What do the 640K memory limitation and the overlay technology from the 1980s have to do with today's software development? At first glance, nothing at all. Back then, both topics were answers to technical constraints that made developing hardware and software challenging. At a second glance, however, there is very much a connection. We still have many challenges. The numbers and drivers may have changed, but we still have boundaries to confront and overcome. This keynote reflects in an anecdotal and personal way on the journey that software development has been on over the past decades and the lessons learned along the way: from programming paradigms and languages to software architecture and agility to technologies like the cloud and the edge to topics like business agility and sustainability. There and back again.