Wine, Wisdom & What Now?

Finding Happiness After Loss: Grief, Faith and Choosing Yourself Again

• Yolanda Holliday • Episode 9

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0:00 | 24:02

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 and caring for everyone around her while quietly carrying her own pain.

Through grief, reflection, faith, and learning when to pull away, she began giving herself permission to live differently—to set boundaries, protect her peace, and choose happiness without apology.

In This Episode, We Discuss:

  • Navigating grief while giving yourself permission to keep living
  • Finding happiness and moments of joy after losing a loved one
  • The difference between appearing happy and truly being happy
  • Learning to say no and knowing when to pull away
  • Finding strength through faith
  • Why supportive relationships matter during difficult seasons
  • Choosing yourself after years of caring for everyone else

Whether you're grieving a loss, carrying the weight of everyone around you, or realizing you've spent too much time putting yourself last, this conversation is a reminder that you can still find joy and create a meaningful life in the season ahead.

As Pastor Keevi reminds us, don't give up on yourself.

The Pairing

Peach in Love Peach Bellini by Tabitha Brown—a sweet, peach-forward Bellini that complements a conversation about finding joy again and embracing the season you're in.

A Question to Reflect On

When was the last time you stopped taking care of everyone else long enough to ask yourself, "Am I truly happy?"

Continue the Conversation

If this episode resonated with you, share it with another woman who may need encouragement as she navigates grief or a major life 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

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.

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.