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Choosing the right show is the first hurdle to putting up your own work, and the best advice I can give is this: be realistic. Do you really have enough money to pull off The Crucible? Can you assemble the cast needed for a Shakespeare? Do people actually want to see your interpretation of Waiting for Godot? Are you too young/old/short/tall to play that leading role you always wanted? Has the show been done recently in your city, and if so, are you going to do it differently enough to warrant staging it again? Tough questions, but you need to be honest with yourself.