In this episode of Creativity Connects with Mikki Wilson, we sit down with Alyssa Conary, Membership Director at Creative Collective, for a grounded conversation about what it really means to hold community.

Rather than focusing on growth for growth’s sake, Alyssa reflects on community-centered leadership as a practice rooted in care, consistency, and responsibility. Drawing from her work supporting women entrepreneurs and her involvement with Historic Salem, Inc., she shares how history, place, and stewardship shape the way she approaches leadership—both formally and behind the scenes.

This conversation goes beyond surface-level ideas of connection and explores the quieter labor of maintaining trust, setting boundaries, and making decisions that honor both people and institutions over time. Alyssa offers a thoughtful perspective on sustainability, reminding us that not everything needs to scale—some things simply need to be held well.

What community-centered leadership looks like in practice

How history and place influence modern leadership decisions

Holding institutions, not just moments or momentum

The unseen labor of maintaining trust and sustainability

Why care, boundaries, and pacing are strategic leadership tools

“Community isn’t just about bringing people together. It’s about what you’re willing to hold when people show up as their full selves.”

“A lot of the work I do is invisible. It’s listening, following up, remembering details, and creating a sense of safety people don’t always realize they need.”

“You can’t build trust through systems alone. Trust comes from consistency, presence, and doing what you say you’re going to do.”

“Holding community doesn’t mean carrying it all yourself. It works best when responsibility is shared.”

“People think community is events, but it’s really about relationships — and relationships take care.”

Alyssa Conary is the Membership Director for Creative Collective, where she supports and nurtures a community of entrepreneurs and creatives across the North Shore. Alyssa is known for her human-centered approach to community care, helping members feel welcomed, supported, and connected while strengthening the relationships that make the creative economy thrive. She is also involved with Historic Salem, Inc., bringing a place-based and preservation-minded lens to her leadership work.

Mikki Wilson is the host of Creativity Connects with Mikki Wilson and the founder of Dot Connector Consulting. Known for her ability to facilitate meaningful connections, Mikki cultivates conversations that go beyond the brand to highlight the lived experiences, leadership, and “messy middles” behind women’s entrepreneurial journeys.

Creativity Connects with Mikki Wilson is a Creative Collective podcast that goes beyond the brand to explore the authentic journeys of women entrepreneurs in the creative economy. Produced by Randyll Collum for Peabody TV, the series amplifies the voices of Creative Collective members and the moments, motivations, and pivots that shape their work. Sponsored by Jenni Stuart Fine Jewelry.

Website: creativecollectivema.comLinkedIn: https://www.linkedin.com/in/alyssa-conary-1b59173b/Email: [email protected]Instagram: @alyssagaconary

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