Making HERstory: Bold. Brave. Feral AF Stories from Female CEOs

Body Image, Boy Moms, and Breaking the Script with Jackie Kelley (Part 1) | Episode 21

Ashley Crabb

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0:00 | 32:17

Welcome back to Making Her Story — the space where women stop shrinking, speak their truths, and share the moments that roar.

Today’s conversation is with the one and only Jackie Kelley (aka “Stay At Home Jackie” in my world) — a mother, creator, illustrator, and walking permission slip for the quirky, the tender, and the wildly honest. Jackie and I have a long-distance friendship with zero polish and a lot of heart, and this episode feels exactly like that: real, funny, deeply grounding, and unexpectedly powerful.

In Part 1, we talk about what it actually means to show up as yourself online (and in real life) when the world keeps handing you a rulebook. Jackie shares how her content started out light and fun… and how honesty, feedback, and bravery built into something bigger: a community of women who just want to be seen without judgment.

We also go all the way in on body image — not in a performative “love yourself” way, but in the real-life, day-to-day work of existing in a body without letting shame run the show. We talk about how postpartum bodies get treated like “before and after” projects, why “you’re so brave” can sting, and how confidence can be an act of exposure therapy.

And because we’re both raising boys, we talk about what it looks like to model body neutrality and self-trust in real time — in dressing rooms, in workout routines, in conversations our kids are always listening to.

In this episode, we talk about:

  • Jackie’s “origin story” as a creator
  • Why curated “aspirational” content can quietly make you feel like shit
  • The power of being 30% good at a lot of things — and going all-in anyway
  • Body image, postpartum pressure, and the exhaustion of constant self-editing
  • Why “you’re so brave” isn’t always a compliment
  • Shaving your head, beauty standards, and the fear of not being “classically feminine”
  • Dressing for dopamine vs. dressing for the male gaze

Connect with Jackie Kelley:

Also check out:

If you loved this episode, share it with the friend who needs permission to exist louder — and come back for Part 2 where we keep going deeper into the stories we carry, the rules we break, and the rooms we’re building.

RESOURCES + CONNECTION:

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