sail close to the wind

verb2

1. •
   To sail in a direction close to that from which the wind is blowing, while still making headway.

   • As the Syrene vvas seen to fall to leevvard in the afternoon, the signal vvas made to her to sail as close to the vvind as possible. — 1781
2. •
   (figurative) To behave in a manner that is on the verge of being dangerous, illegal, or improper.

   • But he received only indifferent remuneration, in those days, and found himself to "sail close to the wind," to meet his current expenses. — 1876