PEOPLE PLEASER REHAB: 10 challenges to finally put yourself first

LATE BLOOMERS

Rich & Rox Pink

Self-improvement, Education

5.0 • 599 Ratings

🗓️ 11 February 2026

⏱️ 36 minutes

🔗️ Recording | iTunes | RSS

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Summary

In this episode of LATE BLOOMERS, Rich and Rox take on people pleasing head-on and introduce 10 real-life challenges designed to interrupt the habits that keep you putting everyone else first. They talk honestly about how people pleasing shows up day to day — over-explaining, apologising unnecessarily, saying yes when you mean no, and managing other people’s emotions at your own expense.

They walk through the discomfort that comes with breaking these patterns, including the guilt, anxiety, and fear of being seen as rude, selfish, or difficult. Rich and Rox share personal examples of how deeply ingrained these behaviours are, where they came from, and why “being nice” often costs far more than we realise.

This episode isn’t about becoming cold or uncaring — it’s about learning to tolerate discomfort, stop abandoning yourself, and practice choosing your needs without justification. If you’re exhausted from overgiving, overthinking, and constantly putting yourself last, this is your rehab.

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Transcript

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0:00.0	Are you a people pleaser? I've got a challenge for you. In fact, I've got 10 challenges for you to make you stop being a people pleaser. It's going to be uncomfortable, but you're going to agree to it because you're a people pleaser.
0:10.6	You are a mean, mean man and I'm scared. This is the late bloomer's podcast where we are getting our lives together.
0:20.3	Eventually, brought to you by our sponsor's Loop Earplugs.
0:24.5	Are you ready for this challenge?
0:26.6	Don't think.
0:29.5	I'm really looking forward to this episode.
0:32.4	Yeah, I bet you are.
0:34.8	I guess one thing I will say,
0:37.4	I'm a self-identified people-pleaser.
0:40.6	That doesn't end up pleasing anybody, neither the other person or myself.
0:46.9	We understand people pleasing is bad and gets in the way and build secret resentments
0:50.6	and relationship issues, a blocker of true intimacy.
0:55.2	It probably comes from trauma. So like we are in agreement that we want to get rid of people pleasing. Yeah.
1:01.3	So like we're on the same page there. I just don't know where these challenges are going to take
1:07.2	us. Well, look, I'm going to, I'm going to ease in nice and gently to start with, okay?
1:13.7	A nice, simple one for you. Number one of curing your people-pleasering is you've got to start
1:23.6	sending back the wrong meal.
1:29.4	Right.
1:35.6	I, if a waitress has delivered me the wrong meal.
1:36.4	Yeah.
1:42.8	But actually, I wasn't 100% set on what I was going to have.
1:45.2	And I like what she's put in front of me. the restaurant is busy and she's stressed. It can actually feel really nice. Actually, don't
	...

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