When Is a Win Podcast is about pausing to reflect on the moments that shape us. Each episode starts with a simple “when” question and unfolds into an honest conversation about growth, resilience, joy, and everything in between. From laughter over reality TV to deep dives into wellness, work, and family, this is a space for curiosity, care, and connection—because sometimes just recognizing when we’ve learned or shifted is already a win.
When I Met My Best Friend Nancey Pt.1 Ft. Nancey B. Price
Warning: Grown people language.
In this episode, I’m joined by my best friend Nancey as we look back on the moment we realized our friendship was built for the long haul. From uncontrollable laughter to hard-earned lessons—and yes, a little chaos—we unpack what it really means to grow alongside someone who knows all your chapters.
4 Feb 2026
When I Found Mindfulness through Meditation, Gratitude & Movement Ft. Julie R.
Mindfulness is the practice of actively and openly paying attention to the present moment, without judgment. It involves observing thoughts, feelings, and sensations as they arise, accepting them without getting carried away by them. Essentially, it's about being fully present in your experience, rather than being lost in worries about the past or future. Join me for a full conversation with Julie R., a wellness coach and Chopra Global certified Meditation teacher.
Connect with Julie:
https://www.balancedleap.com/ (https://www.balancedleap.com/)
https://www.instagram.com/balancedleap/ (https://www.instagram.com/balancedleap/)
26 Jan 2026
When Grief Changed Everything: A Conversation on Loss, Love, and Spirituality Ft. Jazz J.
In this heartfelt conversation, I sit down with my cousin Jazz to talk openly about grief, loss, and spirituality. We share our personal experiences of losing people we love and how navigating that loss has changed the way we understand love, connection, and life itself. We reflect on the complicated emotions that come with grief—the moments that feel heavy, the ones that surprise you, and the ways it shows up when you least expect it.
Throughout the conversation, we lean into the importance of family, the comfort we find in memories, and the spiritual connections that continue even after our loved ones are gone. Through laughter, tears, and honest reflection, we talk about what our losses have taught us and how they’ve shaped who we are today. At its core, this conversation is about honoring the people we’ve lost by choosing to live fully, love deeply, and carry their lessons with us every step of the way.
20 Jan 2026
When I Found What Love Meant to Me Ft. Nanny
Love doesn’t always arrive the way we expect it to. In this episode, I sit down with my Nanny to reflect on when I began to truly understand what love means in my own life—romantic love specifically. Together, we explore the lessons that shaped my perspective, the myths that fell away, and the moments that helped redefine what love is and what it isn’t.
This conversation is thoughtful, honest, and evolving—about learning love over time, unlearning what no longer fits, and allowing your definition of love to grow with you.
20 Oct 2025
When I Had to Trust God, the Process & Myself Ft. Kim M.
"Having a relationship built in love and not fear with God changed everything for me."
This one is personal. My soul sister, Kim M., joins me for a conversation about the importance of trusting the process in life. We discuss our personal experiences of overcoming challenges, the role of spirituality and our ancestors in our journeys, and the significance of making decisions that align with our true selves. This conversation emphasizes the powerof joy, the necessity of self-trust, and the impact on personal growth.
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For Questions & Inquiries: contact.alenat@gmail.com
12 Oct 2025
When I Started Dealing with Chronic Pain Ft. Brittany A.
In this episode, I speak with my close friend, Brittany, where we share our personal journeys with chronic pain, discussing the challenges, misunderstandings, and the importance of community and advocacy in healthcare.
We talk about the emotional and physical impacts of chronicpain, the role of anxiety, and the significance of finding supportive medical professionals.
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For Questions & Inquiries: contact.alenat@gmail.com
28 Sept 2025
When I Reminisced With My 96 Year-Old Great Grandma Ft. Christine Beards
In this heartfelt conversation, I talk with my 96-year-old great-grandmother, Christine Beards, exploring themes of love, community, motherhood, and the importance of education.
Grandma reflects on her life experiences, the impact of her community, and the joy of helping others. She shares her dreams, the challenges of motherhood, and the significance of faith and support in family life. The conversation highlights the wisdom passed down through generations and the enduring bonds of love and care.
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For Questions & Inquiries: contact.alenat@gmail.com
22 Sept 2025
When I Got Serious About My Wellness Journey Ft. Eleanor Foley, Licensed Acupuncturist
My licensed acupuncturist, Eleanor Foley, joins me to discuss our personal wellness journeys. We discuss the importance of mental, physical, and spiritual health, the role of community support in healing, and the significance ofacupuncture in maintaining overall wellness.
Eleanor shares her experiences with health struggles from a young age and how they shaped her approach to healing. The conversation emphasizes that healing is not a linear process and highlights the importance of finding joy in the present moment.
You can book an appointment with Eleanor Foley at Lakeside Spine & Wellness in Chicago, IL: https://www.lakesidechicagochiro.com/meet-the-doctor/eleanor-foley/ (https://www.lakesidechicagochiro.com/meet-the-doctor/eleanor-foley/ )
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For Questions & Inquiries: contact.alenat@gmail.com
15 Sept 2025
When We Became Obsessed with Nicolandria & Love Island during Unprecedented Times Ft. Avery & Faith
What does it mean to be completely hooked on Love Island when the world around you feels like it’s falling apart? In this episode, Faith, Avery, and I dive into Season 7, our obsession with Nicolandria, and the rollercoaster of toxic drama that kept us glued to the screen.
We unpack why this season felt different, how watching reality TV together became a form of joy and escape, and why sometimes leaning into a little chaos is exactly what gets us through uncertain times.
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For Questions & Inquiries: contact.alenat@gmail.com
2 Sept 2025
When I Was Honest About My Relationship with My Mom Ft. Nanny
Nanny and I reflect on when I got real about my relationship with my mom. We talk about honesty, healing, and what it means to face family stories with both truth and love.
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Being honest about family can be hard, but it can also be freeing. In this episode, I open up about when I decided to be honest about my relationship with my mom - naming the truths, the struggles, and the love that lives alongside them. With Nanny by my side, we talk about what honesty looks like in family relationships, how it can hurt and heal, and why telling the truth is sometimes the first step toward understanding and growth.
For Questions & Inquiries: contact.alenat@gmail.com
2 Sept 2025
When I Decided to Use My Voice
Sometimes the most powerful choice we can make is to speak up. In this first short episode, I share when I decided to use my voice - what pushed me to stop holding back, what it felt like to speak my truth finally, and why claiming your voice is a win in itself. This episode is about courage, honesty, and the small but life-changing moments when you choose to stand in your own story.
Questions or Inquiries: contact.alenat@gmail.com
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