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22 posts tagged with "lead"

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Strong Opinions, Loosely Held

· 5 min read
Calvin Cheng
Shape what gets built and the value it creates.

An old friend of mine queried, over hot mocha at a hipster cafe: "So Calvin, what is the most challenging technical skillset or programming language that you think I should master, to grow my tech career?",

I was most tempted to answer - "Haskell", "Erlang", "Rust", "electronics design", "cryptography" or "AI".

But I decided otherwise.

The most challenging technical ability to master is the ability to hold contradictory ideas in your head, remain zen regardless of uncertainties and execute despite a lack of clarity. To be fair, one can argue that this isn't really a technical skill and it sounds a lot more like soft skills. (This connects to how imagination helps us hold multiple possibilities simultaneously.)

Hear me out.

Systems Optimize for Control, Not Meaning

· 4 min read
Calvin Cheng
Shape what gets built and the value it creates.

Watterson was openly critical of rote education, productivity worship, commercialized childhood, advertising, and mass culture. In Calvin and Hobbes, school isn't evil - but it is rigid, joyless, and indifferent to curiosity.

The takeaway: systems are optimized for control, not for meaning. (This is part of a series exploring Calvin and Hobbes.)

Childhood Truths Adults Rationalize Away

· 3 min read
Calvin Cheng
Shape what gets built and the value it creates.

Calvin asks questions adults stop asking. Not because adults know the answers, but because we've learned to stop asking. (This is part of a series exploring Calvin and Hobbes.)

"Why should I do homework?" isn't a lazy question. It's a fundamental challenge to the system. "Why is being 'good' defined by convenience?" cuts to the heart of how we've structured society. "Why do adults say one thing and do another?" exposes the gap between stated values and actual behavior.