To prepare students to imagine desirable futures amidst current planetary level challenges, design educators must think and act in new ways. In this paper, we describe a pilot study that illustrates how educators might teach K-12 students and university design students to situate their making within transitional times in a volatile and exponentially changing world. We describe how to best situate students to align design thinking and learning with future foresight. Here we present a pilot test and evaluate how a university-level Dexign Futures course content, approach, and scaffolded instructional materials – can be adapted for use in K-12 Design Learning Challenges. We describe the K-12 design-based learning challenges/experiences developed and implemented by the Design Learning Network (DLN). The Dexign Futures course we describe in this paper is a required course for third year undergraduate students in the School of Design at Carnegie Mellon University. The “x” signifies a different type of design that aligns short-term action with long-term goals. The course integrates design thinking and learning with long-horizon future scenario foresight. Broadly speaking, we ask how might portions of a design course be taught and experienced by teachers and students of two different demographics: within the university (Design Undergraduates) and in K-12 (via DLN). This pilot study is descriptive in nature; in future work, we seek to assess learning outcomes across university and K-12 courses. We believe the approach described is relevant for lifelong learners (e.g., post- graduate-level, career development, transitional adult education).