Abstract: This article explores the "glass walls" women freelancers and entrepreneurs perceive as barriers to their professional advancement and business development, through an examination of existing research on unconscious gender biases and social norms that delineate how subtle stereotypes associate leadership more readily with masculine traits, undermining some women's confidence in their expertise while also revealing studies that show this dynamic hinders women's self-promotion and willingness to position themselves as prospective business owners. Additionally, the piece investigates how closely-knit 'old boy's clubs' and networking traditions privileging stereotypically masculine social activities disadvantage women seeking clients within their industries, while organizational dynamics like homogenous cultures and family-unfriendly policies unintentionally exacerbate these issues, limiting women's access to opportunity. The article concludes by outlining practical, research-backed strategies organizations can implement to break down glass walls through inclusive practices such as auditing for biases, establishing mentorship programs, and showcasing female role models, sending a strong message that all entrepreneurs will find supportive communities where talent alone determines success through a judicious, data-driven approach that progressively advances equity within the freelance sphere.