Wine, Wisdom & What Now?
Life after 40 comes with new questions, unexpected transitions, and opportunities to rediscover yourself.
Join host Yolanda Holliday for honest conversations about reinvention, relationships, menopause, wellness, and everything that comes next.
Real conversations. Good wine. A little wisdom for the journey.
Episodes
19 episodes
Self-Worth After 50: Choosing Yourself, Healing and Finding Love
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 Li...
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Rediscovering Your Identity: Letting Go of Expectations and Embracing Yourself
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 Cla...
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Redefining Success After 40: Leaving Corporate Life and Choosing Freedom
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,...
Identity After Job Loss: Rediscovering Yourself Beyond Your Career
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 abo...
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Celebrating Your Wins: Why Every Milestone Deserves Recognition
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?,...
Authenticity After 40: Letting Go of the Mask and Being Yourself
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 ...
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Finding Your Community After 40: Why Sisterhood and Connection Matter
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 Holl...
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Choosing Peace in Relationships: Setting Boundaries and Trusting Yourself
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 occupat...
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Starting Over at 50: Why It's Never Too Late to Reinvent Your Life
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 embraci...
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Finding Happiness After Loss: Grief, Faith and Choosing Yourself Again
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...
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Reinventing Your Career: Leaving Corporate Life to Pursue Your Purpose
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...
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Navigating Menopause and Empty Nesting: Embracing Life's Next Chapter
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 str...
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Overcoming Imposter Syndrome After 40: Finding the Courage to Start
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 impos...
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Healing and Rediscovering Your Identity: Becoming the Woman You're Meant to Be
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...
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Rediscovering Yourself After Divorce: Rebuilding Confidence and Choosing Happiness
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 hones...
Perimenopause Symptoms: Brain Fog, Anxiety and What Women Need to Know
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' Bi...
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Self-Care After 40: Choosing Joy, Healing and Rediscovering Yourself
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 brea...
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From Survival Mode to Self-Preservation: Setting Boundaries and Choosing Yourself
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 journe...
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