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.
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Ep 006 | Show Up for Yourself | Wine, Wisdom & Courage
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday reflects on the journey of launching the podcast, celebrating six episodes, and the courage it takes to keep showing up despite self-doubt.
From overcoming imposter syndrome to choosing herself the same way she's always chosen everyone else, Yolanda shares why courage isn't the absence of fear—it's deciding to move forward anyway.
If you've ever questioned whether you're good enough, too old, or qualified enough to pursue your dreams, this conversation is for you.
The Pairing: LVE Cabernet Sauvignon
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.
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.
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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.
SPEAKER_00
When I had to do it for my kids, it wasn't a question in the world if it would get done. When I have a client expecting something from me, there's not a question in the world that I am not going to execute. I am going to get this done for them. But when I have to show up for myself, where does that same courage go? Why can I not show up for myself the same way that I show up for everyone else? Yolanda Holiday, and I thank you for joining me. As usual, we're going to kick off this episode with the pairing. That is our segment where we pair a black hole wine brand with our conversation. Today's wine is going to be LBE Cabernet Sauvignon. It is John Legends brand. This is a medium-body carabinet. It has notes of blackberries, dark chocolate, some oak. It is a drinking carabonet. If you have tried it, I'd love to think we know what you think. Please put it in our comments. If not, you can find this at your local wine store. When you do try it, leave us a comment. Let us know what you think. We love to know what you think about the wines that we are sharing on our episodes. For today's conversation, it is going to be a solo episode. It is going to be me. After five episodes, I feel like it was time to come and reflect and celebrate and talk about just what's important to me at this point. I've had four amazing women on. It was a great conversation. I have completed this is my sixth episode. I have met my first month's goal of 100 downloads. That's not listens. Those are just what people have downloaded, downloaded to their device. I have a goal of 100 episodes and I ended it with 102. So I exceeded the goal. I don't know why it is as women. We often will look in the mirror and our hair will fire. But we'll see that one piece of hair out of place, and that is what we'll focus on. Or we will have just done a bomb job at something. But instead of celebrating the greatness in it, we focus on the one thing that didn't get that didn't go quite right. And this season, I'm being intentional to not just focus on the bad. So I'm going to take time to celebrate. I am going to review the bad because, or it's not even bad. I'm going to review the areas where processes can be improved, but I'm also going to take the time to celebrate it. The areas where processes can be improved are important because that's the only way we get better. But I'm also going to show up and I'm going to celebrate. I think for me, imposter syndrome kicks, so it's important that I celebrate. Because there is a voice in my head that says, can you do this? Why are you doing this? Are you good enough? Are you qualified? And sometimes I give credit to that voice and I will shrink myself. And this season I'm being intentional and not doing that. I am showing up. I am doing the things. I am quieting the noise in my own head. What is the worst thing that can happen? In the case of this podcast, I love, I love a big podcast. When I look at the podcast that I enjoy, usually black women, mid 30s to early 40s, and here I am at 50, thinking about launching a podcast. Of course, I'm going to say, Am I too old for this? Apostle syndrome is going to say, Am I too old for this? Being intentional and not listening to that voice, I showed up anyway. So I'm patting myself on the back for doing that. Because I'm obviously not too old for this because there is an audience. There's great conversation coming out of this. And that is that is enough to make me realize that imposter syndrome had had a little control, but I am taking my control back because I'm pushing through regardless of the doubts in my head. I feel it's important for me to celebrate that. I challenge you, I ask you, what is something that you wanted to try that attempted but didn't follow through because imposter syndrome got in your way? What is that thing? Go back and read. I challenge you to pull out your journal, write it down, just step out of faith and try it anyway. What is the worst thing that can happen? I always say if it doesn't kill you, you're gonna get a great lesson out of it. So give it a try because you never ever know how it will be received once you get out of your own head. Today's episode, partly about imposter city, but it's about the main title, the main thing, it's about courage. I did an event back in May. It was a virtual event for black women over 40, and we talked about all the things. We talked about perimenopause, we talked about starting over. We talked about all of the things. But there was one common theme that came out of that, and that was courage. I don't care how strong we are, I don't care how we walk around, we have a superwoman cape on our back. It is very common for us to get in our own head and stop us from doing the things that we are really passionate about or that we really, really want to do. It takes courage to step out there and say, I don't care what anyone else thinks, I don't care about the self-doubt that I have, I am going to push through and do it anyway. That is a level of courage that always showed up for me when I was doing it for others. When I had to do it for my kids, it wasn't a question in the world if it would get done. There was not a thing that can stop me from at least trying. When I have a group or a client that's expecting something from me, there's not a question in the world that I am not going to execute. I am going to get this done for them. But when I have to show up for myself, where does that same courage go? Why can I not show up for myself the same way that I show up for everyone else? That is something that I had to really sit with. And I don't believe that I am alone in this. I believe if you think through your life, you think through the things that people expected from you, how you showed up without any doubt, but then you think about the things that you actually wanted for yourself, how you had all the doubt in the world. Why is that? And I don't have the answer to why that is a thing. But what I do have is the courage to push through that. I matter just as much as anyone else. I love my children with everything in me. And there is no doubt that I won't go to the end for them. I want that same love and determination for myself. I am in a season where I am learning to love myself with everything in me. I am in a season where I am willing to gamble any and everything on me because I know I can do it. And I know I deserve it. The same as you, I challenge to really think about. And when I challenge you, let me know that you hear it. Comment, comment in the comment section. Let me know that one, you feel what I feel that I'm not in this alone. And two, what do you plan to do for yourself? Because we deserve it. We deserve it just as much as we give it to everyone else. I don't know what it was about turning 50. I will tell anyone, it was empowering. And it was empowering in the fact that I felt free, free to speak for myself. And that freedom to speak for myself, to live out loud, it doesn't just come with doing it in front of others. It comes when I look in the mirror as well. When I look in the mirror and say, you set a go, you did not stop, you did not give into the noise, you pushed through, and you are still pushing, and the vision is growing. There is no doubt in my mind that this podcast is going to be a rated podcast. Because if I don't believe that, who's going to believe it? I have no doubt in my mind that this is going to be rated. That this is going to be exactly what I envisioned it. A platform for black women over 40 to feel, seen, to be heard, to know that we're not on home, to pull each other up. When I'm on social media, when I'm on TikTok or in these Facebook groups, I'm encouraged by the amount of momentum I see being poured into women, black women over 40. And the one thing I think about is what greatness would come out of collaboration. Now, there are some clinical doctors and successful business owners that are driving these movements. And in my mind, I am not a clinical doctor. Although I have planned some successful events and done some amazing things, I don't give myself enough credit, or I wasn't giving myself enough credit to say that I belong at the table with a bunch of successful entrepreneurs. But at this scene, I'm going to be at the table. I'm going to push aside the doubt. I'm going to reach out to these women who are doing great things for the same demographics that serves this podcast. For the same demographics that curated living serves black women over 40 because I'm mad again the greatness that will come out of us collaborating. So instead of allowing imposter centric to say to me, maybe you shouldn't reach out to her, I'm going to reach out. Now, how they receive it, I don't know. What is the worst that can happen? They ghost me, they silence me, they block me. I don't know. But I guarantee you, there is going to be someone who is open and imagine the greatness that comes out of that. I am giving myself grades and decisions to step out and have courage. And it takes a lot to have courage because with courage comes rejection. With emotional maturity comes the understanding that rejection is not the end all to anything. Rejection is just lesson learned, move forward, maybe pivot, go another direction, but don't give up. That's all that is going to mean to. The women that I have spoken with in the previous episodes, all great women, all doing great things. Imagine outside of the podcast, women coming together, healing, knowing that we're not in this alone, encouraging women who are starting over, encouraging women who may not be in a happens, happy season of life to get to that happy season. Because those were all of the themes from that previous episode. So in my mind, I'm thinking, how do I bring everyone together and make it happen in a room where we come together and we all grow and we all learn? Imposter syndrome will stop me from doing that. I am going to push forward. I, in this season, will be intentional about doing all of the things because I know killing imposter syndrome is going to bring nothing but greatness. I believe that in my heart, and I know that that is what will happen. I want you to think about the areas where you are depriving yourself because imposter syndrome is winning out. Again, I challenge you, take it on, do the thing. What is the worst thing that can happen? If it doesn't kill you, then nothing. You will either learn a great valuable lesson, pivot to do it differently, or it will be a bigger success than even you can imagine. That is what I want for us. We often play silent. We don't want to come through as the angry black woman. We don't want to come through as too controlling. We don't want to come through as the woman that just doesn't fit at have a seat at the table. Let that noise go. Just do it. Just go out there, be yourself, live your dream, know that you deserve it. You deserve it as much as you deserve it. You deserve it as much as anyone else deserves it. You deserve it as much as I deserve it. Let's make it personal. You deserve it as much as I do. I will celebrate and cheer you on, and I ask that you celebrate and cheer me on when you see that woman who may be by herself or walking down the street. Smile and say hello because you never know what your sister's going. Your sis couldn't have just been beat down by corporate America and just in her head about if she's making the right decisions, if she should just let it go, if she is too old for what she is doing now. That smile and encouraging nod from you can change the mindset of her in that moment. And the same thing applies. When you give out, you there's someone that will pour into you. And this may sound a little hypocritical because we always say we can't pour from an empty cup. This is not pouring from an empty cup. This is finding someone to take with you on the journey. You're not carrying them, you're encouraging them. The same encouragement that's going to be fed into you, you're feeding into others. And if we start encouraging each other, then we can't be stopped. We just cannot be stopped. The currents of the world cannot stop us in anything that we able to do. I did not know what I was going to talk about in the solo episode. What I knew was I wanted to take the time to come on and celebrate the win. I wanted to take the time to review processes that could be improved. But I also wanted to take the time to encourage not only myself, but to encourage you. And the one word that kept coming to mind was courage. The one word that was an overall theme from that event was courage. So as I started to say, even when we wear our superwoman heat, you sometimes struggle with courage. What is it you need for you to be courageous today? What is it you need from you as well as from the people around you for you to be courageous in this season? Because in this season, you should be empowered. You deserve it. We have poured so much into everyone else. It's our time. It is our time. The worst thing that I fear is getting close to that day when I will no longer be here and looking back and saying, I wish I had lived out loud. I wish I had done this. Or I wish I could go back and re and have a redo to live out my dream. I'm gonna wake up every day that God allows, and I'm going to be intentional in doing something for that is what I challenge myself to do, and that is what I challenge everything to do. So on this sixth episode, I want to issue you a challenge to show up for you, be courageous, kill impostasync, find that thing that you put to the side because you just thought you were not good enough, not qualified, too old, whatever that thing is. Do it. Just do it. And then come back and share with me. Share it with me. I have said that several times in this episode. One of the things I realize that I don't is encourage you to leave a comment, to follow the podcast, to like, to share. And on my list of things to improve and do better, that is one of them. So this is my opportunity to say to you, please like, share, comment. Have a conversation with me. Put it in the comments. And if it's too personal, you don't want to share it with the world, email questions at winewisdomwhatnow.com. I am the one that reads those emails. I am the one that's going to get it. I would I am very genuine when I say I want there to be a conversation. I want to conversate with you. The other thing that I said I need to work on is I continuously week after week say listeners. You are not listeners at this point. You are my podcast family. You are my sister, you are my supporter. You are important. You are much more than a listener. I am removing that word out of my vocabulary. If I say it again, call me out. You are much more than a listener. I cannot express how much I appreciate you. Because again, when we come together, whether it's me behind the mic and you listening to it, when we come together, there is nothing but greatness. Everyone's life is a story. Everyone has been through something. Everyone should take the time where they sit down and they heal for what they need to heal for, and they find how to intent, be intentional, intentional about living the life they deserve. We all have a story. If you have a story you want to share, I invite you. This podcast is for everyday lived experiences. I invite you, email me. Again, it's questions at winewisdawhatnow.com. We need to encourage each other, especially in this season. Perry Menopause will have you doubting everything. We'll have you think you're going crazy. Imagine what a community of women encouraging encouraging you will do. That is the goal. The podcast is just part of the ecosystem. At the end of the day, I invented a room of us coming together, growing together, learning from each other, encouraging each other, and being the best that we can be, pushing each other to be there for ourselves the way we are there for others. I have so many things that are in the works, and imposter syndrome will not get in the way. It will be launched strategically, because I can't launch everything at the same time, because burnout is real, and I'm not trying to burn out. I want to keep the passion and the joy that I feel when a woman texts me or sends me a message about something she got out of the podcast. I want that. And I encourage you to let me know because that lets me know that this is worth it. Imposter syndrome out the door. I'm not listening to that. I'm listening to the courage in me, but also the feedback from you. It is important. As I said, so now we're on episode six. By episode 10, I would like to officially launch in her season. And in her season is the segment where you will email in any perimenopausal. I said that real slow. Any perimenopausal questions you may have, or we're expanding it. Any retirement financial questions you may have. I have two professions that will answer the question on the podcast. If you want to remain anonymous, let us know in the email and we will make sure that you are anonymous. But any question you have, I'm sure there are hundreds of others that have the same question. So it's not only going to help you, it's going to help others. The email address for that is inher season at winewisdomwhatnow.com. I encourage you to send those emails in. We have been getting some, they've been trickling in. But I know there are questions because I see you on social media asking the social media experts, what do I do for frozen shoulder? When you can get that question answered by a licensed professional. I'm not the licensed professional, so I'm going to bring on the licensed professional. I probably have the same questions as you. So I'm going to probably send in some questions. When it comes to retirement, I've said this before. When we started working in our 20s, we had no idea what retirement would look like. We thought, oh, I'm going to put aside 6% because the company's going to match this percent and I'm going to be good. But then life happens. You didn't account for college tuition for your children. You didn't account for taking care of an elderly parent. You didn't account for life life and having to dip into your savings or take it out alone on that 401k. You didn't account for that. So now in the season, it's time to regroup because we're going to retire and no one should work until their last day. So how do you get back on track? How do you set a game plan? I have a licensed professional that will answer your questions. I will be having events where these licensed professionals will be there to have conversations. Like I ask you to support me. There is a vision, and this vision is for us. It's not for me. It's not even just for you. It is for us because I am in this season with you. I am going through the same things that you are going through. As always, I appreciate you for showing up. This has been a note off of my chest. I feel like coming in, I didn't know and didn't want to overthink what I would discuss. But I feel like what was said needed to be said, not only for me, but hopefully for you. In case no one tells you you are amazing, and I want him to have the most amazing week ever. Again, like, share, comment, tell your friends, send them to the podcast. Join me each week with release at 6 a.m. Thank you.