Understanding it refers to actual wind that helps move something along faster. With a following wind at our backs, our hike will be easier.
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Nautical Origin
It originates from sailing and is mostly used in the context of sea travel or other wind-influenced activities. The ancient mariners relied on a following wind to hasten their voyages.
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Positive Connotation
Gives a sense of ease or assistance, as it implies that external forces are aiding progress. The cyclist reached his destination quickly, thanks to a following wind.