In June 2016, David J. Chard had the honor of delivering the William Cruickshank Memorial Lecture at the annual meeting of the International Academy for Research in Learning Disabilities (IARLD). This article contains the set of questions he asked himself as he prepared the presentation and a brief of the comments that unfolded during his talk. The following questions are discussed: (1) In 1972, William Cruickshank published a paper on the issues facing the field of learning disabilities (LD) at that time. How do the issues that Cruickshank raised in 1972 compare to the issues facing the field today?; (2) What progress has been made and in what areas?; (3) What obstacles and opportunities remain?; and (4) Why does this work remain important 45 years after Cruickshank wrote his paper about the challenges facing this field? [This article is based on the William M. Cruickshank Memorial Lecture delivered in Austin, Texas, at the 40th Annual Meeting of the International Academy for Research in Learning Disabilities, June, 2016.]