This project investigates the intersection between reflection through journaling and Artificial Intelligence (AI), more specifically Conversational Agents (CA) in interaction design. Journaling together with a CA is a relatively unexplored area in HCI and Interaction Design, especially when studying the experiential aspect. Furthermore, designing for reflection has been a rising topic within HCI and Interaction Design. The project used a modified version of the double diamond model as a design process to research, create and test a concept for multimodal interactive journaling using a conversational agent. The results suggest that conversational agents have the potential to play an influential and positive role in evoking reflection in an individual through collaborative and conversational interaction. The project provides design recommendations for designing an interactive journaling experience with a conversational agent and an example of how designers can design using interaction, AI, and language as a design material. The project contributes insights to designing artifacts for reflection and how a design process can be designed to design for AI and conversational interfaces.