Wine, Wisdom & What Now?

What if rest didn’t have to be something you earned after completely exhausting yourself? Burnout recovery after 40 isn’t just about taking a break. It’s about recognizing the patterns that keep us overextended, learning to set boundaries, and giving ourselves permission to live differently. In this episode of Wine, Wisdom & What Now? , host Yolanda Holliday sits down with Dr. Rhonda Tsoi-A-Fa...

What happens when you finally stop questioning whether you’re worthy of the life you want—and start choosing yourself? In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with Pamela Davis-Brown, creator and host of The Well Done Life podcast, for an honest conversation about worthiness, choosing yourself, healing, wellness, love after 50, and giving yourself permission to...

What happens when you stop trying to become who everyone else thinks you should be—and finally give yourself permission to be who you are? In this episode of Wine, Wisdom & What Now? , Yolanda Holliday sits down with transformation speaker, coach, and founder of Transform with Tam, Tamara Clark, for a powerful conversation about identity, expectations, healing, and learning to embrace the woma...

What if the life you worked hard to build no longer feels like the life you want? In this episode of Wine, Wisdom & What Now? , Yolanda sits down with Coach MJ Hunter, a next chapter coach, content creator, author, and solo van lifer who decided she wasn’t going to spend the next season of her life waiting for someday. After more than 20 years in corporate America, MJ sold her home, bought an...

Who are you when the title, the career, or the role that helped define you is suddenly no longer there? In this episode of Wine, Wisdom & What Now? , Yolanda Holliday sits down with Tammy Oglesby for an honest conversation about identity, career transitions, faith, grief, and rediscovering yourself when life takes an unexpected turn. After nearly 30 years of building a successful corporate car...

Big Things Happening | Wine, Wisdom & Celebrating the Journey When was the last time you stopped long enough to celebrate yourself—not because the work was finished, but because you kept going and reached a milestone worth acknowledging? This week’s episode of Wine, Wisdom & What Now? is a special one. Yolanda is popping the Champagne and celebrating the official opening of The Curated Cir...

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 consid...

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, encoura...

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...

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 abou...

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:...

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-changi...

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-...

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...

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-...

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 re...

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 persona...

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 d...

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 perim...

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...