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Surveying the history of citizen environmentalism in the context of environmental law and politics over the past fifty years, this essay hypothesizes five different categories of corporate, governmental, political, and individual actions that deserve to be called “dumb,” and the societal lessons that have been or could be learned from each. If there is truth to the wistful aphorism that “we learn from our mistakes,” then our society is in position to learn a great deal about our world and how it works, which perhaps provides some ground for hope for the years to come. Environmentalism embodies fundamentally rational and realistic principles of analyzing scientific fact, human needs and behavior, values and risks, and issues of policy and governance—so therefore, as in the past, against protracted retrogressive opposition, citizen environmentalism will undoubtedly continue to play an indispensable societal role.