The modern labour economy is fraught with challenges, such as economic inequality, job insecurity, digital intensification and shifting labour market composition along the lines of skills, employer consolidation, and the profile of the average employee. Ownership has emerged as a powerful, growing, and increasingly accessible solution to these challenges, as it enables workers to reap the full material benefits of their labour and generate wealth and security in a digital-first world. However, despite a positive perception towards ownership, few workers participate in ownership models, such as co-operatives and entrepreneurship. This research investigates barriers to ownership optimizing behaviours among workers, the costs, risks, and benefits of transitioning to ownership, and the differences between employees and independent workers. The hypothesis is that experimenting with interoperable digital ownership tools can lead to disruptive worker-centred innovations that increase worker stake, such as capital ownership, capital income, and voice in decision-making. This research employs strategic foresight and design research methodologies to provide a structured approach to understanding complex systems and framing future scenarios and experimentation. Ultimately, this research aims to decrease precarity and increase agency for workers by laying the groundwork for practical innovations that enable ownership-driven security.