Abstract-Modeling people's online behavior in relation to their real-world social context is an interesting and important research problem. In this paper, we present our preliminary study of attrition behavior in real-world organizations based on two online datasets: a dataset from a small startup (40+ users) and a dataset from one large US company (3600+ users). The small startup dataset is collected using our privacy-preserving data logging tool, which removes personal identifiable information from content data and extracts only aggregated statistics such as word frequency counts and sentiment features. The privacypreserving measures have enabled us to recruit participants to support this study. Correlation analysis over the startup dataset has shown that statistically there is often a change point in people's online behavior, and data exhibits weak trends that may be manifestation of real-world attrition. Same findings are also verified in the large company dataset. Furthermore, we have trained a classifier to predict real-world attrition with a moderate accuracy of 60-65% on the large company dataset. Given the incompleteness and noisy nature of data, the accuracy is encouraging.