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 slow down, embrace change, and give herself grace when life no longer looked the way she planned.

If you've ever found yourself adjusting to a new season and wondering, "What's next?" this conversation is for you.

The Pairing: Love Y'all Moscato by Tabitha Brown

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today's conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own "what now" season.

And remember—you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today’s conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own “what now” season.

And remember — you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.

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 deciding to move forward anyway.

If you've ever questioned whether you're good enough, too old, or qualified enough to pursue your dreams, this conversation is for you.

The Pairing: LVE Cabernet Sauvignon

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today's conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own "what now" season.

And remember—you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today’s conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own “what now” season.

And remember — you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.

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 choose peace, trust God's timing, and embrace her purpose transformed her life.

If you've ever wondered whether everything you've been through has a purpose, this conversation is for you.

The Pairing: Brown Estate Red Blend

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today's conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own "what now" season.

And remember—you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today’s conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own “what now” season.

And remember — you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.

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 becoming. Together, they discuss motherhood, boundaries, self-worth, and the peace that comes from living life on your own terms.

If you’ve ever found yourself wondering, “What about me?” this conversation is for you.

The Pairing: Love Corkscrew Cabernet Sauvignon

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today’s conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own “what now” season.

And remember — you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today’s conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own “what now” season.

And remember — you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.

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 herself, and learning that she's not alone.

If you've ever wondered, "Is it just me?" this conversation is for you.

The Pairing: LVE by John Legend Chardonnay

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today’s conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own “what now” season.

And remember — you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.

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 living intentionally, setting boundaries, and choosing joy every day. Together, they explore the identity shifts many women experience after 40, the importance of prioritizing your well-being without guilt, and why therapy can be one of the greatest gifts you give yourself.

If you've ever found yourself asking, "Who am I now?" or wondering if it's time to put yourself first, this conversation is for you.

In this episode, we discuss:
• Navigating the empty nest season
• What true self-care really looks like
• Boundaries as a form of self-care
• Finding yourself during life's transitions
• Breast cancer survivorship and resilience
• Choosing joy with intention
• The benefits of therapy and mental wellness

Guest: Joy Robbins
Licensed Mental Health Therapist, Self-Care Coach, and Founder of Creative Counseling & Consulting and Enjoy Wellness Retreats.

Connect with Joy:
Creative Counseling & Consulting: [email protected]
Enjoy Wellness Retreats: [email protected]

Coming Soon: In Her Season

One of our favorite parts of the show is In Her Season, a listener-driven segment where trusted experts answer real questions from women navigating life's transitions. Whether you're facing changes in your health, relationships, career, finances, identity, or simply wondering "what now?", this space is for you.

Have a question you'd like answered on a future episode? We'd love to hear from you.

Email your question to:
[email protected]

Your question may be featured anonymously on an upcoming episode of Wine, Wisdom & What Now?

If you enjoyed this episode, be sure to subscribe, leave a review, and share it with a woman who needs the reminder that choosing herself is not selfish.

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today’s conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own “what now” season.

And remember — you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.

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 empty, she was forced to confront a difficult truth: survivor's mode was no longer serving her.

In this candid conversation, Yolanda reflects on what it means to move from survival to self-preservation, the importance of boundaries, the power of giving yourself grace, and the freedom that comes from choosing yourself without guilt.

She also introduces listeners to the vision behind Wine, Wisdom & What Now?—a podcast created for Black women navigating reinvention, wellness, identity shifts, relationships, purpose, and all the questions that come with this season of life.

🍷 The Pairing: Brown Estate Rosé

To kick off our very first episode—and in celebration of National Rosé Month—we're raising a glass to Brown Estate Rosé, a Black-owned winery from California known for crafting wines that are bold, vibrant, and unforgettable.

As you settle into this conversation, we invite you to sip, reflect, and consider a question many women find themselves asking in this season: What's next? If you've been pouring into everyone else, struggling to make yourself a priority, or feeling the weight of constant responsibility, this episode is for you.

Have a question for In Her Season?
Submit your perimenopause or menopause questions to:
📧 [email protected]

🌐 www.winewisdomwhatnow.com

Follow, subscribe, and share with a woman who needs this conversation.

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today’s conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own “what now” season.

And remember — you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.

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 conversations, meaningful connection, and community for women learning to rediscover themselves and embrace what’s next.

Through reflective storytelling, real-life conversations, expert insight, and featured Black-owned wine brands that complement the conversation, Wine, Wisdom & What Now? creates space for women to feel seen, supported, and reminded they do not have to navigate this season alone.

🎙 Official episodes begin June 2
🍷 Featuring Black-owned wine brands
✨ Subscribe and join the conversation

Thank you for joining me for another episode of Wine, Wisdom & What Now?

If today’s conversation resonated with you, be sure to subscribe, leave a review, and share this episode with another woman navigating her own “what now” season.

And remember — you do not have to navigate this season of life alone.

Until next time, pour a glass, give yourself grace, and keep becoming.