As the world moves rapidly toward the fourth industrial revolution, and 5G, we analyzed the status of the international shipping industry, particular in Greece, which together with EU, lagged behind in relation to digital management. Throughout history, mankind has dreamed of automating mechanical processes, and succeeded in producing more goods with less power, based on the economic principle. But the quality of goods (and of human life) was left out of the analysis. We tried to correct this oversight in the Appendix. Not much has changed to this day as in the last 270 years, as robots, and other means, are used now to increase productivity. As we show, the tension now is between humans and machines. This antagonism is not about productivity, since there is no doubt that machines are more productive, but about who is more intelligent. Humans have natural intelligence, but machines have artificial one. Some argue that machines are inferior in many areas, such as medicine, agriculture, finance, management, education, distribution, transportation and maritime management.