Brendan O'Bra discusses the journey of migrating a monolithic Java application called Gumby to microservices using Scala and Akka. Originally a single large codebase, Gumby was split into modular microservices composed together into "microliths" to allow incremental development. The microliths helped address challenges of scaling, deployment, and team collaboration. The architecture eventually evolved to true microservices running independently in a Docker swarm. Challenges included understanding Akka clustering, databases, and tooling choices.