Background: The importance of sustainability is growing; however, the mindset of many businesses remains in the profit-driven take-make-waste economy, aiming for limitless growth. Humanity cannot continue with business-as-usual, and a paradigm shift must occur to ensure a future for the planet. SMEs represent 99% of the businesses in the EU, and to ensure a safer tomorrow for all, they need to evolve to reach sustainable development and capture the opportunities of regenerative strategies. Nevertheless, regenerative business practices are not widely appropriated in practice. Purpose: The purpose of the paper is to explore the phenomenon of regenerative businesses on SME level through the perspective of Swedish sustainability consultants. The authors aim to gain an understanding of the transformation processes in order to investigate if SMEs can reach a regenerative stage and, if so, how? Method: The study was conducted with an inductive qualitative approach under the interpretivism paradigm, and a multiple case study approach was chosen to best capture the phenomenon. The primary data was collected through semi-structured interviews with sustainability consultants from various SMEs in Sweden, and a thematic data analysis was conducted to interpret the empirical findings to relate them to the theories presented. Conclusion: The findings pointed to eight factors that enable and restrict SMEs in transitioning to a regenerative phase. Internally, SMEs are impacted in their transition by the mindset, values, sustainability awareness, strategy and communication, and the organizational structure of the business. In addition, the main external factors influencing the transition are the ambiguity regarding the sustainability concept and pressure from various stakeholders. The findings also highlighted the interconnectedness of the factors and the importance of a paradigm shift to whole systems thinking.