Encouraging creative risk to reduce risk to life explores how a collaborative, cross disciplinary design research and teaching methodology can provide a platform for tackling projects in the complex industrial risk at sea scenario. Our research discusses the culture of design engaging with risk in the context of the wicked problems we identified, the methods and techniques used to tackle these challenges, how cross disciplinary projects can lead to novel insights, and how design education can be used to engage with industry and users to bridge the gap between technological innovation and user needs. The Royal College of Art funded by the Lloyds Register Foundation, working with a group of industry stakeholders, investigated two major areas of risk within the maritime context: Safe Sea Transfers from ship to ship, and making the Thames the safest city river by the year 2030. The contrasting questions of the deep, complex design issues in ship to ship transfers and the broad strategic future requirement for the River Thames in 2030 were explored using a range of approaches that encouraged collaboration, innovation and risk taking in design practice. Our conclusions support the view that an approach of increasing creative risk in education can provide insights into the use of design led innovation in order to reduce risk to life. Furthermore, we uncover the implications this has in terms of projects, disciplines and practices in the role of design thinking in general, and more specifically in the context of risk and safety at sea.