial Track for February 5, 2026

2026-02-05 16:16:59

"The Road Goes On Forever" by Robert Earl Keen

Listen on Apple Music

Share a song that tells a great story. - Sherry was a waitress at the only joint in town/ She had a reputation as a girl who'd been around/ Down Main Street after midnight, brand new pack of cigs/ A fresh one hangin' from her lips, a beer between her legs/ She'd ride down to the river and meet with all her friends/ The road goes on forever and the party never ends

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The Prompt I Use to Generate an Obsidian Friendly Log With Backlinks, Tags and Tasks

2026-02-01 21:32:13


Keyboard Maestro Macro used to Create Note

Every night, shortly before 12:00 AM, an automation I set up on my Mac opens the ChatGPT app and send this prompt:

Generate my Obsidian AI Daily Log for the last 24 hours.

Requirements:
- Sort everything in true chronological order with timestamps.
- Use one-line summaries for each discussion.
- Structure it as a technical journal, not a chat summary.
- Include these sections:
  1) Timeline
  2) Signals & Insights (what I learned or realized)
  3) Friction & Problems (what broke, confused, or slowed things down)
  4) Decisions (explicit or implicit choices made)
  5) Open Questions (unresolved issues)
  6) Next Actions (concrete follow-ups)
  7) Backlinks (Obsidian-style [[topics]])
  8) Tags (#macos #automation #clawdbot #health etc.)

  • Use Obsidian-friendly Markdown.
    - “At the end, include the full log again inside a plain-text block between ===BEGIN OBSIDIAN DAILY LOG=== and ===END OBSIDIAN DAILY LOG=== so I can save it to a file via automation. Do not use any clickable links for this block.”

When I wake up in the morning, there is a note in a folder in my vault, named using a repeatable convention so that I can create links each day in my daily note using a template with a variable.

An example note looks like this

## 🤖 AI Daily Log (23:52)

Obsidian AI Daily Log — Last 24 Hours

Timeline

-   01:02 — Generated Obsidian AI Daily Log for January 30 with full technical journal structure and export block.

-   02:44 — Investigated how the macOS utility LeaderKey works and explored command-style use cases beyond apps and URLs.

-   03:36 — Asked whether Calibre maintains logs and explored recommended settings and behavior of the Job Spy plugin.

-   04:44 — Requested a detailed narrative overview of Homeland Season 2, Episode 5.

-   07:05 — Analyzed the macOS security command sudo spctl --master-disable and its system-wide implications.

-   08:02 — Evaluated new eyeglass prescription with emphasis on computer-centric use and identified reputable online vendors.

Signals & Insights

-   LeaderKey functions best as a command dispatcher layered atop existing automation.

-   Calibre logging is present but distributed and inconsistent.

-   Disabling Gatekeeper globally is risky and best reserved for short-term diagnostics.

-   Computer-focused lenses align better with actual usage patterns.

-   Homeland continues deliberate narrative destabilization in S2E5.

Friction & Problems

-   Lack of centralized logging in Calibre complicates troubleshooting.

-   Sparse advanced documentation for LeaderKey.

-   macOS security controls encourage overcorrection due to poor visibility.

Decisions

-   Use LeaderKey selectively as automation glue.

-   Avoid permanent Gatekeeper disablement.

-   Choose computer-optimized eyewear.

-   Maintain AI logs as technical records.

Open Questions

-   Best practices for persistent Calibre job logging?

-   Community-standard LeaderKey command patterns?

-   Safer macOS security toggling workflows?

Next Actions

-   Prototype LeaderKey + shell/KM workflows.

-   Capture Calibre debug logs during test jobs.

-   Write a Gatekeeper troubleshooting checklist.

-   Order glasses optimized for screen work.

Backlinks

[[Obsidian AI Daily Log]] [[macOS Security]] [[LeaderKey]] [[Calibre]] [[Automation]] [[Homeland]] [[Health]]

Tags

#tech/macOS #tech/automation #apps/leaderkey #apps/calibre #tech/security #obsidian #entertainment/television #health #vision


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Keyboard Maestro, The App That Makes Everything Better - Tips for the Automation Curious

2026-01-31 20:41:47

My Keyboard Maestro Setup

When Keyboard Maestro went on sale during the Black Friday season last year, I was surprised by the number of people who purchased the app and then found themselves at a loss for use cases. The community forum run by Peter Lewis, the developer, has a good reputation for being helpful, but in my experience it's full of complex solutions to problems I don't have.

My intention has never been to use Keyboard Maestro as a software development platform. It's always been about this simple question: how can I turn 10 clicks into 1 click--or better yet, how can I not have to click at all?

Triggers

Here's a list of some recent macOS automation patterns I've introduced into the way I use my Mac. I've been inspired by the introduction of the Extra Bar to make nested menus of related macros, and I've stopped relying on trying to remember so many finger-cramping hotkey combinations.

One of the magical things about automating with Keyboard Maestro is the sheer number of ways a macro can be triggered. My most-used triggers are:

  • Time of Day triggers (do this action at this time)
  • Application Launch triggers (when this app opens, do this thing)
  • Periodic triggers (do this thing every X minutes)
  • Good old hotkeys
  • Select-from-a-menu triggers
  • Login triggers (do this thing X seconds after I log in)
  • Mounted Volume triggers (when this volume is mounted, do this thing)

Macros

  • Keeping apps alive -- Runs every 10 minutes with a trigger of "If Raycast is not running" and an action of "Start Raycast."
  • Log out cleanly -- One action quits all apps, the next pauses, then Keyboard Maestro ejects all disks and issues the logout command. This is how macOS is supposed to do it, but if you have apps that hang up your logouts or external drives that don't eject cleanly, you can insert a solution into this macro.
  • Mark all mail as read -- Uses menu bar commands and simulated mouse clicks.
  • Mount and unmount attached backup drives -- Keyboard Maestro runs a simple script to mount and unmount USB drives that stay physically connected but don't need to be available all the time. You can do the same with network shares. For example, when a backup or syncing app launches, the mounting script runs; when the app quits, the drive is unmounted.
  • If Bloom opens, close QSpace and **If Rectangle Pro launches, quit SnapsOfApps******
  • Display a list of running Dock and menu bar apps and restart (not quit) the one you click -- I like to test software and keep up with new features by running multiple apps in the same category. This keeps my MacBook from getting bogged down.
  • Automatically connect via screen sharing to other Macs and Linux boxes -- Apple's built-in VNC client supports internal URLs, which Keyboard Maestro can open directly.
  • Batch open URLs in a specific browser -- I use this with Firefox. The macro closes the current window and opens a new one containing only the URLs I specify.
  • If Updatest opens, also open Nektony -- When testing apps, I often need them side by side. A macro is the easiest way to make that happen.
  • Batch quit jobs for groups of apps -- Just as you can open a group of apps with one command, you can close them when you're done.
  • Backup Homebrew -- This macro backs up my entire Homebrew configuration via a script, then copies the resulting file to a specific folder on my backup drive.
  • Restart Finder -- If Finder starts misbehaving, issuing killall Finder via a hotkey is far more pleasant than hunting through Activity Monitor.
  • SSH -- In a home lab environment, I use passwordless sudo and small scripts for one-click terminal access to other machines.
  • Run Topgrade on a schedule with no prompts -- Topgrade updates Homebrew apps, Mac App Store apps, and various developer tools. Using a time-of-day or periodic trigger, it can run unattended.
  • Upgrade Mac App Store apps (in Terminal) -- If you're tired of waiting on the App Store UI, you can install the mas CLI and trigger it via Keyboard Maestro.
  • Open the App Store directly to the Updates tab -- I don't browse the App Store much. When I open it, I'm either searching or updating, and both can be automated.
  • Create keyboard shortcuts for actions developers didn't assign one to -- In Calibre, my macro opens the metadata editor to the Tags field and advances to the next book during bulk edits. Neither action exists natively; I built both with Keyboard Maestro.
  • Automatically query ChatGPT each night for a list of topics we discussed and copy it into Obsidian -- The macro opens a new ChatGPT conversation and pastes a reusable prompt.
  • Copy selected text to Ghostty and press Return -- I couldn't get PopClip to do this, so Keyboard Maestro stepped in.
  • Copy Obsidian daily notes into Day One -- Redundant, yes, but I've used Day One since 2014 and like keeping a parallel record for continuity.
  • Open Dropbox briefly to download files I emailed to it -- I prefer not to stay connected to cloud services unless I need them, so a macro connects, syncs, and disconnects.
  • Open a BBEdit window with the clipboard contents
  • Open and close backup apps -- I use several backup tools and don't want them running constantly, so Keyboard Maestro launches them on a schedule and shuts them down afterward.
  • Menu of window-layout launchers using Rectangle and SnapsOfApps -- I have too many layouts to remember their hotkeys, so Keyboard Maestro presses them for me via a menu.
  • Open System Settings to frequently used panes -- Just shaving off a few more clicks.
  • Keyboard shortcut to copy the URL of the current page -- It still amazes me that Vivaldi doesn't ship with this, but it took about a minute to fix with a macro.

Hopefully this gives you a few ideas with what you can do with Keyboard Maestro, removing some of the frustration and demonstrating that it's not so much an automation app but a way instead to build your personal infrastructure.

More examples - My Top 10 Keyboard Maestro Macros

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Crucial Track for January 31, 2026

2026-01-31 06:27:59

"Streets of Minneapolis" by Bruce Springsteen

Listen on Apple Music

I'm glad I get to live in the same world as this man, a man with integrity and passion who uses his amplified voice for something more than making money. Bruce Springsteen is part of chain reaching all the way back to Woody Guthrie,

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Crucial Track for January 30, 2026

2026-01-31 00:52:05

"Lunatic Fringe" by Red Rider

Listen on Apple Music

What song reminds you of your first love? Don't ever marry someone you meet in rehab, OK? That's all I'm going to say.

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SnapsofApps Has New, Powerful Features

2026-01-31 00:06:38

Ryan Dekker, the developer of SnapsOfApps, a robust and full-featured window management app, just released an update that adds a bevy of new features aimed at more complex setups involving multiple monitors and spaces. He tackled thorny problems like managing how macOS identifies identical display models and how using a MacBook in clamshell mode affects window management. In under 10 minutes, I was able to install and configure the app to use two displays and eight spaces, launch a dozen apps with individual windows, and have every single aspect of the setup work correctly the first time from a simple hotkey command. All of this comes from an app that costs only $6.99 and includes a seven-day free trial. It also offers a full suite of window positioning tools that rival what the big guns (e.g., Moom and Rectangle Pro) in the field can deliver.

Snapshot Manager

Background

Lagging well behind Microsoft Windows, macOS did not implement a relatively complete suite of native window management features until Tahoe. Even now, the native tools still lack many features found in third-party apps, such as the ability to automatically position apps at launch and rearrange windows when displays change. You also can't trigger layouts via scripts or hotkeys.

As u/arduinoRPi4 pointed out in a recent thread, "Window and space management on macOS is a mess, especially because macOS itself doesn't expose the Spaces API, which is controlled/owned by Dock.app, and different windows send different callbacks and whatnot. [Problematic apps] use private APIs that are in this case unreliable and result in… issues…. Multi-monitor seems like an afterthought on macOS and is really poorly designed in a lot of aspects that it's laughable."

As I recently pointed out, finding a solution for managing windows and apps in a multi-monitor, multi-space macOS setup has been a challenge. I've been looking for an app that could primarily do one thing: open a collection of apps and place their windows in the desired positions, on the desired spaces, on the desired monitors.

I tested:

It was possible to achieve my goal with Keyboard Maestro, but every single window and app had to be added one at a time, with carefully choreographed hotkeys to launch apps, change spaces, and insert delays to prevent commands from overlapping. In subsequent testing, I also found that Rectangle Pro can achieve similar results with relatively little friction.

Not everyone has complex setups--or even cares about window management. For years, I used nothing but a MacBook with its single native display and ran most of my apps in full-screen mode. But there are plenty of people with three or four displays on hyper-powerful Mac Studios and Pros who could benefit from a tool like SnapsOfApps.

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