The impact of human activities is increasingly affecting today’s lifestyle and endangering the capacity of future generations to access natural resources. The need for sustainable practices in business has risen and is becoming a popular trend in the event field. However, the manner in which enterprises around the world embrace sustainability depends on several cultural, economic and political factors. Chile is a developing country that is shifting towards sustainability, but still faces many challenges. This study focuses on two Chilean small event enterprises and aims to investigate and compare their main limitations, mindsets and business models. It analyses their point of view on the future of sustainability in Chile. The method used for the research was a semi-structured interview directed to the managers of these enterprises, designed to gather quantitative information about their perception and business culture. The results were analysed by theme, identifying two areas of conflict. Firstly, a lack of public awareness and environmental education. Secondly, the shortage of governmental auditing tools that are necessary to ensure that environmental laws are met. Consequently, an implementation plan, with both short and long-term goals, was proposed to the enterprises, based on the findings as well as on four model theories. The tentative suggestions are tools for enhancing the culture of collaboration between small enterprises, and to change the environmental awareness of their stakeholders. These recommendations intend to help the small enterprises navigate through Chile’s cultural and political challenges, and meet the country’s sustainability needs.