This paper reports an ethnographic researcher’s shift towards the tech industry while maintaining the purpose of spotting opportunities and problems. It must be emphasized that whether working with remote communities in far-flung corners of the world or sitting in a room full of software developers, the concept remains the same: it is all about the users. Ethnographic researchers may not live with software developers but are getting increasingly closer to them. This paper aims to explain how this is done, i.e., by using participatory methods, such as field diaries. The first author’s initial realization of the full potential of diaries arose in Ethiopia and Mozambique, where efforts by institutions to help people often fail due to the lack of on-the-ground knowledge about the communities in which they operate. To address this, written and photo diaries were implemented so that community members could clearly express what is important in their everyday lives. In the current software company setting, we use the same method to understand what happens when users develop with our platform. The salient difference is that instead of receiving handwritten diaries and photos, we collect digital journals and screenshots from our users’ experience. This enables moving towards a continuous research vision to identify new user needs timely and ensure we are always building the right thing. However, by adopting this and other proactive approaches for generative research, new challenges are emerging regarding the efficient collection and analysis of large amounts of qualitative information.