Chatter about Google’s transition from vanguard to dinosaur is hardly new. The company just turned 25 — roughly two centuries in tech years. It has lived through five presidents and two major market crashes. Its boy-wonder cofounders are now emeritus executives, and it changed its corporate name from a word that telegraphed futurism and brainpower to a word most people learn by age 3. But the past few years have introduced new troubles: lower tolerance for risk, crackdowns on innovation, layoffs, and a narrative that its famed products like search and Gmail are getting worse. They have supercharged the perception that Google, once seen as the most desirable place to work in Silicon Valley, has become the one thing it promised it would never be: boring.

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