Shailey & Katie's Lemonade Stand: Design Moms Finding the Happy Balance as Creative Entrepreneurs

Stop People Pleasing: We Thought We Were Being Helpful. Turns Out… Nope.

Episode Summary

“People pleasing is actually about controlling others.”Wait—what? Rude! But it’s true. When we’re trying to make everyone happy, what we’re really trying to do is control how people see us. This week, we’re unpacking that sneaky truth and learning how to say no (without turning into a soulless- boundary-monster). People pleasing. From apologizing for existing 😆 to saying yes when your soul is screaming no, they get real about why we do it, how it sneaks into everyday moments, and what it looks like to finally break free. They share cringe-worthy personal stories (we’ve all been there), and dig into how to set boundaries without burning bridges. You’ll hear about the power of pausing before reacting, assuming positive intent (even when it’s hard), and how curiosity can diffuse 90% of awkward human moments. And because we love a good game, the episode includes a “Boundary Blitz” — a rapid-fire roleplay where Shailey gets to practice saying no. You’ll walk away with practical ways to stop over-explaining, start communicating clearly, and actually feel confident when you say no — without the shame spiral. 

Episode Notes

“People pleasing is actually about controlling others.”Wait—what? Rude! But it’s true. When we’re trying to make everyone happy, what we’re really trying to do is control how people see us. This week, we’re unpacking that sneaky truth and learning how to say no (without turning into a soulless- boundary-monster). People pleasing. From apologizing for existing 😆 to saying yes when your soul is screaming no, they get real about why we do it, how it sneaks into everyday moments, and what it looks like to finally break free.

They share cringe-worthy personal stories (we’ve all been there), and dig into how to set boundaries without burning bridges. You’ll hear about the power of pausing before reacting, assuming positive intent (even when it’s hard), and how curiosity can diffuse 90% of awkward human moments.

And because we love a good game, the episode includes a “Boundary Blitz” — a rapid-fire roleplay where Shailey gets to practice saying no.

You’ll walk away with practical ways to stop over-explaining, start communicating clearly, and actually feel confident when you say no — without the shame spiral. 

Takeaways

• People pleasing usually starts from wanting to be liked — not evil, just outdated programming.
• Assuming good intent changes how you see people and how you talk to them.
• Curiosity beats judgment every time.
• Confidence is a muscle — and boundaries are your gym.
• A thoughtful pause is your secret weapon in any tough moment.
• Clear is kind. Vague is confusing.
• Saying no doesn’t make you mean — it makes you honest.
• Boundaries protect your peace and your relationships.
• You don’t owe everyone an essay-length explanation.
• Celebrate every time you choose growth over guilt.