Connie Woolsey Teaches Women to Take Ownership of Their Lives

“You are your problem, and you’re also your solution.” Connie Woolsey builds everything around that belief. She calls the work The Ownership Practice: taking 100% responsibility for your life and your impact. In 2025, she held herself to this standard and walked away from a vice president role to build something of her own.

Connie Woolsey is the founder of The CBW Collective, where she coaches high-performing women one-on-one, works with leadership teams and organizations, and speaks on getting out of your own way. She writes a weekly newsletter, The Standard, and her first book, Forge Your Freedom, comes out in 2027. She is also a member of the Entreprenista League.

Different rooms, same pattern

Connie works with 2 kinds of clients. The first is the high-performing woman who looks successful from the outside and knows she has been quietly avoiding her own life: overthinking, saying yes when she means no, waiting to feel ready. She hires Connie for one-on-one coaching.

The second is the builder, a founder or executive who leads a capable team, but keeps bringing everything back to them. Those leaders bring Connie in for workshops, consulting, and keynotes to build a culture of ownership. “Different rooms, same pattern: avoidance of ownership,” she says.

She is proudest of the women she coaches. “Watching a client finally have the conversation she’d been avoiding for years, or take the leap she kept talking herself out of, and then hearing her say, ‘I did the thing.’ That never gets old,” Connie says. “It’s the entire reason I built my business.”

From store manager to retail executive

Before becoming a founder, Connie spent 15 years in retail leadership and reinvented herself more than once along the way, “chasing work that mattered and chasing a ceiling I kept hitting,” she says.

The role that shaped her most was in cannabis. She helped build one of Florida’s emerging cannabis retail organizations from the ground up, rising from store manager to vice president of retail in 3 years. “I learned to build and scale fast without breaking the people doing the scaling,” she says.

Her operator experience is the foundation of everything she teaches now.

Taking her own advice

Connie loved the company she helped build and the people in it. Over time, she noticed that the work lighting her up was coaching someone through the thing they had been avoiding and helping them take ownership of it to move forward.

She had done the work on herself first. “From the outside I looked like I had it figured out, but for years I was quietly avoiding my own life,” she says. “Doing the ownership work changed everything for me, and I couldn’t stop thinking about how many capable women were stuck in the same pattern.”

Eventually, keeping that to herself started to feel like avoidance, the exact thing she teaches against. “So in 2025 I took my own advice, bet on myself, and left to build this full-time,” she says.

“The entrepreneur was always there,” she says. “I met her later than I could have, but right on time.”

A finished book and a letter every Sunday

This year, Connie finished her first book, Forge Your Freedom: Take Ownership, Build Self-Trust, and Break Every Excuse. It is now in copyedit with her publisher, Book Launchers. “It still feels surreal,” she says.

She also launched The Standard and has kept it going every Sunday, which she calls “a discipline win as much as a business one.” She also released The Ownership Starter, a free resource, to get her work into more hands.

On the speaking side, she was selected as a featured panelist for the ShePowered Speaking event and has delivered several keynotes to local organizations. “Each stage still feels like a leap, and every time I take it, I trust myself a little more,” she says. Her summary of the year? “Small and steady, but they’re mine.”

Own that you need people

“I wish I’d known I didn’t have to build alone,” Connie says. As an operator, she was used to being the one who had it handled, so her instinct was to figure everything out by herself.

“What I’ve learned is that isolation is not the same as ownership,” she says. “Taking ownership of your business also means owning that you need people: mentors, peers, other women who are in the arena with you.” If she had reached for community sooner, she says, she would have moved faster and doubted herself less.

Forge Your Freedom arrives in 2027

The next chapter is about reach. Forge Your Freedom comes out in 2027, and Connie wants it in the hands of every capable woman who is tired of waiting to feel ready.

Around the book, she is adding more writing, a podcast, bigger stages, group programs, and organizational partnerships. She wants The Ownership Practice to become the language people reach for, the way they reach for “growth mindset” or “extreme ownership” now. “Whether it’s a book, a keynote, a newsletter, or a client on a hard week, it’s the same standard in a different room,” she says.

You can follow Connie on LinkedIn, sign up for The Standard, start with The Ownership Starter, and find her coaching, speaking, and Forge Your Freedom at conniewoolsey.com.

Connie’s story is a reminder that taking ownership of a business also means owning that you need people. The Entreprenista League is the most supportive community of women founders helping you move faster and doubt yourself less. Learn more about the Entreprenista League right here.