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 wasn't fully prepared to answer: Who am I without my career? Tammy opens up about how much of her identity had become connected to her accomplishments, degrees, promotions, and professional success. She shares the difficult days that followed her job loss, including seeking therapy, grieving the life she knew, and learning how to create structure when she no longer had a workplace determining the rhythm of her days. Together, Yolanda and Tammy talk about learning to hear your own voice, releasing the need for permission, recognizing when you've outgrown a season, and understanding that you can be grateful for what a chapter gave you while still wanting something different. In This Episode, We Discuss: Rediscovering your identity after an unexpected job lossSeparating your self-worth from career titles and accomplishmentsNavigating grief and emotional challenges during career transitionsFinding purpose and structure outside corporate lifeGiving yourself permission to explore a new chapterThe Pairing Theo-patra's Cuvée Blanc from Theopolis Vineyards, a Black-owned winery founded by Theodora Lee. A Question to Reflect On If every title you carry disappeared tomorrow, how would you describe the woman underneath them? Connect with Tammy Tammy is building her personal brand, Becoming Her, along with resources designed to help women reflect on their identity, explore what's next, and begin building something of their own. https://stan.store/ladytami Continue the Conversation If this episode resonated with you, subscribe, leave a review, and share it with another woman navigating an unexpected transition. Join The Curated Circle, a community for Black women 40+ navigating life's transitions through meaningful conversations, resources, and sisterhood. https://circle.curatedlivingbyyh.com Explore The Curated Living Boutique Discover thoughtfully curated apparel, journals, gifts, and Wine, Wisdom & What Now? favorites. https://curatedlivingbyyh.com Until next time, pour a glass, give yourself grace, and keep becoming. Join the conversation — send Yolanda a message. Ready to find your Circle? The Curated Circle is a community for Black women 40+ to connect, learn, grow, and navigate this season of life together. Learn more and join us at Curated Living by YH. The Curated Living Boutique is officially open. Shop thoughtfully curated apparel, gifts, journals, Wine, Wisdom & What Now? favorites, and pieces from our In Her Season Collection — created with women navigating this season of life in mind. Shop the Boutique at curatedlivingbyyh.com. Curated for your journey. ou don’t have to navigate this season alone. The Curated Circle was created to give Black women 40+ a space for honest conversations, meaningful connection, trusted resources, and sisterhood. Come find your Circle at Curated Living by YH. 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.
