Reinvention & Identity 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 stop trying to become who everyone else thinks you should be—and finally give yourself permission to be who you are? In this episode of Wine, Wisdom & What Now?, Yolanda Holliday sits down with transformation speaker, coach, and founder of Transform with Tam, Tamara Clark, for a powerful conversation about identity, expectations, healing, and learning to embrace the woman you are while still becoming the woman you’re meant to be. Tamara opens up about becoming a mothe...

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, and solo van lifer who decided she wasn't going to spend the next season of her life waiting for someday. After more than 20 years in corporate America, MJ sold her home, bought an empty cargo van, converted it herself, and hit the road. But this conversation is abou...

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 about identity after job loss, career transitions, faith, grief, and rediscovering yourself when life takes an unexpected turn. After nearly 30 years of building a successful corporate career, Tammy found herself facing an unexpected job loss—and with it, a question she w...

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 masks we sometimes wear—the smiles, the "I'm fine," and the picture-perfect version of life we present to others while privately knowing that everything isn't okay. Yolanda challenges us to consider the emotional cost of pretending and asks a powerful question: Do you...

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 embracing a season of purpose instead of limitation. After attending a family gathering that stirred unexpected emotions, Yolanda opens up about honoring the relationships that shaped her and why the experience reaffirmed her passion for building Curated Living—a community w...

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 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 career reinvention, faith, boundaries, 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 le...

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 imposter syndrome, finding the courage to start something new, and learning to show up for yourself even when self-doubt tries to hold you back. As she celebrates the first six episodes of the podcast, Yolanda shares what this journey has taught her about courage, confiden...

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 Go Be Her University, Cocoa Pugh, for an inspiring conversation about healing, rediscovering your identity, and embracing the woman you're becoming. Through seasons of heartbreak, rebuilding, and self-discovery, Cocoa shares how learning to choose peace, trust God'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 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 journey that inspired both the podcast and Curated Living by YH. For years, Yolanda wore the Superwoman cape proudly—showing up for everyone, carrying every burden, and believing that strength meant never slowing down. But after years of pouring into others, navigating li...