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

Ashley Crabb
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This is Making HERstory—where bold, brave, feral women share the stories that flip the table, rewrite the rules, and remind us that we’re not here to fit in—we’re here to take up space.

  1. 2D AGO

    Decide, Don’t Choose: The Moment a Mother Steps Into Her Wealth | Episode 24

    In this episode, I’m sharing a shift that cracked something open for me: You don’t choose. You decide. Here’s what we explore: The energetic difference between choosing and decidingWhy decision requires severanceHow keeping doors “cracked open” fragments usThe hidden cost of indecision for mothers in leadershipWhy waiting to feel ready keeps us splitHow fragmentation impacts wealthWhat it means to lead from wholenessThe ripple effect of women connecting womenWhy community is a form of wealthHow deciding steadies your voice and expands your presenceWe talk about: The root meaning of the word decide — to severThe fear of closing the door on old identitiesHow I faced fragmentation in my own visibilityWhy I’m done waiting to feel readyWhat shifts when we decide from the woman we are becomingBecause as mothers, we already decide all day long. We decide the rhythm of our homes.  We decide emotional tone.  We decide how energy moves. But when it comes to ourselves — our leadership, our voice, our visibility — we hesitate. This episode is an invitation to stop choosing and start deciding. To lead from integration instead of fragmentation. To build wealth from wholeness. Reflection Questions Where am I still choosing because deciding feels too final?What door am I keeping cracked open?Which version of me is currently leading?What would shift if I decided from the woman I am becoming?Affirmation from this episode: I am a wealthy woman.  I am a present mother.  I am a leader.  I do not have to prove it. See you next week. RESOURCES + CONNECTION: Find Ashley on Instagram: https://www.instagram.com/itsashleycrabb/ Download the Tell My Story Firestarter: https://ashley-crabb.mykajabi.com/opt-in Book a Vibe Check Call with Me: https://calendly.com/itsashleycrabb/30min

    18 min

  2. FEB 25

    Healing Through Creativity: How Art Supports Mental Health for Teens and Adults with Annie Cullen | Episode 23

    Welcome back babes to another episode of Making Her History — the space where women stop shrinking, share their truths, and turn their moments into roars. Today’s guest is Annie Cullen — a high school art teacher, professional fine artist, and Doctor of Education (EdD) who’s blending research, creativity, and real-life lived experience to create safer, more human spaces for students and adults. Annie’s story is full of pivots (and bold detours): from moving to New York City with a paper resume and portfolio, to wedding photography, to the classroom, to earning her doctorate in May 2024 — not to “move on,” but to better serve the kids she sees every day. This conversation is about so much more than art class. We talk about confidence as a muscle, why relationships shape resilience, what trauma-informed care actually looks like in everyday moments, and how wellness can be as simple as breathing, boundaries, and learning to be kinder to yourself in real time. In this episode, we explore: Why Annie pursued her doctorate so her ideas would be taken seriously — and used locally to help studentsHow art becomes a safe space for teens because it’s expressive and not performance-basedThe role of one supportive adult as a resilience factor for kids experiencing adversityA practical, research-backed approach to confidence building (especially for teens)Why “self-care” doesn’t need to be big — sometimes it’s breathing, unclenching your jaw, and saying noThe need for more spaces where men can experience softness, creativity, and support tooHow Annie’s fine art, workshops, and Wellness Wednesday content all connect under one mission: helping people exist with more compassion, autonomy, and agencyConnect with Annie Cullen Instagram: https://www.instagram.com/annie.cullen.artist/ If you loved this episode, share it with a friend who needs a little more support, softness, and permission to be human. Subscribe to Making Her History so you don’t miss the next story. RESOURCES + CONNECTION: Find Ashley on Instagram: https://www.instagram.com/itsashleycrabb/ Download the Tell My Story Firestarter: https://ashley-crabb.mykajabi.com/opt-in Book a Vibe Check Call with Me: https://calendly.com/itsashleycrabb/30min

    56 min

  3. FEB 20

    Body Image, Boy Moms, and Breaking the Script with Jackie Kelley (Part 2) | Episode 22

    We are not just raising children. We are shaping how the next generation understands bodies, strength, confidence, and worth. In Part 2 of my conversation with Jackie Kelley, we got super real about body image and parenting. We talked about Jackie growing up in a home where body image was loud. We talked about how what our mothers modeled shaped us. And then we asked the bigger question: What are we modeling now? We talk about raising boys and how modeling body image for them matters in so many ways. We talk about what it means to raise sons who respect women, who feel at home in their own bodies, and who don’t equate worth with appearance. This episode is layered. It’s about daughters. It’s about sons. It’s about unlearning. It’s about choosing something different. It’s about realizing that how we live in our bodies becomes part of our children’s story. Part 2 with Jackie Kelley on Making Her Story. If you’re raising kids — or reparenting yourself — this conversation will meet you where you are. Connect with Jackie Kelley: Instagram: Stay At Home Jackie https://www.instagram.com/stayathomejackie/ TikTok: Stay At Home Jackie (she’s trying, okay) https://www.tiktok.com/@stayathomejackieNewsletter: https://www.stayathomejackie.com/Also check out: The Crab Twins and Friends — Ashley’s children’s book illustrated by Jackie: https://tr.ee/W-dzggdqKt RESOURCES + CONNECTION: Find Ashley on Instagram: https://www.instagram.com/itsashleycrabb/ Download the Tell My Story Firestarter: https://ashley-crabb.mykajabi.com/opt-in Book a Vibe Check Call with Me: https://calendly.com/itsashleycrabb/30min

    26 min

  4. FEB 18

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

    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 creatorWhy curated “aspirational” content can quietly make you feel like shitThe power of being 30% good at a lot of things — and going all-in anywayBody image, postpartum pressure, and the exhaustion of constant self-editingWhy “you’re so brave” isn’t always a complimentShaving your head, beauty standards, and the fear of not being “classically feminine”Dressing for dopamine vs. dressing for the male gazeConnect with Jackie Kelley: Instagram: Stay At Home Jackie https://www.instagram.com/stayathomejackie/ TikTok: Stay At Home Jackie (she’s trying, okay) https://www.tiktok.com/@stayathomejackieNewsletter: https://www.stayathomejackie.com/Also check out: The Crab Twins and Friends — Ashley’s children’s book illustrated by Jackie: https://tr.ee/W-dzggdqKt 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: Find Ashley on Instagram: https://www.instagram.com/itsashleycrabb/ Download the Tell My Story Firestarter: https://ashley-crabb.mykajabi.com/opt-in Book a Vibe Check Call with Me: https://calendly.com/itsashleycrabb/30min

    32 min

  5. FEB 11

    Becoming the Woman Who Can Hold More | Episode 20

    Welcome back to Making HERstory! This episode is for the moment when the story you’ve been telling yourself stops working—not because you failed, but because you’re being asked to become someone who can hold more. Not more hustle. Not more pressure. More support. More truth. More wealth in its real forms. This conversation is about the quiet identity shift that happens when you stop performing strength, stop martyring yourself, and finally allow yourself to receive the support you keep saying you want. We talk about what it really means to manifest—not as wishful thinking or perfect routines, but as embodiment. As becoming the woman who can receive what she’s been asking for. In this episode, we explore: The difference between wanting support and being willing to receive itHow control, martyrdom, and “doing it all” quietly block abundanceWhy manifesting is about identity, not forcing outcomesHow other women are essential to building sustainable wealthThe way motherhood reshapes leadership, ambition, and supportThe identity shift required to move from survival into embodied abundanceThis episode is for: Mothers who feel like they’re carrying everything aloneWomen who crave support but struggle to accept itBuilders who are exhausted from proving their worth through burnoutWomen navigating wealth, leadership, and visibility after motherhoodAnyone who knows she’s meant for more but feels stuck between control and trust“In order to receive what you are asking for, you have to become the woman who can hold it.” If this episode stirred something in you, here are a few ways to keep the conversation going: Download the Tell Your Story Firestarter — a free guide to help you get your story out of your head and into embodiment, leadership, and action. Book a 30-minute vibe check if you want clarity, support, or space to talk through what you’re building and becoming. And if you’re here for community, stay close. This podcast is a room for mothers, builders, and leaders who are done doing it alone. You don’t have to earn support by suffering. You don’t have to prove your worth by carrying it all. Wealth isn’t built in isolation. It’s built in rooms. In relationships. In trust. And you were never meant to do this alone. RESOURCES + CONNECTION: Find Ashley on Instagram: https://www.instagram.com/itsashleycrabb/ Download the Tell My Story Firestarter: https://ashley-crabb.mykajabi.com/opt-in Book a Vibe Check Call with Me: https://calendly.com/itsashleycrabb/30min

    27 min

  6. FEB 2

    Mothers of Wealth: Story, Space, and the Power of Community | Episode 19

    Every woman has a story. And so many of us have quietly wondered if ours is even worthy of being told. This episode is an invitation to stop questioning the value of what you’ve lived—and to start recognizing that your story, your motherhood, your everyday experiences are not side notes. They are the foundation of your leadership, your wealth, and the legacy you are building right now. What This Episode Holds • The truth about why so many women doubt the worth of their own story  • How motherhood reshapes identity—and why that does not disqualify us from leadership  • A redefinition of wealth that includes time, energy, community, and support  • Why community does not require sameness—it requires respect and room to be  • The power of women creating intentional spaces without judgment  • How ordinary, everyday moments become life-changing when we recognize their meaning Who This Episode Is For • Mothers questioning whether their story matters  • Women redefining wealth beyond money alone  • Mothers building businesses, communities, or creative work alongside family life  • Women craving connection without comparison  • Anyone longing for rooms where judgment is replaced with support “Motherhood doesn’t disqualify us from wealth. It qualifies us for leadership.” We don’t need more pressure. We need more space. Space for different stories. Different ways of mothering. Different ways of building and belonging. This is what wealth looks like when women create rooms together. And we are just getting started. RESOURCES + CONNECTION: Find Ashley on Instagram: https://www.instagram.com/itsashleycrabb/ Download the Tell My Story Firestarter: https://ashley-crabb.mykajabi.com/opt-in Book a Vibe Check Call with Me: https://calendly.com/itsashleycrabb/30min

    14 min

  7. JAN 26

    {Flashback Episode} Gratitude Isn’t the Opposite of Wanting More | Episode 11

    Women are so often taught that gratitude and desire can’t coexist. That if you want more, you must not appreciate what you have. That ambition is a threat. That desire is dangerous. That wanting more makes you ungrateful. But the truth is this: Gratitude isn’t the opposite of wanting more. Gratitude is what prepares you to receive more. In today’s episode, Ashley breaks down the difference between survival gratitude (the kind women inherit to stay small) and embodied gratitude (the kind that expands you). She shares her own story of how motherhood, identity, spirituality, and desire collided — and how women can reclaim the truth about wanting more. Inside this episode, you’ll explore: • Why women are conditioned to treat desire as a threat  • The difference between survival gratitude and embodied gratitude  • How gratitude can ground you instead of shrink you  • Why desire is a sign of alignment, not selfishness  • How abundance begins with noticing the pull toward what’s next • The role of spirituality, intuition, and identity in desire • How daily gratitude rituals shift your capacity to receive • Why wanting more isn’t discontent — it’s becoming If you’ve ever felt guilty for wanting more — more space, more purpose, more fulfillment, more abundance — this episode will meet you right where you are. RESOURCES + CONNECTION: Find Ashley on Instagram: https://www.instagram.com/itsashleycrabb/ Download the Tell My Story Firestarter: https://ashley-crabb.mykajabi.com/opt-in Book a Vibe Check Call with Me: https://calendly.com/itsashleycrabb/30min

    20 min

  8. JAN 19

    The Journey Into Style After Motherhood with Erica from The Wardrobe Staple | Episode 18

    Motherhood changes everything — including the way you see yourself when you catch your reflection on a random Tuesday and don’t recognize the woman staring back. If you’ve ever felt lost in the “sweats and survival” season, this one is a reminder that finding your style isn’t about vanity. It’s about coming home to yourself. About redefining your normal. About being seen — by you first. What This Episode Holds • The identity shift that happens after kids and why it can feel like whiplash • Why getting dressed can be a form of self-care, not performance or pressure • How “influencer culture” can turn into overbuying, overwhelm, and a closet full of clothes you don’t even like • What it looks like to rebuild style with intention, sustainability, and self-trust • Erica’s journey from CPA to full-time stylist — and what it takes to choose the path you actually want • The truth about style after motherhood: it’s not about trends, it’s about how you want to feel in your own life Who This Episode Is For • Moms who feel like they lost themselves somewhere between diapers, deadlines, and survival mode • Women who want to feel confident in what they wear without chasing trends or buying more random shit online • Women craving a “new normal” that feels like them — not who they were before kids • Women who want to feel seen in their clothes again, without pressure to be a “fashion girl” • Women ready to choose themselves in small, tangible ways that actually change everything Resources & Next Steps If Erica’s story hit home and you’re ready to start reconnecting with your style: Follow Erica on Instagram: The Wardrobe Staple — https://www.instagram.com/the.wardrobe.staple/ Take the free Iconic Mom Style Quiz — https://www.thewardrobestaple.com/quizIf you enjoyed this episode, follow Making Her Story, leave a five-star review, and stay close. More feral stories from female CEOs are coming. You don’t have to become someone new to feel good in your skin again. You get to rebuild from where you are — in this season, in this body, in this life. And if style is part of how you find yourself again, you deserve that too. RESOURCES + CONNECTION: Find Ashley on Instagram: https://www.instagram.com/itsashleycrabb/ Download the Tell My Story Firestarter: https://ashley-crabb.mykajabi.com/opt-in Book a Vibe Check Call with Me: https://calendly.com/itsashleycrabb/30min

    50 min
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This is Making HERstory—where bold, brave, feral women share the stories that flip the table, rewrite the rules, and remind us that we’re not here to fit in—we’re here to take up space.

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