Human mobility has been studied from different perspectives. One approach addresses predictability, deriving theoretical limits on the accuracy that any prediction model can achieve in a given dataset. This approach focuses on the inherent nature and fundamental patterns of human behavior captured in the dataset, filtering out factors that depend on the specificities of the prediction method adopted. In this paper, we revisit the state-of-the-art method for estimating the predictability of a person's mobility, which, despite being widely adopted, suffers from low interpretability and disregards external factors that have been suggested to improve predictability estimation, notably the use of contextual information (e.g., weather, day of the week, and time of the day). We also conduct a thorough analysis of how this widely used method works, by looking into two different measures (one proposed by us) which are easier to understand and, as shown, capture reasonably well the effects of the original technique. Additionally, we investigate strategies to incorporate different types of contextual information into predictability estimates, and show that the benefits vary depending on the underlying prediction task. Finally, we propose and evaluate alternative estimates of predictability which, while being much easier to interpret, provide comparable results to the state-of-the-art.