sail close to the wind
Flirt with trouble
To sail close to the wind is to behave in a way that skirts the edge of what's acceptable, legal, or safe—risking trouble without quite crossing the line.
From the nautical maneuver of sailing as nearly into the wind as possible, which risks stalling.
The accountant sailed close to the wind with those deductions, but nothing was technically illegal.
Pushing conflicts to disaster's threshold
- recklessnessCareless disregard for danger
- gambleStake on uncertain outcome
- perilSerious threat of harm
- hazardSource of potential harm
jeopardize · precarious · high-stakes · tightrope · daredevil · audacity · boldness · venturesome
Reducing effort improperly
- gray areaAmbiguous, ill-defined situation
- loopholeExploitable gap in rules
- borderlineEdge of acceptability
- questionableOf uncertain validity
dubious · shady · unscrupulous · sharp practice · dodgy · skating on thin ice · indiscretion · impropriety
brinkmanship
Pushing conflicts to disaster's threshold
- recklessnessCareless disregard for danger
- gambleStake on uncertain outcome
- perilSerious threat of harm
hazard · jeopardize · precarious · high-stakes · tightrope · daredevil · audacity · boldness · venturesome · thrill-seeking
cutting corners
Reducing effort improperly
- gray areaAmbiguous, ill-defined situation
- loopholeExploitable gap in rules
- borderlineEdge of acceptability
questionable · dubious · shady · unscrupulous · sharp practice · dodgy · skating on thin ice · indiscretion · impropriety · misconduct
- Nautical Idiomsbatten down the hatches, all hands on deck, three sheets to the wind, in the same boat, rock the boat
- sea idiomsall at sea, dead in the water, sink or swim, miss the boat, rock the boat
- risk phrasestake a chance, take a gamble, risk it all, go for broke, roll the dice
sail close to the windplay it safe
Avoid unnecessary chances
err on the side of caution · hedge one's bets · tread carefully · proceed with caution · leave nothing to chance
sail close to the windkeep one's nose clean
Avoid misconduct or scandal
toe the line · play by the rules · color inside the lines · follow the rules · play fair
sailor, winding, sailing, winded, sailed, sailboat, sails, downwind, tailwind