Wine, Wisdom & What Now?
Wine, Wisdom & What Now? is a lifestyle podcast for Black women navigating reinvention, identity shifts, wellness, and the “what now” season of life. Through honest conversations, reflective storytelling, and expert insight, host Yolanda Holliday creates a space where women feel seen, supported, and reminded they don’t have to navigate this season alone.
Episodes
What happens when the version of you everyone sees doesn’t match what’s really happening behind closed doors?
In this solo episode of Wine, Wisdom & What Now?, Yolanda Holliday gets honest about the masks we sometimes wear—the smiles, the “I’m fine,” and the picture-perfect version of life we present to others while privately knowing that everything isn’t okay.
Yolanda challenges us to co...
Who is in your circle—and do you have the kind of community that challenges you, supports you, and reminds you that you don't have to figure everything out alone?
In this solo episode of Wine, Wisdom & What Now?, Yolanda Holliday opens up about why community has become such an important part of her life and why she believes every woman deserves a space where she can be supported, encouraged, challenged, and understood.
From...
What happens when you finally trust the feeling that tells you something isn’t right—even when walking away means stepping into the unknown?
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with occupational therapist Shayla for an honest conversation about choosing peace, trusting yourself, setting boundaries, and finding the courage to make difficult decisions.
After years of naturally putting...
What if your best chapter isn't behind you—but still waiting for you?
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday shares one of her most personal solo conversations yet, reflecting on grief, family, community, and why turning 50 has become a season of purpose instead of limitation.
After attending a family gathering that stirred unexpected emotions, Yolanda opens up about navigating changing family dynamic...
What happens when you’ve spent years taking care of everyone else and finally realize it’s time to choose yourself?
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with Pastor Keevi Worthy for a deeply personal conversation about grief, faith, healing, and the decision to make happiness a priority.
After losing her husband, Keevi found herself facing a difficult truth: she had spent much of her...
What happens when you stop pouring from an empty cup and start pouring into your purpose?
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with entrepreneur and Horton Cellars owner Denise Horton for an inspiring conversation about faith, boundaries, reinvention, and having the courage to bet on yourself.
After spending 19 years in healthcare, Denise made the life-changing decision to leave a stable career ...
Ep 007 | Life Looks Different Now | Wine, Wisdom & New Seasons
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with entrepreneur, event strategist, and business owner Pamela Howard for an honest conversation about navigating the unexpected transitions that come with this season of life.
From menopause and empty nesting to becoming a grandmother and redefining self-care, Pamela shares how she learned to...
Ep 006 | Show Up for Yourself | Wine, Wisdom & Courage
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday reflects on the journey of launching the podcast, celebrating six episodes, and the courage it takes to keep showing up despite self-doubt.
From overcoming imposter syndrome to choosing herself the same way she's always chosen everyone else, Yolanda shares why courage isn't the absence of fear—it's decidi...
Ep 005 | It's Going to Be Worth It | Wine, Wisdom & Becoming Her
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with certified coach, author, speaker, and Founder of Go Be Her University, Cocoa Pugh, for an inspiring conversation about healing, identity, and becoming the woman you were always created to be.
Through seasons of heartbreak, rebuilding, and self-discovery, Cocoa shares how learning to cho...
Ep 004 | I Need to Get Back to Me | Wine, Wisdom & Reinvention
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with Fariyda “Free” Burgess for an honest conversation about divorce, rediscovery, and finding the courage to choose yourself.
After 15 years of marriage, Free shares her journey of reclaiming her happiness, redefining self-care, and creating a life that reflects who she is becomin...
Ep 003 | Nobody Prepared Me for This | Wine, Wisdom & Perimenopause
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with Anita "Lil' Bit" Lindell for an honest conversation about navigating perimenopause and the symptoms many women aren't prepared for.
From brain fog and anxiety to sleepless nights and heart palpitations, Anita shares her personal journey of searching for answers, advocating for hersel...
In this episode of Wine, Wisdom & What Now?, Yolanda sits down with licensed mental health therapist, self-care coach, and breast cancer survivor Joy Robbins for an honest conversation about what happens when life shifts and you're forced to rediscover yourself.
From navigating the empty nest season to redefining self-care beyond spa days and bubble baths, Joy shares how a breast cancer diagnosis deepened her commitment to livin...
In the very first episode of Wine, Wisdom & What Now?, host Yolanda Holliday shares the personal journey that inspired both the podcast and the Curated Living by YH movement.
For years, Yolanda wore the Superwoman cape proudly—showing up for everyone, carrying every burden, and believing that strength meant never slowing down. But when years of pouring into others, life transitions, and perimenopause left her running on em...
Welcome to Wine, Wisdom & What Now? — a lifestyle podcast for Black women 40+ navigating reinvention, wellness, identity shifts, healing, purpose, and the “what now” season of life.
In this official trailer, host Yolanda Holliday shares the heart behind the podcast and the journey that inspired its creation. What began as personal reflection during a season of uncertainty evolved into a space for honest convers...
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