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We explore the nature of the practice of collaboration, focusing in particular on some of the reasons why collaborative initiatives tend to challenge those involved. Two concepts are central to this exploration. The first is collaborative advantage. This captures the synergy argument: to gain real advantage from collaboration, something has to be achieved that could not have been achieved by any one of the organizations acting alone. This concept provides a useful "guiding light" for the purpose of collaboration. The second concept, collaborative inertia, captures what happens very frequently in practice: the output from a collaborative arrangement is negligible, the rate of output is extremely slow, or stories of pain and hard grind are integral to successes achieved.