Girls Night #306: How to Prepare Your Career for Motherhood
(You can also listen right here!👇)
ABOUT THIS EPISODE
What happens when two of the biggest parts of your life collide—your career and your desire to start a family?
That’s exactly what we’re talking about in today’s Girls Night episode. I’m joined by my dear friend Jena Dunay—a mom of two, business owner, and career strategist who has spent years helping women navigate big transitions in their work lives.
Jena knows firsthand what it looks like to juggle both career ambitions and motherhood dreams, and she’s here to share the wisdom she’s learned along the way.
In this conversation, we cover:
How to prepare your career for baby before you’re even pregnant
What to do if you love your job but also know you want to start a family soon
Whether you should “pull back” at work before baby—or lean in until it’s time to pivot
How to know if your workplace will really support you as a mom
The truth about maternity leave (paid vs. unpaid, how it works, what to ask your HR team)
When and how to tell your employer you’re pregnant
Practical ways to set boundaries and actually enjoy your maternity leave
How to define “success” in your career during different motherhood seasons
This episode is full of encouragement and practical advice for anyone who’s in what I call The Everything Era—that stretch of life when so many big decisions seem to come at once. If you’ve ever wondered how to hold space for both a career you love and a family you’re dreaming of, this conversation will be such a gift.
LINKS FROM THE SHOW
→ "We Need to Talk" guide with scripts for 44 difficult conversations
→ Love Your Single Life course for building confidence and navigating dating conversations
→ Just Married course for newlyweds learning to navigate conflict and communication
→ Becoming Mama course for advocating for yourself during pregnancy and early motherhood
Connect with Girls Night:
📱 Follow @SMayWilson on Instagram
💌 Weekly newsletter with exclusive content
10 Questions to Ask Your HR Team Before Maternity Leave
1. What type of leave am I eligible for?
Clarify if you qualify for FMLA, short-term disability, paid parental leave, or any state-specific programs.
2. How is maternity leave pay structured?
Ask about percentage of pay, waiting periods, and how different benefits (PTO, short-term disability, parental leave) stack together.
3. How do I formally request my leave?
Confirm the paperwork, notice period, and any documentation (like a doctor’s note) that’s required.
4. Can I use PTO or sick days before/after leave?
See if you can extend your time off by combining paid leave, vacation days, or sick time.
5. How will benefits work while I’m out?
Ask how health insurance, retirement contributions, and other benefits are handled—and if you’ll owe any payments while on leave.
6. What happens to my role while I’m gone?
Clarify whether your position is guaranteed, if duties will be reassigned, and how reentry will be handled.
7. What is the process for returning to work?
Understand if you can request flexible scheduling, remote work, or a phased return.
8. Will my performance goals be adjusted?
Make sure expectations and reviews account for your time away.
9. What should I do about ongoing projects?
Discuss transition plans, coverage, and how you’ll hand off work before leaving.
10. Who will be my main point of contact during leave?
Decide how (and if) you want to be contacted about work matters while you’re away.
CONNECT WITH STEPHANIE
Instagram // Website // Courses // Join her email list