A generally unheralded development in human history that has had profound impact is the mastery of the understanding of uncertainty. Rather than have the future being the domain of oracles, and outcomes attributed to the gods, events could be assessed in terms of their likely occurrence with consequences evaluated. While gambling provided the early impetus, understanding and assessing uncertainty has transformed research in many fields and unleashed achievements in economic growth, games, engineering, biology and medicine. This understanding has led to rational approaches to risk taking that form the basis of the insurance industry and the calculation of annuities. These approaches have also impacted engineering wit the move away from 'factor of safety' design. The research has developed into how we view and assess risk and how we make choices, both of which are fundamental to the modern market economy. This presentation will cover a potted history of understanding uncertainty and its links to gambling, its characters, and its development into wider fields. In parallel, the presentation will describe my personal journey in making sense of living in an uncertain world. With the advent of near ubiquitous computing, huge data sets now exist covering nearly every aspect of human endeavour. This has opened up the field of data mining and the power of pattern recognition with concomitant opportunities and challenges. I'll touch on some exciting developments in these areas.