Given that the contemporary world is changing substantially and enduringly, there is now an increasing call for transforming learning landscapes to actualize future-ready education, which equips students with the diversified knowledge, skills, and qualities to cope with the unforeseeable and ever-evolving future. In recent years, many crises, especially since the unprecedented global pandemic outbreak of coronavirus disease 2019, have put a spotlight on the weaknesses associated with the conventional learning landscape, especially in terms of preparedness planning. A fundamental problem lies in the tendency of the overall landscape to remain lagging behind rather than looking forward, such that students lack the readiness to confront the future ahead of them. Nonetheless, the lingering paradox is that in what ways could the future learning landscape be unfolded and planned by educators when the future remains complex and unknowable. This conceptual article borrows the concepts of "preparedness" commonly found across disaster response and emergency management as well as "future of education" with relevant trends and changes, to reveal the possible directions for equipping students with uncertainty preparedness. This can facilitate and empower all students to recognize and embrace all the unknowns and to remain resilient and responsive.