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Craig McCaskill
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Everything

Books and Ideas

4 posts

Communication and Influence

6 posts

Leadership and Culture

8 posts

Product and Strategy

10 posts

Systems and Scaling

5 posts

Technology and Future

6 posts

Thinking and Learning

10 posts
19 Apr, 2026
Featured
Technology and Future
19 Apr
Technology and Future
Featured

Toothpaste Back in Tubes: On opportunity cost, art, and what stays human →

The AI debate keeps leaving out the part that matters most: what gets made with the time it gives back. On opportunity cost, art, and what stays human.
08 Mar, 2026
Featured
Leadership and Culture
08 Mar
Leadership and Culture
Featured

The Games Your Organization is Actually Playing →

Most organizational dysfunction comes from rational people responding to badly designed games. Before you blame the players, check the rules.
22 Feb, 2026
Featured
Leadership and Culture
22 Feb
Leadership and Culture
Featured

The Case for Being Wrong Faster →

Most organizations punish people for changing their minds. The ones that win are the ones that learn fastest.
25 Jan, 2026
Technology and Future
25 Jan
Technology and Future

When Seeing Is No Longer Believing →

We spent years worrying about deepfakes. Then we watched authentic video get contradicted by official statements, with media treating both as valid perspectives.
24 Aug, 2025
Featured
Technology and Future
24 Aug
Technology and Future
Featured

The Bubble That Knows It's a Bubble →

Railway Mania, dot-com, AI. Technology bubbles follow a pattern older than any of them. What's different this time is that everyone knows the script.
11 Jun, 2025
Featured
Product and Strategy
11 Jun
Product and Strategy
Featured

Sensing and Sensemaking: The Hidden Skills of Product Management →

The best product managers develop two underappreciated capabilities that turn ambiguous signals into strategic clarity: sensing what others miss and making sense of what it means.
24 May, 2025
Featured
Thinking and Learning
24 May
Thinking and Learning
Featured

Writing is still thinking →

A blank page doesn't lie about what you actually know. In a world of AI shortcuts, writing is still the best way to really think.
25 May, 2024
Featured
Technology and Future
25 May
Technology and Future
Featured

Playing Favorites - How AI Shapes Our Knowledge Without Us Noticing →

We're building a world where AI increasingly decides what information we see. These systems have a built-in bias toward the average, and it's narrowing what we collectively know.
30 Jul, 2023
Books and Ideas
30 Jul
Books and Ideas

Truth in a Post-Truth World, Revisiting Frankfurt's On Bullshit →

Revisiting Harry G. Frankfurt's 'On Bullshit' in a world where attention matters more than accuracy, and bullshit is louder than both.
06 Aug, 2013
Product and Strategy
06 Aug
Product and Strategy

Mental Models →

A 2013 note on mental models and the ways we borrow, misuse, and forget them when designing for people.
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