Confidence in Women Is Still Interpreted Differently
There was a recurring theme throughout the Breaking Barriers fireside chat at the 2026 Connecticut Women in Insurance Summit: leadership for women often comes with a different set of expectations.
Not because women are less capable.
Not because they lack ambition.
But because many women still find themselves navigating industries where leadership has historically looked, and sounded, very different.
During the conversation, Angela Ripley, Owner and President of VW Brown Insurance Service and 2025–2026 Big “I” Chair, and Lisa Lounsbury, President of Big I Connecticut and Big I New York and Co-Founder of Catalyit, shared honest reflections on leadership, visibility, mentorship, and the realities of growing into positions of influence within the insurance industry.
What made the discussion resonate so deeply was not just their accomplishments, but the honesty behind the journey.
Leadership Doesn’t Always Start with Certainty
One of the most relatable moments from the conversation came when Angela shared that insurance was never originally part of her plan.
“I graduated with a degree in marketing with a concentration in advertising, and I really wanted to do sports marketing.”
After struggling to find the right opportunity immediately after graduation, Angela eventually joined her father’s insurance agency and started in claims, an experience she candidly described as difficult, but incredibly foundational.
“Great foundation, worst job for me ever.”
From there, she transitioned into marketing, sales, and eventually agency leadership.
What made this part of the conversation so compelling was how deeply human it felt. Leadership journeys rarely begin with certainty. Many begin with simply being willing to learn, adapt, and say yes to opportunities before feeling fully ready.
The Visibility Gap Still Matters
One of the most significant moments of the fireside chat centered around Angela becoming only the second female national chair of the Big “I” in more than two decades.
Lisa reflected on the significance of that accomplishment while also acknowledging how overdue that representation feels.
“She’s the second female leader of it… that by itself — drop the mic.”
Angela herself addressed the milestone with humility and honesty.
“It’s sad that it took 22 years for another woman to come along.”
That moment resonated deeply throughout the room because it highlighted two truths simultaneously:
1. The industry has made meaningful progress and 2. There is still more work to do.
Representation matters. Visibility matters. Seeing women step into influential leadership positions helps create a clearer path for future generations entering the industry.
The Confidence Gap Isn’t Always About Capability
Throughout the conversation, both Angela and Lisa spoke openly about the nervousness and self-doubt that can accompany leadership opportunities, even for highly accomplished professionals.
Angela described walking into construction-focused client meetings earlier in her career and feeling the pressure of needing to establish credibility immediately.
“I had to learn how to walk in there with confidence.”
Later in the discussion, Lisa connected those experiences to the broader issue of imposter syndrome that many women continue navigating professionally.
“I think women suffer a lot from imposter syndrome.”
What made this conversation powerful was that neither speaker framed uncertainty as weakness. Instead, they normalized it.
Leadership confidence does not always arrive before action.
Often, it develops because of action.
Balancing Leadership and Life
Another major theme from the discussion was the reality of balancing leadership responsibilities alongside personal and family life.
Angela spoke candidly about raising her daughters while simultaneously managing agency leadership, national leadership commitments, mentoring responsibilities, and a demanding travel schedule.
Rather than describing balance as something perfectly achievable, she offered a more realistic perspective.
“It’s never a balance… balance means a scale.”
Instead, she described leadership and life as something closer to harmony, continuously adjusting, prioritizing, and moving forward without expecting perfection.
That perspective resonated strongly because it reflected the lived reality of so many professional women in the room.
The Importance of Stepping Forward Anyway
Perhaps the most impactful takeaway from the entire conversation came toward the end of the fireside chat, when Angela shared advice for women considering leadership opportunities.
“Stop doubting yourself.”
And then, more importantly:
“Just go. Just go enjoy yourself… just walk in the door.”
It was a simple message, but one that clearly resonated throughout the room.
Not because leadership suddenly becomes easy.
Not because fear or uncertainty disappear.
But because waiting to feel perfectly ready often means never starting at all.
At the Connecticut Women’s Summit 2026, Angela Ripley and Lisa Lounsbury didn’t just speak about leadership. They modeled what thoughtful, supportive, authentic leadership can look like and reminded attendees that growth often begins the moment we decide to step forward anyway.
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