Alyson Caffrey

Growing Pains |  Where Business Owners Come to Plan Maternity Leave

Business EN ↓ 142 episodes

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 m...

Author

Alyson Caffrey

Category

Business

Podcast website

alysoncaffrey.com

Latest episode

Aug 20, 2025

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Episodes

You Never Really Come Back From Maternity Leave 20.08.2025

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 expectat...

Motherhood Isn’t a Side Note with The Millionaire Mother, Cait Scudder 13.08.2025

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.  C...

How to Take a Second Maternity Leave in Your Business 06.08.2025

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 p...

What if Motherhood Didn’t Require You to Suffer? with Heather Chauvin 30.07.2025

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-...

How Didiana De La Osa Took a Real Maternity Leave Without Pausing Her Mission 23.07.2025

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 clini...

$10K Weeks, Two Kids, and No Childcare with Leah Gervais 16.07.2025

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 playbo...

What No One Tells You About Postpartum Mental Health with Dr. Emily Guarnotta 09.07.2025

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...

How Janea Kannett Launched a Diaper Bag Brand in the Middle of Postpartum and Toddler Chaos 02.07.2025

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...

Healing Your Gut for a Stronger Pregnancy, Postpartum, and CEO Life with Bridgitte Mallinson, MS RDN 25.06.2025

When I first met Bridgitte Mallinson, MS, RDN, I knew I needed to bring her voice to Growing Pains. Bridgitte is the founder and CEO of GutPersonal, a female‑founded supplement company that helps women heal gut issues with personalized testing and targeted formulas. She’s also a registered functional dietitian, a mom to Lily, and currently pregnant with baby girl number two. I invited her on becau...

How Deborah Collazo Planned Maternity Leave Across Two Businesses 20.06.2025

When Deborah Collazo first started planning her self-employed maternity leave, she was overwhelmed. She was convinced she’d either have to shut down her business completely or skip taking time off altogether. But after joining my maternity leave planning program, Deborah created a plan that gave her clarity, support, and confidence. Now she’s preparing to welcome her baby this fall, with her busin...

Taking the Shame Out of Your Finances with Tiffany Vogel 11.06.2025

What if getting a handle on your business finances didn’t have to feel so heavy? In this episode, I’m joined by financial coach Tiffany Vogel, who has made it her mission to simplify the money side of entrepreneurship, especially for moms. We talk about why so many of us avoid looking at the numbers, how to rebuild trust in yourself as a business owner, and what it means to build a life (not just...

Let This Be the Beginning – Maternity Leave Roadmap #30 06.06.2025

If you’ve made it here, you’ve done something powerful. You’ve committed to rethinking what maternity leave can look like as a business owner. In this final episode of the series, I’m reflecting on what we’ve covered, what it really means to lead yourself through this season, and how to keep going. Because this work isn’t just about creating a plan. It’s about becoming the kind of leader your busi...

Flexibility Is the Plan – Maternity Leave Roadmap #29 04.06.2025

When you're building a plan for maternity leave, it’s easy to assume that once it’s in place, it’s set in stone. But the truth is, your needs, your baby’s rhythms, and your business might ask for something different. That’s not a sign you did it wrong. It’s a sign you’re paying attention. In this episode of the Maternity Leave Roadmap series, I’m talking about flexibility. Not the kind that t...

Protect Your Energy While Prepping for Leave – Maternity Leave Roadmap #28 02.06.2025

What if growth didn’t have to be loud, measurable, or tied to a to-do list? In this reflective episode of the Maternity Leave Roadmap series, I’m sharing what early postpartum really felt like and how disorienting it was to go from clear, daily business progress to the invisible work of motherhood. If you’ve ever felt like you’re falling behind just because your growth doesn’t look the same, I hop...

Choose Your Anchor Activity – Maternity Leave Roadmap #27 30.05.2025

When your whole life is shifting, you need something that keeps you grounded. That’s what an anchor activity is for. In this episode of the Maternity Leave Roadmap series, I’m introducing one of the very first things we build inside The Bond coaching program: the anchor activity. Whether it’s journaling, stretching, walking, or simply breathing, this practice helps you reconnect to yourself as eve...

Working on Maternity Leave – Maternity Leave Roadmap #26 28.05.2025

Some people want to fully unplug during maternity leave. Others feel pulled to work, and that doesn’t have to be a bad thing. In this episode of the Maternity Leave Roadmap series, we’re talking about how to think through working during your leave. Whether it’s out of desire or necessity, this episode walks you through how to assess your time, your capacity, and your energy so you can say yes to w...

Train People How to Treat You – Maternity Leave Roadmap #25 26.05.2025

Boundaries aren't just about protecting your time. They are about teaching others what to expect from you. In this episode of the Maternity Leave Roadmap series, I’m sharing what it really looks like to create boundaries that stick. I walk through how to set expectations with yourself, your team, and your clients, especially during maternity leave. From turning off notifications to creating d...

5 Boundaries to Set Before Baby Comes – Maternity Leave Roadmap #24 23.05.2025

The closer you get to maternity leave, the more valuable your time and energy become. And the only way to protect both is with boundaries. In this episode of the Maternity Leave Roadmap series, I’m walking you through five boundaries that have helped me save my sanity during pregnancy, maternity leave, and early motherhood. These aren’t just “nice to have” tips. They’re clarity-setting, calendar-c...

The Power of Community and Intuition – Maternity Leave Roadmap #23 21.05.2025

It’s easy to feel like you should have a village around you during motherhood and business. But what happens when that village doesn’t show up? In this episode of the Maternity Leave Roadmap series, I’m talking about the two forms of support that matter most in this season: community and intuition. I share personal stories of navigating early motherhood and entrepreneurship without nearby family s...

The Identity Shift of Motherhood and Business – Maternity Leave Roadmap #22 19.05.2025

The biggest shift in your maternity leave plan isn’t logistical. It’s personal. In this episode of the Maternity Leave Roadmap series, I’m sharing what that identity shift looked like for me, how it caught me off guard, and why it ultimately made me a stronger, more focused business owner. Whether you’re about to become a mom for the first time or you’re navigating this transition again in a new s...

The Frontload Fallacy – Maternity Leave Roadmap #21 16.05.2025

You’ve probably heard it before: just get everything done before baby comes. But what if trying to frontload your entire business is actually setting you up to fail? In this episode of the Maternity Leave Roadmap series, I’m breaking down what I call the “frontload fallacy” and why I believe one of the most important parts of preparing for maternity leave is learning how to slow down before the ba...

Block a Day to Implement – Maternity Leave Roadmap #20 14.05.2025

You’ve done the planning. Now it’s time to actually start building. In this episode of the Maternity Leave Roadmap series, we’re entering the implementation phase. I’m sharing one of the most effective tools I’ve used (and that we use inside The Bond) to help you get momentum when it’s time to put your plan into action: blocking a full day. You’ll learn how to structure your time, where to go to g...

The Only 3 Problems in Your Business – Maternity Leave Roadmap #19 12.05.2025

By now, you’ve probably uncovered a few areas in your business that need support. But what if diagnosing the real problem was simpler than you think? In this episode of the Maternity Leave Roadmap series, I’m sharing what I’ve learned from a decade of operations consulting: almost every issue in your business falls into just three categories. I’ll walk you through how to tell the difference betwee...

Audit Your Finances Before Leave – Maternity Leave Roadmap #18 09.05.2025

You don’t need to sell more to afford your leave. You need to start with the money you already have. In this episode of the Maternity Leave Roadmap series, I’m walking you through a step-by-step financial audit that helped me return from maternity leave with a more profitable and sustainable business. You’ll learn how to review your expenses, identify what’s not serving you, and make decisions tha...

Should I Get Insurance? – Maternity Leave Roadmap #17 07.05.2025

Most business owners wait until something goes wrong before they think about insurance. But when you’re planning maternity leave, thinking ahead is a gift to your future self. In this episode of the Maternity Leave Roadmap series, I’m breaking down my own business insurance setup and explaining how I use a mix of state programs, private policies, and tax strategy to create financial stability duri...

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