We have improved considerably our scientific understanding of the key solar drivers of Space Weather, i.e., Coronal Mass Ejections, flares, in the last 20+ years thanks to a plethora of space missions and modeling advances. Yet, a major breakthrough in assessing the geo-effectiveness of a given CME and associated phenomena still escapes us, holding back actionable medium-term (up to 7 days) forecasting of Space Weather. Why is that? I adopt a two-pronged approach to search for answers. First, I assess the last 20+ years of research on solar drivers by identifying lessons-learned and paradigm shifts in our view of solar activity, always in relation to Space Weather concerns. Then, I review the state of key observation-based quantities used in forecasting to isolate the choke points and research gaps that limit medium-term forecasting performance. Finally, I outline a path forward along three vectors—breakthrough capabilities, geo-effective potential, and actionable forecast—with the strongest potential to improve space weather forecasting horizon and robustness.