How to Break Free from People Pleasing with Anna Stewart
In this episode of The Ready Enough Podcast, host Lauren Beane sits down with Anna Stewart, a Board Certified Coach and expert in personal growth, leadership development, and boundary-setting, to discuss how to break free from people-pleasing, build confidence, and start living authentically. Anna shares her powerful ABCs of Authenticity framework—Alignment, Boundaries, and Conflict Management—to help recovering people-pleasers set healthier boundaries, communicate with confidence, and reclaim their time, energy, and self-worth. If you’ve ever struggled with saying “no,” putting yourself first, or dealing with conflict, this episode is packed with practical strategies to help you stop seeking approval and start living life on your terms.
About our guest
Anna Stewart is a board certified coach who has taught her clients how to build amazing relationships with themselves and live their lives by design. Through her podcast, speeches, YouTube videos, and social media posts, she has inspired recovering people pleasers from all over the world to build better boundaries and prioritize themselves so they can live the life they deserve.
Anna is a recovering people-pleaser who, as a teen parent, used to struggle with her identity and confidence.
She lacked faith that she could stand up for herself. She sought to seek others approval through her actions and self sacrifice. This led to her not applying herself and limited her ability to reach her full potential. Through training and experience, Anna has discovered the necessary principles to thrive through authenticity in life and work.
She now teaches others to how to improve their wellbeing and relationships and realize their potential with the ABCs of authenticity.
Ever catch yourself saying “yes” when you really want to say “no”? Or bending over backward to make everyone else happy—only to feel drained and resentful afterward? If you’ve ever struggled with people-pleasing, this episode of The Ready Enough Podcast is for you!
I sat down with Anna Stewart, a Board Certified Coach and leadership expert, to talk about the sneaky ways people-pleasing holds us back and, more importantly, how to break free and start living life on your terms.
Ready to stop seeking approval and start owning your confidence? Let’s dive into the biggest takeaways from our conversation.
🚨 The Hard Truth: People-Pleasing is NOT Kindness
One of the biggest myths Anna debunked? People-pleasing isn’t the same as being kind—it’s actually a form of manipulation (ouch!). When we constantly prioritize others' needs over our own, we’re not truly being selfless—we’re trying to control how people perceive us, often out of fear of rejection.
Instead of focusing on being nice, Anna encourages us to focus on being kind—which means setting boundaries, being honest about our needs, and communicating openly.
Ask yourself: Am I saying “yes” because I genuinely want to—or because I’m afraid of how someone will react if I say no?
🎯 The ABCs of Authenticity: The Ultimate Framework for Confidence
Anna introduced her powerful ABCs of Authenticity, a framework designed to help people-pleasers step into their power:
✔️ A - Alignment: Get clear on your core values and make decisions that support them. If something doesn’t align, it’s an easy “no.”
✔️ B - Boundaries: Boundaries aren’t selfish—they’re necessary for protecting your time, energy, and well-being.
✔️ C - Conflict Management: Conflict doesn’t have to be scary. When done right, it actually strengthens relationships and builds trust.
This simple framework can help you shift from approval-seeking to living authentically, unapologetically, and with confidence.
🚦 Setting Boundaries (Without Feeling Like a Jerk)
Let’s be real—setting boundaries feels uncomfortable at first, especially if you’ve spent years saying “yes” to everything.
Anna’s advice? Start small.
✅ If you’re constantly answering late-night work emails, set a hard cutoff time and stick to it.
✅ If friends or family ask for favors, practice saying, “I’d love to help, but I can’t right now.”
✅ If someone reacts negatively? That’s a them problem, not a you problem.
Boundaries are about teaching others how to treat you—and trust me, the people who respect you will respect your boundaries.
💡 The Power of Saying “No” (Without the Guilt)
Still feeling guilty about putting yourself first? Anna shared this perspective shift:
👉 Every time you say yes to something that drains you, you’re saying no to something that could energize and fulfill you.
Next time you hesitate to set a boundary, ask yourself:
🔹 Is this aligned with my values?
🔹 Will saying yes bring me joy—or resentment?
🔹 What would I tell a friend in this situation?
Saying “no” is an act of self-respect—and it actually creates space for the right opportunities to come your way.
✨ Final Takeaway: You Are Enough (Exactly As You Are)
One of the most powerful moments in our conversation? When Anna reminded us that we don’t have to prove ourselves to anyone.
"You are absolutely enough, exactly as you are."
Let that sink in.
It’s time to release the pressure, stop seeking external validation, and step into your power.
🎧 Listen to the Full Episode
Ready to ditch people-pleasing for good? Tune in now for even more insights, strategies, and real talk on setting boundaries, managing conflict, and stepping into your most confident, authentic self.
Listen to the full episode now: APPLE PODCASTS | SPOTIFY | AMAZON MUSIC
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