Skip to main content

The holidays are a time for togetherness, laughter, and the occasional awkward family question: “So, where are you applying to college?”

While these conversations can feel pressure-packed, the holiday break offers parents a golden opportunity to connect with their students about their college journey—if approached carefully and creatively. This season, let’s sleigh the stress with meaningful conversations that build rapport, unpack what you don’t know, and set the stage for ongoing dialogue about their future.

Setting the Stage: Creating a Relaxed Atmosphere

Before discussing college topics, ensure the environment is festive and inviting. Think of these conversations as unwrapping a gift—you want to savor each layer, not rip through the paper in a rush.

  • Pick the right moment: Look for natural opportunities, like a quiet evening by the fire or a cozy car ride to see holiday lights. Avoid the stress of multitasking during holiday prep.
  • Start light: Use the season’s spirit to keep things playful. Try a fun question like, “If college was a holiday gift, what’s on your wish list?”
  • Listen first: Approach with curiosity, not pressure. Your student should feel heard, not interrogated.

Key Topics to Unwrap

The goal isn’t to solve everything in one conversation—it’s to gather insight, understand their perspective, and keep the lines of communication open. This season, anchor your conversation around these two areas:

1. Reassessing the College List: Like Santa’s list, your student’s college options may need updating. What seemed like a dream school last summer might no longer sparkle, and priorities might have shifted. Use this time to dig a little deeper into their thinking.

  • Ask open-ended questions: Start with, “What excites you most about the schools on your list?” or “Have any of your preferences changed recently?” This invites them to share without feeling judged.
  • Look for patterns: Listen for themes as they talk. Are they more interested in schools with strong programs in a specific field, or are location and campus culture taking center stage?
  • Highlight balance: Ensure their list includes a mix of reach, match, and safety schools. For example, “Do you feel like your list has a good mix of options, or should we tweak it?”
  • Unpack the why: If a school seems less exciting now, ask why. Are they worried about cost, feeling unsure about fit, or overwhelmed by admissions expectations?

This isn’t the time to make decisions but to gather information and understand their thinking. By showing genuine curiosity, you build trust and set the stage for future conversations.

2. Personal Readiness: The transition to college is about more than academics. It’s also an emotional and social leap; your students may have concerns they haven’t shared yet. Use the warmth of the holiday season to explore how they feel about this significant change.

  • Check the excitement meter: Ask what they’re most excited about when considering college. Is it making new friends, living independently, or diving into a favorite subject? Their answers can give you insight into their priorities.
  • Address concerns gently: Follow up with, “What’s one thing about college that feels a little scary or uncertain?” Normalize their anxieties by sharing a story about a challenge they overcame at their age without making it overly drawn out and biographical.
  • Encourage reflection: If your student struggles to articulate their feelings, suggest they think about it and revisit the topic. Sometimes, it takes time for teens to process their emotions.
  • Keep it collaborative: Frame this as a team effort. “No matter what, we’ll figure this out together” can go a long way in easing their worries.

These conversations aren’t about fixing everything today but showing your teen that you’re there to support them—both now and as they navigate the road ahead.

Navigating Challenges and Emotional Moments

Not every conversation will be smooth. If emotions or fear start to flare, keep these tips in mind:

  • Pause, don’t push: If the conversation turns tense or pivots into another aspect of the college process, take a break. Revisit it later when everyone’s in a better mood.
  • Stay supportive: Avoid correcting, criticizing, or giving unsolicited advice. Instead, focus on validating their feelings and showing empathy.
  • Be transparent: If you feel stressed about finances or deadlines, calmly share your concerns. Transparency fosters trust, but avoid overwhelming them with your worries and return the conversation to them.

Wrapping Up: Ending on a Positive Note

At the end of your holiday college talk, focus on building momentum rather than tying everything up in a bow:

  • Acknowledge their efforts: Celebrate their progress so far, even if it’s just adding a few schools to their list or working on an essay draft.
  • Verbalize your gratitude: Tell your kid you are thankful for the conversation you just had with them and look forward to continuing it.
  • Express confidence: Remind them that you believe in them. A simple “I’m so proud of who you are and how you’re handling this” will mean the world to your kid.

Conclusion

The holidays are more than presents and carols—they’re about the gifts of time and connection. Having these merry and meaningful conversations gives your kid a gift far beyond the season: your guidance, trust, and support. So, pour some cocoa, settle by the twinkling tree, and start unpacking their college dreams. After all, every incredible journey begins with a single step—or, in this case, a sleigh ride powered by love, respect, and understanding.

4083371-0626

David Q. Hao, MA, JD is a college & career coach, author, education leader, and all-around nerd. He has fifteen years of educational leadership experience, including being the Head of School, Associate Vice President of Student Affairs, and Dean of Student Success & Advising. David earned his Doctor of Jurisprudence and Master of Higher Education Administration degrees from Boston College and his Bachelor of Business Administration degree (economics major) from Baylor University. He is the co-author of the book “The Maximizer Mindset: Work Less, Achieve More, Spread Joy” and the co-author of the article “Thinking Theologically About Student Success: Higher Education with a Higher Calling.”