The energy transition is a complex problem that requires a comprehensive and structured approach to policymaking. Such an approach is needed to ensure that transition pathways and policies enable greener energy alternatives whilst ensuring prosperity for people living in the region and limiting environmental degradation to the local ecosystem. This paper applies a qualitative approach based on systematic literature research and review analysis to identify and analyse previous work within this interdisciplinary field in order to understand the complexity of energy transitions and identify key variables and sub-sectors that need to be addressed by policymaking. The paper then looks at the problem from a regional level and uses the Tees Valley region in North East England as a reference case for the energy system and potential proposed policies for the energy transition. A system dynamics methodology was employed to help visualise and emphasise the major complexity of the energy transition and the challenges that policymaking needs to tackle for the successfully enable implementation and application of the energy transition policies. The results of this study identified that in relation to the Tees Valley energy system, its development and transition towards decarbonisation, the major challenge for the policymakers is to ensure that proposed policies foster growth in job creation without leading to job losses within the local employment market.