Episode 4: Three Things I Regret with My Oldest

When my oldest left for college, I thought I was ready.

I'd spent years helping other families through this process — I knew the forms, the timelines, the essays. What I didn't know was how it would feel when the checklist ended and the quiet started.

I've replayed that senior year so many times — not the grades or the acceptance letters, but the moments in between. And if I'm honest, there are a few things I regret.

Here's something I don't say out loud very often: I'm a self-proclaimed helicopter mom. I hover. I check. I remind. I manage. For years, I told myself this was what good parenting looked like — staying on top of things, making sure nothing slipped through the cracks, being involved.

But now that Jake's been at college since August, I'm starting to wonder if all that hovering served my kids as well as I thought it did. Or if it mostly just served me — my need to feel in control, my fear of watching them fail, my anxiety about whether I was doing enough.

In this episode, I'm sharing three things I regret about how I parented during Jake's senior year — not to beat myself up, but because maybe you're doing some of the same things right now. And maybe, like me, you can still course-correct before it's too late.

This is a raw, honest episode about overfunctioning, rushing through the year, letting fear drive your parenting, and what I'm learning to do differently with my younger son. If you're standing at the edge of senior year — or already in it — this one's for you.

In This Episode:

• Why I'm a self-proclaimed helicopter mom (and why I'm questioning if that's been helpful)
• Regret #1: Trying to protect my son from every discomfort — and what I wish I'd done differently
• Regret #2: Rushing through senior year instead of savoring it (and the Target moment that broke my heart)
• Regret #3: Letting fear drive my parenting after he left for college — and how I'm still learning to let go
• What I'm doing differently with my younger son (including the program application I didn't nag him about)
• Practical steps you can take RIGHT NOW if you're in the middle of this season

Key Takeaways:

• Every time you swoop in to fix things, you send the message that you don't think they can handle it
• The ordinary moments — Tuesday night dinners, home videos, cereal before the game — those are the real milestones
• Silence from your college student doesn't always mean something's wrong; it usually just means they're living
• You can course-correct right now. Today. It's not too late.
• The goal isn't to be a perfect parent — it's to be a parent who learns, adjusts, and tries again

What You Need to Hear: You are allowed to feel the grief and the joy at the same time. You're allowed to miss them before they even leave. And you're absolutely allowed to get it wrong sometimes. They'll still turn out okay.

Connect with Lindsay:

• Website: thecollegecounselingmom.com
• Instagram: @thecollegecounselingmom
• Email: lindsay@thecollegecounselingmom.com

About This Podcast: The College Counseling Mom Podcast is a weekly show for parents of high schoolers. Hosted by Lindsay Phillips — school counselor, independent college counselor, and mom living this journey in real time — each episode offers real talk, practical strategies, and the reminder that you're doing better than you think.

A Note from Lindsay: If this episode hit a nerve, share it with another mom who's staring down that final year. We're all figuring it out as we go.

You've got this — and I've got you.

If you’re a parent navigating high school, college admissions, or the many transitions that come with raising teens, you’re in the right place.

I’m Lindsay, a college counselor and parent who believes thoughtful guidance matters—especially for the awesomely average kid. The student who isn’t chasing prestige, but still deserves smart planning, clear strategy, and a path that truly fits.

You can explore ways to work with me, learn about upcoming programs, or find additional resources at www.thecollegecounselingmom.com and sign up for my weekly newsletter here. 

If this episode was helpful, I’d be so grateful if you’d follow the show, leave a review, or share it with another parent who could use steady, grounded support.

Thanks for being here. I’m honored to walk this season with you.
Lindsay | The College Counseling Mom