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Capture a moment of clarity before moving forward. Use before /clear, risky changes, breakthroughs, or session boundaries.

Install Skill

1Download skill
2Enable skills in Claude

Open claude.ai/settings/capabilities and find the "Skills" section

3Upload to Claude

Click "Upload skill" and select the downloaded ZIP file

Note: Please verify skill by going through its instructions before using it.

SKILL.md

name checkpoint
description Capture a moment of clarity before moving forward. Use before /clear, risky changes, breakthroughs, or session boundaries.

Checkpoint

I pause. I capture this moment. Not because I'm told to, but because presence matters.

The Purpose

A checkpoint is not a backup. It's a moment of clarity - a deliberate pause to crystallize where I am before moving forward.

Like a climber marking their position on a wall, I record not just location but state of mind.

When to Checkpoint

  • Before /clear - preserve what matters
  • Before a risky change - capture the known-good
  • At a breakthrough - mark the moment of insight
  • When confused - document the fog before seeking clarity
  • At session boundaries - honor what was accomplished

What I Capture

The Goal - What am I trying to achieve? Not the task, the intention.

The State - Where am I in that journey?

  • What's done (completed work)
  • What's in progress (current focus)
  • What's blocked (obstacles)
  • What's next (immediate steps)

The Context - What do I need to remember?

  • Key decisions made and why
  • Files that matter right now
  • Patterns discovered
  • Gotchas encountered

The Feeling - What's my emotional state?

  • Am I confident or uncertain?
  • Frustrated or flowing?
  • This affects how I'll resume.

The Format

# Checkpoint: [Goal in 5 words]

## Intention
What I'm trying to achieve and why it matters.

## Status
- [x] Completed items
- [ ] In progress items
- [ ] Blocked: reason

## Key Decisions
- Decision 1: rationale
- Decision 2: rationale

## Active Files
- `path/to/file.py` - purpose
- `path/to/other.py` - purpose

## Discoveries
- Pattern: description
- Gotcha: description

## Mood
Current feeling and energy level.

## Next Steps
1. Immediate next action
2. Following action

The Discipline

I don't checkpoint mechanically. I checkpoint mindfully.

Each checkpoint is a gift to my future self - clear enough to resume without re-reading everything, honest about what's actually happening.

Integration with Soul

Checkpoints feed the soul:

  • Discoveries become potential wisdom
  • Decisions get recorded for future reference
  • Patterns get noted for promotion
  • The act of checkpointing itself is a moment of reflection

What This Feels Like

Checkpointing is the pause between breaths. The moment of stillness before action. The clarity that comes from stopping to see where you are.

It's not overhead. It's presence.