Sunday Letters

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Dangerous metrics

The right amount of bullshit

Why do you want to convince them?

VCs sell money

Don't panic

Self-fufilling worry

How to Make Your Organization Run Like a Well-Oiled Machine

Look for the next bottleneck

Planning for 35 years

Do the more rare thing

Goal versus Process

Descriptivism

Is the team for you or are you for the team?

What guarantees are you making?

Undeveloping conviction

Manager or short order cook?

Managing..up?

Asking versus telling

The power of yes

Principles and discomfort

Something fun...

The value of iteration

Which derivative are you?

Against "talent"

Culture is what you put up with

In praise of glorious messes

Why won't they give us the resources?

In praise of small weirdos

Fear and metrics

No smooth discontinuities

The rainbow of disgust and joy

The abstraction trap

Language isn't the cure

Humility in leadership

New tools or old?

Fit then optimize

Bad communication is always your fault

Solve the right problem

Let's cut some cake

Desire isn't a strategy

Humility in leadership

Be a brave fool

Don't lie to the computer

Useful skepticism

Bonus post - Noisy Monitors

The power of patterns

Understanding, explaining and simplicity

To hack or not to hack

Absolute vs Relative

Proof is in the doing

© 2025 Sam schillace
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