Wine, Wisdom & What Now? is a lifestyle podcast for Black women navigating reinvention, identity shifts, wellness, and the “what now” season of life. Through honest conversations, reflective storytelling, and expert insight, host Yolanda Holliday creates a space where women feel seen, supported, and reminded they don’t have to navigate this season alone.
Ep 009 | Now It's My Time | Wine, Wisdom & Choosing Happiness
•Yolanda Holliday•Episode 9
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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 grief, faith, healing, and the decision to make happiness a priority.
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.
Together, they discuss:
Navigating grief while giving yourself permission to keep living
The difference between appearing happy and truly being happy
Learning to say no and knowing when to pull away
Finding strength through faith
Why the right people matter during difficult seasons
Choosing yourself after years of taking care of everyone else
Whether you’re grieving a loss, carrying the weight of everyone around you, or simply realizing that you’ve spent too much time putting yourself last, this conversation is a reminder that you can still find joy, choose yourself, and create happiness in the life that is still ahead of you.
This Week’s Pairing:Peach in Love Peach Bellini by Tabitha Brown — a sweet, peach-forward Bellini that pairs beautifully with a conversation about finding joy again, embracing freedom, and allowing yourself to enjoy the season you’re in. As always, we’re proud to highlight another Black-owned wine brand and encourage you to support the brands helping diversify the wine industry.
Reflection Question: When was the last time you stopped taking care of everyone else long enough to ask yourself, “Am I truly happy?”
If this episode encouraged you, be sure to follow, rate, and share Wine, Wisdom & What Now? with another woman who may need the reminder that it’s okay to have hard days, it’s okay to grieve, and it’s okay to choose yourself. As Pastor Keevi reminds us: don’t give up on yourself.
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.
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.
SPEAKER_00
I spent a lot of time alone and being happy on the outside so other people can see it. But when I get home and I get by myself and I get in my bedroom, that's when the tears come. I can sit in the house and cry all night long, but don't nobody will see it. So I'm putting on an act for everybody else. Even for family.
SPEAKER_01
What was your aha moment? What was it that made you really? I'm not happy.
SPEAKER_00
I don't think I ever truly been happy in my life until now.
SPEAKER_01
For those that are new here, welcome. For those that have come back, and this is your second, third, fourth, or sixth episode, I appreciate you. Thank you for following me on this journey. With every episode, we kick it off with the pairing, and the pairing is our segment where we feature a black-owned line brand. This week we have a Peach in Love Peach Bellini by Tabitha Brown. This is Tabitha Brown's line. It is produced in Germany and sold only at Target. I know we are boycotting Target, but think about all of the black-owned brands that are currently in Target that are not getting our support. So if nothing else, just consider your support in these brands. The reason we do this is because black-owned wine brands, the wine industry itself, it is set up so that we don't have success amongst black-owned wine brands. We don't have the dollars, we don't have the support. So it's important that if you are someone that enjoys wine, you at least consider supporting a black-owned brand. Seek them out, they are in stores. This one is only sold at Target, but we featured others that are sold at your local wine stores. Today's guest is a widow, pastor, business owner, and mayor whose life has been shaped by faith, resilience, and a deep commitment to serving others. After years of pouring into her family and community, she's now embracing a new season of rediscovering joy, choosing herself, and finding happiness without apology. Her story is one of perseverance, reinvention, and the courage to keep moving forward no matter what life brings. Pastor Keeve Worthy, welcome to this episode.
SPEAKER_00
Thank you.
SPEAKER_01
It's good to be here. I'm so excited. I know it's going to be a good conversation. I have the pleasure of knowing, I call assist, but Pastor Worthy outside of this podcast, so I know it's going to be a really, really good conversation and one that I hope pours into not only our assist listening, myself and you, because I don't think you realize how much you influence, encourage, and inspire others. So I'm going to ask you, what season are you currently navigating?
SPEAKER_00
Um now I am currently navigating to be happy. I just want to be happy and take care of myself. I have taken care of everybody else. And now is it's my time. I I want to be happy. I'm making sure that I'm good, you know. So yeah. Let's see.
SPEAKER_01
What I'm finding a common theme is that women get to a certain point, and it's usually around 50 where they realize I poured into everyone else, and now what about me? I feel empty. I felt guilty, but now it's like we're taking back our power and recognizing that we deserve it as well.
SPEAKER_00
Right. I always felt like I had to take care of everybody else. Siblings, mom, just people around me. I always wanted to make sure everybody else was good. And it will drain you, and it did drain me. And I didn't realize how drained I was until after my husband passed. So now I just want to live for me. And don't get me wrong, I still take care of mommy, I still take care of my children, but I make sure that I'm good. I make sure that I'm happy and I'm taken care of.
SPEAKER_01
That's important. Something that you deserve, something that we all deserve, and something that a lot of black women struggle with because I believe our generation at least, we are trained almost to take care of everyone else. We are taught that it is selfish to put yourself first. So it's almost changing the mindset to what our new realities is. What we were taught was not necessarily the correct thing. We don't have to lose ourselves for everyone else.
unknown
Right.
SPEAKER_01
What does happiness look like to you?
SPEAKER_00
Oh God. Just worry free. I spent most of my life worrying. And I I mean, just to not worry anymore. To go wherever I want to go, to do whatever I want to do. I don't have to answer to nobody but God. That's the way I want it. That's the way I'm planning on keeping it. I just want to just to be free. To be free to to live with no regret. You know, don't worry about what nobody else has to say, because it don't matter what nobody. As long as I'm happy. And I I spent most of my life worrying about what other people think about me or what they would say. But it don't matter anymore. I just want to make myself happy. I just want to be free. And that's what I that's what I'm doing. I'm embracing that. It's something that I'd never done before. So now I'm embracing it. And I like it. I like it. Good.
SPEAKER_01
Good. I can see it in your smile. What was your aha moment? What was it that made you realize I'm not happy?
SPEAKER_00
Well, after Lee passed, I wasn't happy. And honestly, even before he passed, I wasn't happy. But after he passed, and some time after, I started to just sit down and I had to just like look at myself in the mirror and and just see that I haven't been happy for a long time. We I guess when you're by yourself for so long, you have time to sit and think. So I spent a lot of time alone and being happy on the outside so other people can see it. But when I get home and I get by myself and I get in my bedroom, that's when the tears come. That's when the sadness comes. Because I'm putting on the act for everybody else. Even for family. I can sit in the house and cry all night long, but don't nobody will see it. So I had to really just take a step back and say, okay, you're going to really have a nervous breakdown if if you don't get to the root of this problem. I haven't been, I I don't think I ever truly been happy in my life until now.
SPEAKER_01
That is that just to sit down and have that real conversation with yourself, it is powerful. And it's something that I think everyone needs to get into a space where you do truly reflect. Because, like you said, what you put on out in the streets, you gotta go home at night. And then what does that look like? And if that is how you are like, if you are going home sad, crying, you deserve better. And like you said, you're gonna have a nervous breakdown because you're so busy putting on a front for everyone else that when you get home, you gotta really deal with reality, and that's that's a hard place to be, and it takes a certain amount of strength to pull yourself up out of it. Where do you get your strength from to pull yourself up out of it?
SPEAKER_00
I get my script from most of all from God because I have to stay connected to God. If I don't stay connected to God, I'll fall apart. And not only God, but God put people around me that I can that I can truly be honest with. I had one lady ask me one day, right after Lee Dy, she said, How are you doing? She said, Tell me, how are you really doing? And she said, How are you managing? I said, I I do good. I said, I just take two tall 9 p.m. and I drink some wine and I go to sleep. And she just looked at me and she was like, and I said that at a church. So she was like, I think you said that. But then she said, but then she said, thank you. She said, I want to thank you for being honest with me. So it's been around people that I can be honest with and I can open up to and I can tell them, you know what, I'm not doing good right now. I drank wine to help me to keep my sanity. I had to take pills at night in order for me to get a good night's rest. And I did that for so long to I had to stop and say, okay, God, I need for you to step in. Because if you don't step in, I'm gonna end up hurting myself. It wasn't a good thing what I was doing. It was just something to keep me, to try to keep me going, but it wasn't good. So I have to stay connected to God in every way that I can because on top of going through what I'm going through, I'm not only carrying mine, I'm carrying everybody's. I'm carrying the entire church. I'm carrying the entire town. I'm carrying everybody's. I'm carrying an entire household. So I have to stay connected to God. I have to.
SPEAKER_01
So you mentioned you even though you still have a lot on your plate, you are putting you first and prioritizing your happiness. Right. What is it you do for you to make sure that you're staying on your journey for happiness and not getting lost in all of the responsibilities? Because again, you're a mother, a grandmother, a mayor, a pastor, a caregiver. What are you doing to make sure you don't get off track from your journey?
SPEAKER_00
I have to pull back vacation, vacation, vacation. I like to go. When somebody says let's go, I go. I don't even think twice. I'm like, yeah, I'm going. I don't even think twice about it. I like to go. My phone is one thing that I have to just take it, and I have more than one phone, but I have to take them and I have to just say, okay, not today. The biggest thing for me is I have to know when to pull away. And I pull away and I had to take a day and say, no, I'm not doing it today. Because I get so overwhelmed with the phone calls, so overwhelmed with word and people that sometimes I feel like I can't breathe. So I have to say, I'm not doing it today. So for me, that's what I had to do. I just have to just disappear for a while.
SPEAKER_01
That is the power of no. A lot of people think that no is such a bad word, struggle with saying it, but you lose a lot of you when you don't know how to say no.
SPEAKER_00
Right. I hope that word.
SPEAKER_01
That word, that's a whole sentence, but I hope that you are in these moments taking the time to applaud yourself for where you are because there are so many women who can't pull themselves up out of the darkness. And if you had to give a word to these women who are out smiling, life's great, but at home in the dark, can't pull it together, can't see any hope. What word would you give to them?
SPEAKER_00
I would want to encourage them to don't give up on yourself. Don't give up on yourself. You can do it. There is life out of grief. You can still live, you can still be happy, you got to remember the memories and take the memories with you, but you got to get up and you have to continue to keep going. You cannot let nothing or nobody stop you from being the best you you can be. This is a beautiful world that we have, and we have to get up and we have to tell God, thank you, even in the midst of what we're going through, and we have to keep going. So I would say to you, get up, rise up, and keep going. It's not gonna be a good day every day. It's not. Sometimes I say, you know what, I just don't feel like it today. I'm just gonna be to myself. But I get up and I keep going.
SPEAKER_01
So I mentioned it in the intro, but we haven't directly discussed it. So for the sister that's listening, that is hearing your story, how long have you been a widow and how long did it take you to get to this place?
SPEAKER_00
Lee died April 12th of last year. So I've been a widow a year. It took me a minute. Um this year, things have gotten better. Like the beginning of this year start to get a little bit better. Like I said, I still have my moments to where I don't want to be bothered or just like it hit you at a certain time. It's not something that you can just stop and say, okay, I'm over it. You'll never be over it. I'm outside cutting grass, and I'm like, I can have a nurse break down and cutting grass because I'm like, you know what, my husband did this. If I can't reach something in the cabinet, and I'm like, you know, I can say, Lee, will you come get this? But he's not there to do that anymore. So you have your moments, but it took me to be able to get up and to be how I am now. To be honest, I I did start it immediately after he died. I hadn't stopped running. My feet haven't stopped going since he died. The day, I mean, week after I became the mayor like two weeks after my husband passed. And it helps me, we are all different. It helps me to keep going, to stay busy. I have been busy ever since he passed. So I can say two weeks after he's gonna be.
SPEAKER_01
So there are points where someone may be grieving and thinking, I should be over this now. It's been six months, it's been a year. That's just not how grief works. And it works differently for everybody. So your story may be a year, and somebody else's story may be five years, and it works differently for everyone. I think the most important thing to do, I feel like the most important thing to do is own your grief, and then speak to someone, get some grief counseling, speak to your minister, pastor, best friend. Like, don't hold it in, but then allow yourself to have those bad days because they are this person was important in your life, your husband, whoever it is you're grieving, was important in your life. So of course you're gonna miss them.
SPEAKER_00
You are, and and don't let like don't let nobody tell you how long it's gonna take for you to grieve. Every relationship is different. I met a lady and she said her husband has been dead over 30 years, and she hasn't been able to move forward. It's different for everybody. Everybody's different for me. I have to just stay busy. If I stay busy, I'm fine. But if I get to myself, if I get on that phone and if I start looking back at old memories, then I'll break down. But that's okay. It's okay to have those moments, it's okay to break down, so it's okay to cry. I just pray that you don't stay there. Just don't stay there.
SPEAKER_01
Right, right. You have overcome so much in life, and you are again an inspiration to many. Oftentimes, we're so busy in the journey we don't actually stop to give ourselves credit for the journey. If you had to look back to young Kiwi, what would you say to her?
SPEAKER_00
I would say, you go girl. That's what I would say, cause young Kiwi was rough. Young Kiwi was hard-headed, young Kiwi didn't listen at nobody, young Kiwi was out there doing whatever young Kiwi wanted to do. You couldn't tell me nothing. A lot of people look down on young Kiwi. A lot of people talk bad on me. And to be Mayor Great Falls, I never imagined that I would because I didn't think that they would want me because as a child I didn't feel wanted. So I would have to, you know, give give give Kiwi a high five and say, good job, for not giving up and and not throwing in the towel. Good job.
SPEAKER_01
Based on your journey and all that you are experiencing, the wins, the losses, however hard it was, what is it you want to leave us with? What is it you want to share for someone who may be listening and going through anything and just looking for a little bit of hope?
SPEAKER_00
I would say to you, don't give up. Trust in the Lord with all of your heart. Put your trust in God and lean not to your own understanding. That's what messes us up a lot. Your thoughts, what you're thinking, it will mess you up. A lot of times it's not even what you think. Just continue to trust in the Lord, lean to not understanding, acknowledge Him, and let Him direct your path. It's gonna be alright. We all experience some rough times, we all experience some hard times. We all feel like we want to give up at one point in our life. But since don't give up. There's need of you. There's somebody out there that needs you. Somebody out there needs to hear your story, somebody out there needs to draw for your strength. So don't give up and don't throw in the towel.
SPEAKER_01
Amen. I would uh diddle that. Just I think you said the most important thing that don't give up. You are needed. Somebody needs you, you need you. There is no season that lasts forever. That this is just one season. Do the work, lean on your people, whatever it takes to get you to, as you said, your happy place.
SPEAKER_00
Yeah. Now lean on your people. Your people. Don't lean on the wrong people. You know, your people. I had to learn that too. There's some good people out there. And you just got to to know. You got to know who to lean on. You got to know who you should trust. Yeah, you have to.
SPEAKER_01
Yeah, use your discernment and time doesn't matter. You could have known someone for 30 years and have met someone for six months. That person of 30 years may not have your best interest, where that person for six months is really caring about you.
SPEAKER_00
Right, right. And when Lee died, God put this young lady in my life, and she has been one of my best friends, and I never imagined that she would be. But she has been there for me more than people that I have known my entire life. Well, that's true.
SPEAKER_01
Yeah, yeah. Okay, well, I knew this was going to be a really, really good conversation. And I said I couldn't wait to get to the point where I said, I told you so. But it was a really good conversation, and I feel like it is going to touch so many people who need to hear it. Sometimes we don't see people who have gone through it. So when you don't see it, you just you just don't know. But to actually see someone who has not gone through it but has is still currently going through it, but also in that journey of going through it, making happiness a priority, making yourself a priority. So I think that this would help a lot of women. I hope it does. I appreciate all those that listen and follow. If you have any comments, questions, whether it's for myself, whether it's for Pastor Worthy, or any of the guests that have come on, you can always email them to questions at winewisdomwhatnow.com. We do have a segment which will kick off in episode 10 called In Her Season, and that is where we will have a trusted professional come on to answer your questions about Perimenopause, menopause, and we've added financial retirement planning, financial planning, whatever financial questions you may have. You email those into in her season at winewisdom whatnow.com. We will provide them to the expert, and they will provide an answer that we will feature on a future episode. I'm asking that you like, follow, share, let everyone know about Wine Wisdom and What Now. It is because of you that we keep coming back. We did meet our first month's goal, and we're looking to exceed our second month's goal. There is a newsletter for the podcast that gives you snippets of what is happening at this week's episode. It is released every Tuesday. Before you even listen, you can read this newsletter. It is a short newsletter that comes to your email. You can go to our website to sign up, and it is winewisdomwhatnow.com, and it is just a box that you put your email address in. This way we can keep you updated. And again, episodes are released every Tuesday at 6 a.m. I greatly appreciate you for taking this journey with me. If you have a story you want to tell, email me. Let me know. Everybody has a story, and this is about everyday black women sharing their lived experiences. So even if you think no one wants to hear it, I can guarantee you there is somebody that's going to be encouraged by your story. If no one has told you, you are amazing, and I hope you have the best week ever. Thank you for joining.