The primary area of investigation is the overlap between the Canadian Creative Economy and the Fourth Industrial Revolution. The digital environment is constantly changing, and businesses need to adapt and plan for possible futures. This research will focus on small business owners in the creative industries as the primary audience. Canadian entrepreneurs will benefit from the research findings to take full advantage of the new tools to discover untapped business opportunities. The goal of the toolkit developed in this project is to invite creative entrepreneurs to reflect on their existing business model and envision new possible futures. It provides a simple approach to generate alternative business models using prompts focusing on three main pillars: offering, audience, and revenue streams. By using prompts, the toolkit stimulates a conversation that encourages entrepreneurs to engage in problem-solving and explore innovative approaches to leverage new solutions. Through this process, the toolkit aims to facilitate discovery and inspire creative entrepreneurs to consider new ways of approaching their business endeavors.