The Shift To Freedom


The New Prescription for People Pleasing: From Vibe to Tribe with Clayton Olson

Ep. 36

“People pleasing brings a ton of limitations and really gets in the way of us being able to create adult relationships where there's vulnerability, authenticity, transparency, and a resilience in the connection where both people can be seen and actually loved,” explains co-host Clayton Olson. If you have a tendency toward people pleasing, you are likely not being your authentic self and may even be struggling to find your tribe. Truthfully, it takes a lot of inner work to reverse the childhood conditioning that reinforces people pleasing behaviors, but it is worth it to build better relationships. Today, co-host Ben Easter talks with Clayton about why people pleasing exists and how to stop people pleasing and start forming more authentic relationships. 

When we are children, we rely on the relationship with our caregivers for everything. This means that we tend to learn pretty quickly that it works in our favor to try to please them. However, this type of relationship is very unbalanced and doesn’t work in adulthood. If we constantly try to please everyone, we can never show our true selves. And instead of attracting our tribe, we will attract the tribe that fits the false self that we created to please others. In order to stop people pleasing and start living authentically, we must figure out what our own principles are and stick to them. 

People pleasing can be a really problematic tendency for many people because it is a survival technique we learn in childhood. Even though people pleasing may seem harmless, it tends to lead to resentment, poor boundaries, and inauthentic relationships. 


  • “People pleasing brings a ton of limitations that we're creating and really gets in the way of us being able to create adult relationships where there's vulnerability, authenticity, transparency, and a resilience in the connection where both people can be seen and actually loved.” (12:07-12:23 | Clayton)
  • “At its essence, people pleasing is about love. It’s a desire for love. It’s a desire to feel worthy of love.” (12:27-12:34 | Ben)
  • “People that are not people pleasers typically have a set of principles that they operate from regardless of what the external world is doing.” (29:56-30:02 | Clayton)
  • “Your authentic self is the homing beacon that dog-whistles out the people that are your actual tribe.” (35:10-35:18 | Clayton)


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