The Chi-Sao exercise can be a great source of progress but it can also be its worse enemy!
It all depends on how it is practiced. It is not supposed to be a fight. The idea behind it should be about infusing the Wing Chun principles into free action and not about scoring hits on some Gung-Fu brother.
It should be also about disconnecting that left brain and allowing the body to express freely what he knows and can do without thinking about it. There should never be planning ahead or strategy in Chi-Sao, things that can take the practitioner away from the here now.
There should never be physical tensions in Chi-Sao. Stay away from the “sumo” type of Chi-Sao! A stiff arm is as bad as a stiff mind. The easiest route should always be looked for in attack. (Primordial WCK skill) The opponent force should be avoided in the best ways possible. (Again primordial WCK skill) Trying to score hits at all costs by using crazy moves should be avoided too.
Good Chi-Sao practice should be like an animated but controlled conversation where questions and answers are flowing effortlessly back and forth.
The more skilled your practice partners will be, the more difficult it will be to touch them but it goes both ways because there is a point where attack starts to provide for its own defence. This skill doesn’t come by being forceful.
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