Jess Freeman spent years being pretty sure she wasn’t going to have kids.
Not in a dramatic, announcement-to-the-world way. More like a quiet, steady conclusion she carried after losing her mom in a car accident at 24, two months into running her business full time, two weeks before Christmas.
Her brain did what a lot of our brains would do. No mom. Can’t be a mom. Not happening.
And for a long time, that felt like the answer.
The Workbook That Changed Everything
Years later, after a fostering experience that was equal parts meaningful and traumatic, after watching close friends have babies, after sitting in the tension of “I genuinely don’t know if I’m supposed to do this,” Jess did what any type-A woman would do.
She found a workbook on Amazon.
Somewhere around chapter eight, there was a prompt: Write a letter to the child you’re choosing not to have. (yes, we all got chills.)
And she couldn’t do it.
That was the answer.
“You Could Just Have One”
Jess brought this realization to a mentor, a friend about ten years older who knew she’d been wrestling with this. Jess told her she thought she was supposed to have kids, and that it was terrifying.
Her friend said two things. First: I know you can do this. Second: You could just have one.
And Jess said something on the podcast that stuck with us. She said she knew she didn’t need permission. But in that moment, the permission opened a door she didn’t know was available.
She got pregnant a month later.
“She Has the Best Advocate in Her Back Pocket”
Jess is a type 1 diabetic, diagnosed at three. One of her biggest fears about having a baby was passing it on. There’s no guarantee either way, and the not-knowing is its own kind of weight.
But when we asked how she navigated that surrender, she said something that wrecked us:
“Well, she has the best advocate in her back pocket if it happens.”
That confidence didn’t come from nowhere. It came from watching her own mom advocate fiercely for her. Standing in the hallway at school going to bat for her. Making sure her daughter was seen and cared for, even when the systems around her didn’t get it.
Jess is carrying that forward now.
Designing a Life, Not Just Running a Business
Jess has been running Jess Creatives for 15 years. She also founded The Ordinary Business, a podcast and community for business owners who want to do good work and work with cool people without chasing a million-dollar goal.
What stood out to us in this conversation wasn’t just her business success. It was how intentionally she’s built her life around it.
She doesn’t work Fridays. She has a clear revenue ceiling she’s comfortable with. She turns down projects when she’s full, even when the money is tempting. She’d rather be present at bedtime than answering one more email.
And she said something we think every mom building something needs to hear: she’s not willing to say yes to work just for money if it means missing bedtime, staying up until midnight, or skipping the park. “You can wait until my next availability, or you can go find someone else.”
That’s not luck. That’s 15 years of designing a life on purpose.
The Thing About Mother’s Intuition
At the very end of our conversation (the part that wasn’t even supposed to be recorded), Jess said something that we couldn’t not share.
She expected mother’s intuition to be loud. Like a clear signal. A flashing sign. And for months after her daughter was born, she thought she didn’t have it.
Then she realized: for her, it’s quiet. It’s the small thought that crosses her mind, like “maybe I should take her to the doctor.” Not a dramatic knowing. Just a nudge.
She followed one of those nudges once. Double ear infection.
That was her intuition. She just didn’t recognize it because she was waiting for it to shout.
Why This Episode Matters
This is a conversation about grief and motherhood and entrepreneurship and identity and what happens when you stop waiting for life to feel certain and start designing it anyway.
If you’ve ever felt like you needed permission to want something, or like your instincts were too quiet to trust, or like you had to have it all figured out before you could take the next step, this one’s for you.
If This Episode Hit Close to Home
Sometimes you hear a story and realize you’ve been carrying something similar. If you’re in a season where you’re navigating big decisions, identity shifts, or just trying to figure out what you actually want, our coaches get it and would love to help you build a life that fits the season you’re in.
You can learn more about coaching by booking a call with Meredith or send us a DM on Instagram @getmomready.
Find Jess
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