One of the most common assumptions regarding indoor positioning systems based on Wi-Fi fingerprinting is that the Radio Map (RM) becomes outdated and has to be updated to maintain the positioning performance. It is known that propagation effects, the addition/removal of Access Points (APs), changes in the indoor layout, among others, cause RMs to become outdated. However, there is a lack of studies that show how the RM degrades over time. In this paper, we describe an empirical study, based on real-world experiments, to evaluate how and why RMs degrade over time. We conducted site surveys and deployed monitoring devices to analyse the radio environment of one building over 2+ years, which allowed us to identify significant changes/events that caused the degradation of RMs. To quantify the RM degradation, we use the positioning error and propose the RM degradation ratio, a metric to directly compare two RMs and measure how different they are. Obtained results show that the positioning performance is much better when RMs are collected on the same day as the test data, and although RM degradation tends to increase over time, it only leads to large positioning errors when significant changes occur in the Wi-Fi infrastructure, making previous RMs outdated.