milk and cookies

milk and cookies

a complete guide to breaking the people-pleasing pattern

ayushi thakkar's avatar
ayushi thakkar
Jan 31, 2026
∙ Paid

breaking the people-pleasing pattern sounds straightforward in theory; just start saying no, set boundaries, prioritize personal needs over others’ comfort but anyone who’s tried to stop people-pleasing learns pretty quickly that the hard part is sitting with the discomfort that follows when you actually do. the fear of disappointing people isn’t rational and it doesn’t respond to rational arguments about why boundaries are healthy or why personal needs matter. it translates into a deep psychological response that’s been trained through years or decades of learning that other people’s comfort is more important than personal wellbeing, and changing it requires working with that nervous system response rather than just trying to override it with willpower.

Subscribe

what follows is a framework for actually changing people-pleasing behavior in ways that account for how difficult and uncomfortable it is, strategies that work even when the terror of disappointing someone feels unbearable. this is about recalibrating a system that’s been completely out of balance, where all the care and accommodation flow outward and nothing flows back in.

1. start tracking automatic yeses for two weeks without trying to change them

the first step is to become aware of how often automatic agreement happens without any conscious decision-making. for two weeks, just notice every time a yes comes out automatically in response to a request or suggestion, and make a simple note of it. the tracking can be as basic as a tally mark in a phone or a note that says “agreed to lunch with sarah, agreed to help noor move, agreed to take on extra project at work.”


paid posts go into the how. there’s 20% off right now if you want access.

User's avatar

Continue reading this post for free, courtesy of ayushi thakkar.

Or purchase a paid subscription.
© 2026 Ayushi Thakkar · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture