The design process is full of judgment, especially around successes and failures that occur through each iteration. Decisions about how to proceed when ideas do not work can be especially challenging for beginning designers. Yet, experts are able to demonstrate more natural regulation of the process. This research focused on the experiences of beginning designers to qualitatively explore how self-regulation practices of forethought and self-reflection are manifest when completing iterative design. Think aloud data and design artifacts were collected from four design teams as they completed a design challenge in their introductory engineering design course. Abridged accounts of the design show a range of approaches toward planning and reflection through successive iterations. Qualitative themes from the accounts illustrate insight from thinking of design through a lens of self-regulation. In forethought phases, there is harmony between the goal setting and visualization encountered in both design and self-regulated learning. Such planning can serve as a catalyst for improved performance when integrated into an upcoming design cycle. Themes also suggest that evaluation occurs throughout the design process, with a range of informal to formal moments. In these reflective moments, the interpretation of this accumulated information influences whether designers iterate or interrupt their design cycles. This research affirms parallels between design thinking and self-regulation processes, and speaks to the benefits of holding these in tandem during the education of beginning designers.