The Canadian Women’s Chamber of Commerce (CanWCC), in partnership with Highwire Collective, will deliver a program to support and economically elevate diverse mature women over 55 who are chronically unemployed or underemployed and seeking to start a viable solo enterprise. Mature women, particularly Black, newcomer, and racialized women, face systemic barriers in both the labour market and self-employment ecosystem, and are often excluded from programming geared toward younger founders or small- and medium-sized businesses. This program directly addresses those gaps with a tailored, community-based model that supports mature women at the earliest and most critical stages of business development. Phase One is an eight-week, facilitator-led business viability and planning program. Participants will learn foundational skills in business modelling, financial literacy, pricing, customer discovery, and sales readiness. Programming is efficient and designed to help participants assess business feasibility, understand startup costs, and identify pathways to sustainable income. Instruction reflects the lived experiences of diverse mature women, with subject-matter experts who represent the communities being served. The program includes hands-on workshops, peer learning, and individualized coaching. Phases Two and Three extend support for five months through communication and sales skill practice (Phase Two) and monthly workshops on intermediate business topics focused on finance and operations (Phase Three). The workshop topics include financial management, operations, pricing and getting paid. Participants will receive a free annual CanWCC membership upon completion of Phase One. This extended learning model, combined with CanWCC membership, reinforces core skills, reduces isolation, and fosters a long-term community of peers, an essential support for self-employed women who would otherwise navigate entrepreneurship alone.