In this episode of Uncharted: Your Sidekick for Life, Ann Kelley shares her journey to becoming a psychologist, author, and podcaster. Her path wasn’t straightforward, defined instead by a series of decisions to step away from what didn’t feel right until she found what did. Ann’s life was marked by exploration—testing out different careers, learning what didn’t fit, and gradually uncovering the work that connected with her sense of purpose.
Pre-med was an early contender, but one encounter with a needle was enough to send her running in the opposite direction.
“Turns out,” she laughs, “when you almost faint watching a needle go into someone, medicine might not be your thing.”
So much for that chapter.
Physical therapy seemed promising, at least for a while, until her mother quipped, “You’re more of a chief than an Indian.” Outdated phrasing aside, Ann realized she needed a career where she could use her creative and analytical mind. Cue more exploration, more trial runs, and eventually—after enough detours to make even Frodo feel like he had it easy—Ann found her place in psychology.
The irony of becoming the very thing she’d once sworn off wasn’t lost on her.
“I didn’t want to be a psychologist,” she admits, “and here I am.”
Growing up, she saw the family psychologist navigate a room full of chaos, and the sheer weight of it convinced her that it was a job she would never want.
“It just seemed impossible,” she reflects, “like walking into a tornado and thinking you could calm the storm.” And yet, life has a way of rewriting the scripts we think we’re following.
But arriving at her destination didn’t mean the challenges were over.
Ann struggled with the ethics of charging people for therapy, a tension she describes with characteristic honesty.
“Someone comes into my office, they need help, and I charge them? It felt wrong, like I was closing the door on people who couldn’t afford it.”
A sentiment that resonates deeply. In a world where therapy can feel like a luxury item, Ann’s frustration is a reminder of how far we have to go to make mental health services truly accessible.
Her response to this tension was to create something that didn’t require a price tag. Enter Therapist Uncensored, the podcast she co-hosts, where she shares tools and insights from her work as a psychologist.
“Not everyone can afford therapy, but everyone can listen to a podcast.”
It’s the kind of practical solution that feels both inspiring and refreshingly simple.
Her book, Secure Relating: Holding Your Own in an Insecure World, expands on her goal of helping people navigate relationships and cultivate meaningful connections.
As Ann explains, feeling secure in ourselves and in our relationships is essential for building bridges instead of walls. It’s a perspective that becomes even more relevant when the conversation shifts to cancel culture, a modern phenomenon that often prioritizes disconnection over dialogue.
“If we disconnect from differences, how do we grow?”
she asks, cutting through the noise with a simple truth.
The hosts weigh in, exploring how cancel culture can stifle connection and promote fear. Ann points out that fear is often the driving force behind these behaviors.
“When we’re in fear, we’re not curious. We’re not open. We’re just trying to survive.”
It’s a survival mode that leaves little room for nuance—or humanity.
Cancel culture, Ann suggests, reflects a deeper issue—our growing discomfort with staying in tough conversations. It’s a dynamic she’s seen both in her work as a psychologist and in her personal reflections. She contrasts this with the concept of connection, where curiosity and openness lead to growth. The hosts agree, riffing on how cancel culture often feels like “Thanos snapping people out of existence.”
A swift and dramatic response, sure, but maybe not the most constructive approach.
Ann also shares her thoughts on Gen Z, describing them as a generation under unique pressures. Between the ubiquity of social media and the constant comparison it fosters, they face challenges that earlier generations never did.
“They’re always worried about how they’re coming across, and if you’re always performing, it’s hard to connect with what you’re really feeling.”
It’s a poignant reminder that authenticity isn’t just about being seen—it’s about feeling seen, even by yourself.
The discussion circles back to fear and opportunity, themes that have defined much of Ann’s own journey. She speaks about the importance of recognizing fear as a natural response, but not letting it dictate our actions.
“Discomfort doesn’t mean stop, sometimes it’s the signal to keep going.”
For Ann, it was this willingness to sit with uncertainty that allowed her to move forward, both in her personal life and her career.
By the end of the episode, it’s clear that Ann’s story isn’t just about her. It’s about the broader human experience—the messy, imperfect process of figuring things out.
And as the hosts wrap up the conversation, one question lingers: “What opportunities for connection are we missing because we’re too busy running from discomfort?”
Perhaps the answer isn’t to silence fear, but to acknowledge it—and move forward anyway. Or, as Yoda wisely said, “The greatest teacher, failure is.”
Listen to Ann Kelley on Uncharted: Your Sidekick for Life – Episode 10, Season 2
Ann Kelley: Dr. Kelley: A Career Rooted in Connection
Dr. Kelley is a licensed psychologist specializing in individual and couples therapy. She blends modern attachment theory, relational neuroscience, and depth psychology to help clients build inner security and deepen relationships. Beyond her practice, she co-hosts Therapist Uncensored, a top-rated podcast with over 10 million downloads across 172 countries. The show brings relational science to a global audience, fostering security and connection.
As co-author of Secure Relating: Holding Your Own in an Insecure World (HarperCollins, 2024), Dr. Kelley offers fresh insights on navigating relationships in today’s world. She also delivers advanced clinical training and public speaking engagements, sharing her expertise with professionals and communities worldwide.
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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