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Dive into a collection of past posts and rediscover timeless content.
Checking, Not Guessing

Aug 20, 2026

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4 min read

Checking, Not Guessing

How I decide when to trust Claude's answer — and when to ask a human instead

Simon Cooper
Simon Cooper

The Weekly

The AI advice nobody's giving you: do less, not more.

Aug 13, 2026

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5 min read

The AI advice nobody's giving you: do less, not more.

You don't need to understand everything, just the things that help you.

Simon Cooper
Simon Cooper
I didn't write a to-do list after my time off

Aug 6, 2026

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5 min read

I didn't write a to-do list after my time off

Back from a few days off, I handed my inbox and Slack to Claude and asked it to triage. Would you?

Simon Cooper
Simon Cooper
I Shared My AI Chat With My Boss. Should You?

Jul 30, 2026

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4 min read

I Shared My AI Chat With My Boss. Should You?

Sharing Claude and ChatGPT conversations saves time, but this week's news shows why it's not risk-free

Simon Cooper
Simon Cooper

The Weekly

One Designer, Ten Iterations, Zero Job Loss

Jul 23, 2026

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4 min read

One Designer, Ten Iterations, Zero Job Loss

Inside a designer's first real experiment with AI-assisted prototyping

Simon Cooper
Simon Cooper

The Weekly

Don't Settle with the Initial Answer

Jul 16, 2026

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4 min read

Don't Settle with the Initial Answer

How follow-up questions turn AI from useful to genuinely indispensable

Simon Cooper
Simon Cooper

The Weekly

My AI Budget Just Shrank by 98%

Jul 9, 2026

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5 min read

My AI Budget Just Shrank by 98%

What a shrinking AI budget taught me about spending discipline — and what it says about AI's ROI problem

Simon Cooper
Simon Cooper

The Weekly

Is Your Team's AI Chaos Quietly Draining Productivity?

Jul 2, 2026

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5 min read

Is Your Team's AI Chaos Quietly Draining Productivity?

What happens when 10 desks means 10 different AI tools

Simon Cooper
Simon Cooper

The Weekly

Is Your Boss Using AI More Than You?

Jun 25, 2026

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4 min read

Is Your Boss Using AI More Than You?

A senior leader sat near me this week, and I got a front-row seat to how they actually use AI.

Simon Cooper
Simon Cooper

The Weekly

Is AI really coming for your job?

Jun 18, 2026

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4 min read

Is AI really coming for your job?

It doesn't have to if you engage with it.

Simon Cooper
Simon Cooper
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