A server comprises a communications module; a processor coupled to the communications module; and a memory coupled to the processor, the memory storing processor-executable instructions which, when executed, configure the processor to receive, via the communications module and from a remote computing device, user input indicating a response to one or more prompts; generate an aspirational profile for a user based at least on the received user input; receive, via the communications module and from a monitoring application installed on the remote computing device, monitoring data; generate a behavior profile for the user based at least on the monitoring data; and when the behavior profile is misaligned with the aspirational profile, send, via the communications module and to the remote computing device, a notification indicating that the behavior profile is misaligned with the aspirational profile.