In this article, the author discusses the challenge of the "transient" and the "timeless" problems of educational assessment and describes how to survive a lifetime of policy and practice in assessment. He first presents a personal retrospective from 1960s to 2000. Then he talks about assessment in transition and conflicting philosophies. Next, he discusses variables in the evolution of assessment and identifies some of the sources of conflict that lie inside one's every changing world of assessment. The list has arisen partly from his experience and partly from looking up "assessment" in dictionaries and thesauri. Lastly, the author looks at assessment through the lens of a post-modern critique.