Table of Contents

• 1 Fifteen Years to Fifteen Minutes
• 2 My First Prompt Was Embarrassingly Bad
• 3 The Dream That Died at 3 AM

• 4 Setting Up the Orchestra Pit
• 5 From Paragraph to Protocol

• 6 When Agents Collide
• 7 The Ticket That Broke Everything
• 8 The Testing Specialist
• 9 The Economics of Amnesia
• 10 Living Documentation

• 11 The Child Ticket Dance
• 12 PR Review in Ninety Seconds
• 13 The Process That Runs Itself

• 14 Watching the Watchers
• 15 The Hard Limits

• 16 The Oversight Economy

• A Tool Setup
• B CLAUDE.md Template
• C Workflow Command Reference

• About the Author

• CLAUDE.md Starter Template (ready-to-use file)
• Workflow Command Cheatsheet (one-page PDF)
• Pre-Flight Checklist (printable PDF)

It AI'nt That Hard

A Developer's Guide to Directing AI, While Pretending You Know What You're Doing

1. Copyright
2. Preface
   1. Who This Book Is For
   2. Who I Am
   3. What This Book Isn't
   4. What This Book Is
   5. The Uncomfortable Parts
   6. How to Read This Book
   7. The Wife
   8. The Stakes
3. Dedication
4. Acknowledgements
   1. The Inner Circle
   2. The Tools
   3. The Ones I've Forgotten
5. Chapter 1 Fifteen Years to Fifteen Minutes
   1. The Demo
   2. The Long Road Here
   3. Midnight Reckoning
   4. The 2 AM Scenarios
   5. First Contact
   6. The Seventy Percent
   7. The Decision
6. Chapter 2 My First Prompt Was Embarrassingly Bad
   1. The Skeleton Closet
   2. The Junior Developer Moment
   3. The Week of Iteration
   4. The Power of Negation
   5. Requirements Engineering by Another Name
   6. The Clarity Tax
   7. The Prompt in the History
7. Chapter 3 The Dream That Died at 3 AM
   1. The Vision
   2. The Architecture That Made Perfect Sense
   3. The Integration That Wouldn't
   4. The Desperation Phase
   5. Acceptance
8. Chapter 4 Setting Up the Orchestra Pit
   1. The Invisible Foundation
   2. The Amnesia Problem
   3. Context Feng Shui
   4. Boring Infrastructure, Essential Infrastructure
   5. Commands That Compound
   6. The Local CI Decision
   7. The Legacy-Proof Principle
   8. The Integration Layer
   9. The Compound Effect
9. Chapter 5 From Paragraph to Protocol
   1. The Document That Grew
   2. The Iceberg Beneath the Iceberg
   3. The Architecture of Context
   4. From Context to Tickets
   5. The Highlight Reel of Failure
   6. The Disasters Behind the Dashboard
   7. The Current State
   8. What the Workflow Taught Me
   9. The Monolith Wearing a Trench Coat
   10. The Pre-PR Step That Nearly Wasn't
10. Chapter 6 When Agents Collide
    1. The Monday Morning Massacre
    2. The Anatomy of a Collision
    3. The Naive Solutions
    4. The Isolation Principle
    5. The Workspace Protocol
    6. Conflict Detection
    7. True Parallelism
    8. The Lessons
11. Chapter 7 The Ticket That Broke Everything
    1. The Pride Before the Fall
    2. The Unravelling
    3. The Anatomy of Failure
    4. The Evening Reckoning
    5. The Ticket Analysis Protocol
    6. The Pre-PR Validation
    7. The Red Flags
    8. The Irony
12. Chapter 8 The Testing Specialist
    1. The Test I Called Overkill
    2. The Problem with "Add Tests"
    3. Building a Paranoid Persona
    4. The Pyramid That Isn't Optional
    5. What Paranoia Produces
    6. Tests Before Code
    7. The Hollowing Problem
    8. The Coverage Controversy
    9. The Vanity Metric Problem
    10. The Semantic Gap
    11. The Bouncer at the Door
    12. The Quiet Wins
13. Chapter 9 The Economics of Amnesia
    1. The Usage Report That Ruined My Morning
    2. The Budget Conversation
    3. The Model Tiering Revelation
    4. The Living Documentation Breakthrough
    5. Context Window Hygiene
    6. Memory Bloat and Session Discipline
    7. Compaction Resilience
    8. The Compound Effect
    9. The Actual Cost
    10. The Cost I Wasn't Counting
    11. The Mindset Shift
14. Chapter 10 Living Documentation
    1. The Endpoint That Already Existed
    2. The Problem Nobody Solves
    3. Documentation That Updates Itself
    4. The Structure
    5. What the Index Contains
    6. The Wrong Structure First
    7. Keeping It Fresh
    8. Temporal Context
    9. Managing the Index
    10. The Transformation
    11. The Meta-Lesson
15. Chapter 11 The Child Ticket Dance
    1. The Agents That Didn't Talk to Each Other
    2. The Amnesia Coordination Problem
    3. Contracts Before Code
    4. The Workflow Adaptation
    5. The Umbrella Branch Adaptation
    6. The Dependency Dance
    7. The Handoff Problem
    8. The Integration Verification
    9. The Failure I Didn't Prevent
    10. The Choreography Mindset
    11. The GPS in the Tesco Car Park
    12. The Diplomatic Interpreter
    13. Why Defensive Code Is Worse Than No Fix
    14. Trace, Don't Patch
    15. Why AI Loves Defensive Code
    16. The Contract Enforcement Loop
    17. Handling Contract Changes
    18. The Transformation
16. Chapter 12 PR Review in Ninety Seconds
    1. The Files That Weren't There
    2. The Problem with Human Reviews
    3. The Requirements Matrix
    4. The Five Phases
    5. The Review File
    6. The Ninety-Second Claim
    7. What AI Catches, What Humans Catch
    8. The Results
    9. The Deeper Lesson
17. Chapter 13 The Process That Runs Itself
    1. The Meeting That Didn't Happen
    2. The Uncomfortable Question
    3. The Accountability Shift
    4. What Every Textbook Describes
    5. The Enforcement Mechanism
    6. The Productivity Illusion
    7. What Disappeared
    8. What Remained
    9. The Cost of Autonomy
    10. The Meta-Lesson
18. Chapter 14 Watching the Watchers
    1. The Silent Failure
    2. The Observability Gap
    3. What Needs Watching
    4. The Dashboard That Doesn't Exist
    5. The Honest Bit
    6. The Alerts That Matter
    7. The Audit Trail
    8. The Human Checkpoint
    9. The Meta-Observability Problem
    10. The Learning Loop
    11. The Trust Calibration
    12. The Cost of Watching
19. Chapter 15 The Hard Limits
    1. The Command That Almost Ran
    2. The Problem with Capability
    3. The Guardrail Architecture
    4. The Enforcement Mechanism
    5. The Bypass Temptation
    6. The Incident That Shaped the Rules
    7. The Allowlist vs Blocklist Debate
    8. The Human Override
    9. The Trust Gradient
    10. The Security Blind Spot
    11. Constraints as a Form of Love
    12. The Living Document
    13. The Final Layer
20. Chapter 16 The Oversight Economy
    1. The Job That Changed Shape
    2. What I Actually Do Now
    3. The Oversight Economy
    4. The Skills That Matter
    5. The Existential Question
    6. Keeping the Hands Warm
    7. The Control Group
    8. The Productivity Paradox
    9. When the Oversight Fails
    10. The Selection Bias
    11. The Team-of-One Question
    12. The Craft Question
    13. The Future We're Building
    14. The Personal Note
21. Summary
    1. The Chapter Overview
    2. Key Concepts
    3. Who Should Read This
    4. Who Shouldn't Read This

1. Title Page
2. Cover
3. Table of Contents