In this rich and grounded conversation, Kathy sits down with Teddy Stripling, a school counselor, therapist, and host of the Talking Emotions podcast, to explore the emotional lives of boys through the lens of Gestalt therapy, fatherhood, and years of experience in both schools and private practice.Teddy brings over a decade of experience working with children and teens, and shares how his journey—from wanting to become a chef to becoming a therapist—was shaped by curiosity, creativity, and a deep desire to help young people feel seen and understood.
Reflecting on his early work with younger children, Teddy describes how his role was initially framed around “fixing” kids to help them function in the classroom. But with time, he came to realize that real change starts with connection. By slowing down and getting curious about who the student is, he found more meaningful ways to support emotional growth and partner with educators.
The conversation dives into the rising levels of anxiety among adolescents, especially in high-performing school environments, and how shame, peer pressure, and subtle messages around masculinity can shape a boy’s sense of identity.
Drawing from his Gestalt therapy training, Teddy explains why awareness—especially awareness of body sensations and inner experiences—is the foundation for emotional change. He speaks to the importance of giving kids space to be bored, creative, and independent, and why modeling calm and curiosity as parents is often more powerful than solving every problem.
Teddy also shares the story behind his podcast Talking Emotions—a creative outlet that lets him reach students, parents, and mental health providers alike—and recounts a memorable interview that left him both inspired and a little starstruck.
This conversation is full of grounded insights for parents navigating school life, identity development, and emotional presence with their boys.
**********
Feeling motivated? Here's a short, powerful coaching experience to help you tune in, connect, and understand your son—one tiny step at a time.
Join my free 1:1 Tiny Challenge™: 3 Days to a Stronger Connection With Your Son
✨ In just 3 days, you’ll take one small step each day to understand, connect, and affirm your son—no overwhelm, no pressure, just powerful parenting in action.
Here’s how it works:
✔️ I’ll send you one simple action + reflection each day
✔️ You’ll message me back with your experience
✔️ I’ll support you personally with insights, encouragement, and next steps
👉 Ready to get started? You can just send me a note at kathy@sonhoodcoaching.com and say “I’m in!” and I’ll take care of the rest.
**********
Teddy Stripling is a Licensed Clinical Professional Counselor (LCPC) and high school counselor based in Chicago, IL. He brings over 14 years of experience working with children and adolescents, both in schools and private practice. Teddy is trained in Gestalt therapy, certified in Shame-Informed Treatment, Anger Management, and Executive Functioning strategies. He presents at conferences in the midwest and nationally,andconsults with schools to help support youth with diverse needs.
He is also the host of the podcast Talking Emotions, which bridges conversations between teens, parents, educators, and mental health providers.
