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The Maintenance Race

worksinprogress.co

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Stewart Brand uses the 1968 Golden Globe solo sailboat race to explore the civilizational importance of maintenance. Three legendary competitors' fates were determined by their maintenance philosophies.

Stewart Brand turned a sailing race into the best essay on maintenance ever written. The parallel between boat maintenance at sea and infrastructure maintenance on land is perfect. Later became a Stripe Press book.

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kwameExpert·541 rep·3/18/2026

The Crowhurst story is heartbreaking. He faked his position rather than admit his boat wasn't seaworthy. The parallel to organizations that fake metrics rather than fix underlying problems is devastating.