In this paper we will point to implications for designers who support organizations in the transition process from products to services based business models. These implications are based on four important challenges when designing for services: the designerly mindset, collaboration, empathy with stakeholders and implementation. These challenges have been identified by analysing the previous work of the second author, in which interviews were conducted with people in practice that consider themselves self-trained service designers and work as design consultants in service design projects. To further explore these challenges we will compare them with the experiences of the first author, who has been trained as product designer specialized in the design of intelligent products, and is currently part of the Smart Textile Services project as design- researcher. This project deals with the textile industry, which is traditionally focused on manufacturing but now in the transition towards delivering services. We will reflect on the moments that the design researcher felt uncomfortable as product designer and ran into similar challenges as the self-trained service designers. Based on the comparison of the self-trained service designers and the design-researcher we will point to implications for designers who are designing services in transitioning industries.