The Chicago Journal

Midlife Women Reclaim Power at Transformative Retreats

Midlife Women Reclaim Power at Transformative Retreats
Photo Courtesy: Lisa Callahan / Kari Morin

For many women, life between the ages of 30 and 70 is a balancing act. Between demanding careers, raising kids or caring for aging parents, and running households, even vacations can feel like work—often centered on everyone else’s needs. The result? Women end up depleted, disconnected from themselves, and unsure when they last had the space to ask: What do I really want?

With their Best Chapter Yet Retreats, Lisa Callahan and Kari Morin have discovered something powerful: women heal and grow best in community. Their next gathering, “Brave and Boundless,” takes place October 3–5, 2025, in Chicago, and it’s designed to give women something they rarely grant themselves — a pause.

When women arrive, the agenda is already set. Thoughtfully prepared meals appear without anyone needing to plan or prep. Time is structured yet spacious, with room for both reflection and connection. 

Surrounded by like-minded women, attendees are free from the mental load of making sure everyone else is happy. Instead, the only requirement is to show up — and allow themselves to be seen, supported, and inspired.

Born From Conversations That Matter

These retreats were born out of the podcast they co-host, “The Things We Know.” Two coaches, speakers, and women in midlife themselves, Lisa and Kari explore the truths, struggles, and possibilities of this life stage. Week after week, they heard from listeners who resonated deeply with their conversations but longed for something more than just listening. They wanted to experience that sense of belonging and encouragement in real life.

“The Best Chapter Yet” retreats were born from that need—a way to turn inspiration into action and create a welcoming space where women can gather, be real, and leave with renewed clarity and confidence. 

Held in inspiring locations like Laguna Beach, CA, Chandler, AZ, and Chicago, these retreats offer the perfect backdrop for transformation. 

A Counter-Current to Today’s Cultural Messaging

This space for self-reclamation feels especially urgent in today’s climate. Across the United States, women are watching their rights erode, from reproductive freedoms to workplace equity. 

In subtle and not-so-subtle ways, the message many receive is that their value lies in nurturing others versus honoring their own dreams.

But women aren’t standing for that. They are seeking ways to reclaim autonomy, agency, and joy—not just for themselves, but for their daughters, nieces, and granddaughters.

“The Best Chapter Yet” philosophy is simple: when a woman reconnects with what matters to her, she not only changes her own life — she becomes a catalyst for change in her family, workplace, and community.

Why “Time for Yourself” Isn’t Selfish

At their past retreats, they have explored the transformative ripple effect of self-prioritization. For example:

  1. Saying No Means Saying Yes to Yourself – Boundaries aren’t walls; they’re doorways to your own well-being. When women say “no” to constant overextension, they create space for rest, creativity, and purpose.
  2. Your Purpose Evolves – Many attendees discover their life’s purpose isn’t static. Whether they’re entering a new career phase, becoming empty nesters, or navigating personal reinvention, they leave with clarity on what they want now — not just what they wanted 20 years ago.
  3. Your Story Has Power – They walk participants through the arc of their lives, helping them see how much they’ve already overcome and accomplished. This process unlocks the belief that their next chapter can be the best one yet, regardless of age.

The Power of Women in Community

There’s something irreplaceable about gathering with women who understand your life stage. Stories are shared without judgment. Laughter flows easily. The burdens of “keeping it together” fall away.

Attendees often say they leave feeling lighter, more grounded, and more hopeful—not just because they’ve set new goals, but because they’ve felt the solidarity of others who believe in their potential.

Why Now Matters

In a culture that often asks women to “be everything for everyone,” taking intentional time away to focus solely on yourself is a radical act. Doing it in a room full of other women doing the same? That’s revolutionary.

The Best Chapter Yet” retreats aren’t about escape—they’re about return. Return to yourself, your voice, and your vision for the future. Because when women are brave enough to claim what they want, they become boundless in what they can create.

Join “The Things We Know” mailing list to be the first to hear about upcoming retreats—with dream destinations like Palm Springs and Costa Rica on the horizon.

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