Episode 139

Sofi Madison: Building a Creative Career Around Family, From Retail Shop Owner to Independent Consultant

This week, we're sitting down with Sofi Madison, a former shop owner turned independent consultant who's redefining what work-life balance looks like in the North Shore. Sofi shares her journey from running Olives and Grace—a beloved retail destination—to consulting for independent retailers and hospitality teams, all while raising two boys (ages 3 and 5) in Manchester by the Sea.

In this honest conversation, Sofi opens up about the intentional decision to become a "working plus stay-at-home mom," her 9am-2:30pm work window, and why she chose to close a successful business she loved to create space for motherhood. We dig into the messy realities of balancing creative work with the demands of young children, why she's slow to sign her kids up for sports, and how she's finding creative expression through social media and Substack in this season of life.

What We Cover:

  • Seasonal routines: Why Sofi's a 5am coffee-on-the-porch person in summer but hits snooze until 6:45 in winter

  • The luxury of a single school drop-off and what slow, wholesome mornings look like at Waldorf school

  • Working compressed hours (9am-2:30pm) while running an independent consulting practice

  • Why she closed a thriving retail business when her "lens of love completely shifted" after kids

  • Navigating witching hour, car snacks, and the All Star soundtrack on repeat

  • Dinner struggles with picky eaters and the dream of everyone eating the same meal

  • The invisible labor of household management and how she and her husband divide responsibilities

  • Shrinking friend circles for quality over quantity in the mom phase

  • Using AI for dinner prep advice and vitamin guidance (but never for personal communication)

  • Being honest about romantic relationships taking a backseat when kids are young

  • Why she doesn't miss her kids when she travels for work (and the freedom in saying that out loud)

Guest Bio: Sofi Madison lives in Manchester by the Sea with her husband Tom and two sons. She's an independent consultant working with retailers and hospitality teams, helping them create intentional, human-centered experiences. Previously, she owned Olives and Grace, a curated retail shop. Sofi is also a content creator for Meet Boston (airing on NESN) where she profiles small businesses and tells the stories of Boston's creative community. You can find her thoughtful long-form writing on Substack, where she explores how hospitality spaces create connection in an increasingly digital world.

Connect with Sofi:

Key Timestamps:

  • 01:26 Meet Our Guest: Sofi Madison

  • 02:13 Rapid Fire Questions with Sofi

  • 03:50 Sofi's Morning Routine

  • 07:43 Navigating Work and Family Balance

  • 19:03 Dinner Time and Evening Routines

  • 25:54 Choosing Activities for the Kids

  • 28:33 Choosing the Right Sports for Kids

  • 32:14 Balancing Self-Care and Parenting

  • 35:45 Household Management Strategies

  • 44:19 Navigating Friendships and Relationships

  • 47:57 Embracing Creativity and Social Media

  • 50:52 The Role of AI in Daily Life

  • 56:08 Current Obsessions and Joys

  • 59:03 Conclusion and Farewell

Resources Mentioned:

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