Who Made You the Boss?

What if the key to your next breakthrough wasn’t in another how-to guide, but in trusting yourself? In the Season 4 finale, host Lindsey Epperly challenges you to let go of the step-by-step formulas and lean into your own intuition.

This episode is for anyone who has ever felt stuck in the “supposed to” and is ready to explore what happens when you trust what you already know. If you’ve been waiting for a sign to step into something bigger, this is it.

What you'll learn in this episode:

• Why trusting yourself is the key to growth, both personally and professionally.

• How the "riff over recipe" mindset can apply to your career, leadership, and creativity.

• The staggering statistics on mental health struggles in entrepreneurship—and how O’nr is stepping in to help.

• What it means to be in an "open-handed" season and why forcing outcomes may be holding you back.

• How to recognize and embrace your next train car in life, even when you don’t know exactly where it leads.

  
  

Links & Mentions:

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.

  
  

In this episode, you'll discover how to navigate the challenges of life and business with purpose and intention. Lindsey dives deep with Pauleanna Reid, a communications executive, celebrity ghostwriter, and new mom, to uncover actionable insights from her journey. Learn how to transform personal struggles into opportunities for growth, balance mental health while achieving big goals, and leverage mentorship to shape your future. From candid stories about career pivots and dating to practical advice on thriving as an entrepreneur and parent, this episode is packed with takeaways to help you align your passions with your purpose.

What you'll learn in this episode:

• How to Turn Struggles into Strengths: Discover actionable strategies for transforming personal challenges into career and personal growth opportunities.

• The Power of Intentionality: Learn how to align your goals, values, and actions to create a life and career that feels purposeful and fulfilling.

• The Role of Mentorship: Explore how finding the right mentors—and mentoring others—can shape your journey and impact future generations.

• Balancing Mental Health with High Performance: Get insights on managing mental health while maintaining focus and achieving success in both personal and professional life.

• Lessons from the World of Celebrity Ghostwriting: Gain a behind-the-scenes look at how Pauleanna carved out her niche and what it takes to build a unique, thriving career.

  
  

ABOUT PAULEANNA:

This week, join Lindsey for a heartfelt and empowering conversation with Daisy Auger-Dominguez, a trailblazing author and leadership expert, as she shares strategies to combat burnout and reignite your passion for your work. Discover how to maintain your personal identity in leadership roles, foster empathy in communication, and handle the emotional toll of public criticism. With practical techniques for managing stress and inspiring stories—including a heartwarming moment from Daisy’s "happy folder"—this episode is packed with actionable advice to help you lead with purpose and resilience. Tune in for insights that will transform the way you approach leadership and self-care.

What you'll learn in this episode:

• Strategies for providing tough feedback with empathy to ensure it is constructive and well-received.

• Insights into reframing negative internal narratives and combating self-doubt to manage burnout effectively.

• Methods for creating nurturing workplace environments that prioritize employee well-being and productivity.

In this transformative episode, personal branding coach Allison Hare shares her powerful insights on navigating life’s biggest transitions and reinventing yourself with purpose. Discover her framework for addressing burnout, learn how to balance masculine and feminine energies for greater alignment, and uncover the key to setting boundaries that protect your time and energy. Whether you’re facing a major life change or simply looking to step into a more empowered version of yourself, this episode is packed with actionable advice and inspiration to help you thrive. Don’t miss this opportunity to redefine what’s possible for your life and career!

What you'll learn in this episode:

• Strategies like the "Happy Calendar Challenge" for assessing and rebalancing energy-draining and energizing activities.

• Insights into balancing masculine and feminine energies for a holistic approach to success.

• The importance of boundaries, creative experimentation, and finding energy through setting limits.

• The value of mentorship and having a trusted advisor to support transitions and break down emotional barriers.

  
  

ABOUT ALLISON:

Allison Hare is the creator and host of the award-winning globally ranked podcast, Late Learner. She is a former corporate sales executive who purposely left the corporate world to coach high-performing women to redesign their best lives without burnout. As a lifestyle and career coach and keynote speaker specializing in navigating transitions, personal branding, and even operates as an undercover podcast coach. Allison lives in Atlanta with her beloved husband and 2 children and is an endurance challenge fanatic, among other exciting hobbies keeping her dopamine levels high.

Connect with Allison: