The global demographic context of contemporary society is characterized by an increasing percentage of elderly people. In fact, currently in Portugal 22% of its total population is over 65 years of age with an average retirement age of approximately 64 years of age. As a result, it is considered one of the countries in the world with the highest proportion of elderly people, which are consequently labelled as a socially vulnerable group. This prevalent situation presents a current social problem described by the lack of inclusion and sense of meaning among the elders and retired in civil society, shaping the embedded negative attitudes and stereotypes attached to these societal groups as invalid and dependent. In this way, the continuous growth of the elderly population requires the introduction of social organizations, such as the Portuguese social organization The Grandmas Came to Work, centered in the elderly and retiree’s inclusion in society and on their well-being. The main focus of this social organization is to promote ageing as a continuation of development and learning through creative methods and activities, as well as to fill the gap between generations by offering the elderly and retired a place where they can learn from each other, discuss and meet. Hence, this study aims to understand the social and economic sustainability of this particular organization to support the inclusion and well-being of the elderly. This will be done by analyzing the viability of using artistic methods and activities in the context of elderly and retiree's social inclusion. This issue is relevant in the context of Portugal given its predominance of an elderly population and the lack of this group's social inclusion. In fact, it is predicted that by 2050 Portugal will be the country in the European Union with the highest percentage of elderly people (32%) and lowest percentage of working population. This complex issue was studied by using qualitative methods for the data collection, namely through the conduction of semi-structured interviews done to one of the organization’s founders and to its participants. This data provided an updated version of the situation of the elderly and retired population living in Portugal, especially of their possible social inclusion by participating in this specific type of social organizations. The results confirmed the role of such organizations for contributing to the social inclusion of the elderly and retired and for their increased sense of meaning, affecting positively both theirs and society’s perception of the continuous value and contribution of this group. Nevertheless, as what happens in many social and non-social organizations, some limitations were found in the project’s management and respective suggestions were made to face those limitations.