The lack of security and assurance in our computer systems and supporting network and system infrastructure is clear. What to do about it is not clear. The difficulty is rooted in the social, political and economic environment in which computing occurs. Marketing forces, societal pressures, and most especially peoples' varying needs for safety and security exacerbate the difficulties of applying technical remediations to improve security. Numerous solutions have been proposed, each dealing with one or more aspects of the problems in security but none of which engage with what it means to be safe and secure in contemporary society. We have to simultaneously understand security from the societal, individual and technical perspectives and wrestle a position on information security from those three perspectives. This talk takes a historical position to understand how environmental forces influence security technology, policy, and procedures. It asks how information security grew as a practice and where it will go. It will also provide thoughts on how to improve information security.