“Playing to win” is different than “playing not to lose.” The actions you would take to win are different than the actions you would take to “not lose.”
Playing to Win
If you are playing to win, you do whatever is necessary to move things forward. You aggressively try to put points on the board. You’re not reckless, but you’re certainly not passive.
When you play to win, you make the call that you fear. You have the difficult conversation. You deal with the tricky issues that may put your outcomes at risk if things go south on you.
Playing Not to Lose
If you are playing to “not lose,” you’re cautious. Probably overly-cautious. You want to avoid mistakes, so you hold back. Instead of doing what you know you need to do, you wait to react. Instead of using all of your power to tilt things in your direction, you wait.
You don’t make the call to your dream client because they said they needed time to think things over. You avoid talking about your price because you worry that your prospect will say it’s too high. You don’t act because you are fearful that anything you do will put your deal at risk.