Parenting Tweens and Teens: Setting Boundaries Without Breaking Connection with Aliah Singh, Caitlyn Severin, & Hannah Takajo

“Let them. The clothes, the style— it’s going to change. The point is they want to be seen and they want to feel understood. You, accepting whatever from they’re in that moment and rolling with the changes gives them that freedom to figure out who they truly are.” —Caitlyn Severin

“What’s important is, at the end of the day, what is the feeling that your daughter walks away with when she thinks about you and your relationship, not the little nitty gritty day-to-day things.” —Aliah Singh

"It's not too late. This is your child and you’ll hopefully have a strong adult relationship with them. This is the foundation of that." —Hannah Takajo

Parenting a teenager isn’t about control, it’s about connection— even when connection feels impossible.

If you’ve ever wondered why your once-chatty child now slams doors or retreats behind headphones, you’re not alone. The truth is, raising tweens and teens means navigating a maze of shifting moods, boundary-testing, and moments that challenge everything you thought you knew about being a parent.

 Cultivateen Roots was founded by therapist Caitlyn Severin, special ed teacher Hannah Takajo, and school counselor Aliah Singh to support parents through the challenges of raising teens. Combining empathy with practical guidance, they empower families to strengthen relationships and confidently navigate adolescence. 

Tune in as Heather sits with Aliah, Caitlyn, and Hannah to unpack the real challenges of parenting teens and tweens, share actionable strategies for building trust, setting boundaries, and handling tough conversations—so you can stop surviving and start connecting.

Connect with Heather: 

Website

Facebook 

Instagram

LinkedIn

Episode Highlights:
02:41 Parenting in the Fast Lane
09:32 Ditching the Fear: Celebrating Teen Years
16:19 Hormones and the Teen Brain
21:09 Shame, Repair, and Connection: The Emotional Rollercoaster of Teens
25:24 Guiding Teens in the Digital Age
31:08 Listening Over Lecturing and Navigating Friendship Drama
38:27 Supporting Identity, Style, and Self-Discovery and Addressing Mean Behavior
42:41 The Sex Talk and Beyond
51:59 Advice for Raising Amazing Teens 
01:00:43 The Importance of Self-Care for Parents  

Connect with Cultivateen Roots: 

The Founders

Aliah Singh
Aliah holds a Master’s in Counseling Psychology from the University of San Francisco and has over a decade of experience as a school counselor. She specializes in guiding middle and high school students and their families through the emotional and developmental challenges of adolescence, with a focus on building resilience, confidence, and independence.

Caitlin Severin
Caitlin is a Licensed Marriage and Family Therapist with 13 years of experience supporting teens and families across private practice, nonprofits, and schools. She helps families navigate adolescence through emotional resilience, healthy communication, and personal growth.

Hannah Takajo
Hannah holds a Master’s in Special Education and has spent the past 10 years teaching and case-managing high school students. She specializes in inclusive education and works closely with families to advocate for students with diverse learning needs, promoting collaboration and student success.

Website

Support the show