A method and system provides personalized user experiences to users of a tax return preparation system, at least partially based on likelihoods of occurrence of life events for the users in a tax year, according to one embodiment. The method and system applies the user data to one or more predictive models to determine the likelihood that one or more available life events occurred in a user's life in a tax year, according to one embodiment. The method and system display life event icons that represent the one or more available life events, and the life event icons are ranked, sorted, and/or emphasized, based on the likelihood that the one or more available life events occurred in a user's life, to increase a user's confidence in the tax return preparations system's capability to address the user's life changes while preparing the user's tax return, according to one embodiment.