About Connie

You Keep Your Word to Everyone but Yourself. I Know, Because I Did Too.

Author, speaker, and founder of CBW Collective. Being capable is exactly what makes it easy to put yourself last.

Connie Woolsey seated and smiling in a black leather jacket
Connie Woolsey with a short mohawk, arms crossed, standing in a cannabis greenhouse during her years as a retail Vice President

My Story

An Unconventional Career

0115 years in sales, leadership, and operations.
02Waitress, 911 dispatcher, then healthcare staffing manager.
03Store manager to Vice President of Retail in three years.
04Led a team of 700 people across two states.
05Opened 32 stores.

The Woman Who Stopped Showing Up for Herself

I was so good at showing up for everyone else that I stopped showing up for me. Then a health scare involving a tumor made the cost impossible to ignore.

I started telling myself the truth and rebuilding self-trust, one small action at a time.

Ownership isn't blame. It's deciding what happens next.

The Work

What I Do Now

Cover of Forge Your Freedom by Connie Woolsey: Take Ownership, Build Self-Trust, and Break Every Excuse.

Here's an early look at the cover. The final version may look a little different.

The Book

Forge Your Freedom

Take Ownership, Build Self-Trust, and Break Every Excuse. Coming January 2027, with a foreword by Becca Powers.

Learn about the book

When I'm not writing, you'll find me on our ranch in Northwest Florida with my husband Brandon, our bulldog Duke and a 350-pound pig named Pig. Yes, really.

In Their Words

"I partnered closely with Connie for over three years as her HR business partner. She is a leader who balances empathy and operational excellence, making tough decisions while remaining relatable and inspiring. I witnessed her growth in accountability and ownership, making her not just a respected operator but a mentor who commanded trust and attention from hundreds. When Connie spoke, the team listened, and followed. She is truly one of the most talented leaders I've worked alongside in my career."

Headshot of Alicia CatataoAlicia Catatao, Vice President of HR

“Connie is an effective operator and builder of teams. She built Sunnyside's Florida retail from the ground up into a market leader, then successfully translated those learnings across states, no small feat in a complex, fast-moving environment. What sets her apart is how she does it: with a genuine, people-first approach that develops strong teams and prepares leaders for what’s next. Connie doesn’t just drive results, she builds organizations that can sustain and scale them. Any business navigating transformation would benefit from her leadership.”

Cory Rothschild, President of Retail, Cresco Labs

The Standard, on Sundays

A quiet place to start keeping your word to yourself

Every Sunday I send one short letter about the promises we make to ourselves and how to actually keep them. When you join, you'll get the Ownership Starter free.

One email a week. Unsubscribe anytime.

One Kept Promise at a Time

I can't hand you a different life. I can help you keep your word to yourself.

You are your problem. You are your solution.

Meet ConnieGet the Ownership Starter

Get the Ownership Starter. You'll also get The Standard, my Sunday newsletter. Unsubscribe anytime.

Connie Woolsey with arms crossed and a soft smile, wearing a black blazer

CBW Collective

Become someone you can count on.

The CBW Collective LLC, PO Box 17, Clarksville, FL 32430
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