The MIT Playful Journey Lab explores frontiers in lifelong, lifewide learning with the goal of understanding the ways we can strengthen future-ready skills. With a focus on learner-centered assessment and playful exploration, we design and investigate new ways to prepare schools, teachers, students, and members of society to thrive in a rapidly-changing world. Through the design of both digital and non-digital tools, design-based research with learners and practitioners, and a growing community of passionate educators, this work will map out new pathways for the future of learning.