Stop People-Pleasing — A Masterclass on Boundaries That Actually Hold

Negotiate Anything

American Negotiation Institute

Business, Education, Self-improvement

4.7 • 748 Ratings

🗓️ 15 December 2025

⏱️ 87 minutes

🔗️ Recording | iTunes | RSS

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Summary

People-pleasing feels generous… until it destroys your energy, your time, your confidence, and your relationships. In this masterclass, three experts break down why setting boundaries is so hard — and how to finally create limits that protect your peace instead of collapsing under pressure. Featured Episodes Kwame Christian opens with a solo lesson on political conversations at work — one of the hardest boundary-setting challenges we face. He explains why these discussions spiral, how to disengage without escalating, and how leaders can mediate conflict without losing trust. Next, negotiation coach Minson Vo joins Kwame for a raw, behind-the-scenes training session on saying no with clarity, confidence, and authenticity. Through live roleplay, they reveal the psychology behind hesitation, the power of emotional self-awareness, and how to use the “positive no” to protect your time without damaging relationships. Finally, career strategist Eliana Goldstein shares the emotional side of boundaries — burnout, guilt, fear of disappointing others, and how people-pleasing quietly sabotages your life and career. She teaches the mindset and communication skills needed to say no with compassion, stay firm during pushback, and create boundaries that actually hold.

Transcript

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0:00.0	Most small business owners only think about insurance after something gets wrong.
0:04.6	Don't be that person.
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0:10.3	No calls, no waiting, and no nonsense.
0:13.3	Protect your business today at nextinsurance.com.
0:17.2	You know you want to start a business.
0:18.9	What you may not know is how to make it a reality. Just visit goaddy.com to get started. That's goaddy.com. Premium features require paid subscription. See terms on site. Welcome to this negotiation masterclass edition of Negotiate Anything. With over 1,600 episodes featuring some of the world's brightest minds, we've
0:38.8	carefully curated three powerful conversations for you. What makes this so special is that you'll
0:44.3	hear how different experts from different industries approach the same challenge in their own unique ways.
0:50.6	Our goal is to give you multiple perspectives so you can build your own unique style.
0:55.5	Success doesn't look the same for everyone, and in this masterclass, you will see exactly why.
1:00.8	Let's dive in.
1:02.3	Unresolved conflict, or our inability to resolve conflict, is the greatest existential threat to humanity.
1:09.1	We are more likely to tear ourselves apart from the inside
1:12.5	than any foreign invader that we might face, right? And it's we are our own greatest adversary,
1:20.9	but also our own greatest advocate. And if we can collectively as a society get better at having
1:26.5	these difficult conversations, get better at having these difficult conversations, get
1:28.3	better at collaboratively problem solving, and not seeing each other as enemies, but seeing
1:32.8	each other as two imperfect people, just sharing our versions of the truth, trying our best
1:39.3	to make it through the day, I think we can make the world a better place. All right, everybody, welcome to a solo
1:47.6	episode. It has been a long time since I've done a solo episode, maybe years, potentially years
1:54.2	since I've done a solo episode. So it's good to be back and I think this is a good time to
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