Headwind/ˈhedwɪnd/ Definition 1 of 2Pro Tip 1/3Literal Meaning Refers to actual wind against a ship or plane, making travel harder. The pilot reported a strong headwind, delaying our flight. Pro Tip 2/3Physical Challenges Used to describe physical struggles similar to facing wind while moving. They faced a real headwind while biking uphill. Pro Tip 3/3Not Just Weather While related to nature, it often explains difficulty in a journey or mission. Her headwind was the mountain terrain, not the actual wind.