Monthly Review and Planning
ballred/obsidian-claude-pkm
Runs a monthly review in an Obsidian vault: rolls up weekly reviews, checks quarterly milestones against yearly goals and sets next month's focus.
Interactive trail review and update process for Obsidian vault at ~/Brains/brain.
Install Trail Checkin
$ npx skills add glebis/claude-skills --skill trail-checkin -a claude-codeProject install by default; add -g for ~/.claude/skills/.
$ gh skill install glebis/claude-skills trail-checkin --agent claude-codeProject scope by default; add --scope user for a personal install. Needs GitHub CLI 2.90.0 or later (public preview).
$ git clone --depth 1 https://github.com/glebis/claude-skills.git skills-src && mkdir -p .claude/skills && cp -r skills-src/trail-checkin .claude/skills/trail-checkin && rm -rf skills-srcUse ~/.claude/skills/ instead of .claude/skills for a personal install. The folder must contain SKILL.md.
Claude Code skills documentation · loads skills from .claude/skills/
Install the "trail-checkin" agent skill from https://github.com/glebis/claude-skills/tree/main/trail-checkin into .claude/skills/trail-checkin/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "trail-checkin", then confirm the skill loads.Claude Code copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
$skill-installer install https://github.com/glebis/claude-skills/tree/main/trail-checkinType this inside Codex. $skill-installer <name> installs a curated skill from openai/skills. The installer writes to $CODEX_HOME/skills (default ~/.codex/skills). Restart Codex if the skill does not show up.
$ npx skills add glebis/claude-skills --skill trail-checkin -a codexProject install goes to .agents/skills/; add -g for ~/.codex/skills/.
$ gh skill install glebis/claude-skills trail-checkin --agent codexProject scope by default (.agents/skills/); add --scope user for a personal install.
$ git clone --depth 1 https://github.com/glebis/claude-skills.git skills-src && mkdir -p .agents/skills && cp -r skills-src/trail-checkin .agents/skills/trail-checkin && rm -rf skills-srcUse ~/.agents/skills/ instead of .agents/skills for a personal install.
Codex skills documentation · loads skills from .agents/skills/
Install the "trail-checkin" agent skill from https://github.com/glebis/claude-skills/tree/main/trail-checkin into .agents/skills/trail-checkin/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "trail-checkin", then confirm the skill loads.Codex copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
$ npx skills add glebis/claude-skills --skill trail-checkin -a cursorProject install goes to .agents/skills/; add -g for ~/.cursor/skills/.
$ gh skill install glebis/claude-skills trail-checkin --agent cursorProject scope by default (.agents/skills/); add --scope user for a personal install.
$ git clone --depth 1 https://github.com/glebis/claude-skills.git skills-src && mkdir -p .cursor/skills && cp -r skills-src/trail-checkin .cursor/skills/trail-checkin && rm -rf skills-srcUse ~/.cursor/skills/ instead of .cursor/skills for a personal install.
Cursor skills documentation · loads skills from .cursor/skills/, .agents/skills/, .claude/skills/, .codex/skills/
Install the "trail-checkin" agent skill from https://github.com/glebis/claude-skills/tree/main/trail-checkin into .cursor/skills/trail-checkin/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "trail-checkin", then confirm the skill loads.Cursor copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
$ gemini skills install https://github.com/glebis/claude-skills.git --path trail-checkin--scope user (default) or --scope workspace; --path is the subfolder of the repo that holds the skill; --consent skips the security confirmation prompt.
$ npx skills add glebis/claude-skills --skill trail-checkin -a gemini-cliProject install goes to .agents/skills/; add -g for ~/.gemini/skills/.
$ gh skill install glebis/claude-skills trail-checkin --agent gemini-cliProject scope by default (.agents/skills/); add --scope user for a personal install.
$ git clone --depth 1 https://github.com/glebis/claude-skills.git skills-src && mkdir -p .gemini/skills && cp -r skills-src/trail-checkin .gemini/skills/trail-checkin && rm -rf skills-srcUse ~/.gemini/skills/ instead of .gemini/skills for a personal install, then run /skills reload.
Gemini CLI skills documentation · loads skills from .gemini/skills/, .agents/skills/
Install the "trail-checkin" agent skill from https://github.com/glebis/claude-skills/tree/main/trail-checkin into .gemini/skills/trail-checkin/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "trail-checkin", then confirm the skill loads.Gemini CLI copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
$ gh skill install glebis/claude-skills trail-checkinInstalls for Copilot at project scope by default; add --scope user for a personal install. Preview a skill first with gh skill preview. Needs GitHub CLI 2.90.0 or later (public preview).
$ npx skills add glebis/claude-skills --skill trail-checkin -a github-copilotProject install goes to .agents/skills/; add -g for ~/.copilot/skills/.
$ git clone --depth 1 https://github.com/glebis/claude-skills.git skills-src && mkdir -p .github/skills && cp -r skills-src/trail-checkin .github/skills/trail-checkin && rm -rf skills-srcUse ~/.copilot/skills/ instead of .github/skills for a personal install. Commit .github/skills so cloud agent and code review can use it.
GitHub Copilot skills documentation · loads skills from .github/skills/, .claude/skills/, .agents/skills/
Install the "trail-checkin" agent skill from https://github.com/glebis/claude-skills/tree/main/trail-checkin into .github/skills/trail-checkin/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "trail-checkin", then confirm the skill loads.GitHub Copilot copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
$ npx skills add glebis/claude-skills --skill trail-checkin -a opencodeOpenCode documents no install command of its own. Project install goes to .agents/skills/; add -g for ~/.config/opencode/skills/.
$ gh skill install glebis/claude-skills trail-checkin --agent opencodeProject scope by default (.agents/skills/); add --scope user for a personal install.
$ git clone --depth 1 https://github.com/glebis/claude-skills.git skills-src && mkdir -p .opencode/skills && cp -r skills-src/trail-checkin .opencode/skills/trail-checkin && rm -rf skills-srcUse ~/.config/opencode/skills/ instead of .opencode/skills for a personal install.
OpenCode skills documentation · loads skills from .opencode/skills/, .claude/skills/, .agents/skills/
Install the "trail-checkin" agent skill from https://github.com/glebis/claude-skills/tree/main/trail-checkin into .opencode/skills/trail-checkin/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "trail-checkin", then confirm the skill loads.OpenCode copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
Facts
- Skill name
trail-checkin- GitHub stars
- 391
- Token cost
- ~838 tokens
- SKILL.md length
- 262 words
- Files
- 3 (incl. scripts)
- Skills in repo
- 92
- Repo updated
- First seen
- Licence
- MIT
At a glance
Interactive trail review and update process for Obsidian vault at ~/Brains/brain.
- Works in 4 steps: List Trails → Select Trails → Check-in Questions (per trail) → …
- Milestone moments
- SKILL.md covers Prerequisites, Usage, How It Works and Output, plus 3 more sections
- Runs Python scripts from its folder; calls python3
What it does
Trail Checkin is an agent skill from glebis/claude-skills. Interactive trail review and update process for Obsidian vault at ~/Brains/brain. Lists available Trails, lets you select which to check in with, then walks through structured questions for each (progress, markers, tasks, metrics, open questions, status, next review date) and updates the trail file. Use for weekly reviews, milestone moments, context switching, or monthly reflection. Triggers on /trail-checkin.
Its SKILL.md is about 840 tokens, which your agent loads only when the skill is triggered. The skill folder holds 3 other files, including scripts (for example `prompt.md` and `scripts/trail_checkin.py`).
It sits in Knowledge Management, covering Project management and Journaling and reflection. It works with Obsidian. The repository describes itself as: Collection of Claude Code skills for enhanced AI workflows. The licence is MIT.
When your agent uses it
- Milestone moments
- Context switching
- Monthly reflection
Example prompts
- “/trail-checkin”
Requirements
- Python 3
Workflow steps
4 steps, taken from the step headings in SKILL.md.
What it can do on your machine
Read from SKILL.md and the folder at commit 3b88261. It shows what the files ask for, not the result of running them.
Tool permissions
Pre-approves nothing: there is no allowed-tools line, so your agent's usual permission prompts apply.
From allowed-tools in the SKILL.md frontmatter.
Runs code
Ships 1 file in scripts/ (Python), which the agent can run.
Shell commands in SKILL.md call:
python3
From the folder's file list and the shell code blocks in SKILL.md.
Network
No URLs in SKILL.md.
From URLs in SKILL.md, links to its own repository left out.
Credentials
Names no API keys, tokens, secrets or passwords.
From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.
Context cost
Trail Checkin loads about 838 tokens when it runs. Until then it costs about 107 tokens; SKILL.md has 262 words of instructions outside code blocks.
Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.
Safety
Auto-check passed
The automated check found no risky patterns in SKILL.md.
Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); the scripts in this folder are not scanned.
SKILL.md
The full file from glebis/claude-skills at commit 3b88261, republished under its MIT licence (© glebis). 262 words, ~838 tokens.
Download SKILL.mdSave it as
.claude/skills/trail-checkin/SKILL.md (or your agent's skills folder). This skill also uses 2 other files; get the full folder from GitHub.- name
- trail-checkin
- description
- Interactive trail review and update process for Obsidian vault at ~/Brains/brain. Lists available Trails, lets you select which to check in with, then walks through structured questions for each (progress, markers, tasks, metrics, open questions, status, next review date) and updates the trail file. Use for weekly reviews, milestone moments, context switching, or monthly reflection. Triggers on /trail-checkin.
Base directory for this skill: ~/.Codex/skills/trail-checkin
Trail Check-in Skill
Interactive trail review and update process. Lists available trails, lets you select which to check in with, then walks through structured questions for each trail to capture progress, update markers, and reflect on direction.
Prerequisites
- Obsidian vault at
~/Brains/brain - Trails located in
~/Brains/brain/Trails/ - Trail files follow naming pattern
Trail - *.md
Usage
Run the skill to start an interactive check-in:
/trail-checkinOr invoke directly:
python3 ~/.Codex/skills/trail-checkin/scripts/trail_checkin.pyHow It Works
Step 1: List Trails
Script scans Trails/ folder and extracts:
- Trail name
- Status (active/paused/completed)
- Last updated date
- Objective (first line summary)
Returns JSON with trail list.
Step 2: Select Trails
Codex uses AskUserQuestion with multiSelect to let you choose which trails to check in with.
Step 3: Check-in Questions (per trail)
For each selected trail, Codex asks:
- Progress made - What happened since last check-in?
- Markers to add - Any new milestones reached?
- Tasks completed - Which tasks can be marked done?
- New tasks - What needs to be added?
- Metrics update - Any numbers to update?
- Open questions - New questions or resolved ones?
- Status change - Still active? Paused? Completed?
- Next review date - When to check in again?
Step 4: Update Trails
Codex updates each trail file with:
- New progress markers
- Updated metrics
- Task status changes
- New open questions
- Updated
last_updateddate - Next review date
Output
Returns summary of updates made to each trail.
Example Session
User: /trail-checkin
Codex: Found 5 trails. Which would you like to check in with?
[multiSelect: Mental Health Tech, Codex Lab, Telegram Agent, Salience, Voice Codex]
User: [selects Mental Health Tech, Voice Codex]
Codex: Let's check in with Trail: Mental Health Tech
What progress have you made since last update (2026-01-19)?
[short answer input]
User: Published Vastaamo hack post, drafted privacy ethics analysis
Codex: Should we add any progress markers?
[yes/no]
[continues through questions...]
Codex: Updated Trail: Mental Health Tech
- Added marker: Vastaamo hack post published
- Updated posts metric: 78
- Marked task complete: Publish privacy post
- Updated last_updated: 2026-01-19
Now checking in with Trail: Voice Codex...Script API
# List all trails
python3 scripts/trail_checkin.py list
# Get trail details
python3 scripts/trail_checkin.py show "Mental Health Tech"Returns JSON for programmatic use.
When to Use
- Weekly reviews
- Project milestone moments
- When switching contexts between trails
- Monthly reflection sessions
- When a trail needs status update
© glebis, MIT. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file
Files
SKILL.md and 2 other files (scripts) in trail-checkin of glebis/claude-skills.
- SKILL.md
- prompt.md
- scripts/trail_checkin.py
Open the folder on GitHubat commit 3b88261
Compare with similar skills
Trail Checkin next to the 5 skills that share the most tags, products or categories with it. Stars are the repository's; “used in” counts other GitHub owners with a copy.
| Skill | Stars | Used in | Tokens | Auto-check | Licence | Repo updated |
|---|---|---|---|---|---|---|
| Trail Checkin this skillglebis/claude-skills | 391 | — | ~838 | Automated safety check: Pass | MIT | |
| Monthly Review and Planningballred/obsidian-claude-pkm | 1.9k | — | ~1.4k | Automated safety check: Pass | MIT | |
| LLM Wikilewislulu/llm-wiki-skill | 655 | — | ~3.7k | Automated safety check: Pass | None | |
| Journalthoreinstein/gemini-obsidian | 102 | — | ~283 | Automated safety check: Pass | ISC | |
| Daily Notes Workflowballred/obsidian-claude-pkm | 1.9k | — | ~2k | Automated safety check: Pass | MIT | |
| Solomdzhitongblog/solomd | 1.2k | — | ~2k | Automated safety check: Pass | MIT |
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Related
Works with
Categories
Questions about Trail Checkin
What does Trail Checkin do?
Interactive trail review and update process for Obsidian vault at ~/Brains/brain. Trail Checkin is an agent skill from glebis/claude-skills. Interactive trail review and update process for Obsidian vault at ~/Brains/brain.
When should I use Trail Checkin?
Trail Checkin fits situations like: milestone moments; context switching; monthly reflection.
How do I install Trail Checkin in Claude Code?
Run `npx skills add glebis/claude-skills --skill trail-checkin -a claude-code`. Or copy the skill folder (trail-checkin in glebis/claude-skills) into .claude/skills/trail-checkin in your project. Claude Code loads it when a task matches its description.
How do I install Trail Checkin in Codex?
Run `npx skills add glebis/claude-skills --skill trail-checkin -a codex`. Or copy the skill folder (trail-checkin in glebis/claude-skills) into .agents/skills/trail-checkin in your project. Codex loads it when a task matches its description.
Can I use Trail Checkin in Cursor, Gemini CLI or GitHub Copilot?
Cursor, Gemini CLI, GitHub Copilot and OpenCode also load SKILL.md folders. With the skills CLI, run `npx skills add glebis/claude-skills --skill trail-checkin -a cursor` (or -a gemini-cli, github-copilot or opencode for the others). To copy it by hand, put the folder in .cursor/skills/trail-checkin, .gemini/skills/trail-checkin, .github/skills/trail-checkin and .opencode/skills/trail-checkin in your project.
What does Trail Checkin need to run?
Going by SKILL.md and its folder, Trail Checkin needs Python for the scripts in its folder and the command-line tools its instructions call (python3). Our summary lists: Python 3.
Does Trail Checkin access the network?
SKILL.md contains no URLs. Any network use would come from the scripts or tools the agent runs. This is read from the text; nothing was executed.
Is Trail Checkin safe to install?
Our automated static check of SKILL.md found no risky patterns, such as piping downloads into a shell, reading credential files or hidden Unicode. It is not a guarantee. The check reads SKILL.md only: the scripts in the folder are not scanned, so read them before running anything.
What licence does Trail Checkin use?
Trail Checkin is published under the MIT licence (the repository's licence). It allows redistribution, so the full SKILL.md is shown on this page.
How many tokens does Trail Checkin use?
About 838 tokens (SKILL.md is roughly 3.4k characters). Agents keep only the skill's name and description in context until a task matches; then they load SKILL.md in full.
What are the alternatives to Trail Checkin?
Skills that share tags, products or a category with Trail Checkin: Monthly Review and Planning (ballred/obsidian-claude-pkm, 1.9k stars), LLM Wiki (lewislulu/llm-wiki-skill, 655 stars), Journal (thoreinstein/gemini-obsidian, 102 stars) and Daily Notes Workflow (ballred/obsidian-claude-pkm, 1.9k stars). The comparison table on this page puts their stars, adoption, token cost, safety result and licence side by side.
Who maintains Trail Checkin?
glebis (a GitHub user) maintains it in glebis/claude-skills, which has 391 GitHub stars. The repository holds 92 skills in this directory. The repository was last updated on October 8, 2026.
Source: glebis/claude-skills on GitHub. Facts on this page come from the repository at the commit we read; the author's words are quoted as theirs.