• 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

Register for the Live Event

Zoom Live Event Registration
Name
Name

Watch the On-Demand Session

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

Finding Your Center: Building Resilience to Withstand Any Storm

June 17, 2025 2:00 PM PT 05:00 PM ET

Join us for an immersive live conversation with Pico Iyer, bestselling author and one of our most trusted voices on finding peace in turbulent times.

Kari Cardinale and Pico will explore how to transform life’s inevitable chaos into unshakeable inner calm. Pico’s decades of study with spiritual masters like the Dalai Lama and immersion in cultures across 80+ countries has revealed timeless practices for staying centered when everything around us feels uncertain.

In this live chat, learn how to:

  • Access deep calm: no apps or lengthy rituals required, just tools that work when you need them most
  • Transform chaos into your teacher: learn to see disruption as an opportunity for growth rather than something to fear
  • Find your authentic center: not the calm you perform for others, but the unshakeable peace that becomes your foundation

This is about becoming so grounded in yourself that external storms can’t shake your inner foundation.

You Are Enough: The Courage to Feel Complete

July 8, 2025 12:00 PM PT 03:00 PM ET

What if success isn’t about doing more but finally feeling enough?

Blake Mycoskie – entrepreneur, philanthropist, author, and founder of TOMS – joins us for an unfiltered conversation about what happens when chasing achievement stops working.

After building a $600M brand and giving away millions of shoes, Blake hit a wall that success couldn’t fix. What followed was a personal reckoning and a complete rewrite of what it means to live a meaningful life.

In this candid live session with MEA CEO Derek Gehl, Blake shares the hard-won lessons behind his shift from relentless striving to grounded self-worth. You’ll hear how he helps other high performers step off the hamster wheel and reconnect with who they are beyond the résumé.

If you’ve ever asked yourself, Is this it?, this conversation is for you.

Rewilding: Reclaiming Your Self-Agency in a World That Wants to Tame You

July 16, 2025 1:00 PM PT 04:00 PM ET

What if the parts of you that feel “too much” or “not enough” are actually the truest signals of who you are?

Join author, horse whisperer, and founder of the EQUUS Experience®, Kelly Wendorf, for a live, warm conversation with MEA’s Derek Gehl on reclaiming the voice you muted, the instincts you second-guessed, and the self you edited to fit in.

This is a callback to the wilderness within – a space where ancient earth wisdom meets modern neuroscience, and the animals still know something we’ve forgotten: how to live in full alignment with our nature.

Here’s some of what might rise to the surface:

  • The hidden ways your body remembers old survival strategies and how to teach it new, more expansive ones.

  • What harmonious assertiveness looks like in real life (and why it’s not the same as people-pleasing or powering through)

  • Ways to dissolve the inherited roles, rules, and survival masks that keep you small

  • How to reconnect with your body’s deep intelligence through nature-based and equine-guided practices

Come if you’re ready to shed the scripts and step back into the wild wisdom of your true self.

Discovering the Hero’s Journey in Midlife

July 30, 2025 12:00 PM PT 03:00 PM ET

Join us for an intimate talk with Ben Katt, meditation teacher, former minister, and author of The Way Home: Discovering the Hero’s Journey to Wholeness in Midlife, as we explore how ancient wisdom traditions can guide us through the challenging transitions of midlife and beyond.

Hosted by MEA’s Kari Cardinale, this session offers a unique opportunity to learn from Ben, whose compassionate approach has helped countless individuals transform their lives and discover deeper joy, purpose, and meaning.

In this live chat, you can learn how to:

  • Identify where you are on your own Hero’s Journey
  • Embrace vulnerability as a pathway to personal power
  • Connect with your inner wisdom even during times of uncertainty
  • Incorporate simple contemplative practices to gain clarity and direction

This is more than just a discussion – it’s an invitation to embark on your own Hero’s Journey toward wholeness and fulfillment.

Life Reimagined: Unlocking the Power of Purpose

August 6, 2025 12:00 PM PT 03:00 PM ET

What if purpose isn’t something you chase but something you live, one moment at a time?

World-renowned purpose pioneer Richard Leider joins MEA’s Kari Cardinale for an inspiring conversation about how to move from asking “What’s next?” to “What really matters?”

Drawing from decades of coaching, research, and his own lived experience, Richard shares how everyday choices — what he calls “little p” purpose — can lead to big shifts in how we live, age, and connect. You’ll hear why purpose is essential not just for meaning, but for well-being and longevity, and how to begin reconnecting with it now, no matter your stage of life.

If you’re standing at a crossroads and craving clarity, this conversation is your invitation to start living on purpose.