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Growing Pains |  Where Business Owners Come to Plan Maternity Leave

Alyson Caffrey
Growing Pains |  Where Business Owners Come to Plan Maternity Leave
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  • You Never Really Come Back From Maternity Leave
    Over the years of supporting hundreds of business-owning moms, I’ve noticed a truth no one wants to say out loud: the version of you that existed before maternity leave isn’t the one who returns. You don’t bounce back. You bounce forward. And the sooner we stop trying to fit into old routines that no longer serve us, the more freedom we’ll find.This episode is an invitation to shift your expectations, rework your systems, and let yourself be changed. Because that’s where the magic really happens. If you’ve ever felt like you should be doing it all like you used to, this one’s for you.In This Episode, You’ll Learn: • Why bouncing back is the wrong goal and what it means to bounce forward instead • How I trained my team to stop texting me when I was with my baby (and how you can too) • The unexpected way I use “version ones” to reduce decision fatigue and lighten my load • The myth of “just wake up before your kids” and what I do instead • How to use season-based decision-making to confidently say no • The one system I wish I had built before having my first son_______________ You don't have to choose between growing your business and your family. Grab the Maternity Leave Roadmap for $29: www.mastermaternityleave.com/roadmap Send in your maternity leave questions! [email protected] xx Alywww.instagram.com/alycaffreywww.mastermaternityleave.com
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  • Motherhood Isn’t a Side Note with The Millionaire Mother, Cait Scudder
    We’re told not to make any big business decisions postpartum. But what if that’s actually when everything becomes the most clear?In today’s conversation with Cait Scudder, business mentor, TEDx speaker, and founder of The Millionaire Mother, we discuss the deep personal transformation that occurs after birth and how Cait’s own postpartum reckoning led to a complete reinvention of her business. Cait shares exactly how she knew it was time to shut down a wildly successful mastermind, what it took to create a brand that fully reflected her evolution, and why motherhood is not something she hides in business. It’s the center.In This Episode, You’ll Learn: • Why Cait shut down a multi-7-figure mastermind just months after giving birth • Why trying to “just add a baby” to your old business model almost always backfires • What changed between baby one and baby three, especially in how Cait allowed herself to be supported • How to advocate for your needs without guilt and model that strength for your kids • The mindset shift that completely redefined legacy for her (hint: it’s not just about money)Connect with Cait:www.themillionairemother.comwww.instagram.com/themillionairemotherwww.themillionairemother.com/podcast_______________ You don't have to choose between growing your business and your family. Grab the Maternity Leave Roadmap for $29: www.mastermaternityleave.com/roadmap Send in your maternity leave questions! [email protected] xx Alywww.instagram.com/alycaffreywww.mastermaternityleave.com
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  • How to Take a Second Maternity Leave in Your Business
    Planning a second maternity leave isn’t just a repeat. It’s a whole new equation.You’re already a mom. You’re already running a business. And when you’re preparing for another baby, the bandwidth just isn’t the same. In this episode, I’m sharing what I did differently the second time around, not just because I knew more, but because I needed different support. From navigating state programs and private disability insurance to managing toddler care and carving out space for myself, this is the real story behind what it takes to plan a second leave as a self-employed mom.This episode is especially for second-, third-, or fifth-time moms who are trying to plan leave in the midst of already parenting. It’s for those of you who feel like you should know how to do this by now, but deep down, know that your life and your capacity have shifted. The second time around, the stakes are different. And so is the plan.In This Episode, You’ll Learn:• Why your second maternity leave can’t be planned the same way as your first • How I approached finances, insurance, and short-term disability differently • The systems and team members I leaned on to keep the business running • The self-care non-negotiables I built into my daily rhythm (and how I got support for them) • What I did to help my first son feel secure and seen in those early newborn days • How writing letters to myself during pregnancy helped me navigate postpartum_______________ You don't have to choose between growing your business and your family. Grab the Maternity Leave Roadmap for $29: www.mastermaternityleave.com/roadmap Send in your maternity leave questions! [email protected] xx Alywww.instagram.com/alycaffreywww.mastermaternityleave.com
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  • What if Motherhood Didn’t Require You to Suffer? with Heather Chauvin
    There was a moment in this conversation with Heather Chauvin that stopped me in my tracks. She said, “If you’re not going to create space for how you want to feel, you’re going to have a lot of space for how you don’t want to feel.” And I felt that in my body. Because so many of us, especially in early motherhood, are taught that struggle is part of the deal. That exhaustion, resentment, and self-sacrifice just come with the territory.But what if that’s not actually true?Heather is a leadership coach, former social worker, and mom of three who rebuilt her life after a stage 4 cancer diagnosis. Her work is all about helping women stop abandoning themselves in the name of being a “good” mother, partner, or business owner. This conversation is honest, clarifying, and filled with the kind of perspective shift I wish I had when I was newly postpartum.In This Episode, You’ll Learn:What Heather means when she says “a well-resourced woman is the secret”Why labeling our struggles (like “imposter syndrome”) often blocks true healingThe one journal prompt that changed how she showed up in motherhood and businessHow Heather rebuilt her life from a hospital bed—without financial privilege or backupWhat to do when your body reacts before your brain can explain whyWhy “wouldn’t it be nice if…” might be the most powerful question you ask all weekMentioned in the episode:Time Rich Reset http://heatherchauvin.com/alyson Connect with Heather:Website: heatherchauvin.comEmotionally Uncomfortable Podcast: heatherchauvin.com/podcastInstagram: instagram.com/heatherchauvin________________ You don't have to choose between growing your business and your family. Grab the Maternity Leave Roadmap for $29: www.mastermaternityleave.com/roadmap Send in your maternity leave questions! [email protected] xx Alywww.instagram.com/alycaffreywww.mastermaternityleave.com
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  • How Didiana De La Osa Took a Real Maternity Leave Without Pausing Her Mission
    When Didiana De La Osa joined my maternity leave program, she was pregnant, growing a mission-driven business, and determined to take real time off after her son was born. Just a few months later, she’s wrapping up her first maternity leave, and she did it without pausing her momentum or compromising her values.Didi is a board-certified behavior analyst and university professor who supports clinicians and parents in building ethical, effective autism therapy practices. When we first connected, she was preparing to step away for the arrival of her baby boy while onboarding a new clinical contractor, setting up systems, and making sure her team could keep delivering high-quality support in her absence. In this episode, she walks us through the decisions she made to protect her family time, professionalize her operations, and return to a stronger, more sustainable business.In This Episode, You’ll Hear: • How IVF shaped Didiana’s perspective on asking for support and creating space for recovery • Why she applied for our Bond Fund and what she did with the grant • The operational systems she put in place to delegate confidently and avoid burnout • How her maternity leave helped her expand her long-term vision (including credentialing in new states) • What it actually looked like to be present with her baby for 3 months while still staying connected to her mission • Her honest advice for Type A business owners who struggle to let goConnect with Didiwww.premierbhconsulting.comwww.instagram.com/pbhcgroup_______________ You don't have to choose between growing your business and your family. Grab the Maternity Leave Roadmap for $29: www.mastermaternityleave.com/roadmap Send in your maternity leave questions! [email protected] xx Alywww.instagram.com/alycaffreywww.mastermaternityleave.com
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About Growing Pains |  Where Business Owners Come to Plan Maternity Leave

You’re running a business and dreaming of growing your family, but when you search for how to take maternity leave as a self-employed mom, the answers just don’t exist.You’ve pieced together advice from HR blogs, asked your friends, downloaded generic templates, and tried to “figure it out later.” Meanwhile, you’re left wondering: Can I really step away from my business without losing momentum...or my mind?Here’s the truth: You can. And Growing Pains is here to show you how. Hosted by maternity leave strategist and business operations expert Alyson Caffrey, this podcast helps self-employed moms plan for maternity leave during the trying to conceive, pregnancy, and postpartum seasons—without burning out or ghosting their business.Each week, you’ll hear honest solo episodes, expert interviews, and real-life maternity leave stories from moms who are building legacies and raising babies. No fluff. No one-size-fits-all advice. Just grounded guidance to help you navigate life and business on your terms.Alyson has helped hundreds of entrepreneurs streamline their operations and take actual time off for maternity leave, while returning to businesses that thrive.Ready to take maternity leave like a CEO? Follow Growing Pains and let’s build a business that supports your motherhood journey.
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