Affirm That Sh!t

What happens when you're doing everything right, but the people around you still think you're too damn much?

On this episode of Affirm That Sh!t, I sit down with Caroline Esterson, leadership consultant and host of Unshakeable Her, for a raw conversation about workplace misogyny, confidence, resilience, leadership, and the pressure women face to make themselves smaller. At just 23, Caroline was thriving in a regional leadership position when a brutal performance review nearly cost her the job. She was told she was too bold and moved too fast. Rather than abandoning her ambition, she learned how to build trust without sacrificing her strengths.

But that wasn't the last time her confidence would be tested. While leading a workplace transformation project, Caroline faced hate mail, vandalism to her car, and resistance from people who didn't want change. She opens up about learning to separate other people's reactions from her own worth, embracing vulnerability, and recognizing that being confident doesn't mean you aren't shaking on the inside.

Today, Caroline helps women build confidence, strengthen their leadership skills, and navigate career challenges without losing themselves. Her message is one worth remembering: You can be ambitious, vulnerable, curious, and capable without apologizing for who you are. And maybe it's time to stop asking whether you're too much and start asking why you've been expected to be less.

Connect with Caroline: https://inspireyourgenius.com/

What happens when the life you thought was yours suddenly disappears?

On this episode of Affirm That Sh!t, I sit down with Sarah Barnes Humphrey, entrepreneur, podcast host, and author of I Buried Her in a French Press. Ten days before her 37th birthday, Sarah watched the family logistics business she thought she would eventually take over close its doors. She went from being a Director of Sales and Marketing to taking part time jobs, including working as a receptionist and mopping floors, while quietly building the podcast that would eventually become Let’s Talk Supply Chain.

Sarah gets real about the power we give titles, status, and other people’s opinions. We dig into finding your voice, setting boundaries, code switching, entrepreneurship, releasing control, and why waiting until everything is perfect can keep you stuck. Her advice is refreshingly simple: just do it. People probably aren’t paying nearly as much attention to you as you think, and if you hold too tightly to what something should become, you might miss what it could become.

But growth also means accepting that not everyone gets to come with you. Sarah shares the affirmation hitting closest to home in this season of her life: “I release the people who love the old version of me, but can’t handle the healed one.” Finding your voice isn’t a finish line. You may lose it, find it, and redefine it again. The point is giving yourself enough grace to keep becoming.

Connect with Sarah: https://sarahbarneshumphrey.com/

What happens when the title disappears and you’re left staring at the person underneath it?

On this episode of Affirm That Sh!t, I sit down with Becca Pearce, former CEO of the Maryland Health Benefit Exchange, executive coach, and author of You Don’t Have to Achieve to Be Loved. After pouring herself into launching Maryland’s health insurance marketplace, Becca lost her job publicly and found herself wrestling with shame, failure, and a terrifying question: Who am I if I’m no longer my job?

Fourteen months later, another blow came. Years of ignoring hearing loss led Becca to the doctor, where she discovered a brain tumor the size of a ping pong ball growing into her brainstem. Surgery left her with facial paralysis, deafness in one ear, vision loss, and a long recovery that included learning to walk again. Yet even after surviving all of that, Becca initially returned to the same achievement treadmill, determined to prove she could still do the job.

Then came a choice between an important morning meeting and watching her daughter make little hearts through the school bus window. That moment changed everything. Becca began rebuilding her life around family, connection, emotion, and the things no job title could ever give her. Today, she helps others untangle their worth from what they accomplish and reminds us of something worth affirming: You don’t have to achieve to be loved.

Connect with Becca: https://morebeccapearce.com/

What if you built the perfect life... only to realize it belonged to someone you were pretending to be?
On this episode of Affirm That Sh!t, I sit down with Jane Garnett, author of This Time with Feeling and host of Sex, Psychics & Psychedelics, for a raw conversation about identity, external validation, consciousness, spirituality, and the courage it takes to stop performing and become real.

Jane seemingly had it all: a successful Hollywood career, a wealthy producer husband, two children, and a beautiful life in Santa Monica. On paper, it was perfect. Inside, she could feel something wasn't right.

Jane calls what happened next her “reverse Cinderella story.” She began dismantling the life she had been taught to want without knowing exactly what would replace it. That search took her through psychotherapy, psychedelics, spirituality, sexuality, shamanic traditions, and a deeper exploration of what separates the identity we're given from the essence of who we actually are.

This conversation challenges the idea that success automatically equals fulfillment. Jane reminds us that finding yourself isn't always about adding something new. Sometimes it's about stripping away the stories, expectations, and identities that were never yours in the first place. And maybe awakening isn't one giant moment. Maybe it's choosing, again and again, to actually be here for the life you're living.

Connect with Jane: janegarnett.com

What happens when you finally realize the voice inside your head telling you that you’re worthless was never yours? On this episode of Affirm That Sh!t, I sit down with Shannan Kym for a raw conversation about childhood trauma, addiction, family dysfunction, people pleasing, grief, and what it takes to stop surviving and finally start living.

Shannan grew up surrounded by addiction, mental illness, and abuse. Those experiences followed her into adulthood, where shame became people pleasing, alcohol became an escape, and maintaining the perfect image hid what was really happening underneath. After reaching one of the darkest points of her life, a longtime friend helped Shannan enter treatment and confront a powerful truth: what she had spent a lifetime calling “normal” wasn’t normal at all.

Today, Shannan is the author of Find the Answers Within You: 10 Pathways Towards Self-Discovery. Her story is a reminder that your past may explain parts of you, but it doesn’t get to decide who you become next. As Shannan says, “My purpose was in my pain.” Maybe the person your younger self spent years waiting for has finally arrived. Maybe that person is you.

Connect with Shannan: shannankym.com

One drunk driver. Six and a half hours. One grieving mother who decided something had to change.
On this episode of Affirm That Sh!t*, I sit down with Christine Olson for a conversation about unimaginable grief, a mother’s love, surviving the darkest moments of loss, and what can happen when you refuse to let tragedy have the final word.

On December 7, 2005, Christine’s 22-year-old daughter, Tiffany, was heading to dinner with her boyfriend, Dustin, when a drunk driver ran a stop sign. Tiffany was killed on impact, and Dustin also died from his injuries.

Christine was only about 15 minutes away.

But law enforcement didn’t know who to call.

It took six and a half hours before Christine learned her daughter was gone.

That delay planted a question in the middle of her grief: Why couldn’t emergency contacts be connected to a driver’s license or state-issued ID so first responders could quickly reach the people who matter most?

Christine wasn’t a politician. She didn’t work in government or law enforcement. She was a restaurant server on Anna Maria Island who admits she didn’t even own a computer.
But she knew something was wrong.

So she started asking questions.

People started signing petitions. Her community stepped forward. Florida listened.

Eventually, TIFF, To Inform Families First, was born in honor of Tiffany. Christine became the first person to register emergency contacts through the program in Florida, and she says approximately 22 million people in the state have since registered. The initiative has also expanded into other states as Christine continues advocating for broader access across the country.

But behind those numbers is still a mother who misses her daughter.

Christine opens up about the side of this story that advocacy doesn’t erase. She shares the depth of her grief, the suicidal thoughts she experienced after Tiffany’s death, the role her faith played in helping her survive, and why she still seeks grief counseling nearly 20 years later.

Her purpose didn’t erase her pain.

It gave the pain somewhere to go.

Christine chose to become the change she desperately wished had existed on the night Tiffany died. Now, she wants other families to have access to something she didn’t: the possibility of being reached quickly when every second matters.

And maybe that’s the biggest affirmation inside this entire conversation.

You don’t need the perfect plan to create change.

You don’t need political connections.

You don’t need to know exactly how the story ends.

Sometimes you start with one question, one step, and one stubborn belief that what happened to you should not have to happen to somebody else.

Christine says she is approaching the finish line of her work with TIFF, but she intends to finish well.
This is Tiffany’s legacy.

This is Christine’s fight.

And this is what happens when love refuses to stop moving.

Connect with Christine: https://toinformfamiliesfirst.org/

What do you do when the pain doesn’t end?

You stop waiting for life to get easier and discover just how damn strong you can become.
On this episode of Affirm That Sh!t, I sit down with Rick Cram to talk about chronic pain, resilience, mental strength, and what it really means to be your best when your body has other plans.

Rick’s journey began during the final minutes of his last high school football game. One tackle changed the trajectory of his life, eventually leading to seven knee surgeries, including a total knee replacement. More than 50 years later, Rick continues to experience unpredictable blasts of intense pain every day.

But Rick refuses to call this a journey of pain.

He calls it a journey of resilience.

And there’s a difference.

Rick opens up about reaching a point where he sat in doctors’ offices shaking, fighting back tears, and admitting he was desperate for relief. Yet somewhere inside that struggle, something shifted. He began asking a different question: What if thriving doesn’t require the pain to disappear?

That question helped shape *Plan to Be Your Best*, Rick’s framework for helping people understand and strengthen their own unique resilience while navigating chronic pain, stress, grief, pressure, and uncertainty.

We dig into why resilience is a choice you make again and again, how celebrating even the smallest victories can change the way you see yourself, and why being your best isn’t about pretending everything is okay. It’s about putting your greatest strengths into action when everything isn’t.
Rick also shares how additional health challenges tested that philosophy and forced him to practice the very resilience he teaches.

His perspective stopped me in my tracks: What looks like a setback might actually become a setup for something you haven’t seen yet.

Pain happens in the moment.

So does resilience.

And Rick leaves us with an affirmation worth carrying long after this conversation ends:

My best is greater than the pain.

If you’re living with chronic pain, grief, stress, burnout, or anything else that makes simply showing up feel like a battle, this conversation is for you.

Connect with Rick: https://rickcram.com/

Grief has a way of changing everything. The question is, what will you do with what's left?

This week on Affirm That Sh!t, I sit down with Ashley Simpson, an art therapist whose journey proves that purpose often grows from life's deepest losses.

During her senior year of high school, Ashley was preparing for graduation while watching her beloved stepfather battle heart disease. When he unexpectedly passed away before undergoing surgery, her world changed overnight. Instead of allowing grief to define her future, she chose to keep moving forward, trusting that even the hardest moments were shaping the woman she was becoming.

Everything changed again when Ashley volunteered at an art fundraiser supporting children with pediatric cancer. While trying to protect her own heart, she met a young girl whose words would forever change the direction of her life.

"Don't be scared to be my friend. If I died, I'd miss you too."

In that moment, Ashley realized healing isn't about avoiding pain. It's about choosing connection anyway.

That experience inspired her to become a registered art therapist, dedicating her life to helping children and families express emotions that words often cannot reach.

Together, we explore how grief can become purpose, why vulnerability creates healing, and how creativity can help us process life's most difficult experiences.

This conversation is about more than loss.

It's about choosing love, even when there's risk.

It's about discovering purpose through heartbreak.

It's about believing that the people who cross our path, even briefly, can change the trajectory of our lives forever.

If you've ever wondered whether your pain could become someone else's hope, this episode is for you.

Connect with Ashley: https://cavettkids.org/

Addiction recovery, mental health support, and healing from trauma are not what you think. In this episode of Affirm That Sh!t, Rachel Corbett, CEO of supportgroups.ai, shares how connection, resilience, and second chances can rebuild a life.

This week, I sit down with Rachel Corbett, and this conversation does not whisper—it hits.
Rachel is a CEO, a visionary, and a powerful voice in mental health. Before any of that, she experienced homelessness, addiction, and isolation. She knows what it feels like to be overlooked, dismissed, and written off—and she also knows what it takes to rise.

In this episode, we open up the truth about loneliness, addiction, and what it really feels like to disappear in plain sight. Rachel does not just talk about healing—she lived it. She walks us through the darkness of isolation, the fight to reclaim her identity, and the moment she realized that connection is not optional—it is survival.

Addiction is not the root. It is the symptom.
What people truly need is not judgment, but connection.

Rachel shares how she is using technology, AI, and human empathy to make mental health support accessible, immediate, and real through supportgroups.ai.

This conversation goes beyond recovery.

It challenges the narrative.

It calls you to become the person you needed when no one showed up.

Most importantly, it is a reminder: No one is too far gone. No one is hopeless.

If you have ever felt alone, this episode will meet you there—and walk you out.

Connect with Rachel: [email protected]

On this episode of Affirm That Sh!t, I’m diving into the raw, unfiltered truth about what it really takes to transform your life — not later, not “when things calm down,” but right now.

Connie, Portia, and I open up about the retreats that changed us, broke us open, rebuilt us, and handed us back to ourselves. We talk about the power of stepping into a room full of women who look like you, feel like you, and carry the same silent weight you’ve been pretending doesn’t exist.

Connie shares the story of how she trusted a retreat host before even meeting her — how she scraped pennies together, made sacrifices, and bet on herself because growth demanded it. I bring the fire when I talk about hosting retreats and watching women transform right in front of my eyes. And Portia and I crack open the idea of “investment,” flipping the script from money to energy, commitment, readiness, and self-worth.

This episode is for the woman who feels the pull.
The woman who knows she’s meant for more.
The woman who’s tired of waiting for the “right time.”

We talk vision boards.
We talk affirmations.
We talk fear — the good kind — the kind that tells you you’re standing at the doorway to your next era.

And we end with the hardest question of all:
Are you ready to stop being the version of you that’s exhausted, overwhelmed, and hiding… and finally become who you were always meant to be?

If you’ve been craving sisterhood, healing, breakthroughs, or your “I’m done shrinking” moment — this episode will hit you right in the gut in the best possible way.

Reserve your spot today: https://www.sacredyutoricollective.com/