Sometimes a conversation starts in one place and ends up taking you somewhere much deeper.

That’s exactly what happened when I had the opportunity to sit down with Whitney Knox Lee, host of the Impostrix Podcast, for a conversation appropriately titled “Stop ‘Shoulding’ All Over Yourself!”

And let me tell you—there was plenty to talk about!

From being an early childhood educator and grandmother to creating an award-winning children’s podcast, living in a multigenerational home, setting boundaries, taking care of ourselves, and learning to release the pressure of what we think we should be doing, our conversation became much more than a discussion about What’s Poppin’ Penny?

It became a conversation about life.

Sometimes We Need to Stop “Shoulding” on Ourselves

How often do we tell ourselves:

I should be doing more.

I should have accomplished that by now.

I should be further along.

I should be able to handle everything.

I should say yes.

I should be doing it the way everyone else does.

Whew!

That little word—should—can carry a whole lot of weight.

Whitney and I talked about the pressure we put on ourselves and how easy it can be, especially for women and caregivers, to become so focused on everyone else’s needs that we forget to check in with ourselves.

For me, that conversation hit home.

I have spent much of my life caring for other people. I spent more than two decades working in early childhood education. I became a mother, a grandmother, and a creator. I have worn a lot of hats throughout my life.

And somewhere along the way, like so many of us, I had to learn that being there for other people doesn’t mean I have to abandon myself.

Sometimes the most loving thing we can do is create a boundary.

Sometimes we have to say no.

And sometimes we simply have to give ourselves permission to say, “This is enough for today.”

Life Inside a Multigenerational Home

One of the most meaningful parts of my conversation with Whitney was talking about multigenerational family life.

For me, family has always been more than a word. It is an experience.

Living in a multigenerational family environment can be beautiful, joyful, supportive, and deeply enriching. It can also require communication, patience, flexibility—and yes, boundaries!

There is something incredibly special about generations sharing life together. Children have opportunities to learn from grandparents. Grandparents get to experience the world through the eyes of their grandchildren. Parents receive support, and family stories and traditions can be passed from one generation to the next.

That spirit of connection is also at the heart of What’s Poppin’ Penny?

Penny’s world is filled with family, history, love, imagination, and the everyday experiences that help children understand who they are and where they come from.

From Early Childhood Educator to Podcast Creator

My journey to creating What’s Poppin’ Penny? didn’t happen overnight.

Before I was a children’s podcast creator, I was an early childhood educator.

Working with young children taught me something I continue to carry with me today:

Child Development IS Human Development.

What children learn about emotions, relationships, communication, empathy, problem-solving, and resilience during their early years becomes part of the foundation they carry into the rest of their lives.

That belief is one of the reasons I created What’s Poppin’ Penny?

I wanted to create stories that children could enjoy while giving parents, grandparents, teachers, and caregivers opportunities to talk about the big feelings and big questions that come with growing up.

Penny isn’t perfect.

She gets frustrated. She gets curious. She makes discoveries. She experiences joy. She asks questions.

And most importantly, she has trusted adults around her who help her navigate the world.

That’s intentional.

Why I Created What’s Poppin’ Penny?

At the heart of What’s Poppin’ Penny? is a simple belief:

Children deserve stories that see them.

I wanted to create a world where children could hear authentic family experiences, explore social-emotional learning, and encounter characters and relationships that reflect the richness of real life.

Penny’s story also gives children an opportunity to explore subjects that adults sometimes think are “too big” for preschoolers—including grief, family history, ancestry, identity, and change.

Children are already experiencing these things.

They’re asking questions.

They’re noticing when someone is missing.

They’re trying to understand their families.

They’re learning how to manage feelings that can sometimes feel much bigger than they are.

Stories give us a safe place to begin those conversations.

The Importance of Boundaries for Caregivers

One of the biggest takeaways I hope listeners get from my conversation with Whitney is that caregivers need care, too.

Parents, grandparents, teachers, and other trusted adults spend so much time pouring into children that it can become easy to believe that taking time for ourselves is selfish.

It isn’t.

Rest isn’t selfish.

Boundaries aren’t selfish.

Asking for help isn’t selfish.

Taking a breath isn’t selfish.

We can’t pour endlessly from an empty cup.

And perhaps most importantly, we don’t have to measure our worth by how much we accomplish in a day.

That lesson applies to parenting. It applies to caregiving. It applies to entrepreneurship. And it certainly applies to creating something from the ground up.

Building What’s Poppin’ Penny? Has Been a Journey

Creating an independent children’s podcast has been an incredible journey.

There have been exciting milestones, unexpected opportunities, challenges, recognition, and moments when I had to remind myself why I started in the first place.

What’s Poppin’ Penny? was created because I believe children’s stories matter.

The recognition is wonderful. The awards are wonderful. The growing audience is wonderful.

But the reason I keep going is the children.

It’s the family who tells me they listened together.

It’s the educator who uses an episode as a conversation starter.

It’s the grandparent who sees their own family reflected in the stories.

It’s the child who hears a character experiencing a feeling and realizes, “I’m not the only one.”

Those are the moments that matter most.

So, Brownstone Buddies… Let’s Stop “Shoulding”!

If there’s one thing I hope you’ll take away from this conversation, it’s this:

You don’t have to live your life according to a never-ending list of “shoulds.”

You don’t have to do everything.

You don’t have to be everything to everybody.

You don’t have to have every answer.

And you don’t have to compare your journey to someone else’s.

Give yourself permission to pause.

Give yourself permission to grow.

Give yourself permission to change your mind.

Give yourself permission to set boundaries.

And give yourself permission to celebrate how far you’ve already come.

That lesson is important for adults—but it’s also a lesson we can model for children.

When children see trusted adults practicing self-respect, healthy boundaries, patience, and self-compassion, they learn that caring for yourself is part of caring for others.

And that is a lesson worth passing down.

Watch the Full Conversation

I’m grateful to Whitney Knox Lee and the Impostrix Podcast for creating space for such an honest and meaningful conversation.

We talked about far more than a children’s podcast.

We talked about family.

We talked about purpose.

We talked about boundaries.

We talked about caregiving.

We talked about the journey.

And yes—we talked about learning to stop “shoulding” all over ourselves!

So grab a cup of something good, get comfortable, and join us for the conversation.

And remember, Brownstone Buddies:

You don’t have to be perfect. You just have to keep growing.

With love,

Toni Kennedy