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Digitalization is essential for companies looking to stay afloat in a changing business environment. However, lots of enterprises still do not take advantage of this opportunity, which may be due to several factors, such as lack of knowledge, leadership style, high costs or sustainability. Focusing on the controversial link between digitalization and sustainability, this paper seeks to explore the potential of digitalization for enterprises and to propose new development strategies. The primary research was based on a quantitative questionnaire survey conducted among business managers and entrepreneurs in the V4 countries, in Bulgaria and Serbia, focusing on the impact of digitalization on sustainability. Based on the results, the businesses surveyed were divided into two groups: Concerned Committed and Indifferent Conservatives, whom with different preferences, have the potential to achieve a balanced state of ‘digital sustainability—sustainable digitalization’ (digitainability), enabling enterprises to deliver outstanding digitalization performance with a sustainable strategy. [ABSTRACT FROM AUTHOR]