Taking risks in education can lead to positive outcomes for both educators and students fostering innovation, growth, and creativity in the learning process. Failing forward helps us to analyze what went wrong, learn from it, and use the knowledge to improve and move closer to the goal. It takes both risks and failing forward to cause disruptive innovation in education. The literature supports the advantage of transforming our education system from traditional assessment models to project-based learning incorporating e-portfolios as a technological tool for student reflection. The world is continuously changing and innovation stands at the face of education. It is time we adapt and embrace change in order to transform our student's learning in the 21st century.