Test your patience....

[zebrasectomy]

So how many times do I have to throw myself off these barrels, and when will I know when I'm done? Will the trainer tell me or do I have to guess and talk to him?

[steelcoresoviet]

You're doing it wrong.

[Ajogamer]

Hmm, seeing as you mention barrels and "Test your patience", it sounds like you're at the dojo near the construction yard, in area 2. If so, you don't have to throw yourself off at all, but rather, you need to prove your patience, by standing still at the top of the tower for 3 minutes. If you're actually at the Dojo at area 1 however, (which has a cliff with a rope leading up it, rather than barrels), then you gotta drop off the right side of the cliff somewhere around 15 times total.