This Was Supposed to be Easy Podcast

S2: Episdde 64: We Thought the Next Chapter (College) Was Supposed to Be Easy

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This week, Amy and Cheryl sit down with residence hall director and higher education professional Jessa Heroux-Croy for an honest conversation about the transition to college - not just for students - but for the families and supporters who love them.

From roommate dynamics and campus culture to homesickness, connection, and learning how to support young adults without rescuing them, this episode offers practical advice and emotional reassurance for anyone navigating the college transition season.

Whether you’re preparing to send a student off for the first time, welcoming one back home for the summer, or remembering your own experience of figuring out who you were in those years, this conversation is full of warmth, wisdom, and perspective.

Guest Introduction

Jessa Heroux-Croy is a residence hall director working in higher education and student affairs. She lives and works on campus alongside university students and supports them through everything from move-in and roommate conflicts to leadership development, connection, and personal growth. Passionate about student belonging and communication, Jessa brings both professional expertise and personal experience to conversations about what it really means to transition into college life.

 

Key Topics & Takeaways

  • Why campus “fit” matters more than prestige alone
  • Questions families should ask during college visits
  • The hidden emotional transition of coming home after freshman year
  • How roommate conflicts are often really communication conflicts
  • Why students need the act of connection to be intentional, not passive
  • What residence hall staff actually do to support students
  • Ways parents can shift from “fixer” to “coach”
  • The evolving culture of dorm life after COVID and technology changes
  • Creative ways families can stay connected beyond care packages
  • What students really need before moving into the dorms
  • Common dorm shopping mistakes and overlooked essentials
  • Why getting involved on campus early on matters so much

    • Memorable Lines

    “You can’t wait for connection to come to you. You have to meet it halfway.” Jessa Heroux-Croy

    “Who do you need me to be for you right now?” Amy Bond

    “Sometimes students are communicating, you’re just not understanding the way they’re trying.”-Jessa Heroux-Croy

    “College is 100% what you make it. What you’re open to is what you get out of it.” - Jessa Heroux-Croy

    “You’re always the parent, but you start transitioning more into the coach.” - Amy Bond

    “What does communication mean to you?” - Jessa Heroux-Croy

    “Say yes to everything and figure out what works for you.” - Jessa Heroux-Croy

    Challenge for the Week

    If you know a child, student, or young adult preparing for a transition this year, ask them one intentional question this week:

    • What are you most excited about?
    • What are you nervous about?
    • What kind of support feels most helpful to you right now?

      • And if you’re the one entering a new season yourself, consider:

      What would it look like to stay open instead of trying to have everything figured out already?

       

      Additional Resources

      • Explore your future college’s housing and residence life webpages before move-in
      • Look for orientation events, involvement fairs, and student organization showcases
      • Review residence hall prohibited items lists before shopping
      • Encourage students to fill out roommate compatibility forms honestly
        • ...more
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        This Was Supposed to be Easy PodcastBy supposedtobeeasy