261. How to Stop People-Pleasing Without Becoming Rigid ft. Dr. Paula Freedman-Diamond
Finding Mr. Height: The Podcast
Ali Jackson
3.9 • 712 Ratings
🗓️ 16 February 2026
⏱️ 83 minutes
🧾️ Download transcript
Summary
Dr. Paula Freedman-Diamond joins Ali to discuss people-pleasing and how it relates to control in dating and relationships. Paula, a therapist and author of Toxic Striving, breaks down how people-pleasing and rigid boundary-setting are two sides of the same coin: both are attempts to control outcomes and avoid uncomfortable feelings. The conversation explores how to identify when you're prioritizing external validation over your own values and what the middle ground looks like between being overly accommodating and overly rigid. Paula also shares insights on acceptance and commitment therapy, learning to hold your desires lightly while staying grounded in your values.
In Updates, Ali shares a vulnerable conversation that originally aired on the Patreon about societal expectations around women's appearance.
This week's Media Mention is: "The New Rules of Dating for Ambitious Women" from the Ambition 2.0 podcast (by Girlboss), featuring breakup expert and friend of the pod Amy Chan.
Where to find Dr. Paula: On Instagram @mindfuldrpaula, on TikTok @mindfuldrpaula, at www.paulafreedmandiamond.com and www.humankindpsych.com.
Grab Dr. Paula's Book "Toxic Striving" here: www.paulafreedmandiamond.com
Timestamps: Dr. Paula joins us at around minute 33.
Ask questions, make a Storytime submission, or give feedback here: https://tinyurl.com/fmhpodqs
If you'd like to hear Ali’s personal updates before everyone else as well as exclusive episodes every week, ad-free listening, monthly lives, and more…join FMH on Patreon: www.patreon.com/findingmrheight .
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Transcript
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| 0:00.0 | Everyone has shit. |
| 0:01.3 | This is just the one that I happen to have right now. |
| 0:04.3 | At this moment. |
| 0:04.8 | This is what I'm carrying. |
| 0:05.7 | At this moment, it doesn't mean no one else has struggles and it doesn't mean that this is going to be my struggle forever. |
| 0:11.4 | It's just the one. I'm your host, |
| 0:28.3 | Ali Jackson, and I am bringing you my positive and practical approach to dating relationships |
| 0:32.2 | and a whole lot else about life from my lived experience. Thank you for being here. Thank you for almost five years of the |
| 0:38.9 | pod. Actually, by the time you're listening to this, it will be nearly five years to the day. February 18th |
| 0:44.7 | is our technical five year anniversary. Thank you. And I want to celebrate you. I want to give |
| 0:49.9 | appreciation for the listeners that have built the last five years. If you were going to be anywhere |
| 0:54.7 | near New York City on Saturday, February 28th, you haven't heard already. I'm throwing a listener |
| 0:59.3 | appreciation party, an anniversary party. It's going to be at the Folly NYC. Doors open at |
| 1:04.5 | 7 o'clock for patrons and 8 o'clock for public pod listeners. And I'm going to have a |
| 1:09.3 | sponsored bar tab that's first come for a serve, |
| 1:11.3 | so patrons will get first dibs, some welcome gifts or people that show up early. It's going to be a lot of fun. Entry is free, by the way. All you need to do is RCP at tiny URL.com slash fmh five years, the number five. That's how you'll get access to the bar tab. So you RCP for free, and I will have wristbands to access |
| 1:29.6 | that sponsored bar tab with that free RSP. So I really hope to see you there. It's going to be super, |
| 1:34.9 | super fun. This week we have an awesome interview with Dr. Paula Friedman Diamond. She is the author of a |
| 1:40.6 | book, Toxic Striving. She's also a licensed therapist. She talks a lot about people pleasing, which is the original topic that we came on to the |
| 1:48.1 | interview to discuss, but we end up talking about a lot of other stuff too. |
| 1:51.5 | It's a really juicy interview. |
| 1:53.3 | We talk a lot about how people pleasing really comes down to control and that for especially |
... |
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