Issue 42: The System is Not Broken

January 13, 2026

The System is Not Broken

2026 - Week 2

📌 Pinned Manifesto

Work In Progmess is not a newsletter for finished thoughts.

It is a place for ideas that are still forming, questions that do not resolve cleanly, and observations that feel slightly uncomfortable once you sit with them.

We are not here to provide step by step instructions for life, leadership, or success.

We are here to challenge assumptions that have quietly overstayed their welcome.

If you are looking for certainty, this will disappoint you.
If you are willing to sit in the middle of becoming instead of rushing to arrive, you are in the right place.

Still in Progmess.

🧾 This Week, In Brief

The system is doing exactly what it was designed to do
Completion is rewarded because it is measurable
Readiness is ignored because it is inconvenient
The problem is not effort. It is definition

🤔 This Made Us Curious

Every year we ask the same questions.

Why are students unprepared?
Why do new hires struggle?
Why do smart, capable people feel lost after doing everything right?

The answers usually show up on schedule.

“They lack motivation.”
“They are not resilient enough.”
“They were not challenged.”

The solutions follow quickly. Almost reflexively.

Add another requirement.
Tighten the rubric.
Create a new checklist.

This is the part where everyone nods seriously.

And for a moment, it feels productive. Which is incredibly satisfying. Briefly.

🧠 The Assumption Beneath It

The assumption is simple.

If we just make the system more rigorous, readiness will follow.

So we add more.
More credits.
More assessments.
More boxes to check.

At no point do we pause to ask whether the system was ever designed to produce readiness in the first place.

It was not. And that is not a secret.

✅ A Simple Visual Metaphor

The expectation is doing a lot of work here.

Somewhere in this flow, we all agreed this would hold.

🔎 What This Reveals

The system is not broken.

It is highly optimized. Impressively so. Almost suspiciously.

It produces completion at scale.
It creates comparability.
It rewards consistency.

Those are not flaws. They are features.

But readiness is not a feature of the system.
It is something we hope happens, not something the system is built to create.

Self awareness.
Judgment.
Values.
Decision making under uncertainty.

These things do not fit neatly into a process built for efficiency.

So we treat readiness like a side effect instead of the goal.

Then we act surprised when it does not show up on time.

💬 Worth Sitting With

A system optimized for completion will always outperform one designed for readiness.

Especially at producing completion.

❓ A Question to Carry

If the system keeps producing the same outcomes, what definition is it actually serving?

And what definition are we quietly hoping for instead?

📅 Next Week

We will look at why checklist readiness feels so responsible and why it quietly falls apart when the world gets messy.

Still in Progmess.
M and N

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