The author discusses fixing the "Iceberg Problem" of gaps and unfinished learning lurking beneath the surface of math students. Math is cumulative, with new learning resting atop earlier mastery. Year by year, students learn interconnected concepts in a coherent progression, building a foundational body of knowledge that undergirds new understanding in the grades ahead. When a student starts the school year with unfinished learning from prior years, the challenge of both covering grade-level material and addressing unfinished learning can be daunting. The author asserts that today's assessment and accountability policies that incentivizes grade-level instruction may be inadvertently working against the interests of the very students they were designed to help. This is not a call to reverse the principles of standards, accountability, rigor, transparency, and equity that form the basis of education policy and practice today. But it is a candid acknowledgement of the tradeoffs and costs that a focus on annual grade-level expectations creates. In math, preparing students for college or a career requires honestly confronting any gaps in learning that lie beneath the surface. That does not mean lowering expectations for students; rather, given the inherently sequential nature of mathematics, it means designing viable paths that can connect students from where they are starting from to where they need to be. Ensuring all students can access a tailored path to college and career readiness will require the development of a variety of innovative learning models with different philosophies and pedagogical approaches underpinning them.