Free Failing

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 the turning point that changed everything. Allicia unpacks how unhealed childhood wounds shape our thoughts, relationships, and faith—and why avoiding your emotions may be the very...

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 so many high-achieving women hit a wall in midlife, especially after divorce. Dr. Julie shares her own story of divorce, burnout and “crashing hard” in her 40s, and how that exper...

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 helping women survive (and rebuild after) divorce… because she’s lived it too. As always, we talk about stuff people don’t say out loud—why divorce can feel so isolating, what women ac...

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 show in our adult relationships—especially after divorce. If dating keeps triggering old wounds or you find yourself stuck in the same relationship dynamics, attachment theory might...

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: • Why some “red flags” are actually trauma responses • How to slow down and build real trust • Why dating multiple people isn’t necessarily wrong • The surprising role faith...

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 what anxiety actually feels like, how it manifests in different seasons, and how faith and practical tools can coexist when you’re trying to hold it together. Courtney shares her...

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 why so many Christian women struggle in silence. Christy shares her story—college drinking, stress in law school, expat pub culture, postpartum darkness, grief after losing her m...

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 exhausting, humbling, occasionally humiliating., and very tempting to just delete the apps, buy a weighted blanket, and emotionally retire. But in true quasi-delusional fashion, Jess delive...

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 mini reward moments, the girls share real-life strategies that actually work for divorced moms juggling everything. If your to-do list feels overwhelming, this episode is your perm...

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 labor, and still find joy in the middle of the madness. This episode is equal parts honesty, validation, and reminder that strength doesn’t always look polished.#Momburnout #invi...

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 ourselves grace, and also take time to celebrate the victories we often overlook or minimize through the business of everyday life. Jess K. is vowing to t...

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 rebuilding instead of reinventing after divorce or major life transitions. Maybe this year we choose stability and peace in a season that asks for something gentle...

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 unexplainable vibes you get on a date that your brain tries to talk you out of. Why do some men look perfect on paper but your body says absolutely not ? Why does “fast and exciting” som...

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 admits she has 100% blamed Santa for a last-minute toy swap. It’s hard enough holding down the fort in regular life, let alone juggling the absurd holiday pileup of shopping, cooking...

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 common denominator among divorced women, it’s this: men in their 40s and 50s often seem to be missing the emotional intelligenc e required for a truly satisfying relationship. Di...

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 dive into how modern women are redefining identity, confidence, and love beyond relationship status. Let's talk about... How to handle the “boyfriend demotion” and whether we’re t...

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 the inside out. Admittedly. It's not easy. Jess K. sometimes wears her engagement ring in secret (it's just so pretty). Jess T. crashes out sometimes, juggling the stresse...

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 walking a similar road that healing takes time—and that patience and grace for yourself is key. Please follow this show on Spotify. It really helps! xo #Divorcehealing #Divorcedwome...

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 limit—to settle for less than what we’ve been praying for? This convo gets real about what settling actually looks like, why we keep getting hooked on the same unhealthy patterns, and...

This week, Jess T. and Jess K. get real about whether cuffing season —aka that magical time of year when even the most independent women start wondering if Netflix feels better with someone’s son hogging the blanket-even works for divorced moms. We break down why cuffing hits different when you’re 40+, and whether a placeholder relationship is ever worth the emotional hangover. From laughing at ou...

Jess T. and Jess K. dive into the power of “reframing” — the simple but life-changing practice of flipping negative thoughts and hard circumstances into fresh, hopeful perspective s. From navigating loss and heartache to the everyday chaos of parenting and life stress, shifting your mindset can make all the difference. With a mix of faith, science, and a good dose of humor, this episode gives you...

Jess and Jess dive into what it really looks like to rediscover yourself at midlife (ish!) after divorce. From juggling motherhood with society’s never-ending expectations to holding onto the passions that make you you , change doesn’t have to mean losing ourselves. Let's unpack the power of names and identity, the confidence that comes from personal growth, and why it’s never too late to star...

Divorce can leave us asking, “Who am I now?” In this episode, Jess and Jess sit down with professional Enneagram coaches Jasmin Beeney and Theresa Krupicka to explore how we can rediscover our true selves in the aftermath of loss and transition. Whether you’re navigating grief, rebuilding your identity, or longing to step into a new season with clarity, the Enneagram offers a roadmap for healing a...

Jess and Jess sit down with bestselling author Ashley Henriott to talk about her powerful journey through heartbreak, healing, and unexpected reconciliation. Less than a year ago, Ashley and her husband were on the brink of divorce—living apart, with papers ready to sign. But through raw self-reflection and honest conversations with God, Ashley discovered a deeper kind of freedom and faith that ca...

Jess & Jess rewind the clock and spill the tea on what they wish they could tell their 20-year-old selves . From learning to love the body you’re in, to breaking free from toxic beliefs, to ditching the dating apps and putting family first—the wisdom list is long (and sometimes a little spicy ). But instead of drowning in regret, this conversation is about growth, grace, and moving forward ......