From the “office” party for entrepreneurs to Who Da Boss?! The Brunch…and the community growing in between.

I can’t believe it’s been nearly 10 years since I randomly hopped on Instagram and invited strangers to meet me for lunch.

I was a lonely freelance journalist, watching my friends and family post about all the Christmas events they were enjoying with their co-workers.

Three days later, about a dozen girl bossess met me for the first “I Work For My D*mn Self” Christmas luncheon in 2017. I hosted another the following year and about 30 people showed up.

I threw a virtual party in 2020 (thanks to COVID) where more than 50 people logged on. The event was shelved for about three years, as I figured out what I really wanted to do with it.

I decided to bring the party back in 2025 and the turnout proved this event was here to stay.

What began as a community for people building businesses, careers, side hustles and lives on their own terms has grown into something much bigger.

And over the past year, we’ve seen that come to life twice.

First, the Holiday Party

We gathered to celebrate the wins, laugh about the chaos and simply enjoy being around people who understand what it means to work for yourself.

Entrepreneurs. Professionals. Creatives. Side hustlers. Seasoned business owners. People just getting started.

People who had different journeys but same need: community!

Then came, Who Da Boss?

This funny moment with my daughter inspired the name for our first summer brunch: Who Da Boss?!

And what happened in that room exceeded anything I imagined.

More than 50 people, from their 20s through their 60s, representing industries from law and medicine to media, finance, beauty, travel, food, education and entrepreneurship.

Two people even flew in to be there.

One attendee described the experience as “more than just a brunch.” Another said the room gave her the encouragement to finally take a leap she’d been hesitant to take.

That’s what I want IWFMDS to be.

A place to connect, grow, share, refer, collaborate and remind each other what’s possible.

Two Signature Gatherings. One Growing Community.

The rest of the year is about keeping the room alive through meeting virtually and in-person, celebrating members, sharing opportunities, creating connections growing our social platform and building community between gatherings.

From a hair-brain idea one day in 2017 to a thriving and growing community nearly 10 years later is the kind of “overnight” success story I love!

And I’m building a room where we don’t have to do it alone. 🤎

That’s the spirit of the I Work For My D*mn Self community.