Wine, Wisdom & What Now?

Yolanda Holliday

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

  1. Ep 004 | I Need to Get Back to Me | Wine, Wisdom & Reinvention

    Jun 23

    Ep 004 | I Need to Get Back to Me | Wine, Wisdom & Reinvention

    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.

    38 min
  2. Ep 002 | We Get to Choose Joy: Reinvention, Self-Care & Starting Over | Wine, Wisdom & Choosing Yourself

    Jun 9

    Ep 002 | We Get to Choose Joy: Reinvention, Self-Care & Starting Over | Wine, Wisdom & Choosing Yourself

    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: joyrobbins@creativecounselinggroup.com Enjoy Wellness Retreats: jrobbins@enjoywellnessretreats.com 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: inherseason@winewisdomwhatnow.com 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.

    19 min
  3. Ep 001 | From Survivor's Mode to Self-Preservation | Wine, Wisdom & Grace

    Jun 2

    Ep 001 | From Survivor's Mode to Self-Preservation | Wine, Wisdom & Grace

    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: 📧 inherseason@winewisdomwhatnow.com 🌐 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.

    21 min

About

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.