Growing Pains |  Where Business Owners Come to Plan Maternity Leave

Alyson Caffrey
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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.

  1. 08/20/2025

    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! connect@mastermaternityleave.com xx Aly www.instagram.com/alycaffrey www.mastermaternityleave.com

    22 min

  2. 08/13/2025

    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.com www.instagram.com/themillionairemother www.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! connect@mastermaternityleave.com xx Aly www.instagram.com/alycaffrey www.mastermaternityleave.com

    52 min

  3. 08/06/2025

    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! connect@mastermaternityleave.com xx Aly www.instagram.com/alycaffrey www.mastermaternityleave.com

    26 min

  4. 07/30/2025

    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.com Emotionally Uncomfortable Podcast: heatherchauvin.com/podcast Instagram: 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! connect@mastermaternityleave.com xx Aly www.instagram.com/alycaffrey www.mastermaternityleave.com

    33 min

  5. 07/23/2025

    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 go Connect with Didi www.premierbhconsulting.com www.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! connect@mastermaternityleave.com xx Aly www.instagram.com/alycaffrey www.mastermaternityleave.com

    39 min

  6. 07/16/2025

    $10K Weeks, Two Kids, and No Childcare with Leah Gervais

    Leah Gervais makes $10,000 a week, and she does it while staying home full-time with her two boys in New York City. In this conversation, she shares what it looked like to let go of childcare, simplify her business, and step fully into a version of motherhood she didn’t even know she wanted when she started. What I loved about this conversation is how expansive it felt. Leah didn’t follow a playbook. She asked better questions. She made intentional choices to slow down, focus on fewer offers, and rethink how she defined ambition. And the result? A business that still thrives and a motherhood experience that feels fully her own. In This Episode, You’ll Hear: • Why Leah chose to let go of her nanny and what shifted in her business as a result • The moment she realized she didn’t need to “earn” the stay-at-home mom title • What her work hours actually look like now (and how her hourly rate went up) • How she navigated maternity leave differently with each baby • The mindset shift from growth at all costs to depth, sustainability, and trust • Why she’s doubling down on doing less in 2025 and what that really looks like Connect with Leah: www.leahgervais.comwww.instagram.com/leahgervais________________ 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! connect@mastermaternityleave.com xx Aly www.instagram.com/alycaffrey www.mastermaternityleave.com

    42 min

  7. 07/09/2025

    What No One Tells You About Postpartum Mental Health with Dr. Emily Guarnotta

    Some moms know they’re struggling postpartum. Others just feel “off” but don’t know why. I brought on Dr. Emily Guarnotta, a licensed clinical psychologist and certified perinatal mental health provider, to talk about the signs of postpartum anxiety and depression that often go unnoticed. Her perspective helped me name parts of my own journey I hadn’t fully understood until years later. If you’ve ever felt snappy, restless, or overwhelmed as a new mom and wondered if it’s just part of the job, this conversation is for you. Emily specializes in maternal mental health and works with families navigating the full arc of parenthood: from infertility to pregnancy, postpartum, and beyond. What I love about her approach is that it’s both clinical and deeply personal. She started this work after walking through postpartum depression herself. In This Episode, You’ll Learn: • The most common symptoms of postpartum anxiety (that go far beyond worry) • Why some moms struggle more after baby #2, even if baby #1 felt “easier” • How your relationship with self-care activities may need to evolve postpartum • A smart, proactive way to book postpartum therapy even if you’re not sure you’ll need it • What to say when help doesn’t feel helpful (and how to advocate for the support you actually want) • Why it’s never “too late” to get support, even if you’re a year or more postpartum Connect with Dr. Emily: Phoenix Health Instagram: www.instagram.com/_phoenix_health Phoenix Health Facebook: www.facebook.com/JoinPhoenixHealth Instagram: www.instagram.com/dr_emily_guarnotta Linkedin: www.linkedin.com/in/emily-guarnotta _______________ 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! connect@mastermaternityleave.com xx Aly www.instagram.com/alycaffrey www.mastermaternityleave.com

    35 min

  8. 07/02/2025

    How Janea Kannett Launched a Diaper Bag Brand in the Middle of Postpartum and Toddler Chaos

    When Janea Kannett couldn’t find a diaper bag that actually worked for her, she designed one herself. She was in the thick of postpartum anxiety, with a baby on her hip and zero business background. Less than a year later, she’s shipping hundreds of orders from her home, showing up online daily, and slowly rebuilding a version of motherhood she actually wants to live in. I wanted to bring Janea on not because her business is perfect or finished, but because she’s in it right now. She’s growing something real, from scratch, in the middle of everyday life with two little kids. If you’re wondering whether you need a detailed plan, a massive audience, or the confidence to “show up” before you start something, this episode is a generous, honest permission slip to begin exactly where you are. In This Episode, You’ll Hear: • What postpartum anxiety taught Janea about identity, independence, and asking for help  • How she launched her product without a long-term plan (or full inventory)  • What’s working and what’s not as she juggles mom life, marriage, and business  • Why she shows up online six days a week, even when imposter syndrome creeps in  • How she’s redefining success through micro-wins, not milestones Connect with Janea + Mother and Kub: www.motherandkub.com www.instagram.com/motherandkub _______________ 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! connect@mastermaternityleave.com xx Aly www.instagram.com/alycaffrey www.mastermaternityleave.com

    43 min
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Trailer

5
out of 5
13 Ratings

About

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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