Talking To Teens: Expert Tips for Parenting Teenagers

Ep 321: Tips for Teenage People Pleasing


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Amy Wilson, author of Happy to Help, joins us to discuss the complexities of people pleasing, her personal journey of overcoming it, and strategies for teaching teens to listen to their own voice and set healthy boundaries.

Full Show Notes


As parents, we want to raise teens who are confident, grounded in their values, and capable of standing up for themselves—even when it's difficult. Yet in a world that often rewards people-pleasing behavior, teaching our teens to cultivate authenticity can be a tricky endeavor. From a young age, many individuals are socialized to put others' needs before their own, ignore their inner voice, and aim to please. The challenge for caregivers lies in guiding teenagers to embrace their own desires and make decisions based on their personal truths, even when faced with societal pressures to conform.

This is the backdrop of today's discussion, as we delve into the nuances of people pleasing and the importance of empowering teens to connect with their inner voices. Our guest, Amy Wilson, an actor, writer, podcaster, and author of Happy to Help: Adventures of a People Pleaser, shares her journey from an eighth-grade people pleaser to a conscious parent teaching her children the value of self-advocacy. Amy brings a wealth of experience, not only from her own life but from hosting the podcast What Fresh Hell: Laughing in the Face of Motherhood.


Throughout the episode, Amy emphasizes the role of parents in modeling boundary setting and advocating for personal wants and needs. She reflects on the importance of letting kids experience natural consequences and the discomfort of unmet expectations to encourage problem-solving skills and personal growth.

The Consequences of Over-Reminding

One common struggle shared by parents is the habitual reminder—a seemingly well-intentioned effort to guide teens through their obligations can sometimes backfire. When reminders become incessant, teenagers may develop resistance or rely on their parents for motivation, detracting from their sense of responsibility and autonomy. Amy openly discusses her own struggles and how she has navigated this territory with her children, offering valuable insights on striking a balance between gentle guidance and fostering independence.

Eighth Grade Diaries and Emotional Intensity

Amy also takes us on a nostalgic journey through her eighth-grade diary entries, which she uses as a lens to explore adolescent self-awareness and emotional experiences. This segment highlights the significance of strong emotions and first-time experiences during young adolescence, encouraging parents to validate their teens' feelings while providing the perspective that comes with age and maturity.

Tackling Perfectionism and Gender Expectations

A notable theme in Amy's discussion is perfectionism, specifically the concept of socially prescribed perfectionism imposed by societal standards. This pressure is particularly pertinent to the expectations placed on women and girls, and Amy eloquently addresses how parents can combat these external pressures by reinforcing their teens' intrinsic worth and personal boundaries.

As we explore these themes, Amy shares anecdotes from her experiences—both personal and as a parent—alongside actionable strategies for helping teenagers honor their authentic selves. 

In the Episode…

Join the conversation as we uncover:

  • The importance of providing teens with space to fail and learn from mistakes.
  • How to identify and combat people-pleasing tendencies in yourself and your teens.
  • Strategies for breaking the cycle of responding to social expectations.
  • Ways to empower teens to articulate and pursue their true desires.

Amy Wilson's episode is a deep dive into the realm of people pleasing and the crucial skills parents can foster to help teens lead authentic, self-assured lives. Tune in to share some laughs and gain insights that bridge the gap between generational boundaries. Don't forget to subscribe for more enlightening conversations on Talking to Teens!

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