After decades of progress, database management systems (DBMSs) are now the backbones of many data applications that we interact with on a daily basis. Yet, with the emergence of new data types and hardware, building and optimizing new data systems remain as difficult as the heyday of relational databases. In this paper, we summarize our work towards automating the building and optimization of data systems. Drawing from our own experience, we further argue that any automation technique must address three aspects: user specification, code generation, and result validation. We conclude by discussing a case study using videos data processing, along with opportunities for future research towards designing data systems that are automatically generated.