Season of Discovery — A Women's Life Design Retreat

Event Summary

Set in the heart of Boston at the Canopy by Hilton Boston Downtown, Season of Discovery is a thoughtfully designed retreat for women ready to design their next chapter—blending the proven Designing Your Life framework with meaningful conversation, embodiment, and restorative practices. You don't need the woods to reconnect with yourself; sometimes the clearest reflection happens in the middle of a vibrant, walkable city.

Through interactive exercises, you'll explore and reframe the beliefs that shape your choices — personal and social — while building creativity, confidence, and clarity. We'll use tools like energy and balance mapping, surface the narratives that keep us stuck, and design Odyssey Journeys, where you'll imagine three potential futures and prototype the most compelling elements of each.

Drawing on the same design thinking principles introduced in the New York Times bestselling book Designing Your Life, you'll explore practical tools to help you craft a future filled with purpose and possibility. Alongside these life design tools, you'll experience coaching practices that help quiet your inner critic—offering more than one pathway toward clarity and meaningful action.

Season of Discovery is led by Catherine Dalipe, founder of Indigo & Magenta Consulting and a Certified Designing Your Life Facilitator and Coach. Drawing on more than 30 years of experience in international education, leadership, and coaching, Catherine brings together evidence-based life design tools with thoughtful facilitation to help women navigate change with greater clarity and confidence. She is joined by Lauren Kayserman, founder of LGK Coaching and a fellow Certified Designing Your Life Coach. Together, they create a warm, engaging, and supportive environment where women can reflect, reconnect, and intentionally design what's next.

Who This is For

If you're sensing it's time for this kind of space, this retreat may be for you if you:

• Are navigating a transition—career, life chapter, identity, or simply wondering, "What now?"
• Are craving clarity without pressure or forced answers
• Sense your energy, creativity, or confidence has dimmed and are ready to reconnect with it
• Want time to reflect and leave with a grounded path forward
• Value depth, connection, and thoughtful facilitation

What You’ll Experience

• A welcoming community of women navigating their own next chapter
• A virtual Community Welcome Call before the retreat
• Interactive life design exercises and practical tools
• Coaching practices to quiet your inner critic and reconnect with your own voice
• Guided reflection and meaningful small-group conversation
• Embodiment and restorative practices woven throughout
• Spacious time to reflect, reconnect, and create a path forward

Program Details

A pre-retreat Welcome Call to meet the women you'll be designing alongside

• Meet your community and share what brought you here

Day 1 — Saturday, October 24

• 8:00 AM - 5:00 PM Arrival, grounding, kick off your life design experience, reflection, embodiment and restorative practices, and an optional nature-based reset

Day 2 — Sunday, October 25

• 8:00 AM - 3:00 PM || Deepening the work, integration, clarity, and next steps

A detailed schedule will be shared with confirmed participants.

Retreat Price (exclusive of Eventbrite fees)

Retreat Only:

• Early Bird Ticket: $995
• Regular Ticket: $1,295

Retreat + Coaching Package: (Includes retreat + 2 group coaching sessions and 1 1:1 coaching session; coaching sessions are 1 hour in length)

• Early Bird Ticket: $1650
• Regular Ticket $1950

Note: Early Bird tickets for both the Retreat Only and Retreat + Coaching packages are available to the first 15 registrants.