If We Did Everything Right, Would the Org Collapse?

Here’s the uncomfortable truth:

Sometimes it feels like if we actually did things right—

Asked the hard questions.

Slowed down when it mattered.

Pushed back on fake urgency—

We’d break the very system we’re trying to improve.

And in many orgs, we would.

Because dysfunction isn’t a mistake.

It’s a stabilizer.

Why?

Because fire drills get attention.

Because pressure justifies bad alignment.

Because when something looks fast, people stop asking if it’s right.

We’ve built systems that depend on confusion to keep moving.

And clarity? Clarity threatens the illusion.

So how do you lead in a system like that?

You don’t aim for purity.

You aim for precision.

You insert clarity just early enough to reduce regret.

You ask the real question before the fake deadline wins.

You protect momentum—without protecting delusion.

Because if doing it right threatens the system?

Then doing it wrong is the system.

Use this decision tree to test your next project:

Let’s be real—this is hard.

It’s uncomfortable. It’s political. And it often feels like someone else’s job.

But here’s the shift:

You don’t need a title to lead.

Every engineer. Every PM. Every manager.

Everyone is responsible for calling out risk—even if the system prefers silence.

That starts with questions like:

“What problem are we actually solving?”

“What would we do differently if the deadline wasn’t looming?”

“Who regrets it if it breaks?”

Asking these isn’t blocking.

It’s protecting everyone from future regret.

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— SHIP IT AND REGRET IT