This paper describes a framework for learning where learners undergo experimentations with the phenomena at hand according to progressive and staged goals. Bowling is used as a case study in this paper. The premise for experimentations is that learners can experience hidden efficacies, including the formation of "bad habits." A distinction is made between productivity in learning and performance in terms of learning outcomes. In other words, productivity in learning may not necessarily manifest in successful performance, hence the term productive failure. To emphasize the need for self-regulation during problem-solving process, we discuss the movements within the productive-unproductive and success-failure dimensions through three-staged self-regulatory processes and draw implications to learning and instruction.