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Vision of a fail proof smart grid can be fulfilled using modern control capabilities. To maximize performance on the “edge”, systems often evolve into a subtle mix of order and randomness (e.g., biology or astrophysics). Systems exploiting such “deterministic unpredictability” have been built (e.g., high performance aircraft). This paper proposes to expand the envelope of stable operations into the realm of “managed chaos” in order to realize an agile power grid that is more efficient and reliable with less redundancy in transmission capacity. This involves operation of the system with a string of local ephemeral equilibria created by changing control objectives, strategies and/or algorithms. The shallow potential wells around these equilibria keep the system prone to managed chaos, until reaching an acceptable final equilibrium. Overcoming grid stability problems as proposed would enable end-to-end direct transactions between energy producers and consumers with internet-like market reach, transparency and ease of execution.