This dissertation employed a hermeneutic literature review to seek to understand how Bion’s interpretation of negative capability could support an understanding of the complexity of chronicity when working with the whole person treatment approach (WPTA). What emerged was a roadmap identifying three major obstacles to comprehending how the capacity for not knowing, or negative capability, can support understandings of the complexity of chronicity when working with WPTA. The roadblocks encountered on the roadway are: firstly, the culture of biomedicine, and its inherent mind/body problem, along with our expectation that physicians provide expertise and diagnosis. Secondly, our human tendency to split and treat the resultant dualities and dichotomies as either/or choices. When mind/body becomes an either/or choice, it excludes the richness of the health information available at each pole, and excludes the use of WPTA. The defences of minus knowledge (-K) and dispersal formed the final roadblock. Four vital bridge building materials were identified, for bridging the roadblocks. Firstly, the foundation of any bridge was formed by developing an internal container, essential for sitting with uncertainties and doubt, and enabling the translation of our own beta-elements into digestible alpha-elements. Secondly, curiosity created an openness to self-knowledge and new understandings of the complexity of chronicity. Thirdly, the ability to doubt proved essential in questioning all three roadblocks, and in integrating chronicity in a new way, opening the door to new learning. Finally, patient waiting, an active process at the heart of negative capability, provided a space from which original thought could develop. Importantly, while each patient uses the same building material to bridge the roadblocks encountered, each bridge is painstakingly constructed by each patient, brick by brick. Each bridge is unique, as no two patients will construct exactly the same bridge. Moreover, once a bridge is built, it represents a skill set that remains for life, enabling patients to more quickly bridge future roadblocks. Broader implications of this study include its potential application to other uncertain situations, such as to the current global COVID-19 pandemic.