The Curious Engineer

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The Beautiful Mess

cutlefish.substack.com

The beautiful mess of cross-functional product development. Click to read The Beautiful Mess, by John Cutler, a Substack publication with tens of thousands of subscribers.

Engineering management / careersSoftware / engineering practice

’23’24’25’26
Posts
223 from 29 Sep 2023 to 25 Oct 2026
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weekly (66 in the last year)
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personal blog
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2026 53

  1. TBM 447: Why We Sabotage Our Careers
  2. TBM 446: Halos, Vibes, Causality, and Identity
  3. TBM 445: The Feature Factory: A 10-Year Retrospective
  4. TBM 444: What a Workplace Can’t Promise
  5. TBM 443: The Standard Setter
  6. TBM 442: 10 Career Traps (Thoughtful People Fall Into)
  7. TBM 441: AI, the Loss of Positive Friction, and What to Do About It
  8. TBM 440: The Problem With Putting People in Boxes
  9. TBM 439: Day At The Gig...
  10. TBM 438: Am I the Only Weirdo in This Company?
  11. TBM 437: AI and the Recontextualization Tax
  12. TBM 438: The Right But Early Club
  13. TBM 437: Transition Week (And Some Fun Links)
  14. TBM 437: Tokens, Hours, Points, and Other Curious Proxies
  15. TBM 436: Tension-Based Prioritization (A Non-Framework)
  16. TBM 435: 20 Unfiltered Operating Takes
  17. TBM 434: How Maps Can Hide Problems
  18. TBM 433: The Border Collie Faustian Bargain
  19. TBM 432: Bundling & Unbundling Capabilities (and AI)
  20. TBM 431: The Denominator That Matters
  21. TBM 430: Incubate, Compound, Refinance, Liquidate
  22. TBM 429: How To Thrive At Work When You Think Too Much
  23. TBM 428: Yes, Robot. Yes, Boss?
  24. TBM 427: The Bottleneck Strike Again!
  25. TBM 426: The Trouble With Mirrors
  26. TBM 425: AI and Agency
  27. TBM 424: Why We Help (And How To Stay Helpful)
  28. AI Won’t Save the Kingdoms We Built
  29. TBM 423: Why Defining Teams Is So Hard
  30. TBM 422: Exception, Presence, Delegation
  31. TBM 421: Minimally Viable Consistency (Part 3)
  32. TBM 420: The AI Playbook Puzzle
  33. TBM 419: Stop Being So Negative! Stop Being So Naive!
  34. TBM 418: Campfires, Trails, and Quests
  35. TBM 417: Before You Fire All Your Glue People Because of AI
  36. TBM 416: Investment Stewardship (As Habit)
  37. TBM 415: Demand Mix, Discovery, and AI as a (Dys)function Multiplier
  38. TBM 414: Legibility and Legitimacy
  39. TBM 413: In That Space Is Our Power
  40. TBM 412: Institutionalized Overload (Now With AI)
  41. TBM 411: Messy Docs As Helpful Pattern
  42. TBM 410: Dancing With Problems
  43. TBM 409: Minimally Viable Consistency (Part 2)
  44. TBM 408: Basic Links
  45. TBM 407: The Three Juggling Acts (Strategic, Lazy, and Survival)
  46. TBM 406: Seeing Everything, Understanding Nothing (The Context Trap)
  47. TBM 405: Hope, Context, and Control
  48. TBM 404: Should Teams Use the Same Tracker?
  49. TBM 403: The Seduction (And Folly) Of Rollups, Points, and (Most) Time Tracking
  50. TBM 402: The Real-World Journey to Value and Product-Centricity
  51. TBM 401: Solving Problems the Hard Way
  52. TBM 400: Strategic Portfolio Management Meets Product-Centricity
  53. TBM 399: 10 Prioritization Traps

2025 70

  1. TBM 398: Micromanagement? Or Staying Close to Reality?
  2. TBM 397: The Initiative Shape Activity (And a Favor to Ask)
  3. TBM 396: So You Want To Define “The Problem”?
  4. TBM 395: Words! Damned Words!
  5. TBM 394: Imagine If a Restaurant Behaved Like Your Average Product Team (Extended Edition)
  6. TBM 393: Why Labeling Relationships Is So Important
  7. TBM 392: When (And How) Tools Matter
  8. TBM 391: You’re Not Misaligned. You’re Thinking Differently.
  9. TBM 390: Governance by Principle, Not by Template
  10. TBM 389: Overthinker!
  11. TBM 387: Lenses
  12. New and Past Playbooks (Links)
  13. TBM 386: Understanding Enabling Constraints Using Shape Up (Basecamp)
  14. TBM 385: "We Have To Simplify!"
  15. TBM 384: Prioritization Starts With Strategic Prioritization
  16. TBM 383: Maximizers vs. Focusers
  17. TBM 382: Product-Centricity When You Don't Sell A Digital Product
  18. TBM 381: Stop Trying To Make Prioritization "Easy"
  19. TBM 380: “But We Have To Try Something!”
  20. TBM 379: Vertical vs. Horizontal Org Coupling
  21. TBM 378: How To Effectively Pitch Constraints
  22. TBM 377: Time Allocation ≠ Capacity Allocation
  23. TBM 376: Why Are We Organized Like This?
  24. TBM 375: Minimally Viable Consistency
  25. TBM 374: Strategy & Urgency
  26. TBM 273: What To Do More (And Less) Of
  27. Two POM Transformation Flavors
  28. TBM 272: Three Perspectives
  29. TBM 271: Diagnosing Your Company's Strategy Problem
  30. TBM 370: Dependencies Aren't Your Problem
  31. TBM 369: Sources Of Truth
  32. TBM 368: Goals Take Practice
  33. TBM 367: The Wicked "Big Picture" Loop
  34. TBM 366: Empowered For Delivery, But...
  35. A Cagan Critique
  36. TBM 365: The Problem With Value Hierarchies (Video)
  37. TBM 364: Three Team Vibes
  38. TBM 363: Is Matt A Loser?
  39. TBM 362: How (And Why) We Help
  40. TBM 361: Context, Collaboration, Intent, and Investment
  41. TBM 360: "Wait! I Thought the Team Was Overloaded?!"
  42. TBM 359: Process Person
  43. TBM 358: The Genius of SVPG
  44. TBM 357: Perspectives on Change and Improvement
  45. TBM 356: Product Party Modes
  46. TBM 355: Who Should Care?
  47. TBM 354: The 4 Framework Jobs (And Why It Matters)
  48. TBM 353: Conversation Quality and Scale
  49. TBM 352: Funding, Planning, and Context
  50. TBM 351: The 4 Prioritization Jobs (And Why It Matters)
  51. TBM 350: Connecting Dots
  52. TBM 349: A "Product Transformation" North Star
  53. TBM 348: Shared Understanding At Scale
  54. TBM 347: "Why Don't Our Leaders Care About How We Work?"
  55. TBM 346: Broken Record Models
  56. TBM 345: Back On Track
  57. TBM 344: Context, Possibility, Intent, and Action
  58. TBM 343: "We Kind of Suck at That Right Now"
  59. TBM 342: Who Pays the Ego Toll?
  60. TBM 341: 10 Tips for Turning Around a Platform Team
  61. TBM 340: Path to $
  62. TBM 339: Update and Clarifications
  63. TBM 338: 4 Core Product OS Design Competencies
  64. TBM 337: Pirates and Garbage Cans
  65. TBM 336: Product OS Design Tips and Principles
  66. TBM 335: "Simple" Dependency Coordination
  67. TBM 334: The Capacity Allocation Illusion
  68. TBM 333: Lean Graph Theory
  69. TBM 332: The Last Strategy Framework You'll Ever Need
  70. TBM 331: Strategy & Decisiveness

2024 79

  1. TBM 330: (Un)common Sense Playbook
  2. TBM 329: Deep vs. Broad Context Traps
  3. TBM 328: Beyond Firmographic-Based ICPs
  4. TBM 327: Hot Takes and Parochial Altruism
  5. TBM 326: Adhocracies and Bureaucracies
  6. TBM 325: Skeptoptimism – Thinking Slow, Acting Fast
  7. TBM 324: Goal-O-Rama
  8. TBM 323: Quick Tool Tips
  9. TBM 322: Work Shape Mix
  10. systems *doing* and complexity *doing*
  11. TBM 321: "Reducing Complexity"
  12. TBM 320: From Fluffy Concepts to Concrete Outcomes & Behaviors
  13. TBM 319: Surfing Inertia and Pendulum Swings
  14. TBM 318: Why Orgs Become Too Tall
  15. Keep Product Management Messy
  16. TBM 317: Yes, Or...
  17. The tough reality of being a "glue person"...
  18. TBM 316: Ultra Founder Mode
  19. TBM 315: The Self-Sealing Argument Trap
  20. TBM 314: Using Enabling Constraints for Situational Awareness
  21. TBM 313: Chat, Breathe, and Reflect
  22. Scoping and Shaping Mini-Book
  23. TBM 312: Comparing Areas of Friction and Drag
  24. TBM 311: Roadmapping Miro Board and Question for Subscribers
  25. TBM 310: Trees, Journeys, and Loops (and the Functional Model Trap)
  26. TBM 309: Zombie Practices and Processes
  27. TBM 308: Boundary of Safely Challenged Assumptions
  28. The "X" Files (65.57% of 2024 Edition)
  29. TBM 308: No Unforced Errors
  30. TBM 307: The "P" Word, Legitimacy, and Challenging Our Default Models and Frames
  31. TBM 303: The Current Tech Puzzle (With Diverse Takes)
  32. TBM 305: Stop the (Goal) Cascade Madness
  33. TBM 304: Losing a Day a Week to Inefficiencies?
  34. TBM 303: Official, Real, and the Ideal
  35. TBM 302: Why Reflexive Thinkers Need to Take More Breaks
  36. TBM 301: How to Reconcile Prioritization and $/Time Allocation
  37. TBM 300: How to Think About Operations and Enablement
  38. TBM 299: Underperformer
  39. TBM 298: Retrospective Rationalization
  40. TBM 297: Staying In Touch
  41. TBM 296: Trust Lets You Observe Reality
  42. TBM 295: Going Deep 🤮
  43. TBM 294: Close the Loop. Stop the Drift
  44. TBM 293: Where More Effective Product Teams Spend More (and Less) Time
  45. TBM 292: Friction, Documentation, and Product Tools
  46. TBM 291: Why Your Product Transformation Will Fail
  47. TBM 290: The Failure Threshold
  48. Product Coaching with Petra Wille
  49. TBM 289: The Boring Product Manifesto
  50. 20 Things I've Learned as a Systems (Over) Thinker (Extended Commentary)
  51. TBM 288: Changing Your Swing
  52. TBM 287: Layoffs, Pendulums, Layers, and Gemba Walks
  53. Sociotechnical Maestros with Gene Kim
  54. TBM 286: Narrative Fallacies and the 2024 Narrative Soup
  55. TBM 285: Shared Teams and Apples-to-Oranges Priorities
  56. Software Development As Collective Learning With Hazel Weakly
  57. TBM 284: Why Aren't We Talking About Continuous Improvement?
  58. Octopus Careers & Throwaway Stickies with Chris Butler
  59. TBM 283: Just and But
  60. TBM 282: Three Stages of Org Evolution
  61. TBM 281: Stop Chasing Unicorns
  62. TBM 280: 2-6-4-1
  63. TBM 279: How to Learn and Practice Product Management in a Feature Factory
  64. TBM 278: The Power of Firsthand Experience
  65. Notes on Product management theater | Marty Cagan (Lenny's Podcast)
  66. TBM 277: Bring Back Fun
  67. TBM 276: Leverage Distribution
  68. TBM 275: "Bad" Strategy. Why?
  69. TBM 274: How Capable Leaders Navigate Uncertainty and Ambiguity
  70. TBM 273: Transition and Reflection
  71. TBM 272: The Biggest Opportunity (Part 2)
  72. TBM 271: The Biggest Untapped Opportunity
  73. TBM 270: Important Reader PSA
  74. TBM 269: Three Organizational Design Principles
  75. TBM 268: "Going Deep"
  76. TBM 267: Debt and Bridge Building
  77. TBM 266: Human Load Balancers, Renegades, Insiders, and Platform Saviors (Part 4)
  78. TBM 265: Rebuilding Trust and Breaking Free From Trust Proxies and The Swirl
  79. TBM 264: Dependencies In Fast(er) Growing Companies (Part 3)

2023 21

  1. TBM 263: "I Aspire to Regret How We Used to Work"
  2. TBM 262: Dependencies In Fast(er) Growing Companies (Part 2)
  3. TBM 261: Dependencies In Fast(er) Growing Companies (Part 1)
  4. TBM 260: The Thoughtful HIPPO
  5. TBM 259: The Predictability Trap
  6. TBM 258: "Just Hire Talented People and Empower Them"
  7. TBM 257: How to Make the Case for Slowing Down to Speed Up
  8. TBM 256: The Slide
  9. TBM 255: The New Airbnb (Lenny's Podcast) w/Melissa Perri
  10. TBM 254: Self-Gaslighting and the Doubt Loop
  11. TBM 253: Don't Fix Things. Write a New Story
  12. TBM 252: How to Troubleshoot Status Updates and Syncs
  13. TBM 251: Scale vs. Efficiency
  14. TBM 250: Dear Executive...
  15. TBM 249: Return on Investment (and Allocation)
  16. TBM 248: Project-ish
  17. TBM 247: 15 Metaphors for Waste In Product Development
  18. TBM 245: True Empowerment
  19. TBM 246: Why Didn't They Say No?
  20. TBM 245: The Magic Prioritization Trick
  21. TBM 244: We JUST Need to Align Incentives