We’ve all been there: standing at the crossroads of a parenting decision and wondering, am I making the wrong call? For many of us, the idea of letting our kids quit an activity feels like giving in—or worse, failing them. But what if the word “quit” is the problem in the first place?

In this episode, Leslie Randolph sits down with psychologist Dr. Emily Gordon to reframe what’s really going on when kids want out of something. Together, they swap “quitting” for a new lens: detours, decisions, and opportunities to choose differently. The conversation is equal parts practical and freeing, with guiding questions parents can ask themselves and their kids to figure out whether an activity is helping or hurting, whether resistance is about the activity itself or just the transition into it, and how to know when it’s time to stay the course, or turn down a new road.

They also talk about the deeper goal behind these decisions: raising confident teens who know how to check in with themselves, build resilience, and trust their own judgment. From family values to tween autonomy to the lifelong practice of self-confidence, this episode shows how even small parenting choices can strengthen the foundation for confident women in the future.

The takeaway? There’s no universal “right” answer. There’s only the right decision for you and your family, right now.

Episode Breakdown:

00:00 Letting Kids Quit: Why It Feels So Hard

03:02 Meet Dr. Emily Gordon

05:03 Reframing Quitting as Taking a Detour

07:18 A Framework for Making Parenting Decisions

12:07 Parental Pressure, Fear, and Self-Confidence

14:22 How to Help Adolescents Name Their Feelings

17:09 Anxiety, Transitions, and Building Resilience

20:03 Balancing Parental Control and Tween Autonomy

29:07 Weighing Benefits, Costs, and Family Values

31:08 Protecting the Parent-Child Relationship

34:48 Confidence, Resilience, and Growth

Connect with Dr. Emily Gordon:

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Connect With Leslie:

Help Your Teen Cultivate Confidence

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Podcast production and show notes provided by HiveCast.fm