In the EU a program for implementing a circular approach to the Lifestyle and Fashion Industry dealing with the resource challenges of the massive textile-production has been launched (EU 2020). Consequently, national and international legislation is expected to become reality over the coming 5-10 years. Thus, the industry faces a need for circular and closed-loop approaches and will be challenged in developing and recruiting internal competencies for making the transition from linear to circular production possible. Many lifestyle companies face the transition as a challenging process in which the elements are both interdependent, interconnected and influence simultaneously economic, environmental and social concerns. This affects the companies at a wide variety of organizational levels. The companies often struggle to handle the challenges in conjunction, even as this generates tensions, paradoxes and contradictions in the organization – again challenging the roles of i.e. the designer. (Hahn et al., 2014, Berger et al. 2007). Even so, the tensions and paradoxes have received relatively little attention in the literature, and much of the present research on organizational replies to issues related to sustainable development, are often framed around an instrumental logic, - i.e., what benefits the companies in managerial or economical concerns. (Hahn et al., 2014). Performing circular design approaches require the development and use of both personal but also sustainable and systemic-competencies as they have to implode a new level of complexity in the design- and production process, and this puts the designers in often challenging positions and roles in the companies. Research demonstrates how fashion designers can support the transition towards a circular economy (CE) in the fashion industry (EMF, 2018) but as another study investigated the roles of the fashion designers working in medium and large international fashion companies and summarized a model – Organisational Roles of Fashion Designers for Circular Economy (ORFDCE model) suggesting that designers can take up three central roles in the transition process, it provided the designers can expand their sustainability-related knowledge and are supported by four central systemic organizational changes. (Dan & Østergaard, 2020). This paper explores the challenges of the motivational why and also investigates how the designers can implode change in the organizations in the transition from a linear to a circular Lifestyle industry and what obstructions they encounter. This is done by using a 15 semistructured interviews with designers and managers reflecting on both the ORFDCE model, the organizational theory from ‘Tensions in Corporate Sustainability’ and ‘Sustainable-Wellbeing’ using a Quadrant Model Analyzis, (Nygaard, 2019, Hahn et al. 2014, Nygaard & Tønnesbæk, 2013) The paper finally suggests how to use the research when developing design-Educations for Sustainable Development (ESD’s).