It's generally taken as a sort of blanket acknowledgement that we don't know what's best for us, or as another expression of Murphy's law, but I recently found a new way to understand it.
Towards the very end of Likkutei Moharan (II:118) Rebbe Nachman explains that while in our day and age, it is very easy for someone to reveal new Torah simply by speaking it, without having to think about it, HaShem derives special pleasure from the Torah we have to think about. He used the yiddish word trachtin to emphasize the effort expended on thinking about the Torah.
From this teaching, a new understanding of the Yiddish expression occurred to me: when a man thinks about Torah, HaShem laughs from joy.
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