Compass Coaching Retreats; Navigating Midlife Together

Immersive, Experiential Self-Discovery Programs for Personal Renewal

You’ve spent years taking care of others, building a career, and managing responsibilities. Somewhere along the way, your own needs and dreams may have been pushed to the background. You might not know exactly what you want next—but you know it’s not more of the same.

Compass Coaching Retreats are designed for people in midlife who are ready to press pause, take a breath, and ask: What do I really want now?

This isn’t therapy, and it’s not a vacation. It’s a supportive, guided experience that helps you step away from the noise and reconnect with yourself in a deeper way—through reflection, meaningful conversations, and real-life experiences that bring clarity, direction, and energy back to your life.

About the Retreats

Compass Coaching Retreats are small-group experiences for adults somewhere along the journey through midlife, who are navigating change or simply feeling stuck. Whether you’re contemplating retirement, craving more creativity, or just sensing it’s time for something different, this is a space to begin.

Each retreat blends coaching, experiential learning, and personal reflection in peaceful and inspiring settings. You’ve got a lifetime of experience, all you need is to bring is curiosity, a sense of adventure, and a willingness to explore what’s next for you, because you know, you no longer want to continue doing what you’ve done your whole life.

What Brings People Here

• You feel stuck in your routine and need a fresh perspective.
• You’ve achieved a lot—but something feels missing.
• You’re navigating a big change (retirement, empty nest, a career shift).
• You want more meaning, creativity, and connection in your life.
• You haven’t asked yourself “What do I want?” in a long time.

What You’ll Experience

• A respectful, judgment-free space to reflect and explore.
• Coaching prompts to help you clarify what you want more (or less) of.
• Group conversations that are supportive—not performative.
• Creative and nature-based activities to help you reconnect with joy.
• Quiet time for yourself, and meaningful connection with others.

Program Formats

In-Person Immersive Retreats
These 3–5 day retreats take place in peaceful, inspiring locations designed to help you slow down and hear yourself think.

Includes:

• Daily group coaching and facilitated conversations
• Guided journaling, movement, and creative reflection
• Local exploration and solo integration time
• Evening circles to connect and share
• A private pre- and post-retreat coaching session with one of our Coaches

Upcoming Retreats:

• Northern California Coast – January 2026
• Vancouver Island, Canada – Summer 2026
• Portugal or Spain – Fall 2026

Virtual Compass Circles
If you’re not ready to travel, the Virtual Compass Circle is a welcoming place to begin your inward journey from the comfort of home. It’s especially designed for people new to this kind of work, or who simply want a reflective pause.

A 3-month online group experience for clarity, connection, and next-step direction.

This is for you if:

• You feel the nudge for change but don’t know where to begin
• You’ve never done coaching but are curious
• You’re craving something that feels meaningful and grounded

What’s included:

• Six Zoom sessions (75 minutes, twice a month)
• A personal “Compass Map” to chart what matters to you
• Weekly journaling prompts and creative exercises
• One private 1:1 session with one of our Coaches
• Optional buddy pairings for extra connection

Next Cohort Begins: October 2025
Investment: $895
Early registration: $775 before September 5, 2025

This isn’t a course. It’s a circle.
A place to reconnect with what’s real, what’s possible, and what’s next.

Themes We Explore

• What’s working—and what’s not—in your current life
• Who you are beyond your roles and responsibilities
• What brings you meaning, creativity, and joy
• How to make space for something new—without having to blow it all up

This Might Be for You If…

• You’re in or approaching a major life change (planned or unplanned)
• You want to feel more awake, grounded, and intentional
• You’re looking for thoughtful time for yourself—without guilt
• You want growth that’s real and grounded, not fluffy or overwhelming

How to Begin

You don’t have to have all the answers. You just have to want something different.

Compass Coaching Retreats offer you a supportive space to begin again—with clarity, connection, and meaningful momentum.

Experience immersive self-discovery.
Learn to live deeper and dream bigger.
It’s your time now.
Where will your compass point you next?

To schedule a discovery session, email: jennifer@leadership4life.com

Follow my Midlife Musings on Substack:  https://substack.com/@jennifersilverstein