Ep 009 | Now It’s My Time | Wine, Wisdom & Choosing Happiness
What happens when you realize you’ve spent so much time taking care of everyone else that you’ve forgotten how to take care of yourself?
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with Pastor Keevi Worthy for a heartfelt conversation about grief, healing, faith, and the journey back to happiness after years of putting everyone else’s needs before her own.
After the loss of her husband, Keevi was forced to confront a difficult truth: behind the smile everyone saw was a woman who hadn’t truly been happy in a long time. Together, she and Yolanda discuss navigating grief, learning to say no, leaning on faith, surrounding yourself with the right people, and giving yourself permission to choose joy without guilt.
If you’ve been carrying the weight of everyone around you while quietly neglecting yourself, this conversation is your reminder that it’s never too late to choose happiness. Grief may become part of your story, but it doesn’t have to write the ending.
Ep 008 | Pouring Into Purpose | Wine, Wisdom & Living Intentionally
What does it look like to stop pouring from an empty cup and start intentionally pouring into yourself?
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with entrepreneur, wine educator, and Horton Cellars owner Denise Horton for an inspiring conversation about choosing yourself, setting boundaries, and having the courage to pursue purpose—even when it means walking away from everything you’ve known.
After a successful 19-year career in healthcare, Denise took a leap of faith to build a business centered around her passion for wine. Together, she and Yolanda discuss intentional living, the power of saying no, navigating perimenopause, overcoming fear, supporting Black-owned businesses, and why sometimes the best decision you’ll ever make is to simply do it scared.
If you’ve ever felt called to something greater but fear has kept you standing still, this conversation is your reminder that purpose often begins on the other side of faith. Sometimes the greatest investment you can make is choosing yourself first.
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 embracing a slower pace, Pamela shares how she learned to give herself grace, prioritize self-care, and find joy in life’s new seasons.
If you’ve ever found yourself adjusting to a season you didn’t plan for, this conversation is for you.
Ep 006 | Show Up for Yourself | Wine, Wisdom & Courage
In this solo episode of Wine, Wisdom & What Now?, Yolanda Holliday reflects on the first six episodes of the podcast and the courage it takes to keep showing up, even when self-doubt tries to convince you otherwise.
Through a candid conversation about imposter syndrome, celebrating small wins, and choosing yourself with the same determination you give to everyone else, Yolanda challenges women to stop waiting for permission and start believing in what’s possible.
If you’ve ever found yourself wondering, “Why can I show up for everyone else, but not for myself?” this conversation is for you.
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 Cocoa Pugh for an uplifting conversation about purpose, identity, and becoming the woman you were created to be.
Cocoa shares how embracing life's transitions with faith and courage has shaped her journey, reminding us that growth often requires trusting the process before we see the outcome.
If you've ever questioned your purpose or wondered if the journey is worth it, this conversation will encourage you to keep becoming—because what's ahead is worth it.
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 rediscovery, self-worth, and finding the courage to choose yourself after a major life transition.
After 15 years of marriage, Free shares her journey of reclaiming her happiness, redefining self-care, and creating a life that aligns with who she is becoming.
If you’ve ever found yourself wondering, “What about me?” this conversation is for you.
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 don't see coming.
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 found yourself wondering, "Is it just me?" this conversation is for you.
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 Holliday sits down with licensed mental health therapist, self-care coach, and breast cancer survivor Joy Robbins for a conversation about self-care, boundaries, life transitions, and choosing yourself without guilt.
Joy shares how navigating an empty nest and surviving breast cancer reshaped her perspective on wellness, purpose, and joy.
If you've ever found yourself asking, "Who am I now?" this conversation is for you.
Ep 001 | From Survivor’s Mode to Self-Preservation | Wine, Wisdom & Grace
In the debut episode of Wine, Wisdom & What Now?, Yolanda Holliday shares the personal journey that led her from burnout and survival mode to a season of grace, boundaries, and self-preservation.
If you’ve ever found yourself pouring into everyone else while neglecting yourself, this conversation is for you.
Wine, Wisdom & What Now? | Official Trailer
Welcome to Wine, Wisdom & What Now? — a lifestyle podcast for Black women 40+ navigating reinvention, wellness, identity shifts, healing, 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.