On June 6, women from across Hampton Roads gathered inside the stunning Glass Light Hotel in Norfolk, Virginia, for an afternoon of meaningful conversation, strategic connection, and collective growth.
Brunch with Bosses has never been about collecting business cards or making surface-level introductions. It’s about creating a space where ambitious women can have the conversations they’re craving but rarely find room for in their everyday lives.
For three hours, executives, entrepreneurs, creatives, and changemakers pulled up a seat at the table and did what women do best when they feel safe enough to do so: they shared honestly, challenged one another thoughtfully, and left stronger than they arrived.
The room was filled with women from a wide range of industries, including mortgage professionals, Department of Defense contractors, educators, social workers, filmmakers, entrepreneurs, and nonprofit leaders. Different backgrounds. Different experiences. One common thread.
A desire to grow, lead, and win without having to do it alone.
One of the most powerful themes that emerged throughout the afternoon was the evolving definition of success.
For years, many of us were taught that success meant climbing the corporate ladder, earning more money, collecting titles, and pushing through exhaustion in the name of achievement.
The women at Brunch with Bosses challenged that narrative.
The conversation shifted toward something deeper: peace, fulfillment, alignment, impact, and the freedom to build lives that feel as good as they look. Again and again, attendees spoke about wanting success that doesn’t require sacrificing their health, their relationships, or themselves.
Success isn’t just what you’re building. It’s who you’re becoming while you build it.
After the introductions, we kicked off the afternoon with our LeadHERship Identity Quiz, designed to help women identify how they naturally show up as leaders.
Participants were given a rapid-fire quiz to discover their primary and secondary leadership archetypes.
The quiz divided the room into four distinct archetypes:
The Mogul: Driven by impact, results, and influence. Decisive and strategic, but prone to impatience and burnout.
The Visionary: Magnetic, optimistic, and highly creative. Great at inspiring others, but struggles with overcommitment.
The Architect: Thoughtful, disciplined, and the ultimate behind-the-scenes structural backbone. Analytical and reliable, but prone to analysis paralysis and perfectionism.
The Connector: Leads with empathy, trust, and deep relationship-building. They are the “glue” of any team, but must watch out for people-pleasing and undervaluing their own voice.
The room quickly realized that leadership doesn’t look one way, and there is no single blueprint for influence.
The exercise sparked powerful conversations about strengths, blind spots, and how different leadership styles complement one another. Instead of competing for space, we explored how their differences create stronger teams, stronger organizations, and stronger communities.
Another recurring theme in the room centered around navigating leadership as women, particularly in male-dominated environments.
Many attendees shared experiences of being the only woman or the only Black woman in the room. They spoke candidly about the pressure to prove themselves, the challenges of being heard, and the invisible expectations that often accompany leadership roles.
The takeaway was clear: Your voice does not become valuable because someone else validates it. It is valuable because of the expertise, perspective, and experience you bring to the table.
Attendees exchanged practical strategies for advocating for themselves, communicating with confidence, and maintaining their influence without compromising their authenticity.
One insight resonated across the room: Confidence is not about being the loudest voice in the room. It’s about trusting that your voice belongs there and showing up when it matters.
We began our roundtable discussions with a topic that continues to be top of mind for professionals and entrepreneurs alike – Personal Branding.
Jasmine, our co-founder and brand strategist, challenged attendees to think differently about their brand. She told attendees that your personal brand isn’t something you turn on when you’re ready. It’s already happening in real time.
Every interaction, every opportunity, every conversation is shaping how people experience you. The question isn’t whether you have a personal brand. The question is whether you’re intentionally building it.
For women struggling with visibility or social media anxiety, her advice was simple: Stop treating your content like a broadcast and start treating it like a conversation.
Focus on the expertise you want to be known for. Share your perspective consistently. Allow your personality to be part of the message. People don’t remember everything you do. They remember what you stand for.
If you’ve ever questioned whether you belong in the room, you’re not alone. It’s a conversation that struck a chord with nearly every woman at the table.
Attendees discussed the reality of self-doubt and the pressure many women feel to overperform in order to prove their worth. Together, they shared practical ways to navigate those moments:
Perhaps the most important reminder was this: You don’t need permission to own your expertise. You belong in every room you’re invited to.
Perhaps the most needed conversation of the afternoon centered around over-functioning.
Many attendees admitted they had become the default problem-solvers in their workplaces, businesses, families, and communities. While that level of responsibility can feel admirable, it often comes at a cost:
The discussion challenged attendees to rethink what effective leadership actually looks like.
Strong leaders don’t carry everything. Strong leaders create systems, establish boundaries, and empower others to rise.
A few practical reminders emerged:
Protecting your peace is not selfish. It’s a leadership strategy.
We closed the afternoon with one of our favorite traditions: the Ask & Offer Exchange.
Each woman was invited to share a resource, expertise, opportunity, or connection she could offer the room, along with something she needed support with. Within minutes, introductions were being made, resources were being exchanged, and new partnerships were beginning to take shape.
It was a beautiful reminder of what Boss Up Girl has always believed: When women have access to the right relationships, resources, and rooms, incredible things can happen.
Brunch with Bosses: Hampton Roads wasn’t simply a networking event. It was a reminder that leadership doesn’t have to be lonely. That success gets sweeter when it’s shared. And that every woman deserves a seat at a table where she can be fully seen, fully supported, and fully herself.
To every woman who joined us, thank you for your wisdom, your vulnerability, and your willingness to pour into one another.
We’re already looking forward to the next city – Charlotte, You’re Up Next!
Because when women gather with intention, everybody wins!
Written By:
Jasmine O. Dyson
Marketing Strategist & Co-Founder of Boss Up Girl Co.,
Jasmine helps ambitious women turn their expertise into influence, opportunities, and impact. With a passion for marketing, leadership, and experiences, she shares actionable insights designed to help women win in life, career, and business.
