According to Adam Zerner on LessWrong, Portland's Sandy Boulevard is a street-design puzzle that mirrors software engineering. A diagonal road cutting through the grid, it creates a chaotic six-way intersection with high speeds and a documented history of fatal crashes. When a cycling advocate called it 'world class,' he didn't mean it's pleasant—he meant that given the inherent complexity, the design work is excellent. Zerner draws a parallel to legacy code: decisions that made sense in the past become increasingly expensive to fix as constraints compound. Sandy Boulevard is exactly that—a reasonable choice from Portland's early days that now seems almost impossible to alter. The real cost? Removing it would require millions in spending, disrupt local businesses, and overcome political opposition. Zerner asks: is long-term thinking ever worth the short-term friction?

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