Supporting your family-building journey — however it unfolds..

Welcome to Rebel Pineapple

The pineapple has long symbolized strength, resilience, and fertility.

A Rebel Pineapple is more than a symbol — it's a mindset.

A woman with a rebel pineapple mindset tunes out the noise and listens solely to her intuition. In a world full of opinions about her body and timeline, she trusts herself fiercely. She keeps going — not because it’s easy, but because her soul won’t let her quit.

With hope, grit, and a touch of rebellion, she navigates the unexpected, building her family her way.

Dear resilient, strong, incredible YOU —

I’m so glad you’re here.

If you’re navigating fertility, adoption, or the in-between — I see you. I know the weight you're carrying, the dreams you're holding onto, and the strength it takes to keep showing up.

My own journey to motherhood took 10 years: 13 IUIs, nearly 5 IVF cycles, and adoption. Our miracle son came with a congenital heart defect, and looking back, I now see that every step prepared me to be the mother he needed. But that perspective only came with time — and healing.

That’s why I’m beyond excited to launch this deeply meaningful extension of my coaching work.

Rebel Pineapple was born from that journey.
It’s a space where no woman has to walk this path alone — a space where you can reconnect to your wisdom, find calm in the chaos, and build your family your way — with hope, grit, and a little rebellion.

Together, we’ll focus on you — your well-being, your strength, your intuition. You’ll learn tools to calm your nervous system, shift stuck habits, and make decisions with clarity.

I’m not a therapist (and I always recommend having one as part of your team), but I am a woman who’s lived it — and I’m here to make your path lighter. When you lose hope, I am here to carry that for you, too.

You’re not broken. You’re not alone. You were never meant to do this by yourself.

You belong here.

And I’m honored to walk with you.

With love,
Jen

I shared this picture when I realized I was a Mom.

From IVF to Adoption, and everything in between, it finally happened.

Those are happy tears.

We can work 1:1 or in a group setting.

Whether you’re:

  • Trying to conceive for the first time

  • Navigating the early months or your first year of trying

  • Exploring options like IUI, IVF, or other medical treatments

  • Deep into medical treatments and need extra support

  • Taking a break from fertility treatments or considering alternative paths like adoption

  • Feeling uncertain and seeking clarity on next steps

  • Currently a mom, working to prioritize yourself while healing from the physical and emotional toll of fertility struggles.

  • Healing after infertility

No two journeys are alike. I’m here to meet you exactly where you are and offer support for your body, mind, and spirit throughout your journey.

Rebel Pineapple Workshops & Events

I know you have a million things to do…do this one for YOU.

Connect

THRIVE While Waiting Workshop

Our signature in-person Rebel Pineapple Workshop for Women in the Thick of It

Whether you're in the middle of fertility treatments, waiting on answers, exploring adoption or surrogacy, or just feeling lost — this is your space to breathe, reset, and reconnect.

You don’t have to explain where you are. Just come as you are.

What to Expect

First off, some fun! I promise you will have fun!!

Arrive + Connection
Come as you are. No pressure — just presence.

Real Stories, Shared Truths
Hear Jen’s journey and connect one-on-one in a safe space.

Calm the Chaos
Learn simple breathwork + grounding tools to reset fast.

Intuition = Inner Wisdom
Reconnect with your gut and learn how to trust it again.

Journaling + Gut Check
Get quiet, reflect, and hear what your next step might be.

Surviving the Holidays
We will create a plan to navigate the upcoming holidays.

Close with Clarity
Leave feeling lighter, stronger, and more grounded.

You’ll walk away with tools, insight, a sister friend, and a reminder: you’re not alone, and you’re still standing.

Bring a pen. Bring your whole self.
We’ll take care of the rest.

SIGN ME UP!

Saturday, November 15th
9:00 AM – 12:00 PM
Wheaton, IL
$125 per person

Bring a friend — you both get half off!

Only $75 each.

To Register:

  1. Pay via Venmo or PayPal using the links below.

  2. In the note section, please include:

    Your email address

    Your friend’s name (if applicable)

We’ll follow up with a receipt, a short pre-workshop form, and all the necessary event details.

Prefer to pay by cash or check? Just email us and we’ll arrange it!

Email: jendedekelly75@gmail.com