A fair amount of literature has been published concerning the gaps between HCI and software engineering. However, most of it tends to look at the effects of these gaps rather than their causes. We argue that the use of autoethnographic methods would help us in identifying the root causes of these gaps and can bring us closer to finding potential solutions. In this paper, we focus on issues associated with effort estimation for HCI activities in three projects in three typical engagement models for outsourced software development projects in a mainstream IT company in India, namely Fixed Price model, Mixed model, and Time & Material model. We found that the HCI practitioner needs to negotiate her position with several members of the team, both within the vendor and client organisations. At times, a foot-in-the-door project turns out to be a foot-in-the-mouth project. At other times, it leads to inefficiencies and imbalance of work load. The autoethnographic approach led to reflexive thinking by the HCI practitioner, helping her to develop a deeper understanding of all aspects of a problem, and bringing her closer to potential solutions in some cases. The paper also brings to light several aspects of autoethnography as a method, which can influence effort estimation of HCI activities for future projects.