Graceful Growth & Hard Conversations: Inside the Planning Business

In this honest and insightful conversation, Reagan sits down with longtime friend and fellow planner Tara Skinner to explore the nuanced realities of building—and sustaining—a planning business with integrity. Together, they unpack what experience really looks like in an industry that often rewards surface-level polish over operational depth.They talk candidly about vendor loyalty, pricing structures, client education, and the tricky terrain of team building as your business scales. From flat fees to percentage-based models, from early missteps to multi-million-dollar productions, Tara shares the moments that shaped her sixteen-year career—and the lessons that continue to guide her growth.At its core, this episode is about navigating evolution with grace: growing your team, maintaining standards, and preserving relationships, even when hard conversations are required. For planners, creatives, and clients alike, it’s a compelling look behind the curtain.Want more behind-the-scenes stories, trends, and inspiration?Subscribe to our newsletter for inspiration, updates, and expert advice.Follow us on Instagram and TikTok for behind-the-scenes moments, trending ideas, and so much more.Tune in to our Wine and Dine Me Podcast in Apple Podcast and Spotify, where we explore all things weddings, life, and business.