Stephanie Fairyington, a 50-year-old writer in New York City, has spent most of her life people-pleasing but only recently started resisting the urge. In an essay for The Guardian, she describes how her over-investment in being liked has been emotionally costly and how she is training herself to be OK with letting people down.
A lesson in politeness or servility?
Fairyington recounts an incident at a neighborhood cafe where her 10-year-old daughter failed to greet the owner warmly. Embarrassed, she scolded her daughter about manners, but soon realized the girl was simply in a bad mood and unaware of her expression. Fairyington then reflected on how she was reinforcing society's attempts to mold girls into "automatons who reflexively try to please everyone but themselves."
She notes that psychologists and studies indicate that over-investment in people-pleasing amplifies stress, impedes fulfillment, and can lead to self-alienation. She asks whether her daughter is entitled to be in a bad mood, and argues that lessons in politeness can tip into encouraging servility in girls.
The cost of being likable
Fairyington explains that her deep desire to be likable came partly from feeling abnormal and believing she could hide her queerness with agreeability. As a lesbian, she adopted feminine affectations to offset cultural messaging that lesbians are "angry, ugly freaks." She realized the extent of her people-pleasing when she started substitute teaching at public schools in New York City at age 48.
In the classroom, she desperately wanted students to like her, softening her voice and maintaining a perma-smile even when students were disruptive. She cites feminist journalist Rebecca Traister's book Good and Mad, which notes that "Women's anger will be – as it has long been – cast as ugly, unappealing, dangerous." Fairyington felt that expressing anger would amplify her aesthetic inadequacies as a queer person.
Learning to set boundaries
Fairyington observed seasoned teachers and adopted four core practices: giving clear directives, addressing transgressors immediately, balancing discipline with affection, and not being punitive. These teachers earned respect and trust, not just likability. She applied these practices outside the classroom, becoming more assertive as she turned 50 and experienced perimenopause.
Now she raises her voice, clarifies boundaries, and expresses discontent. She models for her daughter the OK-ness of disappointing others, and sees her daughter doing the same, such as telling a boy she only wanted to be friends or going to the beach alone.
The importance of demarcating limits
Fairyington acknowledges that women often face gaslighting, retaliation, or violence when they refuse mistreatment. She still feels uncomfortable but cares less about how people respond to her assertiveness. She concludes that dropping the mask of accommodation affects not just the individual but society, making it more acceptable to express full humanity.
