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.
Growing Pains | Where Business Owners Come to Plan Maternity Leave
Should I Get Insurance? – Maternity Leave Roadmap #17
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 during time away. Whether you’re planning a few weeks or a full year off, this episode will help you understand how insurance fits into your bigger maternity leave plan—and how to layer your options to reduce pressure and risk.
Want the full Maternity Leave Roadmap now?
Get the complete audio and video series, email prompts, templates, and step-by-step planning tools inside the members area:
mastermaternityleave.com/roadmap
Need more personalized support as you prep for maternity leave?
The Bond is my 1:1 container for business owners navigating leave planning with live support, team delegation, and real-time coaching.
mastermaternityleave.com/bond
In This Episode, You’ll Learn:
• Why insurance often gets overlooked—and why it matters for maternity leave
• What a business owner’s policy typically covers (and how it helps)
• How to layer short-term and long-term disability with state programs
• Why business structure and tax status can impact your coverage
• Tips for talking to your provider and building a flexible support plan
This Episode’s Homework:
Make a list of your current coverage (or lack of it). Then set up one call—to your accountant, state representative, or insurance provider—to get clarity on what your options are and what updates you may need before leave.
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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