Anastasia Boyko on leadership, law school, and reinvention

In this episode of This Legal Life, Ben sits down with legal futurist Anastasia Boyko for a conversation that goes far beyond career pivots.

From emigrating to the States from Soviet Ukraine to navigating Big Law layoffs and personal upheaval, Anastasia traces her own hero’s journey through legal practice, innovation, academia, burnout, and ultimately returning home. Together, they explore what happens when the traditional markers of success fall away and you find yourself in a season without a clear next step, what Anastasia calls “the windless sea”.

This episode dives into law school’s hidden rewiring, the pressures of external validation, institutional breakdown in the age of AI, and the hard but necessary work of defining your own North Star.

About Anastasia

Anastasia Boyko is a legal futurist and product evangelist at Filevine, with over 20 years of experience driving innovation across the legal profession. A Yale Law-trained tax lawyer, her career has spanned private practice at top New York firms, leadership roles at Thomson Reuters, Axiom, and Yale Law School, and a directorship at the University of Utah S.J. Quinney College of Law. Her work sits at the intersection of legal education, talent development, and the future of legal services delivery.

Connect with Anastasia on LinkedIn