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
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
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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
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www.mastermaternityleave.com