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Planning With Files

  • 884 installs
  • 44k repo stars
  • Updated July 27, 2026
  • sickn33/antigravity-awesome-skills

planning-with-files is an agent productivity skill that creates persistent, self-updating task plans in markdown files so AI agents retain context across multi-step work.

About

planning-with-files is a skill from sickn33/antigravity-awesome-skills that teaches agents to maintain living task plans as markdown files such as task_plan.md instead of relying on chat memory alone. Each loop creates a plan with a goal, phased checklist, key questions, and a status section that agents update as work advances through research, synthesis, and delivery steps. Developers reach for planning-with-files when agents lose context on long research tasks, multi-file refactors, or any workflow spanning several tool calls. The included examples walk through phased research summaries, showing how plans evolve from creation through source gathering to final delivery. The pattern works across Claude Code, Cursor, and other agents that can read and write repository files during extended sessions.

  • Creates and maintains a living task_plan.md with explicit goal, numbered phases, key questions and status
  • Agent loops by reading the plan before every action to stay aligned
  • Marks phases complete inside the file as work progresses
  • Works for research, writing, bug fixing, feature building and any complex task
  • Prevents context drift and premature task jumping by enforcing plan-first workflow

Planning With Files by the numbers

  • 884 all-time installs (skills.sh)
  • +23 installs in the week ending Jul 28, 2026 (Skillselion tracking)
  • Ranked #534 of 3,301 Productivity & Planning skills by installs in the Skillselion catalog
  • Security screen: MEDIUM risk (skills.sh audit)
  • Data as of Jul 28, 2026 (Skillselion catalog sync)
npx skills add https://github.com/sickn33/antigravity-awesome-skills --skill planning-with-files

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Listed on Skillselion
Installs884
repo stars44k
Security audit2 / 3 scanners passed
Last updatedJuly 27, 2026
Repositorysickn33/antigravity-awesome-skills

How do agents keep context across multi-step tasks?

Create persistent, self-updating task plans that guide AI agents through multi-step work without losing context.

Who is it for?

Developers running long agent sessions who need file-backed plans that survive context window limits and handoffs.

Skip if: Single-shot code edits or teams that already enforce issue-tracker workflows instead of markdown plan files.

When should I use this skill?

The user starts a multi-step agent task, research project, or refactor that needs a persistent plan file updated across loops.

What you get

Persistent task_plan.md files with goals, phased checklists, key questions, and self-updated status sections.

  • task_plan.md
  • Phased status updates

Files

SKILL.mdMarkdownGitHub ↗

Planning with Files

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

Important: Where Files Go

When using this skill:

  • Templates are stored in the skill directory at ${CLAUDE_PLUGIN_ROOT}/templates/
  • Your planning files (task_plan.md, findings.md, progress.md) should be created in your project directory — the folder where you're working
LocationWhat Goes There
Skill directory (${CLAUDE_PLUGIN_ROOT}/)Templates, scripts, reference docs
Your project directorytask_plan.md, findings.md, progress.md

This ensures your planning files live alongside your code, not buried in the skill installation folder.

Quick Start

Before ANY complex task:

1. Create `task_plan.md` in your project — Use templates/task_plan.md as reference 2. Create `findings.md` in your project — Use templates/findings.md as reference 3. Create `progress.md` in your project — 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

Note: All three planning files should be created in your current working directory (your project root), not in the skill's 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:

  • templates/task_plan.md — Phase tracking
  • templates/findings.md — Research storage
  • templates/progress.md — Session logging

Scripts

Helper scripts for automation:

  • scripts/init-session.sh — Initialize all planning files
  • scripts/check-complete.sh — Verify all phases complete

Advanced Topics

  • Manus Principles: See reference.md
  • Real Examples: See examples.md

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

Limitations

  • Use this skill only when the task clearly matches the scope described above.
  • Do not treat the output as a substitute for environment-specific validation, testing, or expert review.
  • Stop and ask for clarification if required inputs, permissions, safety boundaries, or success criteria are missing.

Related skills

How it compares

Use planning-with-files for lightweight markdown plans inside the repo; prefer issue-tracker integrations when work must sync to Jira or Linear.

FAQ

What file does planning-with-files create?

planning-with-files creates markdown plan files such as task_plan.md containing a goal, phased checklist, key questions, and a status section that agents update after each work loop.

Why use planning-with-files for agents?

planning-with-files gives coding agents a persistent file-backed plan so multi-step research or implementation tasks keep context, track completed phases, and resume without relying solely on chat history.

Is Planning With Files safe to install?

skills.sh reports 2 of 3 security scanners passed. Review the Security Audits panel on this page before installing in production.

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