• Live Event

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

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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Meet Your Hosts

Tim Parr

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

Tim Parr is the CEO and Founder of CADDIS, an eyewear brand that crushes age stereotypes. He believes in defying our society’s addiction to youth and fueling getting older and owning it.

Tim got his start as an entrepreneur when he founded Swobo, a California action sports clothing company that expanded into a bike company. After that he worked for some of the world’s most respected brands, such as Patagonia, L.L. Bean, Filson, and many more. He has lectured at the Stanford School of Design, Modern Elder Academy, San Francisco Academy of Art, and the California College of Arts.

In 2013, he formed a bluegrass band and hit the road touring the Western United States – despite not knowing how to play the guitar. He has made a successful life out of defying norms and expectations and exploring opportunities based on his interests and instincts rather than what mainstream thinking would have us believe is the “proper” way to do things.

Now he’d like you to understand how awesome your life can be when you embrace possibility and “do the thing” you have been dreaming about doing.

Derek Gehl

Chief Executive Officer

Derek Gehl is a serial e-commerce entrepreneur, speaker, and author. After spending the first decade of his professional career growing one of world’s first Internet marketing companies to over $30 million in sales, he decided that leading a company of 100 employees in offices in two countries wasn’t for him – so he sold the company to a private equity group and refocused his life on the things he loved most: spending time with his family, pursuing his passions, and building and growing online businesses. In 2024, after doing some consulting for MEA, Derek had his own transformational experience at a Navigating Transitions workshop, which inspired him to join the company as Chief Marketing and Technology Officer and then take on the role as CEO, spearheading our mission to reimagine midlife and build a global pro-aging community that inspires people to thrive in the second half of life.

Discover Upcoming Wisdom

The Bonus Round: Crafting a Meaningful Post-Work Chapter

May 22, 2025 12:00 PM PT 03:00 PM ET

What happens when your career is no longer the centerpiece of your identity?

Join host Kari Cardinale with special guest Dr. Pam McLean – psychologist and co-founder of The Hudson Institute of Coaching – for a wisdom-rich conversation.

DISCOVER HOW TO:

  • Embrace your “bonus round” with creativity and renewed purpose
  • Transform your relationship with time in this exciting new phase
  • Unlock growth opportunities that weren’t possible during career-focused years

For over four decades, Pam has guided thousands to thrive through life transitions. Her pro-aging mindset replaces outdated retirement thinking with a bold vision for your wisdom years.

Whether you’re planning your next move or already in transition – gain the clarity you need to make this chapter your most fulfilling yet!

The Enneagram as a Key to Creativity & Self-Knowledge

June 3, 2025 12:00 PM PT 03:00 PM ET

Join us for a fascinating live conversation with Russ Hudson, one of the world’s foremost Enneagram teachers, as we explore how this ancient and powerful framework can unlock new dimensions of creativity, clarity, and personal growth.

Hosted by MEA’s Kari Cardinale, this session offers a rare opportunity to learn directly from Russ, whose compassionate and deeply insightful approach has helped thousands navigate their inner worlds and live with greater intention.

Whether you’re craving deeper self-awareness, more authentic expression, or a fresh perspective on your next chapter, this live chat about the Enneagram can offer a transformative path forward.

In this live chat, learn how to:

  • Use the Enneagram to better understand your patterns, motivations, and blind spots
  • Break free from limiting habits and reconnect with your core essence
  • Tap into creative energy that may have been dormant or underused
  • Understand what each of the nine types needs in order to flourish

This is so much more than a personality tool – it’s a path to living with more truth, creativity, and meaning.