Brief Description This talk delves into the intersection of experiential learning and engineering education, beginning with insights from my PhD research on tinkering to address ill-structured problems in design. The research highlights how maintaining learner agency, fostering creativity, and leveraging mentor guidance can uniquely empower students to approach complex challenges. The discussion transitions to my experiences as an instructor in Grand Challenges courses, where the courses are designed for the students to learn by engaging with complex sustainability challenges in the real world, focusing on observation and empathy rather than emphasizing or prioritizing solutions. Through these very initial offerings of such courses, learners are seen to cultivate a deep understanding of problem spaces and develop the ability to ask critical questions stemming out of empathy, helping them build essential skills for understanding future engineering challenges. Such an approach has shown changes in confidence and engagement through open-ended exploration, which we believe will ultimately prepare learners for the unpredictable nature of real-world design problems.