This paper describes the first stage of the ongoing development of two scales to measure online wellbeing and trust, based on the results of a series of workshops with younger and older adults. The first, the Online Wellbeing Scale includes subscales covering both psychological, or eudaimonic, wellbeing and subjective, or hedonic, wellbeing, as well as digital literacy and online activity; the overall aim is to understand how a user's online experiences affect their wellbeing. The second scale, the Trust Index includes three subscales covering the importance of trust to the user, trusting beliefs, and contextual factors; the aim for this scale is to examine trust in online algorithm-driven systems. The scales will be used together to aid researchers in understanding how trust (or lack of trust) relates to overall wellbeing online. They will also contribute to the development of a suite of tools for empowering users to negotiate issues of trust online, as well as in designing guidelines for the inclusion of trust considerations in the development of online algorithm-driven systems. The next step is to release the prototype scales developed as a result of this pilot in a large online study in to validate the measures.