What are the increasing risks of interconnected systems, and what are the utility values? What does it look like to have a job working in the intersection of tech, policy, engineering, and the law? Have the technology advances in the past two decades lived up to the initial promise to transform our lives for the better? Is there anything you should be aware of today that can benefit—or hurt—your career down the road? Four women with different backgrounds explain how their work in tech and cybersecurity has shaped their views of the role of government and the importance of innovation, including the experience of being a woman in tech. Merritt is a Cyber Strategist at DHS’ National Cybersecurity & Communications Integration Center navigating between and among public and private sector entities; Maxine is a US Navy Lieutenant Commander at the Pentagon staffing the Chief of Naval Operations; Deborah is a former Bureau Chief at the FCC now managing a consulting practice; and Gabby is an IP lawyer advising high-tech companies and government contractors. We will explain what we wish we knew 10 years ago and 6 months ago, and we will open the floor to questions about why and how we work the way we do.