The question we address in this chapter follows: How can students leverage Learning Statements collected from former students in a design, build, and test course to enhance their own learning by reflecting on doing? A Learning Statement is a structured [Experience|Learning|Value] text-based construct for students in AME4163 Principles of Engineering Design to record what they learned by reflecting on authentic immersive experiences throughout the semester. The immersive experiences include lectures, assignments, reviews, building, testing, and a post-analysis of an electro-mechanical device to address a given customer need. Over the past four years, at the University of Oklahoma-Norman, we have collected almost 32,000 Learning Statements from about 600 students. Based on these Learning Statements, in our earlier work, we proposed a text-mining framework to improve our understanding of what students have learned by reflecting on doing and thence how we might improve the delivery of the course in the future. Our focus, in the earlier work, was on leveraging the historical data to improve the course from the instructor’s perspective. In this chapter, we look at the data from the student’s perspective and focus on demonstrating how students can utilize the former students’ Learning Statements as a knowledge base to tutor themselves in their own learning through reflection on doing. In this chapter, we describe a self-tutoring system that allows students to compare their own Learning Statements to that of the former students in three ways, namely, Experience, Learning, and Value. The core of the self-tutoring system is a semantics-based similarity metric that enables the automatic searching of historical Learning Statements with similar experience, learning, or value at the semantic level. The value of the self-tutoring system is that it provides an opportunity for students to augment what they have written by reflecting on prompts from the self-tutoring system to augment what they eventually share as experience, learning, and value in their own Learning Statements.