A system and method for promoting, tracking, and assessing mental wellness. The method includes receiving an entry from a subject user, the entry including an input and a mood indicator, storing the entry in within a set of entries, the set including at least two entries received over a period of time, and determining a presence of at least one marker in the input of each entry within the set. The method further includes analyzing the set of entries for occurrences of markers or sequences of markers and alerting a supervisory user if the occurrences of markers or sequences of markers exceed a predetermined threshold. The method further includes associating contextual content from a supervisory user to an entry, the contextual content including a note, an attachment, a form, and/or a flag. The system includes a platform for accessing, managing, and storing data and analytics for implementing the method.