THE FINE LINE | with Anna (Cogswell) Kolwicz
The Fine Line | Anna (CogswelL) kolwicz
Anna (Cogswell) Kolwicz is a connector at heart — of people, purpose, and possibility. As the retreat designer behind some of the most thoughtfully curated gatherings for high-profile entrepreneurs and executives, Anna has redefined what it means to build community with intention.
Today, as the Head of Retreats at Hampton, a private network for high-growth founders and CEOs, she’s applying her expertise to create spaces where leaders can show up as their full selves, and grow because of it. Anna’s work is rooted in a core belief: real connection doesn’t happen by accident — it’s designed. Drawing from her own entrepreneurial journey and experience building retreat companies, she’s known for crafting environments where vulnerability and value go hand in hand. That looks like meeting people where they are — on Slack, in group threads, or inside a well-timed icebreaker before check-in. By intentionally creating the conditions for authentic conversations, Anna shortens the distance between strangers and accelerates trust in record time.
A natural facilitator, Anna brings a rare blend of emotional intelligence and operational rigor to every experience she leads. She understands the dynamics of group energy, and how to shift it toward meaningful engagement. Whether she’s prompting a room of executives to share their proudest moment or guiding a conversation on imposter syndrome, she knows how to hold space while moving people forward.
Anna’s retreats aren’t just offsites, they’re turning points. She curates not just where people gather, but how they gather: with openness, generosity, and momentum. Her work has helped hundreds of leaders shed the pressure to perform, embrace their full stories, and return to work with renewed clarity and connection.
As a multi-hyphenate woman navigating the demands of leadership and life, Anna models what it means to lead with both heart and humor. Her philosophy is grounded in rhythm, not balance — honoring the ebb and flow of intense seasons and slower ones. And in every room she leads, she brings that spirit of realness and joy with her.
In this conversation for The Fine Line, Anna shares the truths that have shaped her approach to community, leadership, and self-worth — from designing for connection before people even arrive, to creating a ripple effect of pride that silences imposter syndrome. Her story is a testament to what happens when we stop waiting to feel ready, and start showing up exactly as we are
What was the missing piece you noticed in how communities connect, learn, and grow together? how did you address that with your retreat company, And now at Hampton?
The biggest gap I saw was that most communities talk about connection, but very few actually design for it.
Too often, they launch custom apps or tools that their members never use. If you’re not meeting people where they already are — Slack, WhatsApp, Discord, Facebook, email — you’re creating barriers to engagement and, ultimately, to community.
At Hampton, we’re a Slack community, so to keep things simple and model the behavior we want from members, we use Slack. I’ll spin up a dedicated retreat channel for every event. It’s where I drop important info, collect intros, and ask fun prompts to get people talking ahead of time. That way, when they show up to the retreat, the ice is already broken, they’re already connected, and we skip the usual two days of figuring out who to talk to and how to fit in.
Connection doesn’t start at check-in. It starts the moment someone RSVPs.
In your experience, what do women leaders bring to the table during retreats that can inspire or challenge the broader group dynamic?
Women show up with a different kind of EQ. There’s less posturing, more perspective.
What I love most is the balance: vulnerability paired with action. Women will share something real and then follow it up with a tool, a framework, or a takeaway. That honesty and “give back” mentality shifts the energy in the room and gives everyone permission to drop the facade, get to what matters, and create an environment of mutual support.
What do you think companies or organizations can do to better support working women?
Treat support as a strategy, not charity.
Build structures that allow women to grow.
That could mean mentorship, flexibility, or simply fostering a culture where vulnerability is welcomed.
Most importantly, prioritize real, ongoing connection. When people feel seen, supported, and heard, they stay. And they thrive. Employee retention is good business.
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Follow Brigade Events and stay tuned for the next iteration of The Fine Line at @brigadeevents.
We’d be honored to include you — or a woman you admire — in this series. If you or someone you know has a story to share, we’d love to hear from you. Reach out to us at carly@ingoodcompanypr.com. Together, we can uplift, support, and redefine leadership for the next generation.
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