The following paper aims at providing a holistic view upon the changes Romania, a developing country with an uncertain but promising future, could witness with respect to its competitive and comparative advantages by the year of 2050. The analysis of Romania’s current position focuses on human and technological capital, two areas with untapped potential. To answer the overarching question, namely Romania’s regional positioning in the upcoming three decades, our team deployed a Wargame framework – a three-phase simulation including groups of actors such as Romania’s State & Public Authorities, Citizens, Business Environment, academic and not-for-profit landscapes, as well as two other nation-level players, namely Core Europe and the Visegrad Group. To this end, considering high-level macroeconomic and behavioral variables, the participants took long-term decisions based on what they have believed posed the best interest of the groups they were representing. After reviewing the actions present in the wargame, this paper concludes that a representative proportion of the players involved reached a consensus in that Romania can bridge the gap with Core Europe and Visegrad by shifting its future focus towards 4 distinct areas, namely education, infrastructure, entrepreneurship and technological investment, whilst highlighting a partial interdependency of the later emerging on the appropriate management of the first three areas.