Can’t Say No to Your Kid? ‘Good Enough’ Says That’s a Bigger Problem Than You Think

You know that feeling when your kid asks for something and you want to say no, but then you picture their little face crumpling and suddenly you’re sweating? Like, actually sweating? You’re not dramatic—you’re just a millennial parent who was raised on “because I said so” and swore you’d do it differently. But now “differently” has turned into “I physically cannot deny this child anything without my body going into fight-or-flight.”

On Good Enough, hosts Natasha Leggero and Sabrina Jalees sit down with comedian Esther Povitsky to talk about the guilt spiral of modern parenting—and one unexpected moment from the Amy Winehouse documentary that completely reframes what it means to say no.

Why saying no feels like a personal crisis

“When I have to say no or take something away, like something comes up within me that is so painful that it’s not even like I could do it,” Povitsky admits. “It’s like I physically can’t. And it’s so clearly about me because I’m like, ‘This is weird.’ Like I’m sweating. I’m so uncomfortable.”

She’s not exaggerating for comedic effect. This is real. And it’s worth asking: why does setting a basic limit with a toddler feel like an emotional emergency?

Part of it is generational. Many parents grew up in households where “no” came without explanation—or worse, with anger. So now there’s an overcorrection happening. We want to be gentle. We want to validate feelings. We want to raise emotionally intelligent kids who feel heard. All good things. But somewhere along the way, “gentle parenting” got confused with “never make your child experience disappointment,” and that’s where things get tricky.

The documentary moment that changed everything

“Something happened to me about three years ago, which is I saw the Amy Winehouse documentary,” Leggero says. “And it was very moving. She was so talented. And the one thing her mother said that I’ll never forget is she said, ‘I could never say no to Amy. I could never say no to anything she wanted.'”

When you say no to your kid, you’re not just setting a limit in that moment. You’re teaching them what “no” looks like so they can use it themselves later. “It made me realize, oh, by saying no, you’re actually modeling no,” she explains. “So they’ll be able to say no when someone tries to give them drugs or whatever it is.”

Kids who grow up without hearing no at home often struggle to use it themselves later, especially when it matters most. Not just in big, dramatic scenarios, but in everyday ones. Saying “no” to a friend who’s pushing their limits. Leaving a situation that feels off instead of people-pleasing through it. Speaking up when something doesn’t sit right, rather than freezing or going along just to keep the peace.

If “no” is never practiced in low-stakes moments—like leaving the playground or turning off the TV—it doesn’t feel neutral later. It feels rude. It feels scary. It feels like rejection instead of self-protection. And that’s when kids grow into teens and adults who say yes out of reflex, not desire.

What happens when no one says no

“I hate the ‘don’t say no’ sort of movement,” Jalees says. “I think that it’s important to teach our kids to be kind people out in the world, which requires a lot of no because our core monkey selves want to eat every banana and knock down every tower.”

She’s half-joking, but the point is serious. Kids aren’t born with impulse control or social awareness. They learn it through friction. Through being told “no.” When there are no boundaries, that’s when the behavior spirals. “We all know that kid,” Jalees adds. “And we don’t want to hang out with that kid.”

She takes it a step further by connecting it to adult relationships. When someone says, “We never fight,” it often doesn’t mean everything’s perfect. It usually means one person is swallowing their needs to keep the peace. “Life is a negotiation,” Jalees explains. “We all have different perspectives.” And kids have to learn that too. Disappointment, pushback, compromise—those are important skills.

At the end of the day, shielding kids from every uncomfortable moment doesn’t make them easier humans later. It just delays the lesson. Limits teach kids that they’re not the only person in the room. How to wait. How to lose. How to hear “not right now” without melting down. And that learning has to start somewhere…usually with a parent who’s willing to sit in a little discomfort so their kid doesn’t grow up expecting the world to bend around them.

Want to hear the full conversation? Tune into Good Enough, streaming now wherever you get your podcasts.

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