What drives someone to uproot their life and move across the country with no safety net? For Krystal Marie Orwig, it was a childhood dream that refused to die.

"I was 12 years old when I said I was gonna live in New York," Krystal shares, reflecting on how she made that declaration long before understanding what it would mean. After moving from Southern California at 26, Krystal built a life in NYC starting as a bartender—a career that introduced her to friends, her fiancé, and a sense of community, but never felt like her final destination.

Krystal takes us through her transformation from practical communications major to creative writing MFA graduate, and now teacher at City College of New York. With remarkable candor, she reveals the challenges of pursuing creative dreams when you've been self-supporting since your teens. "I worked full-time throughout college... I was never able to fully dedicate myself to school because I put myself through my undergraduate degree," she explains, making her later decision to commit to writing all the more significant.

As founder of Must Love Memoir, a NYC reading series dedicated to non-fiction writers, Krystal has created the literary community she needed while elevating a genre often dismissed as mere "navel-gazing." Her insights into teaching today's college students—navigating attention spans, technology shifts, and the AI revolution—offer a fascinating glimpse into higher education's changing landscape.

Through conversations about true crime obsessions, complicated parental relationships, and finding your voice as a writer, this episode explores how we build lives of meaning on our own terms. Whether you're contemplating a career change, struggling with imposter syndrome, or simply curious about the realities of pursuing creative work in your 30s, Krystal's journey reminds us it's never too late to follow your passion.

MUST LOVE MEMOIR Reading Series

Krystal Marie Orwig Substack

Mentions:

Goodbye to All That by Joan Didion

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"I had a fucking panic attack because I was so excited," JD recalls of his first trip to a real skate shop as a child growing up in rural Pennsylvania. This moment marks the beginning of a lifelong love affair with skateboarding that would eventually bring him to Brooklyn, where he now tends bar at Greenpoint Palace.

Far from the stereotype of skaters learning from communities in urban environments, JD's story begins in isolation—no sidewalks, no mentors, just VHS tapes he'd repeatedly pause and play to study techniques. There's something beautifully pure about his dedication, teaching himself with makeshift equipment his dad built from "fucked up trash shit." This self-reliance shaped not just his skating style but his entire philosophy around the activity.

When hosts Rita and Marisa probe whether skateboarding should be considered a sport, art, or something else entirely, JD offers a more nuanced take: "It's more like a relationship with this wooden toy. Sometimes you're like 'this thing is—I'm so glad it's in my life,' and sometimes you're like 'God damn it, I hate my skateboard today.'" The conversation expands beyond skateboarding to explore how our passions evolve as our bodies age, the challenge of monetizing what we love without corrupting it, and the surprising observations JD made while teaching skateboarding to children.

Throughout the episode, JD's authenticity shines—whether discussing his ambivalence about profit from skateboarding, his growing interest in surfing as a gentler alternative to concrete impacts, or his sincere approach to apologizing when he's wrong. His story reminds us that our most meaningful pursuits aren't just hobbies but complex relationships that shape who we become.

Listen to discover how a kid with a VHS player and a dream built a life around his wooden toy, and what lessons his journey might hold for your own relationship with the things you love most.

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Writer, comedian, and storyteller Carly Ann Philbin takes us on a journey through her creative process, revealing how she navigates the complex terrain between performance and writing. With refreshing candor, she shares her experiences self-publishing her memoir "Tears of a Blonde" after realizing traditional publishing timelines wouldn't align with her life circumstances.

"I have dreams of fame and glory, but I don't need it," Carly confesses, perfectly capturing the spirit of creative independence that drives many artists. Her illuminating Play-Doh analogy brilliantly explains how we all contain multitudes but must focus certain aspects of ourselves for storytelling: "We're all juxtapositions... a persona is like a machine. All the contents you want to talk about, you put through this machine... and it comes out with a strong voice." This framework offers listeners valuable insight into developing an authentic voice while crafting compelling narratives.

The conversation takes unexpected turns as we explore the challenges of dating in New York ("I wonder if we say it's hard to date in New York, but really it's hard to date men"), the limitations of therapy and meditation for creative people, and the profound lessons we learn from our pets. Carly's vulnerability when discussing how her dog Saturday has become both her child and a vehicle for reparenting herself creates a deeply moving moment of connection.

Discover Carly's "Written in Brooklyn" storytelling workshop, where she helps others transform life experiences into narratives for both page and stage. Whether you're a writer, performer, or simply someone navigating life's complexities, this episode offers wisdom on finding your voice and sharing your unique story with the world. Follow Carly's journey and find your own creative independence beyond the gatekeepers.

Written in Brooklyn writing workshop

Pour Me Out Substack

Tears of a Blonde: Almost Completely True Stores of Love and Heartbreak by Carly Ann Filbin

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