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

    Awareness Is Not the Work: How to Stop Watching Your Patterns and Actually Change Them | Episode 27

    In this episode, I'm getting radically honest about something I've been confusing for most of my life—and I know I'm not alone. Being aware of your patterns is not the same as changing them. For years, I convinced myself that seeing my limiting beliefs, naming my generational cycles, and acknowledging my habits meant I was doing the work. But I was still in the cage. I just knew what the cage looked like. I talk about: The difference between awareness and accountability—and why confusing them keeps you stuckThe identity I built around being the martyr, the savior, the chaos coordinator—and what it cost meWhat shadow work actually looks like when you stop talking about it and start sitting in itWhy transformation is uncomfortable, painful, and hard—and why that means you're finally movingLetting go of the need to make your dreams smaller so other people can hold themLearning to receive help, support, and accountability without feeling like a failureWhat it means to forgive yourself and stay accountable at the same timeThe hardest truth I had to face: I wasn't doing the work. I was watching myself not do it and calling that growth. This episode is about the moment I stopped abandoning myself. About choosing to be an active participant in my own expansion—not just an aware observer of it. About naming what I want out loud, without softening it, without shrinking it, even when it makes someone else uncomfortable. Because awareness without action is just a really pretty cage. And you were never meant to stay in it. ✨ This week's reflection prompts: Where are you aware but not yet taking action? What patterns are you still feeding? What do you truly want—and what have you been making smaller? Write it down. Name it. And decide. 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

    34 min

  2. MAR 18

    Motherhood, Money Struggles, and Self-Worth: The Story I Was Afraid to Share | Episode 26

    In this episode, I’m sharing a part of my story I’ve never spoken out loud before. A season where I was navigating new motherhood with twins, financial uncertainty, postpartum depression—and carrying it all silently. I talk about:  • Moving across the country with no income  • Becoming a new mom to twins while trying to “figure it out”  • The pressure to be a certain kind of mother  • Trying to force a version of motherhood that wasn’t truly mine  • Living in survival mode while feeling like I didn’t deserve help  • The invisible weight mothers carry—and why we keep it hidden The hardest truth I had to face: I didn’t ask for help… because I didn’t believe I was worthy of it. This episode is about releasing shame, redefining motherhood on your terms, and recognizing the wealth you already carry—even in the hardest seasons. Because motherhood doesn’t disqualify you from wealth. It reveals it. 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

    39 min

  3. MAR 11

    The Hidden Cost of “I’m Sorry” as a Mother | Episode 25

    In this episode, I’m talking about something many of us do without even realizing it: saying “I’m sorry.” Not when we’ve truly done something wrong—but the constant apologies for asking questions, taking up space, or simply existing as a full human. Recently, I had a realization that shifted everything for me:  Every time we say “I’m sorry” to someone else, we’re often saying it to ourselves too. I share a powerful moment from an event that forced me to see how often I had let others narrate my story—and how many times I had stayed silent instead of owning my voice. That moment became a turning point. In this episode, I explore:  • Why mothers are conditioned to apologize  • How constant apologizing can make us disappear  • The invisible weight mothers carry in decision-making  • The power of forgiving ourselves for past silence  • What changes when we stop shrinking and start owning our story This conversation is about reclaiming your voice, forgiving yourself, and choosing not to disappear anymore. Because deciding to show up fully—that’s a form of wealth. ✨ Download the Tell Your Story Firestarter in the show notes to start putting your story into words. 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

    19 min

  4. MAR 4

    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

  5. 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

  6. 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

  7. 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

  8. 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
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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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