With the help of a fellowship generously provided by ATID, I took some time during a mid-career pause in my own work as an educator to ask two questions that I know plague other mechanchim as they have plagued me for the past few decades: How well are we accomplishing our tasks, and what can we do to improve? I determined that the current state of Modern Orthodox education – indeed of Modern Orthodoxy itself – can be described as a paradox: on the one hand, our efforts over the past few decades have been phenomenally successful, and at the same time there is so much that cries out for improvement. Both halves of that sentence are true and neither one negates the other.