Plural of headwind; multiple instances of wind opposing motion, or figuratively, obstacles or difficulties blocking progress.
Same origin as headwind. The plural form developed naturally but gained metaphorical strength in 20th-century business language, where 'facing headwinds' became a standard phrase for economic or market challenges.
When companies report earnings, they often blame 'headwinds'—it's a sports/nautical metaphor that makes difficult circumstances sound like natural forces rather than poor planning!
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