DiscoverPlucky Not Perfect PodcastTraveling Through Uncertainty as a Cancer Mom Turned Midlife Explorer with Jennifer Montgomery-Lay (#33)
Traveling Through Uncertainty as a Cancer Mom Turned Midlife Explorer with Jennifer Montgomery-Lay (#33)

Traveling Through Uncertainty as a Cancer Mom Turned Midlife Explorer with Jennifer Montgomery-Lay (#33)

Update: 2025-11-04
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If you’ve ever wondered whether it’s “too late” to start over—or felt stuck between who you’ve been and who you want to become, this is the episode for you. 


Jennifer Montgomery-Lay’s story is one of unimaginable resilience. As a cancer mom for more than two decades, she’s spent much of her adult life caregiving. Instead of letting fear or past identities define her, Jenn has learned to lean into discomfort to step out into new adventures.


Jenn and Carrie met at a business networking event a few years ago. Back then Jenn didn’t have a business—just a quiet nudge that she was meant for something more. What she did have was courage.


In this episode, Jenn shares how her family traveled the world in the midst of heartbreak, chaos and uncertainty. She talks about how travel became a catalyst for healing, and how she’s now helping others rediscover themselves through adventure. We talk about perfectionism, giving ourselves permission to dream again, and what it really means to be plucky in midlife.


As Jenn said, “You’re gonna be okay. Even if you look silly. Even if you mess up. You can find people who believe in you until you believe in yourself.”


 In This Episode:

  • The uncomfortable moment that sparked Jenn’s reinvention

  • Life as a cancer mom: the raw truth, not the hashtag version

  • How a one-way ticket and a leap of faith changed everything

  • The healing power of travel and curiosity

  • Saying yes to new adventures (even when it feels scary)


Resources & Links: 


www.instagram.com/lifealloverthemap


Connect with your host: www.instagram.com/carriejobradley.

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Traveling Through Uncertainty as a Cancer Mom Turned Midlife Explorer with Jennifer Montgomery-Lay (#33)

Traveling Through Uncertainty as a Cancer Mom Turned Midlife Explorer with Jennifer Montgomery-Lay (#33)

Coach Carrie