With growth in e-commerce, demand for truck deliveries has grown exponentially and so has the demand for truck drivers. Ironically, the trucking industry is struggling to keep up with this demand. In this study, we examine the global nature of the truck driver shortage problem by considering individual sets of demographic, socio-economic, legal and psychographic characteristics in two distinct regions of the world - India and the United States. We present a comparative analysis of reasons, and based on the attempted strategies so far in each country, we provide policies and recommendations to deal with the problem.