TL;DR: As a single mom, birth doula, and Creator, Chelsea spent the last four years building a business that gives women the support she never had. Last year, when money was tight, she entered Dare to Dream at the final hour and became a Top 5 winner—giving her the financial breathing room to keep going. Ready to take your shot? Enter this year’s Dare to Dream Challenge.
Chelsea Eckler is a birth doula and founder of Olive Brand Doula Services. Inspired by her own birth experience as a single mom, she pivoted careers and became a certified doula to give expecting moms the kind of support she didn’t have—especially for women who have experienced trauma in the medical system or are giving birth alone.
She believes the way a woman views her birth experience is the first chapter of her journey into motherhood. If that experience is rooted in trauma, it can impact how a mother views herself for years.
That’s why Chelsea fiercely believes every woman deserves to be protected, supported, and reminded that she matters—it’s what fuels her work. And it’s what drove her to enter last year’s Dare to Dream in the final hours of the challenge.
Discover how Chelsea built a purpose-driven business as a single mom, and why applying to Dare to Dream changed everything.
From Certified Doula to Content Creator
Chelsea’s path into the birth space was born from personal pain. During her own pregnancy, she found herself navigating the world as a single mother. And when the time came, she gave birth alone. While her own birth ended up being a beautiful experience, she realized her story was an outlier.
Through her doula certification and training, she was confronted with staggering statistics regarding maternal mortality, neglect, and abuse within the medical system. She realized that many women were facing the most intense moments of their lives without the care they deserved.
“I wanted to be the type of support that I didn’t have.”
She became a doula to be an advocate, protector, and steady presence for women in labor.
Her Creator journey began when she started sharing content on Instagram to reach local clients. Her initial goal was simply to sustain her doula business, but as she shared her knowledge and advocated for women, she realized a much larger mission.
Her DMs flooded with messages from women all over the globe who felt empowered by her words. She began receiving pictures and videos from women she had never met telling her she’d helped them through their births. These stories shifted her perspective entirely—her business was no longer just about finding clients. It was about changing the birth narrative globally.
Navigating Entrepreneurship as a Single Mom
Before the Dare to Dream Challenge, Chelsea was living in a state of constant financial stress. As a single mom, she was burning the candle at both ends, living on a doula’s income, which ranges from $20,000 to $30,000 a year. She found herself caught in a vicious cycle, trying to figure out how to keep her business alive and pay bills.
“I was not doing well financially. I was still trying to figure out how to sustain myself as a doula. I didn’t want to have to go back to bartending or doing something that I didn’t love.”
This financial pressure took a heavy toll on her most important role: being a mother to her daughter, Olivia.
Chelsea shares candidly that when she was struggling, she couldn’t show up as the mom she wanted to be. She felt distracted and fearful, worried she couldn’t teach her daughter how to be secure if she didn’t feel secure herself. At her lowest point, she felt the sting of disappointment when she had to move back into her parents’ house, feeling as though she’d lost everything.
A Stroke of Fate: Chelsea’s Submission
Chelsea was in a hospital room supporting a client when she learned about the Dare to Dream Challenge from an email. It was the final day to enter. She sat there looking at her laboring client, wondering, “What if?”
The labor was long, and she didn’t know if she’d make it home in time to film a submission. But in a stroke of timing that felt like fate, the baby was born just in time. She rushed home to film and edit her entry in the final 30 minutes before the deadline, and quickly hit ‘submit.’
Her submission video focused not just on her dream, but on how it could impact the lives of other women and their communities.
A few weeks later, she received a message that would change everything.
Dare to Dream Top 5: What Winning Meant for Chelsea
When Chelsea found out she was a top five winner, it gave her a profound sense of validation. She received a personal message from Stan’s CEO, John Hu, which Chelsea says was the first time she truly felt seen as a single mom and entrepreneur.
“It was like seeing Olivia,” she recalls, noting that witnessing John’s success as someone raised by a single mom gave her the peace of mind that her daughter would be okay.
Winning Dare to Dream saved Chelsea’s business, giving her the funds to pay overdue bills, provide for her daughter, continue her mission, and uplevel her content creation. She invested in tools, like a simple tripod, to remove the excuses hindering her consistency.
Today, Chelsea’s business has evolved from a dream into a tangible reality. Its success has helped her reach a milestone she’d been striving toward for four years: getting her own apartment for her and Olivia.
Receiving the keys was a marker of her success—a sign that she had built a stable life by doing exactly what she was meant to do without having to compromise her purpose for a traditional job.
To Chelsea, the most valuable part of her journey isn’t money. It’s the belief system she’s now able to pass down to her daughter: that anything is possible because her mom is doing it.
“She knows that anything is possible because her mom is doing it.”
30 Minutes Could Change Everything
Last year, Chelsea’s life shifted because she decided to take a chance. She didn’t wait for the perfect circumstances and setup, or spend weeks filming a cinematic video.
Instead, Chelsea filmed her Dare to Dream entry in the last 30 minutes of the challenge, with nothing but her phone and a dream she deeply believed in. She won by showing up on camera as her rawest, truest self—straight out of a 24-hour shift at the hospital—and speaking from the heart.
Chelsea didn’t wait to feel ready. Instead, she said, “Why the heck not?”
Winning gave her room to breathe and support to keep going. Enough to pay bills, grow her business, and raise Olivia without abandoning the work she believes in.
If you’re on the fence about joining the challenge, waiting for the perfect moment or more time, remember: Chelsea didn’t have either. She entered at the final hour and won—and it changed the trajectory of her year.
💫 There’s still time to apply to this year’s Dare to Dream Challenge. If there’s a dream you can’t shake, submit a video for your chance at $100,000 and support to make it a reality.
👉 Enter the Dare to Dream Challenge
Follow Chelsea’s journey:
Stan Store: Chelsea’s Stan Store
Instagram: @GrowingWithChelsea
TikTok: @GrowingWithChelsea
Facebook: @GrowingWithChelsea
Website: olivebranchdoulaservices.com
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