ABSTRACT: George Santayana’s statement, “Those who cannot remember the past are condemned to repeat it,” is only half true. The past also includes successful histories. If you haven’t been made aware of them, you’re often condemned not to repeat their successes.In a rapidly expanding field such as software engineering, this happens a lot. Extensive studies of many software projects such as the Standish Reports offer convincing evidence that many projects fail to repeat past successes.This paper tries to identify at least some of the major past software experiences that were well worth repeating, and some that were not. It also tries to identify underlying phenomena influencing the evolution of software engineering practices that have at least helped the author appreciate how our field has gotten to where it has been and where it is.A counterpart Santayana-like statement about the past and future might say, “In an era of rapid change, those who repeat the past are condemned to a bleak future.” (Think about the dinosaurs, and think carefully about software engineering maturity models that emphasize repeatability.)This paper also tries to identify some of the major sources of change that will affect software engineering practices in the next couple of decades, and identifies some strategies for assessing and adapting to these sources of change. It also makes some first steps towards distinguishing relatively timeless software engineering principles that are risky not to repeat, and conditions of change under which aging practices will become increasingly risky to repeat.