To explore new opportunities to promote self-regulated learning (SRL) across a variety of contexts, this study applies a novel assignment called Pink Time in seven different courses at two universities. The assignment asks students to “skip class, do anything you want, and give yourself a grade.” In each case, instructors adapted Pink Time to fit the needs of their course. Altogether, 165 students completed 270 self-directed projects and self-assessments targeting five component behaviors of SRL. Findings show that: (1) students were more likely to perceive success in certain behaviors of SRL than in others; (2) students’ perceptions across courses were similar for some behaviors but not others; and (3) subsequent iterations of the assignment supported higher perceived measures of some SRL behaviors but not others. Together these findings illustrate the value and flexibility of this progressive assignment as well as persistent challenges in supporting students’ SRL.