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A term coined by Bob Ross, he would use it as a way to describe when you have to paint something that could very easily ruin the painting. Typically it'd also be something he'd tell you not to trace or copy the way he does it.

Also usable as any time you need to do something with high risk/reward.
Bob Ross: See, you have to decide where the tree lives. This is going to be your Bravery Test
by Zedek December 06, 2012