PEOPLE PLEASER REHAB: 10 challenges to finally put yourself first

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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