Rationality is winning—or is it?

I feel a bit silly writing an post about connotations on a rationalist website, but I really love the quote “Rationality (is/​is not) winning”. I see a few different ways of interpreting it:

  • “Rationality is winning”—results are more important than following a particular ritual of cognition. If something doesn’t work, abandon it no matter how “rational” is seems.

  • “Rationality is not winning”—exploration is much more fun than just mindlessly going toward some goal.

  • “Rationality is winning”—what matters is how good you are at reaching socially accepted criteria of “success”—I don’t like this connotation at all.

  • And I can think of a few others...

I wonder, the way human brain works, is it common for there to be thoughts that are much better expressed with a short sentence full of ambiguous connotations, that by long and accurate explanations? Give me your favourite ambiguous quotes!