If you’re playing any sort of a game, the question “Am I winning?” is usually quite easy to answer. “Is my score higher than the other guy?” usually covers it (though if you’re playing something like chess it might be a little more complicated than that). If you’re playing a computer game the fact that your character is still alive may well be enough to settle this question in your favour.
In life, though, it is a much harder question to answer. It may well be true that, to the healthy mind, it’s not something which should ever really matter, but as noted before, gamification works really (embarrassingly) well for me.
I suspect that deep down most people have their own ways of keeping score. Their bank balance. Their air miles account. How far they ran today. More abstract things, such as their perceived quality of the of the photos they took this weekend, leaning to less abstract things, actual scores, such as might be gleaned from Fitocracy or Foursquare.