The lack of individualized fitting of hearing aids results in many patients never getting the intended benefits, in turn causing the devices to be left unused in a drawer. However, living with an untreated hearing loss has been found to be one of the leading lifestyle related causes of dementia and cognitive decline. Taking a radically different approach to personalize the fitting process of hearing aids, by learning contextual preferences from user-generated data, we in this paper outline the results obtained through a 9-month pilot study. Empowering the user to select between several settings using Internet of things (IoT) connected hearing aids allows for modeling individual preferences and thereby identifying distinct coping strategies. These behavioral patterns indicate that users prefer to switch between highly contrasting aspects of omnidirectionality and noise reduction dependent on the context, rather than relying on the medium "one size fits all" program frequently provided by default in hearing health care. We argue that an IoT approach facilitated by the usage of smartphones may constitute a paradigm shift, enabling continuous personalization of settings dependent on the changing context. Furthermore, making the user an active part of the fitting solution based on self-tracking may increase engagement and awareness and thus improve the quality of life for hearing impaired users. reasons for not using a hearing aid were that the devices did not provide sufficient benefits in noisy situations and there was a perceived poor quality of sound [9].One may ask, why is it that people do not choose to use hearing aids, given the evidence of a high risk of incident dementia, and knowing that these could potentially alleviate cognitive decline? Studies analyzing outcome measures capturing the user satisfaction indicate that this is largely determined by two factors: (1) whether the user perceives an improved quality of life through use of the devices, and (2) to what degree they help overcome limitations when interacting with others around the user. The degree to which the user feels involved in the traditional clinical fitting process highly impacts the overall satisfaction [10]. Alternative models for selling hearing aids over the counter based on do-it-yourself audiometry tests may technically provide the same fitting as provided in a clinical setting [11]. However, the lack of dialogue and hearing care counseling has been shown to result in lower satisfaction. Actively involving the user in shaping the listening experience when adapting to the devices appears to be crucial.