Let’s Stop People-Pleasing and Start Having Hard Conversations #10 episode artwork

EPISODE · Jul 9, 2026 · 36 MIN

Let’s Stop People-Pleasing and Start Having Hard Conversations #10

from Free Therapy with Ben & Kevin · host iHeartPodcasts

Our guest this week is my former therapist, Koorosh Rassekh! We talk about where people-pleasing actually comes from, why it isn't a flaw you need to fix but something that once kept you safe, and the techniques that actually make hard conversations easier. For most of my life I thought keeping the peace made me a better friend, partner, and person. I'd suppress my needs, avoid the conversations I was dreading, and tell myself I was just being easygoing. But it actually just built quiet resentment and slowly ruined my relationships. If you say yes when you mean no, or you've been sitting on a conversation for months because you're afraid of how it'll land, this one's for you. – Kevin New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it’s not. So if you’re struggling, please reach out to a mental health professional who can help.0:00  Intro: people-pleasing and conflict avoidance6:59  Why you're not broken9:47  Why expressing needs feels impossible13:16 People-pleasing caught in real time24:58 How to have hard conversations41:08 Signs you're people-pleasing, and the costSee omnystudio.com/listener for privacy information.

Episode metadata supplied by the publisher feed · Published Jul 9, 2026

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Let’s Stop People-Pleasing and Start Having Hard Conversations #10

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This episode is 36 minutes long.

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This episode was published on July 9, 2026.

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Our guest this week is my former therapist, Koorosh Rassekh! We talk about where people-pleasing actually comes from, why it isn't a flaw you need to fix but something that once kept you safe, and the techniques that actually make hard conversations...

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