While we all want to work on shiny new software with shiny new technology, the reality is that many developers and teams are stuck maintaining legacy systems. While typically these systems continue to work, maintaining them can be painful. Yet the cost of replacing the old systems with new ones is unimaginable and financially untenable for many companies. How do we deal with this situation without abandoning our clients who are not yet candidates for rewrites or even for lift and shift? A long-time software veteran will share some of their own experiences and tips for keeping clients businesses running while slowly helping them evolve to modern times, blending modern software practices into ancient systems.