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. 18h ago

    EP 010 | It's Not Too Late | Wine, Wisdom & Starting Where You Are

    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 dynamics, honoring the relationships that shaped her, and why the experience reaffirmed her passion for building Curated Living—a community where Black women don't have to navigate life's transitions alone. She also shares why she refuses to let age define what's possible and why every day is another opportunity to begin again. Together, we explore:  Navigating grief while embracing new beginnings  Why community matters now more than ever  Letting go of the belief that you're "too old"  Building the life you've been dreaming about—one step at a time  Overcoming imposter syndrome and trusting your purpose  Choosing courage over comfort in this season of life Whether you're starting over after 40, grieving what was, or wondering if it's too late to pursue the life you've imagined, this conversation is a reminder that your story is still being written—and your next chapter may be your best one yet. This Week's Pairing: 🍷 LVE Cabernet Sauvignon by John Legend — a smooth, full-bodied Cabernet with notes of blackberry, caramelized fig, and dark chocolate. As always, we're proud to highlight another Black-owned wine brand and encourage you to support the businesses helping diversify the wine industry. Reflection Question: What dream have you been putting on hold because you believe you've missed your moment—and what would change if you decided to begin anyway? If this episode encouraged you, be sure to follow, rate, and share Wine, Wisdom & What Now? with another woman who needs the reminder that it's never too late to begin again. 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 010 | It's Not Too Late | Wine, Wisdom & Starting Where You Are
  2. Jul 28

    Ep 009 | Now It's My Time | Wine, Wisdom & Choosing Happiness

    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 life worrying about and caring for everyone around her, while quietly carrying her own pain. Through grief, reflection, faith, and learning when to pull away, she began giving herself permission to live differently—to set boundaries, protect her peace, and choose happiness without apology. Together, they discuss: Navigating grief while giving yourself permission to keep livingThe difference between appearing happy and truly being happyLearning to say no and knowing when to pull awayFinding strength through faithWhy the right people matter during difficult seasonsChoosing yourself after years of taking care of everyone elseWhether you’re grieving a loss, carrying the weight of everyone around you, or simply realizing that you’ve spent too much time putting yourself last, this conversation is a reminder that you can still find joy, choose yourself, and create happiness in the life that is still ahead of you. This Week’s Pairing: Peach in Love Peach Bellini by Tabitha Brown — a sweet, peach-forward Bellini that pairs beautifully with a conversation about finding joy again, embracing freedom, and allowing yourself to enjoy the season you’re in. As always, we’re proud to highlight another Black-owned wine brand and encourage you to support the brands helping diversify the wine industry. Reflection Question: When was the last time you stopped taking care of everyone else long enough to ask yourself, “Am I truly happy?” If this episode encouraged you, be sure to follow, rate, and share Wine, Wisdom & What Now? with another woman who may need the reminder that it’s okay to have hard days, it’s okay to grieve, and it’s okay to choose yourself. As Pastor Keevi reminds us: don’t give up on yourself. 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 009 | Now It's My Time | Wine, Wisdom & Choosing Happiness
  3. Jul 21

    EP 008 | Pouring Into Purpose | Wine, Wisdom & Living Intentionally

    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 and pursue her passion for wine. It wasn't an easy leap, but by choosing faith over fear and intentionality over comfort, she discovered a life filled with purpose, freedom, and fulfillment. Together, they discuss:  What it means to live intentionally  Setting boundaries without guilt  The courage to leave a secure career and follow your calling  Why "do it scared" might be the best advice you'll ever receive  Finding confidence in spaces where you're often the only one  The importance of supporting Black-owned businesses and building community Whether you're considering a career change, learning to choose yourself, or simply looking for the courage to take your next step, this conversation will remind you that your purpose is worth pursuing—even if it requires you to step out in faith. This Week's Pairing: 🍷 House of Brown California Red Blend — a vibrant, fruit-forward red with notes of sugared cherry, hibiscus tea, and strawberry. As always, we're proud to highlight another Black-owned wine brand and encourage you to support the businesses helping diversify the wine industry. Reflection Question: What dream have you been putting on hold because you're waiting to feel ready—and what would happen if you decided to do it scared? If this episode encouraged you, be sure to follow, rate, and share Wine, Wisdom & What Now? with someone who's standing at the edge of a new beginning. Your next chapter may begin with one courageous decision.  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 008 | Pouring Into Purpose | Wine, Wisdom & Living Intentionally
  4. Jul 14

    EP 007 | Life Looks Different Now | Wine, Wisdom & New Seasons

    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 007 | Life Looks Different Now | Wine, Wisdom & New Seasons
  5. 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.

    Ep 004 | I Need to Get Back to Me | Wine, Wisdom & Reinvention
  6. 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.

    Ep 002 | We Get to Choose Joy: Reinvention, Self-Care & Starting Over | Wine, Wisdom & Choosing Yourself
  7. 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.

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

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.