In this article, we introduce an AI-enhanced study planning solution named Careerbot, which is a service designed to help students with their “forecasted self”. We define a new term “forecasted self” to mean a future-oriented digital twin, where a student can explore several future selves equipped with new, acquired skills for projected future jobs. The future jobs domain here includes knowledge-work related jobs related to digitalization, emerging technologies, and Industry 4.0/Society 5.0.