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The challenges that companies face in their internationalization strategy are naturally demanding. If we think that this strategy is no longer exclusive to large companies, we can easily understand all the research that has been carried out on this subject and more specifically on the approach to SMEs. Even so, little has been discussed about the relationship that can be established between the different strategic approaches to internationalization and the factors that entrepreneurs most value in this entrepreneurial process. Based on an exhaustive literature review, in addition to determining the driving factors of the internationalization strategy that Portuguese entrepreneurs most value, this research aims to assess, through a comparative study between the entrepreneurs' perspectives in 2014 and 2019, the possible oscillations in the international strategies of Portuguese entrepreneurs during the period of economic crisis (2014) and a post-crisis period (2019). To achieve these objectives, we used data from a questionnaire sent to "exporting companies and/or companies interested in exporting" from the AICEP - Portugal Global Database, in 2014 and later in 2019.