The financial services industry often paints a grim picture of retirement, particularly for those without pensions. The narrative usually revolves around “cliff-edge retirements,” a term designed to induce fear and, consequently, encourage asset management services that come with fees. However, when we put the consumer first and integrate financial planning, technology, and advocacy against financial exploitation, a different, more hopeful landscape emerges. This article explores a retirement planning strategy that focuses on leveraging productive assets and entrepreneurial opportunities to create sustainable livelihoods.