Beginning a teaching career and working to prepare and support beginning teachers is a roller-coaster of successes and puzzling moments. In this article, author Cassandra (Cassie) Seiboldt shares how she learned to manage her first years of teaching by purposefully planning through anticipating student thinking and solutions, and the positive impact this had on her instruction. Lorraine Males, Cassie's university mathematics teacher educator, and Joshua Males, Cassie's mathematics department chair, reflect on how various assignments and structures may have supported her in the lesson-planning process.