Hosted by Jessica Kastner · 🇺🇸 US · EN-US · 41 episodes
Established thought leaders with verified media credentials.
Gritty, faith-filled, hilarious conversations for women rebuilding after divorce and other hard life transitions. Author and host Jessica Kastner gets unapologetically real about the stuff we rarely admit, let alone say out loud. Covering everything from the impending doom of perimenopause, the thrills of coparenting, emotional healing after divorce, (anxiously attached but still sexy A+) and the fresh flaming hell that is online dating, Jess soaks up wisdom and advice from amazing female experts, who live to tell.
Jessica Kastner hosts Free Failing, a society show with 41 episodes published.
Feeling stuck? It might not be your situation—it might be what you’ve buried. Jess sits down with neuro coach and Christian mindset expert Alicia Michelle to reveal how years of emotional suppression kept her stuck—and t
What if your exhaustion isn’t just hormones… but a completely dysregulated nervous system? Jess sits down with Dr. Julie Merriman—licensed counselor, trauma specialist, and host of Compassion Fatigue Cure—to unpack why s
Divorce isn’t just paperwork and custody schedules—it’s identity-shaking, gut-punching, “am I going to be okay?” energy. Jess sits down with therapist, speaker, and Unhitched author Oona Metz, who’s spent 30+ years helpi
Why do so many of us keep dating the same person… just with a different name? Jess sits down with nationally-recognized therapist and author Jessica Baum to unpack why our earliest emotional experiences quietly run the s
Jess sits down with celebrity matchmaker, psychologist and author Dr. Christie Kederian, a.k.a. the "date doctor" to explore what it really takes to date again after divorce and deep relational wounds. They get into: • W
Anxiety doesn’t always look the same—and for many women, it shows up right when life falls apart. Jess sits down with author and speaker Courtney Devich (Mama’s Got Anxiety) for an honest, unfiltered conversation about w
Jess K. sits down with sought-after sobriety coach, speaker, and author Christy Osborne (Love Life Sober) for an honest, funny, and deeply relatable convo about the “mommy wine” trap, drinking as a coping mechanism, and
Jess K. unpacks why breakups hit differently after divorce — heavier, sharper, and somehow more personal than we expected. You finally put yourself back out there, risk hope again… and then it falls apart. It’s exhaustin
Jess K and Jess T break down habit stacking — the ultimate busy-mom hack for getting things done without burning out. From pairing chores with self-care (hello face masks + folding laundry) to turning boring to-dos into
Jess T. & Jess K. dive into the real cost of single motherhood—the burnout, the emotional whiplash, and the quiet resilience it takes to keep going. They explore how single moms juggle family dynamics, carry invisible la
In a solidary effort NOT to make the same mistakes in 2026, Jess & Jess reflect, laugh and cringe at some of the greater "wins" and "fails" they've experienced this past year. Reflection can be powerful, when we allow ou
Jess T. & Jess K. (a self-professing New Year's "junkie") reframe New Year’s resolutions through the lens of real life after loss and starting over. Traditional resolutions can feel exhausting and defeating when you’re r
Jess T. & Jess K. (a self-professing New Year's "junkie") reframe New Year’s resolutions through the lens of real life after loss, after change, after starting over. Traditional resolutions can feel exhausting and defeat
In this episode, Jess & Jess crack open one of the most underrated superpowers women have: the ability to let your nervous system lead. We’re talking gut feelings, tight chests, instant contractions, and those unexplaina
Jess and Jess dive into the chaos and emotional landmines of being a Type B divorced mom during the holidays. Jess K. confesses to showing up with multiple presents literally duct-taped together, while Jess T. openly adm
Jess & Jess dig into the absolute rodeo of dating in your 40s — where emotional maturity is basically foreplay, intentionality is a green flag, and dating apps have become a full-time unpaid internship. If there’s one co
Jess K. and Jess T. unpack the latest viral Vogue article asking: Is it embarrassing for grown women to have a boyfriend? From the awkwardness of saying “my boyfriend” post-divorce to the freedom of doing life solo, they
What happens when the titles we’ve lived under — wife, stay-at-home mom, stepmom, fiancé— suddenly fall away? Jess K. and Jess T. strip down the illusions of identity and talk honestly about what it takes to rebuild from
Jess K. reflects on her life, now one year after divorce—the heartbreak, the healing, and the surprising moments of hope along the way. She shares what helped her most along the way (and what didn’t!), reminding anyone w
Jess and Jess tackle the dreaded “S” word of dating: settling. We’ve all done it, justified it, or tried to rebrand it as “being realistic.” But after surviving divorce, do we really have the time—or emotional credit lim
Alicia Michelle
certified Christian life coach and award-winning podcast host
1 appearance on this show
Julie Merriman
licensed counselor, trauma specialist, host of Compassion Fatigue Cure
1 appearance on this show
Oona Metz
licensed independent clinical social worker, certified group psychotherapist, author
1 appearance on this show
Jessica Baum
psychotherapist and author of Safe: A New Way of Looking at Attachment · null
1 appearance on this show
Christy Osborne
author of Love Life Sober and co-host of the But Jesus Drank Wine! podcast · But Jesus Drank Wine
1 appearance on this show
Ashley Henriott
bestselling author
1 appearance on this show
Yvette Walker
author, speaker, podcaster · Positively Joy
1 appearance on this show
Dr. Jess
911 dispatcher · The Playful Domme
1 appearance on this show
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Free Failing is hosted by Jessica Kastner. The show is categorised under society (culture) and has published 41 episodes.
Free Failing has published 41 episodes.
Free Failing regularly covers society, culture. It sits in the society category, with a culture focus.
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Episodes of Free Failing average 35 minutes. a focused format where a clear narrative arc and tight preparation matter most.
Our data rates Free Failing's guest bar at 80/100 (Premium tier). Established thought leaders with verified media credentials. Sign in to PitchCentric to see how your own Pod Score compares against this show.
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