Confessions of a "Recovering Jerk" with Jennifer Hill

In this episode of Uncharted: Your Sidekick for Life, we sit down with Jennifer Hill—a woman who has worn many titles: entrepreneur, coach, and, as she calls herself, a 'recovering jerk.'

Success, like life, rarely follows a straight line. It’s a path often paved with sacrifice, pain, and the relentless chase for an elusive “enough.”

Jennifer’s journey is one that resonates with anyone who’s ever climbed the ladder only to ask, Is this really it? You achieve, you check all the boxes, but what happens when the top feels emptier than you expected?"

Jennifer grew up with big dreams. At just five years old, she boldly told her grandfather she’d be the first woman president—a testament to the fierce confidence she carried as a child. But as the years went by, that confidence began to waver under the weight of expectations she could never quite meet. By her teenage years, fitting in felt like an impossible task, and she found herself turning to coping mechanisms that only left her feeling more lost."

At one point, Jennifer says, she hated herself so much that she thought maybe she wasn’t meant to be here.

That feeling of being “a misfit” followed her into adulthood, even as she built a successful career. It was only when a mentor called her out, in a way she could never forget, that Jennifer was forced to confront the person she had become.

These were the first words her mentor spoke to her:

"This happened at a seminar her boyfriend at the time suggested she attend. Jennifer was grappling with bulimia, alcoholism, and depression, yet she entered the class skeptical and judgmental, determined to prove it was worthless.

Throughout the session, she was openly dismissive, her self-assurance bordering on arrogance. At one point, she even raised her hand to accuse the class of being a 'cult,' resisting anything that felt like guidance.

The confrontation that followed was a revelation that stunned her. No one had ever held a mirror up quite like this, and the reflection wasn’t pretty.

The moment ended with her mentor turning to Jennifer’s boyfriend and saying,

before walking away."

From “Recovering jerk” to ”Recovering saboteur” to recovering from pain and herself.

The only way forward was change—a deep dive into learning and stepping out of an uncomfortable comfort zone. She started exploring neuroscience, practicing daily meditation to quiet her mind and soften her edges.

Throughout her journey, Jennifer created mantras that kept her rooted in her learning, she shared a couple with us, but this one in particular is our favorite:

”The anti-asshole prayer”

Life isn’t about bending the world to fit your will. It’s about letting go, trusting that what comes has the right to leave and what remains will have the space to grow with you as well as outside of you. One of the most difficult things to accept in life is that we have control only to a certain extent, and that extent is often shorter than we hope. Once you embrace this view, it becomes much easier to let go and move with change.

An experience worth fighting for. "Committed but not attached"

Moving with intention and releasing it with every step. Trusting that what is meant to follow will. As children, we dream in absolutes. We believe that the world should fit us perfectly, that if we try hard enough, everything will fall into place. But as we grow, life inevitably teaches us otherwise. We experience loss, change, and unexpected twists, and our inner child struggles to understand. The dreams may change, but the longing, the hope for “just right,” remains. It’s a balance between what we were, what we are, and what we want to be—a balance in which acceptance is held in the highest regard. Jennifer reminds us of the importance of listening to our inner child, of taking on the role of the guardian. The place we once left to our parents has always been in our own hands. Creating a space for mistakes, doubts, and fear while choosing compassion over criticism.

It’s a way of telling ourselves that it’s safe to dream but also safe to let go, to trust. When we hold our dreams with open hands, we allow them the space to evolve, just as we ourselves evolve. We learn to find joy in the journey, to make peace with the unknown, and to reassure that part of us that feels small, scared, or unworthy.

Today, Jennifer is committed to helping others create that safe space while cherishing her own:

That’s how she co-founded OptiMatch, a tech company with a mission that goes beyond profit—it’s about fostering human connection.

Jennifer’s story, as many others show us that the path to fulfillment isn’t a straight line, and it isn’t easy. But perhaps, that’s the point. After all, if we gave ourselves the grace to stumble and get back up, who knows what beautiful places that journey could lead to? "Are you ready for your own journey of recovering from yourself?"

Listen to Jennifer Hill on Uncharted: Your Sidekick for Life – Episode 8, Season 2

Jennifer Hill: In 2018, Jennifer Hill sold her first company to a subsidiary of Marcum LLP, where it continues to thrive years post-acquisition. A seasoned speaker, Jennifer has presented on global stages, including to 100,000 people in India, and has shared platforms with luminaries such as Deepak Chopra. She co-hosted the 19-episode series, Conversations at the Intersection of Cutting-Edge Science and Spirituality, alongside Chopra and Don Hoffman, and has led popular podcasts, including "Get Yourself the Job" and "Regarding Consciousness," featuring thought leaders like Bruce Lipton, Gregg Braden, and Chopra.

Jennifer’s impact extends beyond media; she has built schools in Nepal and Senegal and received a Lifetime Achievement Award from the Visioneers. Currently, she is developing OptiMatch, a software platform designed to foster psychological safety within businesses and communities, and she coaches CEOs on business growth.

Natalie Peyton: Peyton studied theatre and film in Australia, New York and LA and performed stand-up on the “three coasts.” She honed her podcast executive skills over the last 4 years developing and producing dozens of podcasts and even hosts a children’s mindfulness bedtime program. If you would like to listen to her work, here it is: Snoriezzz

Leon Vanstone: Leon brings his curiosity and sharp interviewing skills to the table, facilitating insightful discussions with our mentors, extracting valuable lessons and insights to empower listeners on their own path to growth and achievement.

Dan Dillard: Dan, with his thoughtful approach and engaging style, delves into the minds of our mentors on the podcast, crafting compelling interviews that uncover the wisdom and experiences driving their success and impact.

This blog was written by Anais Schmidt, one of the hosts of the Uncharted Podcast. Anais is also an aspiring musician. When not in her studio, she tours Europe with Monte Mai.

If you would like to join the conversation email us at anais@foundingup.com

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