This talk takes a reality check of today's IT paradigm and assesses how cloud computing may help deal with the complexity in the IT solutions. We review the fundamental concept of cloud computing and its evolution in the past few years, followed by an in-depth analysis of the state of cloud and outlook of the mega trends in the space for the next 5 years. Next we anatomize various challenges in the cloud adoptions and implementations, which leads to a methodical approach presented to establish a winning cloud strategy.