In August 2019, I defended the first digital history dissertation at Vanderbilt, an outcome I had worked towards since 2011. But getting to that point took me far longer and further afield than anything I had initially envisioned when I first entered graduate school. To help make visible the process of a DH dissertation, my talk will trace my trajectory into DH, and in turn how this new field radically transformed my dissertation and research. In particular, I will reflect on how I went from a first-year graduate student, with a hobbyist interest in computers, to a postdoc in DH, who uses programming and statistics daily. Though my experiences represent one data point, I believe that commonalities exist across institutions, especially given the unique constraints to undertaking DH research as a graduate student. Some of these pressures that I navigated include: – Encouragement to pursue DH because of its perceived ‘attractiveness’ on the job market, while simultaneously having almost no institutional support for this research. – Undertaking DH summer workshops and fellowships and then facing an absence of any opportunities for advanced DH training. – Attempting to meaningfully integrate DH within my historical research, but then facing criticisms regarding both the time to completion and whether this research ‘counts’ as scholarship. Ultimately, I hope sharing my perspective on conceiving, executing, and defending a DH dissertation will provide insights into how graduate students can *and* cannot push the boundaries of humanities’ disciplinary practices.