The Enshittification Trap: Why I'm Returning to Pen and Paper
Since 2011, I've been observing a disturbing trend: software is systematically getting worse. Not technically inferior – on the contrary, features keep piling up. But functionally, in real working life, it's increasingly becoming a burden rather than a help.
From Productivity Hell Back to Simplicity
Five years ago, I was convinced: highly specialized project management systems are the future. I invested hundreds of hours into the perfect tool landscape. Detailed workflows, automated reports, granular time tracking. On paper, everything was perfectly structured.
The reality? I spent more time maintaining the system than doing actual work. Every update brought new features nobody needed. Every new integration increased complexity. And when something didn't work – which happened increasingly often – all work came to a halt.
Today I work with Things3, Apple Notes, and an analog Moleskine Pro Business & Project Planner. Three simple tools instead of thirty complex systems. And I'm more productive than ever.
The Enshittification Spiral: A Business Model Problem
The term "enshittification" describes the process perfectly: First, tools are good for users. Then good for business partners. Finally, only good for shareholders. Microsoft Windows is the prime example – from an operating system that worked to an advertising platform with OS functionality.
Business software follows a similar pattern:
- Phase 1: Lean, focused, solves a problem brilliantly
- Phase 2: Features get added, complexity increases
- Phase 3: Subscriptions are introduced, lock-in effects emerge
- Phase 4: Features disappear behind paywalls, ads appear
- Phase 5: The tool becomes a burden, but migration is too painful
The Hidden Costs of Digitalization
Digitalization should reduce work. Instead, it creates new work:
Maintenance Overhead: Installing updates, learning features, navigating bugs. I used to invest 2-3 hours per week just on tool maintenance. Today? Zero hours. Things3 just works. Apple Notes has been stable for years. My Moleskine doesn't need updates.
Context Switching: Jumping between five different tools costs focus. Each tool has its own logic, own shortcuts, own quirks. The brain needs seconds to minutes for each switch.
Vendor Lock-in: The deeper you're stuck in a complex system, the harder the exit. Proprietary formats, complex export functions, missing compatibility. You're trapped, even when the tool hinders rather than supports you.
My Return to Simplicity
The turning point came during a stressful project phase when my complex system wasn't available. I grabbed pen and paper. And realized: I was faster. More focused. Clearer in my thinking.
Today my workflow looks like this:
- Things3: For time-critical tasks and GTD
- Apple Notes: For quick thoughts and project notes
- Moleskine: For strategic thinking and weekly planning
Three tools. Three clear responsibilities. No overlaps. No synchronization problems. No feature bloat. And most importantly: No distraction through "optimization of optimization".
The Lesson: Less is More Freedom to Act
The great illusion of the software industry: More features mean more productivity. The truth is the opposite. Every feature is one more decision. Every decision costs mental energy. Every saved decision is energy for real work.
My rule today: A tool must be 80% better than the simpler alternative to justify the complexity overhead. Most tools don't even achieve 20%.
For my clients, this means: I don't help with implementing the latest complex marketing automation monster. I design solutions that will still work in ten years. Without subscription models. Without forced updates. Without enshittification spiral.
Digital transformation should make us freer. Not more dependent on systems that don't serve us but exploit us.