40. How to Stop People-Pleasing & Start Living on Your Own Terms

Are you constantly saying yes when you really mean no? Do you feel weighed down by expectations that aren’t your own? In this episode of Who Made You The Boss?, Lindsey sits down with author and podcast host Amy Wilson to unpack the deep roots of people-pleasing—why we do it, how it affects us, and, most importantly, how to break free. Amy shares eye-opening insights from her new book, revealing how societal pressures, self-help culture, and generational beliefs shape our ability to set boundaries.

Expect a candid, insightful conversation filled with practical strategies to reclaim your time, energy, and sense of self. Whether you struggle with saying no, feel guilty when prioritizing yourself, or want to support others facing the same challenge, this episode is packed with takeaways to help you redefine what it means to show up for yourself.

What you’ll learn in this episode:

• Why People-Pleasing Runs Deep: Explore the cultural and generational factors that make saying no so hard—and why it’s not your fault.

• Breaking the Cycle: Discover the turning point that led Amy to challenge her own people-pleasing tendencies and write a book about it.

• The Self-Help Trap: Learn how personal development culture can sometimes reinforce harmful patterns instead of helping you break them.

• Setting Boundaries with Confidence: Get actionable tips for saying no without guilt and creating space for what truly matters.

• Lifting Others Up: Find out how to support friends, family, and colleagues who struggle with people-pleasing.

  
  

For more information and to connect with our host, Lindsey Epperly, subscribe to our Substack here!