Episode Description
In this soulful and transparent conversation, I’m joined by the incredible Jenna Kennedy to pull back the curtain on what happens when the "dream life" no longer feels like a dream.
Jenna shares her powerful story of achieving seven-figure success only to shut it all down overnight after a battle with shingles and a deep realization of her own unhappiness.
Together, we dive into the messy, beautiful process of an ego death, the intersection of mental health and entrepreneurship, and how to find a sense of safety that isn’t tied to your bank account or your Instagram following.
If you’ve been chasing external markers of success but still feel empty, this episode is a warm invitation to return to your internal fulfillment.
Themes:
We explore why checking all the boxes—the money, the house, the marriage—often leads to an "insatiable hunger" rather than the peace we were promised.
Jenna discusses how her body literally forced her to stop, and why we often don't even realize we're stressed until our physical health reaches a breaking point.
What happens when you strip away your titles and achievements? We discuss the identity crisis that follows shutting down a business and how to rediscover who you are outside of "doing."
A deep dive into how our self-worth becomes dangerously intertwined with metrics like sales and engagement, and how to "diversify your validation."
Why true security cannot be found in a partner or a paycheck, but only through a dedicated connection to something greater than ourselves.
Jenna shares her morning rituals with her daughter and how constant "conversation with God" has replaced the need to white-knuckle her way through life.
A raw look at being "in the thick of it"—understanding that while the branches of our lives want to reach heaven, our roots often have to travel through the depths of "hell" first.
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Connect with Amy:
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Connect with Jenna:
🖤Instagram: www.instagram.com/itsjennakennedy
🖤TikTok: https://www.tiktok.com/@itsjennakennedy
🖤Podcast: https://open.spotify.com/show/1v0RKe0p2fbtREGhp1KXFl?si=o4a64bBoSMG6VGCc73DwoA
Jenna Kennedy is the host of the Hope You’re Well podcast and community, where she shares real, honest conversations to help people feel better, be happier and live more fulfilling lives. After a lifetime of chasing success, she woke up one day and prayed for fulfillment so she closed down her successful 7 figure coaching business and found herself navigating depression, stepping into motherhood, and finding her way through the messy middle of self-reinvention. Now, she’s made it her mission to help others create lives that feel good to live. Through her podcast and social platforms, Jenna blends mental health, personal growth, positive psychology, neuroscience, holistic wellness, and raw honesty to help people reconnect to themselves and find everyday joy.