“Rethinking the Future: satisfying staff and students in times of diminishing resources and rising expectations” challenges us to ask and reflect on those unthinkable ‘what if...’ questions that frequently lead us into speculation, conjecture and disagreement. These ‘problem situations’ seem to be harder to deal with than everyday issues, and solutions are often elusive. Why is this? What can we learn from these problems, these situations, and how do we avoid falling into the trap that 100 years ago, H. L. Mencken identified: “Explanations exist; they have existed for all time; there is always a well-known solution to every human problem—neat, plausible, and wrong.” Rittel, Ackoff and Schön have classified these hard to solve problem as wicked, messes and swamps, and in various ways suggest that our approach to them needs to reflect the complex, dynamic and interconnected nature of the problem situation. Schön also claims that it is in these swampy lowlands that the truly interesting and valuable problems exist, and this is where we need to apply our effort in order to make a real difference. Against a backdrop of library strategic planning and a ‘Digital Adventure’, we will explore the messy, swampy world of wicked problems, their recognition, and ways in which we might improve our chances of solving, resolving or dissolving them