In Ibadan, Nigeria, Olufela Osideko's journey into cybersecurity began not from a traditional tech background but through overcoming personal struggles, including depression and academic setbacks. Her chance introduction to cybersecurity through the CyberGirls 1.0 cohort, a pioneering program for women in Africa, ignited her passion for offensive security, leading her to specialize as a penetration tester at Digital Encode. Osideko's story highlights the transformative power of unexpected opportunities and the importance of diversity in the tech field. She emphasizes the value of self-advocacy and resilience, as well as the potential positive impact of AI on cybersecurity, despite concerns about job displacement. Her involvement with Bugcrowd's HackHers network underscores her commitment to addressing gender disparity in the industry. Osideko balances her challenging career with personal well-being practices and aims to continue honing her skills and contributing to the cybersecurity community, serving as a testament to the strength derived from diverse backgrounds and the impact of representation.