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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We all crave comfort. But the truth is, self-confidence isn’t built in comfort zones, it’s built in the moments when we’re willing to be uncomfortable.

Leslie Randolph introduces the idea of deliberate discomfort and why it’s the key to both confident teens and confident women. Drawing from her own life and her coaching work, Leslie unpacks how stretching beyond what feels easy builds the emotional resilience we need to face challenges, pursue big goals, and show up with confidence in everyday life.

What if nothing changes because nothing changes? What if growth, joy, and genuine self-confidence all live on the other side of discomfort? Whether you’re raising a teen girl or navigating your own season of change, this episode will remind you that confidence isn’t about avoiding fear or struggle, it’s about the willingness to walk through it.

Episode Breakdown:

00:00 Why Comfort Zones Don’t Build Confidence

03:17 How Health Challenges Sparked a Wake-Up Call

05:56 Resistance to Change and Why It Feels So Hard

09:00 What Deliberate Discomfort Really Means

12:24 How Discomfort Builds Emotional Resilience

14:00 Everyday Examples of Practicing Discomfort

18:02 Asking for Help as a Confidence Skill

20:54 Strength, Growth, and True Self-Confidence

Links

The Tween Empowerment Summit

Connect With Leslie:

Help Your Teen Cultivate Confidence

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Instagram

Facebook

Podcast production and show notes provided by HiveCast.fm

Some days feel heavier than others. Whether it’s a personal heartbreak or a tragedy in the news, the weight of the world can be a lot to carry. And if you’re someone who feels deeply, it’s not always clear how to keep moving forward.

In this episode, Leslie Randolph offers a thoughtful perspective on what it means to live with sadness, anger, and grief without letting them take over. She shares how self-confidence plays a role even in the hardest moments, not as a way to power through or shut emotions down, but as the quiet willingness to feel it all. What if confidence isn’t about being fearless or upbeat, but about staying present when things are messy? What happens when we let go of the idea that we’re supposed to be happy all the time?

Leslie invites us to stop “shoulding” ourselves into silence or shame. There’s no timeline for healing and no perfect way to process pain. Whether you’re a teenager building confidence for the first time or a grown woman learning how to trust yourself again, this episode will meet you where you are with compassion, clarity, and a few tools to help you keep going.

Episode Breakdown:

00:00 Why We Need Tools for the Hard Days 01:17 Accepting That Sadness Is Part of Life 03:03 Why Asking “Why” Doesn’t Always Help 05:12 You Have to Feel It to Heal It 06:48 The Pressure to Be Happy All the Time 08:12 Confidence Means Feeling the Hard Stuff Too 10:04 Avoiding Discomfort Isn’t the Same as Staying Safe 11:28 Compassion Over Comparison During Grief 13:18 How to Stay Connected When Everything Feels Heavy 14:56 Big Feelings Don’t Last Forever Even When It Feels Like They Might

Connect With Leslie:

Help Your Teen Cultivate Confidence

Website

Instagram

Facebook

Podcast production and show notes provided by HiveCast.fm