Abstract: Systems and methods are structured to impart an emotional connection to a goal and to generate customized, appropriate challenges that maintain participant engagement by handicapping certain parameters. In one embodiment, a financial health computing system is configured to: generate a first profile for a first participant; generate a first goal for the first participant, the first goal comprising a first plurality of milestones and a first plurality of rewards; assess a participant's progress based on a first status item; and generate an advisory alert for the first participant based on the first status item. The advisory alert comprises a recommended financial health activity and is configured to accept a user input for directing an auxiliary system to perform the recommended financial health activity. The first goal and the first plurality of rewards are customized to the first participant based at least in part on the first profile.