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MY MILESTONE MOMENT: CHOOSING MYSELF

How Choosing Yourself Can Transform Your Life and Open Doors You Never Expected

Rosalind M.  Simmons, Founder and Chief Executive Officer on Influential Women
Rosalind M. Simmons
Founder and Chief Executive Officer
Financial Chaplain Group
MY MILESTONE MOMENT: CHOOSING MYSELF

I had just 90 seconds to introduce myself to the Woodlands Area Chamber of Commerce.

When the program ended, Dr. Stacey Denise, who had never met me, approached me and immediately recommended that I apply for the Greater Houston Black Chamber 2026 Pinnacle Award.

But why?

What had she seen in 90 seconds that made her believe I might qualify?

I had never applied for any type of award before. Still, I decided to take the leap and complete the application.

To my surprise, I became a semifinalist.

Then, on August 31, I became a finalist.

A few days later, I came across a social media post from Tracee Ellis Ross that helped me connect the dots. She said:

“I spent years waiting to be chosen. Well, here’s the thing. I’m the chooser.”

Her message was about something many women understand: we are often taught to measure our lives by whether someone else chooses us. But our worth—and the fullness of our lives—cannot depend upon someone else making that decision.

When I read her words, a lightbulb came on.

I realized that my milestone moment was bigger than becoming a finalist.

I had finally chosen myself.

I had decided to live out loud, tell the truth about who I am and what I have experienced, and allow vulnerability to be part of my strength. That is exactly what I did during those 90 seconds at the Chamber.

And choosing vulnerability changed everything.

One by one, people began introducing themselves and saying, “We are happy to have you as a member of the Chamber.” New relationships are forming. New opportunities to support one another are emerging.

So thank you, Tracee Ellis Ross. Your words mattered.

They helped me recognize something I hope women everywhere will recognize too:

We do not have to spend our lives waiting to be chosen. We can choose ourselves.

After 38 years in publishing and authoring 15 books, I am taking that lesson seriously. I am no longer waiting for someone else to decide whether my work is worthy of recognition.

I am submitting my latest book for a book award.

Whether I win or not, something important has already happened.

I chose to enter the room.

And I hope women everywhere will choose themselves—and pursue what matters to them.


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