Teachers' design of a lesson is critical for helping their students develop academically effective forms of self-regulating learning (SRL) in classrooms. Using a quasi-experimental design, the researchers integrated systematic collaborative learning from problematic and successful experiences into teachers' preparatory programs and examined how such learning was associated with preservice physics teachers' SRL-based lesson design. The participants in this study were 132 preservice physics teachers during the practicum phase of their teacher education at four major research universities. Results indicated that preservice teachers who contemplated both problematic and successful experiences developed better SRL lesson-designing skills compared to preservice teachers who contemplated only problematic experiences. This study provides a new outlook for linking collaborative learning from problematic and successful experiences as a means of nurturing teachers' SRL, as well as suggesting implications and further research avenues.