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

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]]