Recent studies on Estonia’s creative economy show a growth in employment in the country’s creative sector and an overall increase in generated revenue. However, some areas need improvements, such as the international export of talent and art, interdisciplinary collaboration, and digital skills in strategy building and creating ecosystems. This study explores which skills and tools Estonian creatives are using, lacking, and willing to obtain, and focuses on collaboration manners and attitudes towards cross-sectoral ecosystems. The methodology is composed of a participatory co-design approach with quantitative and qualitative data sources, including background research on industry mapping and economic statistical indicators, semi-structured interviews with industry professionals and stakeholders, and co-design workshops with local creatives. Data were collected from recordings and transcribed, and the co-design workshop post-it notes were digitalised. The data were analysed from the bottom-up and mapped top-down with the 21st-century skills and ecosystem approach. Our current studies show that knowledge transfer and collaboration (across industry sectors, NGOs, and academia) are critical in a small country with a small population, intertwined with dynamic ecosystem building. Creative people upscale and continuously deepen their professional skills (digital and non-digital) in a lifelong learning manner. The current study found that specialising is hard since sustainable values, including those that promote degrowth, are involved.