In this inspiring episode of Flying Upstream, host Kristyn Medeiros sits down with Jonathan Rosen, a seasoned multi-published author and podcaster, to explore the raw realities of the writing life — from facing rejection to finding humor and healing through storytelling. Whether you’re an aspiring author or simply passionate about creativity, Jonathan’s story offers a powerful blueprint for perseverance, personal growth, and embracing alternative paths to success.

Discover how Jonathan developed a thick skin to handle rejection, why humor is a crucial tool in storytelling (especially for younger audiences), and how writing can serve as an unexpected form of therapy. This episode dives deep into overcoming common myths about publishing, the value of consistency, and why starting to write is the most important step toward realizing your creative dreams.

🕛 Chapters:
00:00 — Introduction to Alternative Paths
01:29 — The Journey of a Writer
06:45 — The Therapeutic Nature of Writing
09:50 — Perseverance in the Face of Rejection
11:53 — The Role of Humor in Writing
14:41 — Balancing Creativity and Routine
16:52 — Misconceptions About Publishing
18:37 — The Importance of Starting to Write

Connect with Jonathan Rosen:
Website: http://www.houseofrosen.com/
Check out Jonathan's Podcast Pop Culture Retro: https://www.youtube.com/@PopCultureRetro
Facebook: https://www.facebook.com/JRosen18/

Follow Jonathan for more writing tips, insights, and behind-the-scenes stories from his creative journey.

In this powerful episode of Flying Upstream, host Luisa Anderson sits down with Yvonne Caputo—a former teacher turned psychotherapist, corporate leader, and author of two deeply moving books about her father. Together, they explore transformation, healing, storytelling, trauma, relationships, family, and legacy with raw honesty and compassion.

Yvonne shares how her life’s winding path—from the classroom to the therapy room to the corporate world—taught her the profound healing power of understanding and trust. She opens up about her relationship with her father, the impact of exploring family history through storytelling, and why end-of-life conversations are some of the most important we’ll ever have.

⏱️ Chapters:
00:00 – Introduction to Alternative Wisdom
01:36 – Yvonne’s Multifaceted Journey
04:50 – The Power of Storytelling
10:14 – Understanding Trauma and Healing
13:23 – Navigating End-of-Life Conversations
19:29 – The Gift of Trust and Closure

🔗 Connect with Yvonne:

• Check Out Yvonne’s Books Flying with Dad and Dying with Dad: https://ingeniumbooks.com/yvonnecaputo/

Ever felt like you were living life on autopilot? In this episode of Flying Upstream, host Kristyn Medeiros sits down with Bianca Lynch, a bold woman who traded in her 9-to-5 for a passport and a backpack. Bianca shares her transformational journey from corporate burnout to global freedom, breaking down what it really takes to become a digital nomad and build a life around freedom, travel, and purpose.

If you're curious about what it’s like to ditch the American Dream in favor of a more aligned, adventurous lifestyle, this conversation is for you. From navigating fear and identity shifts to funding a remote work lifestyle, Bianca offers real talk and practical insights for anyone craving a life outside the norm.

Whether you're dreaming of living abroad, seeking personal growth, or ready to explore remote work and entrepreneurship, this episode will inspire you to question what’s possible.

🌐 Connect with Bianca Lynch

Want to keep up with Bianca’s digital nomad journey or learn more about creating a freedom-based lifestyle? Here’s where you can find her:

Digital Nomad Takeoff Toolkit: https://bit.ly/usdropout (promo code UPSTREAM for 20% off)

U.S. Dropout Checklist (freebie): https://bit.ly/mylifeabroad

Instagram: https://www.instagram.com/shesbookingtheflight/

TikTok: https://www.tiktok.com/@shesbookingtheflight

YouTube: https://www.youtube.com/@shesbookingtheflight

🧭 Chapters:

• 00:00 Intro to Flying Upstream

• 01:11 Bianca's Journey: Leaving the American Dream Behind

• 04:23 The Wake-Up Call: Realizing the Need for Change

• 09:14 First Steps: Testing Life Abroad

• 11:33 Funding the Adventure: Making Money as a Digital Nomad

• 14:22 Cultural Shifts: Embracing a Slower Lifestyle

• 19:02 Daily Life as a Digital Nomad

• 21:12 Overcoming Fear: Taking the Leap to Change

• 23:07 Conclusion: Embracing Freedom and Possibilities

In this soul-stirring episode of Flying Upstream, host Luisa Anderson sits down with transformational coach and entrepreneur Holly Porter to unpack how a near-death experience during COVID-19 led to an extraordinary spiritual awakening and a completely reimagined life.

Holly shares raw, vulnerable moments from her time in the hospital, and the divine insights that followed—including how breath, love, and legacy have taken on entirely new meaning. This conversation dives deep into the healing power of community, the rise of retreats as transformational containers, and how purpose-driven entrepreneurship can emerge from trauma.

You’ll leave this episode with a deeper appreciation for life, and practical inspiration to pursue your own path of healing, manifestation, and personal evolution.

⏱️ Chapters:

00:00 — Welcome to Flying Upstream: Embracing Alternative Paths
00:51 — The Life-Altering Near-Death Experience
05:57 — Spiritual Awakening and Community Support
12:05 — Transformative Lessons and Shifting Identity
16:58 — Purpose, Legacy & the Rise of Healing Retreats
23:41 — Building a Business Aligned with Soul & Service
29:12 — Final Reflections: Embracing the Power of Breath and Being

🔗 Connect with Holly Porter at hollyporterinternational.com

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In this powerful episode of Flying Upstream, host Luisa Anderson sits down with deaf coach, bestselling author, and fierce advocate Kellina Powell—a woman on a mission to change the way we see disability, identity, and resilience.

At just four years old, Kellina lost her hearing due to an infection. Since then, she’s navigated a world not built for people like her—with grit, grace, and a deep commitment to advocacy. She shares how growing up between two worlds—the deaf community and the hearing world—shaped her identity and inspired her to become a voice for change.

⏱️ Chapters:

00:00 – Introduction: The Power of Alternative Paths
01:19 – Kellina’s Journey: Losing Her Hearing at Age 4
02:57 – Living Between Two Worlds: Deaf and Hearing Identities
09:56 – Writing as a Tool for Healing and Advocacy
15:59 – Representation in Media: The Rise of the Deaf Influencer
17:51 – Looking Ahead: Kellina’s Vision for Bridging Communities

🔗 Connect with Kellina:

📘 Book: Everyday I Am Just Deaf
🌐 Website: kellinaempowerment.com
📸 Instagram: https://www.instagram.com/deafqueenboss
💬 Facebook: https://www.facebook.com/KellinaPowell

In this soulful episode of Flying Upstream, host Kristyn Medeiros sits down with creative alchemist Kristi Casey, whose life and work prove that creativity is not a luxury—it’s a lifeline. Kristi shares how embracing artistic expression led her through personal transformation, emotional healing, and profound self-discovery.

Together, they explore the power of creative alchemy—the process of turning inner turmoil into expressive gold. Whether you're navigating a creative block, seeking a more authentic life, or wondering how to reconcile art with livelihood, this conversation will reignite your creative spirit and remind you that you are the author of your own path.

Chapters:
00:00 – Welcome to Flying Upstream
01:49 – Kristi Casey’s Creative Alchemy Journey
11:50 – Pain, Hope, and Truth in Artistic Expression
18:49 – Writing as a Tool for Emotional Unblocking
24:46 – Navigating the Intersection of Art and Income
29:54 – Reclaiming Your Creative Spark

🔗 Connect with Kristi Casey:

Instagram: https://www.instagram.com/trulykristi

X: https://x.com/trulykristi

Website: https://trulykristi.com

Check out her band Mayberry Wine at mayberrywine.com

In this episode of Flying Upstream, host Kristyn Medeiros engages in a profound conversation with David Ask, an entrepreneur and coach who emphasizes the importance of identity over external success. David shares his journey from a competitive upbringing to discovering his authentic self, advocating for the idea that true transformation begins with understanding who you are rather than why you do what you do. He discusses the significance of raising children with grit and authenticity, encouraging parents to mine for the gold within their kids. The episode concludes with a reminder to embrace curiosity and surround oneself with supportive relationships.

Chapters:
00:00 – Welcome to Flying Upstream
00:51 – David Ask’s Journey: From External Success to Internal Clarity
09:09 – Discovering Authenticity in a Competitive World
16:00 – Why Identity Must Come Before Purpose
20:46 – Parenting with Grit: Raising Uncrushable Kids
29:56 – Final Thoughts: Curiosity, Grace & Being Known

🔗 Connect with David:

Instagram: https://www.instagram.com/thedavidask

X: https://www.instagram.com/thedavidask

Facebook: https://www.facebook.com/DavidAskMusic

LinkedIn : https://www.linkedin.com/in/thedavidask

Website: https://www.davidask.com

Information about David's product StatGuardPlus:

Instagram: https://www.instagram.com/statguardplus

Website: https://statguardplus.com

In this episode of Flying Upstream, host Kristyn Medeiros welcomes Beth Pellino-Dudzic—author, songwriter, and creative force—who proves that it's never too late to tell your story. Beth opens up about the deeply personal journey behind finally writing the book she held in her heart for over 25 years.

Through candid reflections, she shares how life’s toughest chapters became her creative fuel, how music remains a cornerstone in her storytelling, and what it really takes to self-publish when the traditional path doesn't feel right.

Whether you're an aspiring writer, an artist stuck in self-doubt, or simply looking for the courage to start again, this episode is packed with insight and inspiration for navigating alternative creative paths and honoring your inner voice.

⏱️ Episode Chapters:

00:00 — Welcome to Flying Upstream
01:08 — Meet Beth Pelino Dudzik: Author, Musician, Creative
08:03 — Life in Hawaii: Balancing Art, Family, and Healing
14:23 — From Grief to Growth: Writing After Adversity
25:35 — The Soundtrack of Her Story: Music’s Role in Beth’s Writing
35:05 — Self-Publishing Lessons & Advice for Creatives
45:10 — Final Reflections: Honor the Voice Within

Learn more about Beth’s creative work, her debut book, and her music by visiting her website and following her on social media:

🌐 Website: https://perfectionsaga.com
📸 Instagram and 📘 Facebook: @bpellinodudzic
🎵 TikTok: @bethandperfecton1

In this powerful episode of Flying Upstream, host, Luisa Anderson sits down with Ryan DeLena and his father, Rob, to explore how they carved a healing path beyond conventional systems. After Ryan’s traumatic experiences in therapeutic schools and failed interventions, it was the raw terrain of New Hampshire’s 91 ski routes—and the bond between father and son—that set them on a transformative journey of healing, trust, and personal growth.

Ryan’s resilience and Rob’s evolution as a parent challenge the notion that institutions know best. Together, they reflect on the deep healing power of the outdoors, the lessons mountains teach, and what happens when we stop outsourcing our instincts to “experts.” This episode is a must-listen for anyone seeking alternative approaches to mental health, parenting, or rediscovering connection through shared struggle.

Chapters

00:00 — Welcome to the Episode: Challenging the System
01:49 — Ryan’s Early Struggles & Institutional Trauma
03:21 — Rob’s Evolution: Learning to Parent Differently
09:22 — Questioning the Experts: Who Really Knows Best?
11:24 — Skiing as Therapy: Movement as Medicine
16:45 — Conquering New Hampshire’s 91 Ski Routes
25:31 — Fatherhood, Vulnerability & Growth
34:25 — Wisdom from the Wilderness

Follow Ryan on Instagram @extreme_ryan_delena

Check out Rob and Ryan's book Without Restraint at without-restraint-book.com.

In this inspiring episode of Flying Upstream, host Kristyn Medeiros, sits down with storyteller and poet Judge Kemp, whose life journey is a masterclass in resilience, identity, and personal growth. From a structured military upbringing to living abroad, facing memory loss, and eventually discovering poetry during the pandemic, Judge shares how creativity became both a lifeline and a legacy.

This episode explores alternative paths to healing, how LGBTQ+ experiences shape creative work, and the power of storytelling to preserve identity and impact community. Judge’s deeply personal insights will resonate with anyone navigating reinvention, seeking creative expression, or finding strength in vulnerability.

⏱️ Chapters:

00:00 – Welcome + Theme: Embracing Alternative Paths
01:53 – Judge Kemp’s Story: Military Life and Early Creativity
07:06 – Memory Loss & the Journey of Reinvention
10:29 – Poetry as Healing During the Pandemic
18:20 – Crafting Legacy Through Words: Live, Love, Leo
23:45 – Identity, Community, and Living Authentically
30:12 – Final Reflections: Creativity as Survival and Service

Follow Judge on Instagram and keep up with him on his blog.

Find out more about his book of poetry Live. Love. Leo.