Ep 22 - When You’re Happy but Not Happy: Accepting That Pregnancy Isn’t Always Joyful

Jill and Bobby open up about the emotional complexity of early pregnancy, especially the disconnect between outward joy and inward uncertainty. They reflect on how happiness and doubt can coexist, why the “shoulds” of pregnancy can feel so heavy, and how those early feelings can ripple into the postpartum experience. From buyer’s remorse to divine timing, this episode reveals the vulnerable side of expecting a child that often goes unspoken—even to ourselves.

In This Episode, You'll Hear:

• Why early pregnancy doesn’t always feel as joyful as expected
• Jill’s raw description of “buyer's remorse” and how it mirrored past decisions
• How Bobby noticed the emotional disconnect and supported Jill through it
• The tension between being “happy because others were happy” and personal uncertainty
• What it meant to miss out on a certain kind of emotional connection during pregnancy
• How Jill found healing and peace in her bond with Declan now
• The role of divine timing in their story—and how faith reframed their experience

Pregnancy can be both a milestone and a minefield of unexpected emotions. If you’ve ever questioned your feelings or felt disconnected during a time when everyone expected joy, you're not alone. These honest conversations remind us that healing starts when we give ourselves permission to tell the truth.  

Join us at the Vision Board Party, April 28, 7pm EST! Whether you're dreaming big for your personal growth or just need some inspiration, this event is all about community, connection, and manifesting your goals. We’d love to have you there—come create, connect, and feel inspired! RSVP Here (Don't worry if you missed it, we host this party quarterly!)  

We hope you'll join us next time!
—Jill & Bobby  

You are invited to find community with us, check out the Mama Outspoken Village here. To learn more or grab your copy of the book, head here. Remember, you’re not alone in this. One of our favorite resources is the Postpartum Resource Center of New York - you deserve support that sees you.

If you’re ready to get clear on what you actually want your life and business to look like, come dream it into reality with me here.

If you’re a new or future mama who wants a real work‑from‑home option, the internship that taught me virtual assisting and helped me land my first client is this.

If you’re craving an entrepreneur village where you can build relationships, learn core strategies, and grow a business you own (not one that owns you), you’ll want to check out this.