Rittel and Webber (Policy Sci 4:155–169, 1973) describe a wicked problem as an issue that is difficult or impossible to solve because of its complex and interconnected nature. Examples of wicked problems in Global Health relate to issues such as climate change, biodiversity loss, persisting poverty, the growing obesity epidemic, and food insecurity (Walls in Glob Health 14:34, 2018). Along with these wicked problems are equally complex events, with roots in this ‘wicked space’, like the COVID-19, H1N1 and H5N1 outbreaks, the emergence and spread of monkeypox, and the international spread of vector borne disease that are challenging the global health security landscape revealing an inherent fragility in our societal global health systems. How do we design and implement solutions to the spectrum of global and public health problems that are rooted in a ‘wicked space’? This chapter presents possibility thinking/possibility doing defined here as a process and experience of creativity, imagination, and ideation to explore and generate innovative ideas and solutions to complex problems. Within this context, such thinking encourages questioning the status quo approaches and imagining alternatives to conventional thinking. In short, possibility thinking/possibility doing involves more than a methodology but a mindset that challenges assumptions and transcends traditional framing of problems.