Relationships & Boundaries Episodes

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 Life podcast, for an honest conversation about self-worth, healing, love after 50, and giving yourself permission to live fully. Pamela shares why she calls this her season of worthiness, how her perspective on life changed after turning 50, and what it meant to open hersel...

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 occupational therapist Shayla for an honest conversation about choosing peace in relationships, setting healthy boundaries, trusting yourself, and finding the courage to make difficult decisions. After years of naturally putting others first, Shayla found herself facing a de...

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 finding happiness after loss, navigating grief, leaning on faith, and giving yourself permission to experience joy again. After losing her husband, Keevi found herself facing a difficult truth: she had spent much of her life worrying about...

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 strategist, and business owner Pamela Howard for an honest conversation about navigating menopause, empty nesting, self-care, and embracing life's next chapter. From experiencing menopause and adjusting to an empty nest to becoming a grandmother, Pamela shares what it's ...

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 honest conversation about rediscovering yourself after divorce, rebuilding confidence, and finding the courage to choose your own happiness. After 15 years of marriage, Free shares her journey of reclaiming her happiness, redefining self-care, and creating a life that refl...

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 breast cancer survivor Joy Robbins for an honest conversation about self-care after 40, rediscovering yourself, and choosing joy through life's transitions. From navigating the empty nest season to redefining self-care beyond spa days and bubble baths, Joy shares how her ...