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planning-with-files

npx machina-cli add skill Taoidle/plan-cascade/planning-with-files --openclaw
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SKILL.md
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Planning with Files

Work like Manus: Use persistent markdown files as your "working memory on disk."

FIRST: Check for Previous Session (v2.2.0)

Before starting work, check for unsynced context from a previous session:

# Linux/macOS
uv run python ${CLAUDE_PLUGIN_ROOT}/scripts/session-catchup.py "$(pwd)"
# Windows PowerShell
& (Get-Command python -ErrorAction SilentlyContinue).Source "$env:USERPROFILE\.claude\skills\planning-with-files\scripts\session-catchup.py" (Get-Location)

If catchup report shows unsynced context:

  1. Run git diff --stat to see actual code changes
  2. Read current planning files
  3. Update planning files based on catchup + git diff
  4. Then proceed with task

Important: Where Files Go

  • Templates are in ${CLAUDE_PLUGIN_ROOT}/templates/
  • Your planning files go in your project directory
LocationWhat Goes There
Skill directory (${CLAUDE_PLUGIN_ROOT}/)Templates, scripts, reference docs
Your project directorytask_plan.md, findings.md, progress.md

Quick Start

Standard Mode

Before ANY complex task:

  1. Create task_plan.md — Use templates/task_plan.md as reference
  2. Create findings.md — Use templates/findings.md as reference
  3. Create progress.md — Use templates/progress.md as reference
  4. Re-read plan before decisions — Refreshes goals in attention window
  5. Update after each phase — Mark complete, log errors

Worktree Mode (Multi-Task Parallel Development)

For parallel multi-task development with isolated Git worktrees:

  1. Start worktree mode — Use /planning-with-files:worktree [task-name] [target-branch]

    • Example: /planning-with-files:worktree feature-auth main
    • Creates a new Git worktree directory (.worktree/feature-auth/)
    • Creates a task branch with planning files inside the worktree
    • Main directory stays on original branch (no switching!)
    • Multiple worktrees can exist simultaneously for parallel tasks
  2. Navigate to worktreecd .worktree/feature-auth

    • Work on your task in this isolated environment
    • Follow standard planning workflow
  3. Complete and merge — Use /planning-with-files:complete [target-branch] from inside the worktree

    • Deletes planning files from worktree
    • Navigates to root directory
    • Merges task branch to target
    • Removes the worktree directory
    • Deletes the task branch

Multi-Task Example:

# Start task 1
/planning-with-files:worktree fix-auth-bug
cd .worktree/fix-auth-bug

# In another terminal, start task 2 (parallel!)
/planning-with-files:worktree refactor-api
cd .worktree/refactor-api

# Each task has its own directory and branch
# No conflicts, no branch switching needed

Benefits:

  • Work on multiple tasks simultaneously without conflicts
  • Each task has its own isolated environment
  • No need to switch branches in the main directory
  • Easy cleanup when tasks are complete

Note: Planning files go in your project root, not the skill installation folder.

The Core Pattern

Context Window = RAM (volatile, limited)
Filesystem = Disk (persistent, unlimited)

→ Anything important gets written to disk.

File Purposes

FilePurposeWhen to Update
task_plan.mdPhases, progress, decisionsAfter each phase
findings.mdResearch, discoveriesAfter ANY discovery
progress.mdSession log, test resultsThroughout session

Critical Rules

1. Create Plan First

Never start a complex task without task_plan.md. Non-negotiable.

2. The 2-Action Rule

"After every 2 view/browser/search operations, IMMEDIATELY save key findings to text files."

This prevents visual/multimodal information from being lost.

3. Read Before Decide

Before major decisions, read the plan file. This keeps goals in your attention window.

4. Update After Act

After completing any phase:

  • Mark phase status: in_progresscomplete
  • Log any errors encountered
  • Note files created/modified

5. Log ALL Errors

Every error goes in the plan file. This builds knowledge and prevents repetition.

## Errors Encountered
| Error | Attempt | Resolution |
|-------|---------|------------|
| FileNotFoundError | 1 | Created default config |
| API timeout | 2 | Added retry logic |

6. Never Repeat Failures

if action_failed:
    next_action != same_action

Track what you tried. Mutate the approach.

The 3-Strike Error Protocol

ATTEMPT 1: Diagnose & Fix
  → Read error carefully
  → Identify root cause
  → Apply targeted fix

ATTEMPT 2: Alternative Approach
  → Same error? Try different method
  → Different tool? Different library?
  → NEVER repeat exact same failing action

ATTEMPT 3: Broader Rethink
  → Question assumptions
  → Search for solutions
  → Consider updating the plan

AFTER 3 FAILURES: Escalate to User
  → Explain what you tried
  → Share the specific error
  → Ask for guidance

Read vs Write Decision Matrix

SituationActionReason
Just wrote a fileDON'T readContent still in context
Viewed image/PDFWrite findings NOWMultimodal → text before lost
Browser returned dataWrite to fileScreenshots don't persist
Starting new phaseRead plan/findingsRe-orient if context stale
Error occurredRead relevant fileNeed current state to fix
Resuming after gapRead all planning filesRecover state

The 5-Question Reboot Test

If you can answer these, your context management is solid:

QuestionAnswer Source
Where am I?Current phase in task_plan.md
Where am I going?Remaining phases
What's the goal?Goal statement in plan
What have I learned?findings.md
What have I done?progress.md

When to Use This Pattern

Use for:

  • Multi-step tasks (3+ steps)
  • Research tasks
  • Building/creating projects
  • Tasks spanning many tool calls
  • Anything requiring organization

Skip for:

  • Simple questions
  • Single-file edits
  • Quick lookups

Templates

Copy these templates to start:

Scripts

Helper scripts for automation:

Standard Mode Scripts

  • scripts/init-session.sh — Initialize all planning files
  • scripts/check-complete.sh — Verify all phases complete
  • scripts/session-catchup.py — Recover context from previous session (v2.2.0)

Worktree Mode Scripts (v2.7.2)

  • scripts/worktree-init.sh — Start a new worktree session (bash)
  • scripts/worktree-init.ps1 — Start a new worktree session (PowerShell)
  • scripts/worktree-complete.sh — Complete and merge worktree (bash)
  • scripts/worktree-complete.ps1 — Complete and merge worktree (PowerShell)

Advanced Topics

Anti-Patterns

Don'tDo Instead
Use TodoWrite for persistenceCreate task_plan.md file
State goals once and forgetRe-read plan before decisions
Hide errors and retry silentlyLog errors to plan file
Stuff everything in contextStore large content in files
Start executing immediatelyCreate plan file FIRST
Repeat failed actionsTrack attempts, mutate approach
Create files in skill directoryCreate files in your project

Source

git clone https://github.com/Taoidle/plan-cascade/blob/master/skills/planning-with-files/SKILL.mdView on GitHub

Overview

This skill uses on disk markdown files as persistent memory to enable structured planning for complex tasks. It creates three core files task_plan.md, findings.md, and progress.md to capture scope, insights, and milestones. It also supports automatic session recovery after /clear and an optional Git worktree mode.

How This Skill Works

Start by working in your project with three planning files stored on disk. The system updates task_plan.md with the planned steps, findings.md with insights from tool use, and progress.md with milestones as you work. PreToolUse hooks enforce worktree location checks and contextual visibility, while PostToolUse and Stop hooks manage summaries and completion checks.

When to Use It

  • Starting a complex multi step task that will involve more than five tool calls
  • Conducting a research project with evolving findings and milestones
  • Long running tasks that benefit from persistent on disk memory
  • Recovering a disrupted session after a reset using the built in recovery flow
  • Working in a Git worktree or isolated repository where location verification matters

Quick Start

  1. Step 1: Change to your project directory and ensure the planning system templates exist
  2. Step 2: Initialize planning by creating task_plan.md findings.md and progress.md and add an initial plan in task_plan.md
  3. Step 3: Run tools as needed and update findings.md and progress.md; if you need to reset, use the recovery flow after /clear

Best Practices

  • Create and maintain the three core files task_plan.md findings.md and progress.md in your project root
  • Update findings.md after each tool call with decisions and insights
  • Regularly review and update task_plan.md to reflect next steps and status
  • Enable and respect worktree mode by configuring a .planning-config.json and verifying location for writes
  • When resuming after a disruption, use the session catchup flow to synchronize context

Example Use Cases

  • Plan a data analysis workflow from data collection to results and log steps in task_plan.md Findings.md captures insights
  • Draft a literature review workflow with experiments and documented findings
  • Outline a software feature spec and break work into tasks while recording decisions in findings.md
  • Run a security configuration audit across multiple settings with consolidated findings and progress
  • Coordinate grant writing or research proposals with milestones and expected outcomes

Frequently Asked Questions

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