How to Plan for Maternity Leave as an Entrepreneur with Aly Caffrey

The Millionaire Mother

What if your maternity leave could be more than a pause from your business—and instead become a season of transformation for both your life and your company?

In this episode, I'm sitting down with Aly Caffrey, small business operations strategist, bestselling author, founder of Operations Agency, and creator of Master Maternity Leave. Aly helps entrepreneurs—especially mothers—design businesses that thrive without sacrificing family.

Aly opens up about her personal story of juggling client emails just hours after giving birth, how that experience reshaped the way she approaches work and motherhood, and why planning for maternity leave is both a strategic and deeply personal act. She shares her proven Operation Simplified framework, the common mistakes moms make when preparing for maternity leave, and how to set up your business so it grows while you step away.

Whether you’re pregnant now, planning to be, or supporting a friend through this season, this episode is full of practical advice and empowering mindset shifts to help you prepare for maternity leave with confidence.

Tune in to hear:

• Aly’s personal story of becoming a mom while running a growing business

• The three pillars of maternity leave planning: finances, systems, and mindset

• Why “front loading” is a common mistake—and what to do instead

• How to design maternity leave around what you want (not guilt or outside pressure)

• The powerful leadership skills mothers develop during maternity leave

• Why your business can actually grow while you step away

• How to embrace creativity, clarity, and vision in the postpartum season

Resources & Links Mentioned in This Episode:

• Website: https://www.mastermaternityleave.com/

• Follow Aly on Instagram: @mastermaternityleave

• Listen to Aly’s podcast: Growing Pains

If you loved this conversation, please share it with another mama entrepreneur who’s preparing for maternity leave—and don’t forget to tag us on Instagram with your takeaways: @themillionairemother and @mastermaternityleave.