[insightcheck]

This might be simplistic, but the concept of "asymmetric upside" might be captured in any situation where "the worst thing can happen is that the person says no."

This includes: applying to competitive positions when you don't seem completely qualified, cold calls in sales (sales seems to be heavily based on asymmetric upside, where sales people call many different people until they get a few Yes-s), and asking people to hang out just to make friends.

More related to money, I've thought that cheap (and often free) educational material to have a large potential upside. Good books are often time well-spent, as long as there is enough time spent applying the concepts too. A cheap online course on video editing (I think about $10 USD at the time) has also come in handy many times.

[tpoacher]

Of course, this is only trivially true when "the worst thing that can happen is they'll say no" is true.

Typically it's not.

[egghead500]

I've asked a friendly girl who I've known for a while out on a date.

She politely declined.

After that our friendship was never really the same; there was always something awkward.

I regretted asking her out because that ruined an otherwise good friendship.