Abstract: Creativity is often aligned, in the academic literature and in policy, with desired 21st century skills. Creativity is also positioned as a vital part of education for digital futures and for the technology-driven learning settings and work lives that students will inevitably face. However, often missing in the writing and the rhetorics about creativity is the link between creativity and failure. We contend that an affirmative view of failure within education, and the designing of learning environments that recognise productive failure, is vital. The affirmation of failure as a pedagogical principle is an integral part of not only fostering creativity in students but also preparing them for the sorts of adaptations and flexibility they need in an environment of technological change. Research and policy development about the affordances of failure in facilitating creativity within education are much neglected, especially in an educational climate of caution and standardisation. In this conceptual and position paper we critically examine and affirm the place of productive failure as a pedagogical principle for promoting creativity. This pedagogical principle can be supported by four operational strategies: 1. Purposeful learning environments, 2. Assertive agency about mistakes, 3. Possibility thinking, and 4. Reflexivity following failure. We also offer possibilities of what a failure-textured and technological-oriented classroom might look like, including its design features.