Our sense of "winning" isn't entirely up for grabs: we prefer sensory stimulation to its absence, we prefer novel stimulations to boring old ones, we prefer to avoid protracted pain, we generally prefer living in human company rather than on desert islands, and so on.

In one manner of thinking, our sense of "winning" - considered as a set of statistically reliable facts about human beings - is definitely part of the territory. It's a set of facts about human brains.

"Winning" more reliably entails accumulating knowledge about what constitutes the experience of winning, and it seems that it has to be actual knowledge - it's not enough to say "I will convince myself that my sense of winning is X", where X is some not necessarily coherent predicate which seems to match the world as we see it.

That may work temporarily and for some people, but be shown up as inadequate as circumstances change.