sailing close to the wind

The phrase "sailing close to the wind" means to operate or behave in a risky or daring manner, often pushing the boundaries of what is considered acceptable or legal. It originated from sailing terminology, where ships sailing as close to the direction from where the wind is blowing (close-hauled) as possible are navigating the fine line between optimal speed and danger, as any slight deviation could cause the ship to collide with the wind or lose control. This phrase is typically used metaphorically to describe someone who is taking calculated risks or engaging in activities that are on the edge of being unacceptable or in violation of rules or standards.