‘Tis the season of reflection. All the leadership and military blogs are awash with articles from Majors completing their key developmental jobs, capturing fresh insight and prime takeaways from what has likely proven the most demanding 18-24 months of their military careers to date. Every unit is different. Every commander is different. Therefore, every experience is a bit different. The number of articles and essays and the breadth of their focus demonstrate the complexity and challenge of key-developmental assignments. This article deviates from those highlighting the incredibly important processes, roles, and systems that make or break S3s and XOs. Here, the focus is on a matter that is often overlooked or overcome by competing demands: the planning process for post-KD assignments.