Wine, Wisdom & What Now?

What does it mean to finally recognize your worth and start choosing yourself after 50?

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 self-worth, healing, love after 50, and giving yourself permission to live fully.

Pamela shares why she calls this her season of worthiness, how her perspective on lif...

What happens when you stop trying to become who everyone else thinks you should be and finally give yourself permission to embrace who you are?

In this episode of Wine, Wisdom & What Now?, Yolanda Holliday welcomes Tamara Clark, transformation speaker, coach, and founder of Transform with Tam, for an honest conversation about rediscovering your identity, letting go of expectations, healing, and embracing who you are.

Tamara share...

What if the life you worked so hard to build no longer feels like the life you want?

In this episode of Wine, Wisdom & What Now?, Yolanda Holliday 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 empty cargo van, converted...

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 after job loss, career transitions, faith, grief, and rediscovering yourself when life takes an unexpected turn.

After nearly 30 years of building a successful corporate career, Tammy found hersel...

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?

In this solo episode of Wine, Wisdom & What Now?, Yolanda Holliday is popping the Champagne and celebrating the official opening of The Curated Circle, a community created for Black women 40+ to connect, find support and resources, and navigate this ...

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 authenticity after 40 and 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 consider the...

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 explores the importance of finding your community after 40 and why meaningful sisterhood, connection, and support matter during this season of life.

From navigating perimenopause and empty nesting ...

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 in relationships, setting healthy boundaries, trusting yourself, and finding the courage to make difficult decisions.

After years o...

What if your best chapter isn't behind you—but still waiting for you?

In this solo episode of Wine, Wisdom & What Now?, Yolanda Holliday reflects on starting over at 50, navigating grief, changing family dynamics, and embracing a season of purpose instead of limitation.

After attending a family gathering that stirred unexpected emotions, Yolanda opens up about honoring the relationships that shaped her and why the experienc...

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 finding happiness after loss, navigating grief, leaning on faith, and giving yourself permission to experience joy again.

After losing her husband, Keevi found herself facing a di...

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 career reinvention, faith, boundaries, and having the courage to bet on yourself.

After spending 19 years in healthcare, Denise made the life-changing decision to leave a stable ...

What happens when life starts looking different from the way you imagined—and you're navigating several changes all at once?

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 menopause, empty nesting, self-care, and embracing life's next chapter.

From experiencing menopause and adjusting to...

Have you ever questioned whether you're good enough, qualified enough, or too old to pursue something you've been dreaming about?

In this solo episode of Wine, Wisdom & What Now?, Yolanda Holliday reflects on overcoming imposter syndrome, finding the courage to start something new, and learning to show up for yourself even when self-doubt tries to hold you back.

As she celebrates the first six episodes of the podcast, Yolanda sha...

What if everything you've been through is helping you become the woman you were always meant to be?

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, rediscovering your identity, and embracing the woman you're becoming.

Through seasons of heartbreak, rebuilding, and self-discov...

Have you ever spent so much time being a wife, mother, or caregiver that you started wondering, "What about me?"

In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with Fariyda "Free" Burgess for an honest conversation about rediscovering yourself after divorce, rebuilding confidence, and finding the courage to choose your own happiness.

After 15 years of marriage, Free shares her journey of reclaiming her ha...

Brain fog. Anxiety. Sleepless nights. Heart palpitations. What happens when your body starts changing and nobody prepared you for it?

In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with Anita "Lil' Bit" Lindell for an honest conversation about perimenopause symptoms, the confusion that can come with hormonal changes, and the importance of advocating for your health.

From brain fog and anxiety to sleepless...

What does choosing yourself really look like after years of putting everyone else first?

In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with licensed mental health therapist, self-care coach, and breast cancer survivor Joy Robbins for an honest conversation about self-care after 40, rediscovering yourself, and choosing joy through life's transitions.

From navigating the empty nest season to redefining sel...

What happens when the woman who has always been strong for everyone else finally realizes she needs to show up for herself?

In the premiere episode of Wine, Wisdom & What Now?, host Yolanda Holliday shares the personal journey that inspired both the podcast and Curated Living by YH.

For years, Yolanda wore the Superwoman cape proudly—showing up for everyone, carrying every burden, and believing that strength meant never slo...

You've spent years showing up for everyone else. But somewhere along the way, have you started asking yourself, "What about me? What's next?"

Welcome to Wine, Wisdom & What Now?, a lifestyle podcast for Black women 40+ navigating reinvention, wellness, identity shifts, healing, relationships, purpose, and this season of life.

Hosted by Yolanda Holliday, the podcast was born from her own journey of reflection and rediscovery. What...