As a DARPA Program Manager, I have had the opportunity to start cybersecurity programs that have progressively taken me farther from my “native” research areas. The Transparent Computing program aims to make currently opaque computing systems transparent by providing high-fidelity visibility into component interactions during system operation across all layers of software abstraction, while imposing minimal performance overhead. The LADS program is developing new defensive cybersecurity capabilities by exploring the intersection of the analog and digital domains, motivated by advances in side channel analysis techniques. The Enhanced Attribution program seeks to provide high-fidelity visibility into all aspects of malicious cyber operator actions and to increase our ability to publicly reveal the actions of such individuals without damaging sources and methods. In this talk I will reflect on this ongoing journey in the context of my prior work, the changing technology landscape, evolving attacker techniques and tactics, and future trends.