1223: How Motherhood Became Her Breaking Point and Her Greatest Business Transformation with Alyson Caffrey
Release Date: 07/30/2025
1230: 7 & 8-Figure Time & Energy RICH Growth
Emotionally Uncomfortable
In this solo episode, Heather reflects on what she’d do differently as she embarks on a new business venture with time, energy, and sustainability at the center. This isn’t another ‘hustle harder’ talk. It’s a candid conversation about how to build 7 and 8 figure impact without sacrificing your health, your family, or your soul. Whether you’re running a business, raising humans, or both, this episode will challenge the way you’ve been taught to define growth and success. Heather explores: 🩶Why emotional energy not information is the missing link in sustainable business...
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1229: From Proving You’re Good to Being Fully Alive with Elise Loehnen
Emotionally Uncomfortable
In this episode, Heather sits down with Elise Loehnen, New York Times bestselling author of On Our Best Behavior, to unpack what it really means to break free from the pressure to be “good” and start living from a place of wholeness. Together, they explore how generational and cultural conditioning shapes women’s roles, the emotional cost of over functioning, and how to rewrite the stories we’ve been taught to live by. This conversation pulls back the curtain on the invisible scripts running your life and invites you to stop performing, start feeling, and come home to yourself. What we...
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1228: Boundaries That Build Respect in My Marriage
Emotionally Uncomfortable
What does it really take to stay connected in marriage while raising a family, running a household, and navigating the emotional ups and downs of everyday life? In this episode, Heather sits down with her husband Bryan for an honest conversation about partnership, communication, and boundaries inside a real relationship. Together, they pull back the curtain on what it looks like to grow individually while still choosing each other daily. In this episode, we talk about: 💛 Why weekly “marriage meetings” can prevent resentment and build connection 💛 How to navigate discomfort and...
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1227: What a Tumor Taught Her About Speaking Up, Showing Up & Deep Self Trust with Lily Walla
Emotionally Uncomfortable
“She’s so strong.” That’s what people say when a woman holds it all together on the outside but what happens when she’s quietly suffering inside? In this episode, Heather sits down with entrepreneur and mother Lily Walla, the founder + CEO of Auggie, for a conversation about the stories women often don’t tell—the health scares, the quiet fears, the identity crises, and the hidden rage that shapes how we show up as mothers, leaders, and humans. Lily shares how a life-threatening tumor reshaped her sense of self, why she built a parenting community rooted in honesty, and how...
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1226: 3 boundaries I'm Putting In Place Before My Kids Start School
Emotionally Uncomfortable
If you’re feeling the urge to hit the reset button as your family transitions into fall, this episode is for you. Heather is pulling back the curtain on how she’s personally re-evaluating her time, energy, and money boundaries and how you can do the same without guilt, shame, or overwhelm. This isn’t about setting rigid rules or reinventing your whole life from scratch. It’s about refinement, alignment, and real emotional accountability so you can start this season feeling clear and in control. In this episode, Heather walks you through how to: Audit what’s actually working (and...
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1225: Stoic Empathy with Shermin Kruse
Emotionally Uncomfortable
What if empathy wasn’t about absorbing everyone’s emotions but about leading with heart and boundaries? In this episode, Heather sits down with Shermin Kruse for a powerful and timely conversation about stoic empathy, emotional discomfort, and the messy middle between caring deeply and protecting your energy. They explore the spectrum of empathy; from burnout and people-pleasing to disconnection and avoidance. And they discuss what it really takes to lead, parent, and grow from a place of internal strength. In this episode, they cover: 🩶 How to know when your empathy is hurting more...
info_outline![1224. [LIFE UPDATE] He Moved Across the Country… and I Didn’t Break show art](https://assets.libsyn.com/item/37694385?height=50&width=50)
1224. [LIFE UPDATE] He Moved Across the Country… and I Didn’t Break
Emotionally Uncomfortable
The older your kids get, the more they need you. Not for rides to soccer practice or packed lunches, but for leadership, boundaries, and emotional presence. In this life update, Heather pulls back the curtain on a summer filled with big transitions, personal growth, and hard choices. From her oldest son moving across the country on short notice, to restructuring her business and team, to dialing in her health with more intentional energy management, she’s sharing what’s working, what’s not, and the uncomfortable truths she’s had to face to stay in alignment. Listen in as Heather breaks...
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1223: How Motherhood Became Her Breaking Point and Her Greatest Business Transformation with Alyson Caffrey
Emotionally Uncomfortable
What if success doesn’t have to cost you everything? In this weeks episode, Heather sits down with author and entrepreneur Alyson Caffrey to talk about the unseen emotional labor of being "the strong one." From the moment she checked in with clients after giving birth to her first child, Alyson began questioning the cultural narratives that taught her to grind, produce, and prove her worth no matter the cost. Together, they unpack what it really takes to shift out of burnout and into alignment, create systems that support rest, and redefine success on your own terms. In this episode, they...
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1222: Reclaiming Confidence, Health and Strength with Adriana Mastronardi
Emotionally Uncomfortable
What does it really look like to reclaim your power after years of people-pleasing, perfectionism, and putting everyone else first? In this episode, Heather sits down with educator, coach, and mother Adriana Mastronardi to explore the transformation that begins the moment a woman stops asking for permission. From redefining fun and food to building a thriving business and becoming the breadwinner in her household, Adriana shares how she learned to question everything—and create a life that reflects who she really is. In this episode, they cover: 🩶 The identity shift that happens when...
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1221: Revolutionizing Education: From Bored Kids to Passionate Learners with MacKenzie Price
Emotionally Uncomfortable
"I don’t want to watch my kids play the same game I had to play growing up." What happens when a mom watches her bright, curious daughters slowly lose their love of learning in traditional school? MacKenzie Price didn't just complain she revolutionized education entirely. In this powerful conversation, MacKenzie shares how she went from frustrated parent to education innovator, creating Alpha School and the 2H Learning model that's transforming how kids learn across North America. In this episode, we cover: 🩶 How to spot the signs that your child is checked out and what to do about it....
info_outlineWhat if success doesn’t have to cost you everything?
In this weeks episode, Heather sits down with author and entrepreneur Alyson Caffrey to talk about the unseen emotional labor of being "the strong one." From the moment she checked in with clients after giving birth to her first child, Alyson began questioning the cultural narratives that taught her to grind, produce, and prove her worth no matter the cost.
Together, they unpack what it really takes to shift out of burnout and into alignment, create systems that support rest, and redefine success on your own terms.
In this episode, they discuss:
🩶 The hidden cost of tying your self-worth to productivity
🩶 What it really looks like to rest, recover, and still lead powerfully
🩶 How to grieve old identities while raising your standards
If you’re the one everyone leans on but you’re secretly wondering who supports you—this episode will remind you of what you actually deserve.
About Alyson
Alyson Caffrey is a small business Operations Strategist, Bestselling Author and founder of Operations Agency.
Alyson is best known for helping founders escape the bitter day-to-day of running a growing company. Over the last 8 years, Aly and her team have helped streamline the back-end ops for a multitude of brands and using her Operations Simplified™ framework to unleash the power of small teams.
She left the board meetings, consulting 8-figure companies on their operations, to serve founders running small businesses. Alyson believes that if she can return fulfilled founders back to their families, she can generate a much larger impact in the world.
Alyson is committed to using her experience growing businesses and streamlining operations to help founders (mostly parents) have better relationships with their business. Whether navigating a new baby, managing the chaos with young kids, or simply making sure you’re front row at all the wrestling matches, Alyson helps create businesses that give time back to our family, not the other way around.
Alyson is mom to two young sons (yea, it’s crazy) and enjoys spending her time at home with her growing family.
https://instagram.com/alycaffrey/
https://instagram.com/mastermaternityleave/
https://alysoncaffrey.com/handbook/
https://mastermaternityleave.com/workshop/
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