Second Acts: Why Midlife is the Perfect Time to Become an Entrepreneur

Tim Parr & Derek Gehl

Your experience isn’t baggage—it’s your biggest advantage. Midlife isn’t the end of opportunity; it’s the beginning of your most meaningful work.

Join Caddis founder Tim Parr and MEA CEO Derek Gehl for a candid conversation on why entrepreneurship in midlife is not just possible, but powerful.

With decades of wisdom, networks, and real-world insight, you’re better positioned than ever to build something that matters. Midlife entrepreneurs don’t just chase ideas—they execute with clarity, confidence, and purpose.

Why midlife is a strategic advantage in entrepreneurship
How to turn your life experience into a thriving business
What younger founders lack that gives you the edge

If you’ve ever felt the urge to start something of your own—but worried it was too late—this session will change your perspective. The best time to start is now.

Register now for this free live session and take the first step toward building the business you’ve always dreamed of.

January 29, 2025 10:30 AM PT 01:30 PM ET

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Watch the On-Demand Session

Meet Your Hosts

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Tim Parr

Entrepreneur | Startup Founder | CEO | Creative Director | Brand Strategist

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Derek Gehl

Chief Executive Officer

Discover Upcoming Wisdom

The Bonus Round: Crafting a Meaningful Post-Work Chapter

Derek Gehl & Pam McLean

February 5, 2026 10:00 AM PT 01:00 PM ET

With Dr. Pam McLean and host Derek Gehl

Join host Derek Gehl in conversation with Dr. Pam McLean, clinical psychologist and co-founder of The Hudson Institute of Coaching, for a grounded look at the psychological shift that comes after a long career.

This live conversation moves beyond retirement planning to explore deeper questions of identity, contribution, and purpose when familiar roles fall away. Drawing on four decades of experience, Pam offers clear, humane insight into how people can navigate this transition with intention.

In this conversation, we’ll explore how to:

Loosen your grip on work-based identity without losing your sense of worth
Rethink contribution when titles and roles no longer define you
Relate differently to time, structure, and self-direction

Whether you’re planning ahead or already in transition, this conversation offers perspective on shaping a post-work chapter that feels meaningful and engaged.

Learn More & Register

Women Thriving Beyond Transitions: A Conversation on Power, Change, and What’s Next

Kari Cardinale, Leslie Salmon Jones & Carla Goldstein

February 18, 2026 10:00 AM PT 01:00 PM ET

Join us for a deep conversation with Leslie Salmon Jones and Carla Goldstein of the Omega Institute about navigating the uncomfortable in-between of transition, when you’re not who you were, but not yet who you’re becoming.

Drawing on decades of work with women leaders, Leslie and Carla explore what it means to move through change without trying to fix or rush it, and how we can reclaim power that feels grounded and shared rather than depleted.

We’ll explore:

Why the “messy middle” of transition is normal, not something to solve
What “doing power differently” means for women in midlife
How to retrieve the parts of yourself you’ve had to squash along the way

Whether you’re in transition by choice or circumstance, this conversation offers a different way to think about change, power, and what becomes possible when women do this work together.