Research on Cognitive Personal Informatics (CPI) is steadily growing as new wearable cognitive tracking technologies emerge on the consumer market, claiming to measure stress, focus, and other cognitive factors. At the same time, with generative AI offering new ways to analyse, visualize, and interpret cognitive data, we hypothesize that cognitive tracking will soon become as simple as measuring your heart rate during a run. Yet, cognitive data remains inherently more complex, context-dependent, and less well understood than physical activity data. This workshop brings together HCI experts to discuss critical questions, including: How can complex cognitive data be translated into meaningful metrics? How can AI support users' data sensemaking without over-simplifying cognitive insights? How can we design inclusive CPI technologies that consider inter-personal variance and neurodiversity? We will map challenges and opportunities for CPI, considering recent AI advancements, and outline a research road map for the foreseeable future.