This talk aims to describe the journey a systems engineer had as part of an automation assignment with the network management team. building from lessons learned and challenges faced with system automation for the last three years. Where and how to start the journey? what to avoid? what to prioritize? how to overcome the lack of network skills for the automation engineer and lack of automation and Linux/Unix skills for network engineers. what challenges were faced and ho w to overcome them? what fights to win, and which to give up? where do I see network automation and configuration management as a systems engineer? what are the status quo and future expectations?