press (one's) luck(redirected from pressing his luck)
press (one's) luck
To risk losing the good favor or fortune one has garnered thus far by brashly or overconfidently seeking more. I know you're in the boss's good graces now, but don't press your luck: she's been known to turn on people for getting too cocky. I've had some good winnings at blackjack, but I don't think I should press my luck any further.