What does walking a kindergartner into their very first classroom have in common with sending a young adult off to college? More than you’d imagine. In this insightful and heartfelt episode, Jenny and Kristine sit down with college counselor and former Broadway performer Elisa Sagardia—who also happens to be an animal lover with a pet menagerie from dogs and cats to hedgehogs, squirrels, and guinea pigs.

Together, we explore how the earliest school transitions mirror the big ones at 17 and 18. Drawing from decades in early childhood and college counseling, we unpack universal themes that show up at every age: letting go, building independence, emotional readiness, routines, friendships, confidence, and connection.

Elisa offers practical wisdom on supporting teens without taking over, managing family anxiety, and preparing students for whatever comes next—four-year universities, community college, trade programs, or gap years. Along the way, we highlight the shared rhythms between kindergarten and college: new environments, big feelings, fresh relationships, and learning to trust the process.

With stories, humor, and Big Little Lessons from both ends of the educational journey, this episode invites families to approach transitions with compassion, clarity, and confidence.

Out of respect for our students, we want to note that while the stories we share are real, names have been changed for anonymity. In fact, every student we mention is named “Charlie.” We use that name as a way to honor privacy while still sharing authentic classroom experiences.

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