The People-Pleasing Trap: Why Being Liked Isn’t the Same as Being Connected
People-pleasing can look like kindness—but is it actually bringing us closer to one another?
In this episode, Rachel and Jeana examine how people-pleasing shows up at work, in friendships, in romantic relationships and even in hospitality. Inspired by Adam Grant’s writing on the subject, they explore the fear of disappointing others, why saying no can feel so loaded and how trying to earn someone’s approval can create an “authenticity gap” in the very relationships we’re hoping to strengthen.
They also discuss rejection as data, the difference between caring for someone and managing their feelings, and why clear communication may be one of the kindest relationship tools we have. Plus: a simple daily journaling practice, an invitation dilemma involving a Mother’s Day brunch and the question we can ask whenever we feel ourselves slipping into people-pleasing mode: Is this actually bringing me closer to this person—or am I simply trying to avoid discomfort?
Media mentioned in this episode:
- “The Truth About People Pleasing” by Adam Grant — the newsletter that inspired the conversation and includes the Kristen Bell example.
- "I Got Rejected 101 Times” by Emily Winter — the essay Jeana references about intentionally becoming more comfortable with rejection.
- “I Got Uninvited From Mother’s Day Brunch Because I’m Not a Mom” from Kramer & Jess — the call-in segment discussed during Show & Tell.
- Eventually — listeners can use code CONNECT10 for 10% off their first year.