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What ought I hope for? This question guides our pursuit of the good life and its answer is shaped by our political and educational experiences. I suggest not only particular content of what we ought to hope for, but also an enriched understanding of how we hope together. I begin with a Deweyan account of hope as a set of habits that support a disposition toward possibility and change for the betterment of oneself and others. I consider the role hope plays in democratic life and how hope might be taught. This includes considering the ways in which cultivating hope might provide us a shared identity with our fellow citizens through how we hope together and what we hope together.