CWChad Wolpert

Ideas

Ideas on AI, careers and making smarter moves.

Thinking in public about AI and work—what it means for your career, how to position yourself, and how to move with confidence in a changing market.

Themes:Career positioningAI & careersCritical thinkingIntelligenceAI history

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Critical thinkingJun 2025 · 6 min read

The Agreeable AI Dilemma: why ChatGPT sometimes tells us what we want to hear

Large language models lean towards being agreeable — and when that agreement feels intelligent, we stop questioning it. How sycophancy creeps in, and how to become a smarter, more critical user.

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AI historyJun 2025

AI was supposed to boom in the 2010s — why didn't it, and why is it booming now?

From one of the first IBM Watson implementations to today's generative AI wave — why the technology finally caught up with the hype.

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