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The nonreversibility of strategic investment and nondeterminacy of information acquired from inner and outer environment put importance on the strategic choice timing. Whether the conversion timing is chosen correctly or not has become one of the key factors influencing the conversion performance. At first, this paper analyzes the influencing factors and random characters of strategic choice timing, and establishes the theoretic existence of optimal time through real option approach. And then the general principle of conversion timing choice is systematically put forward for enterprise's sustainable development, and either the optimal exit time of current main business or investment time of potential main business is determined. At last, by comparative static analysis, it is further discussed that the change of organizational adaptation involving firm's opportunity identification ability, operational capability, investment ability and assets' complementary ability have an effect on the strategic choice timing.