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 010 | It's Not Too Late | Wine, Wisdom & Starting Where You Are
•Yolanda Holliday•Episode 10
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What if your best chapter isn't behind you—but still waiting for you?
In this episode of Wine, Wisdom & What Now?, Yolanda Holliday shares one of her most personal solo conversations yet, reflecting on grief, family, community, and why turning 50 has become a season of purpose instead of limitation.
After attending a family gathering that stirred unexpected emotions, Yolanda opens up about navigating changing family dynamics, honoring the relationships that shaped her, and why the experience reaffirmed her passion for building Curated Living—a community where Black women don't have to navigate life's transitions alone. She also shares why she refuses to let age define what's possible and why every day is another opportunity to begin again.
Together, we explore:
Navigating grief while embracing new beginnings
Why community matters now more than ever
Letting go of the belief that you're "too old"
Building the life you've been dreaming about—one step at a time
Overcoming imposter syndrome and trusting your purpose
Choosing courage over comfort in this season of life
Whether you're starting over after 40, grieving what was, or wondering if it's too late to pursue the life you've imagined, this conversation is a reminder that your story is still being written—and your next chapter may be your best one yet.
This Week's Pairing: 🍷 LVE Cabernet Sauvignon by John Legend — a smooth, full-bodied Cabernet with notes of blackberry, caramelized fig, and dark chocolate. As always, we're proud to highlight another Black-owned wine brand and encourage you to support the businesses helping diversify the wine industry.
Reflection Question: What dream have you been putting on hold because you believe you've missed your moment—and what would change if you decided to begin anyway?
If this episode encouraged you, be sure to follow, rate, and share Wine, Wisdom & What Now? with another woman who needs the reminder that it's never too late to begin again.
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.
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.
SPEAKER_00
When people post on social media, I'm 50 years old, am I too old to do X? It annoys me, it aggravates me because every day you wake up is an opportunity to do something new. So no, at 50 years old, I am not too old to do anything. I am your host, Yolanda Holliday, and I thank you for being here. If this is your first time joining the podcast, welcome. I personally want to welcome you. This is a podcast for us, by us. This is a podcast for black women, 40 and over, dealing with everyday lives. In this season, we hear a lot about perimenopause, but there's so much, so much more that's happening in this season. So we talk about all the things. This is our true, genuine lived experiences. And if you have been here before, thank you for coming back. I appreciate you. I hope that this is feeding you. I hope that you are getting any and everything out of this because I myself plus the guests are coming for it, and we are sharing our true lived experience, and we want you to share. You can always email me, put a comment, add something to the comment. We want to hear about how these episodes are affecting you, if you're getting anything out of it. I want to hear. So again, I thank you for joining me. With any and everything in life that I do, I always take a step back and look at okay, this is what you're doing, but how can you do it better? When I started this podcast, I wanted to show up. I wanted to share my lived experiences, not only just the guests, my own. And what I find when I listen to the previous episodes is the guests are coming forward, they're being extremely vulnerable and transparent, and we're having conversation, but I don't feel like I'm really showing up as me, meaning I'm not sharing enough as me. I add to the conversation, but I don't feel like you're really getting to know me, my passion, my why. And I've had a moment this weekend where my why really, really was front and center. A lot of us after 40, sometimes before, but after 40, we deal with a change in our family dynamics. For me, I lost my grandmother in 2014. I lost my aunt in 2021. That was family to me. They were everything that family represented. They are the reason that I am a great mom to my two amazing kids. They are the reason I understood what it really meant to be in a family. And my situation is a little different. I mentioned a grandmother, I mentioned an aunt. I also have a mother who is still living, but I'm pretty much 99% no contact with her for valid reasons that we won't discuss in today's episode. We could always discuss it in the future because I'm very transparent about it, but I just don't want to go off task. And it's 99% because I have children, and I'm never going to keep my children away from her because I do feel like she is a good grandma. So that's where that 1% comes in. I'm going to do my part to make sure there's at least a relationship there. So for me, when I look at wanting to ask about perimenopause, menopause, just wanting to feel that connection, it's not there. And that is the main reason that I am really big on community. Because I feel like as black women, we are always wearing the cape we are always doing for everyone else. And then we never stop and think, what about us? But in the seasons that I'm asking, what about us? I know that my community is more than just blood relatives. And that is why I want to build curated living because I want to be that community for the woman that has maybe lost her mom or does not have a relationship with her mom, does not have the elders in her family that she can go to, or the friend circle that she can rely on in moments like this. We do not have to go through this season alone. I am building so that we don't have to go through the season alone. Community has always been important to me, and this has been my passion and the reason that I do the things that I do. I had the pleasure of attending a family event this weekend. It is on the family on my grandmother's side. I grew up knowing who they were. I didn't go to Alabama a lot, but I developed relationships and I was extremely excited and happy to spend time in the same room with family. It brought back a lot of happy memories of when my grandmother was alive and we would go down there, just seeing her sisters thriving. It was joyful. It was joy in my heart. But at 2 a.m. this morning I woke up and grief was heavy on me. Grief was heavy on me because, yes, that is my blood family. But the relationship is not what I am used to when it comes to blood family. Not at any of their faults. I am not blaming them for any of it. My family dynamics has always been my grandmother, my aunt, and those of us that were in New Jersey. Alabama was the distance family. So spending time with them helped me see that, yes, I still have blood relatives. But in hindsight, the relationship that I long for with family is not the relationship that I experienced this weekend. Not any fault of theirs. I am just going through the grief of accepting that family as I knew it growing up will never be not with that family. Not with my grandmother gone, not with my aunt gone. Can I start new traditions? Because I do have adult children. One day I pray to have grandchildren, of course, and I will start those traditions. But that doesn't mean I won't grieve what I feel I no longer have. And it does not consume me, I will say that. I have family that are not blood, that are true family. I have friends that support, listen to, that I could have the conversations with. So I'm not lacking in the area of love. I feel like I am very loved. It's just sometimes the grief of this is not what I'm used to creeps up. And it did, and it was a heavy day. I will share that. It was a heavy day. I did not feel like recording, but I knew I had to record. I had to show up because I want to show up as my true genuine self. So that does not mean I'm going to always show up when I'm feeling perfect. I'm going to show up even if I am feeling heavy in the moment. And that is what I experienced today. So that is my before we pour moment that I want to introduce as a new segment. I am going to share each week what I'm feeling, what I'm going through, just me and you having this conversation. And I'm going to call that segment before we pour because we're going to do it before the pairing. Now that we have shared and I have been vulnerable, let's go ahead and pour because it's time. So now we're going to talk about the pairing. And in the pairing, we feature a black-owned wine each week. Anyone that knows me knows my passion for wine. I love wine. I love supporting black-owned businesses and I love community. So when I look at an industry that I support and love, that I don't see a lot of us, I want to do my part in sharing and bringing awareness so that someone hearing this will then go and support a black-owned brand. It is our support that is going to keep them in stores, that is going to keep them around because they need our support. This week's pairing is LBA Carabinet Sauvignon. It is a smooth red wine. I'm not sure of your palette for me. I like a medium to full body. I like wines that are not sweets. I enjoy wines with pairings. So I always look at a wine and said, What can I eat with this? What would really bring out the flavors? So this LVA Carbonet Sauvignon has rich aromas of blackberry, caramelized figs, and dark chocolate. I personally would pair this with a grilled steak, mushroom risotto, aged cheese, or dark chocolates. If you have experienced this wine, I would love to hear about it. Leave me a note in the comments. Let me know what you think. Did you like it? How was it? Do you agree with the notes that I shared or what would you pair it with? If you have not, you can find this wine in your local wine retailers. I purchased this wine at Tour Wine. The wines I bring for it are I'm going to always share what you can purchase so that you can support. It is LBE Cabernet Sauvignon. I believe I mentioned it in the beginning. And if not, this episode there is no guest. It is me. I'm coming forward to share with you doing life as a 50-year-old. That is what I'm going to discuss today. I have hinted on this in the past, but I really, really want to have a conversation that is focused on doing life after 40. I am 50. And what I found in my journey was I was always told when you get to 40, it's going to be the thing. You are going to speak your mind, not care about what anyone thinks. And then when I was approaching 40, I thought I already speak my mind. And I'm not really big on what others think. I don't know what's going to change. And I can honestly say not much changed when I turn 40. Something happened at 45. It caused me to pause. It caused me to reflect. I can honestly say what happened at 45 is that survivor's mode kicked my behind. And I had to sit it down for a little bit. Then approaching 50, I had these big goals. All of a sudden my energy was renewed, and I had these goals. And when I hear people post on social media, I'm 50 years old, and I'm too old to do X. It annoys me. It aggravates me because every day you wake up is an opportunity to do something new. So, no, at 50 years old, I am not too old to do anything. I, at 50, I started a podcast. I at 50 am growing a business that supports a group that I am passionate about, black women. I at 50 am giving myself a chance to explore love all over again. So I have to say, at 50, no, I'm not too old for any of it. At 50, if you want to change a career, if you want to start a business, if you want to start a family, don't let your age limit you. Figure out how you best operate. For me, it's sitting down, it's writing out my goals, and then executing. That's what works for me. You need to figure out what works for you. You need to figure out what makes you happy. Just because you're a certain age don't mean you have to settle for anything because you do not. I refuse to settle. I just refuse to settle. I don't know what it is that's within me that makes me feel that I can have anything that I want. I can go after anything that I want. I wake up to a sign in my room that says, I am unstoppable. That is the first thing I see, and I feel it in my heart. I don't know if I bought the sign because it spoke to me or if I bought the sign because it represented me. Not really sure because I've had the sign for a couple of years now. But it is so true, and it is the first thing I look at, and I carry that with me in everything that I do. I am unstoppable. At 50 years old, I am going to grow this community. I see all of the things I have to get done to make this happen, but I'm going to take it piece by piece and make it happen. I am not going to let it overwhelm me. I am not going to allow that fear to seep in and say, hey, you're too old for this. Why at 50 are you trying to start something new? Every day that I wake up is an opportunity for me to set a new goal, go after a new goal, and achieve a new goal. What is it in life that you have put on the table that you want to do, but you feel like you might be too old, that moment might have passed. What is it you can go back and look at and bring back up again and put yourself out there and just get it done? Imagine what will happen if you just take all the doubt away, find the confidence within you to move forward and go after that thing. Imagine the greatness that you would release in that moment. I give myself permission to make mistakes because I'm not going to always get it right. And if I do make a mistake, does that mean I should have never tried in the first place? Absolutely not. If I make a mistake or if something is not quite right, that is an opportunity for me to stop, to reflect, and pivot to where I need to pivot. When I started Curated Living, Curated Living is a business that was born from passion. Curated Living is a community for black women over 40. I had a huge roadmap of where I needed it to go, but I did not let the finish line stop me from starting because there are so many phases and different things that I want to do for the community that I, with the grace of God, understood that I need to take it in small pieces. I launched in April. I released the podcast in June, and now I'm building the community. I'm launching the community platform September 1st. I am doing all the things to go after this goal. I'm not thinking I'm 50, I gotta make it happen now because then it'll be too late. I have every day that God allows me to open my eyes to keep going after this goal. Will it be perfect? Absolutely not. First, you have to get to know me. First, you have to know my passion for black women, my passion for community to understand that I truly, genuinely am doing this for us. And then when you realize that, then you have to come in the community and see where you fit, see what areas we can challenge you in, what areas we can support you in. So I know there's gonna be phases to this project. My age is not going to stop me from doing this. Actually, my age gives me an advantage because for a lot of years I lacked the confidence. For a lot of years, I allowed imposter syndrome to come in and take over. And this season, I am doing things and not in survivors mode, which means I am actually taking it in. I'm actually taking a moment to think it through without feeling like if I don't hurry up and implement this, I'm gonna miss out or I'm gonna lose it. I don't look around and see, oh, there are other businesses doing this. Maybe the market is too saturated. You know why? Because together we can make such an impact. And what my vision is is not necessarily the vision of another person that's doing this. What I bring to the table is not what someone else is doing. This you can actually support us both because we're feeding different areas of your life. Before 45, I didn't see it that way. I was in savirus mode. I was just running around with a chicken with its head cut off, just trying to do all the things. And now stop and make sure it makes sense. And now have the confidence that I can speak to you and I can share with you what it is that I'm working on. And I can confidently speak to the success of it. Not quiet my voice because I don't want to come across as too cocky or arrogant, not quiet my voice because I'm not truly confident in it. Like I threw it out there, but now I need the support of others to keep pushing me. I no longer need that because I'm so passionate at what I feel. I'm so passionate at what I believe this community will do that I am letting that passion lead me versus my doubts. I'm hoping to be an example to you to show you that 50 is a number. 50 is a great place to be. It is not a hindrance, it is not a roadblock, it is not a dead end. It is so much more to life at 50. I get so much more out of life at 50 than I did when I started a business at 23 years old. Than I did when I started a new business at 35 years old. Than I did when I started a business at 43 years old. Serial entrepreneur. A lot of experience in business. Some of them very successful, some of them not so much. I've learned from every one of those experiences, and I've carried it into year 50. I carried it into not just business, but into my everyday life. So I want us as women who are of a certain age to not look at it as a hindrance. Celebrate your wins, learn from the things that did not go so well, but find the confidence and do the work to keep pushing through life. This is not our end. If God wakes you up tomorrow, that is an opportunity to keep pushing. And when he wakes you up the day after that, push a little further. Dream big. Don't be afraid to dream big. And then after that, execute. Don't be afraid to execute. You cannot overthink one, think yourself out of what is your destiny. Because we as black women have a tendency to do that. We gotta make sure it's perfect because we gotta show up as our perfect selves. We can't show up looking like we need assistance. We can't show up looking like we don't have it all together. That's all part of that superwoman syndrome that I have always despised. I lived it. I was superwoman for a lot of years. I had kids that had to take care of, and I was not going to fail. I lived it for a long time. But there's so much peace on the other side of that. And when you find that peace and then you start your new journey, it feels like it's your destiny. It just feels so different than it felt those years ago when you were doing it in survivors. So again, my message to you is age is a number. Every day that you wake up, go after your goal. Don't let anyone dictate to you that as of a certain age, you should not be doing the things. And I'm going to step out and say this when I'm on social media, because I love TikTok, when I'm on social media and I see a man say, Lisa Ragis recently had video she released, I think she was at one of her parties and she was dancing and having an amazing time. And someone, a male, black man on TikTok, came forward and was like, Don't you think she's too old for this? Why is she too old for this? And if you feel like she's too old for this, keep scrolling. Why do you have to come out on this platform and try to put a black woman in her place because you feel she should be a certain way at a certain age? We have to stop taking on how others feel about us.
SPEAKER_01
Fuck them.
SPEAKER_00
This is not about them. This is how we feel. And this is where community comes in. Because despite the noise, I saw so many black women speak up for her, and that made me super proud. I actually commented on. Usually I keep swirling, but in that case, I had to go out there and say how amazing and fabulous I thought she was celebrating herself at her age. I thought she brought so much energy that we as black women should be celebrating her. And that's what we need to do for each other. So this message actually was about doing life after 50, but I feel like I keep going back to community. We should be doing life after 40, after 50, after 60, exactly how we see fit to do it. Not as someone else determines we should be doing it, but we should be doing it with the community. I am not the only black woman that are rooting for other black women. There are a lot of us out here rooting for each other. Now imagine if we all came into the room together. Imagine if we all were at the same retreat. Imagine if we were all in the same cohort, just on the same platform, cheering each other on day after day. Imagine what it will do for us. Imagine when we go to corporate America and we have to cold switch, because some of us still have to cold switch, and we have to deal with the Karen's of the world, and then we come together. Imagine how much stress we're relieving. Stress kills. We should not be carrying that by ourselves. So we need to use our community. We need to celebrate each other. I am so passionate about Curia Livin. I feel like if I could only sit down and have a conversation with you and just tell you about it, that you would be equally as passionate. It is not a money grab. It is not fluff getting you to buy something. It is not social media energy. I want the real. Imagine what areas of life you can benefit from that. And I challenge you, this was not anywhere in my players, but I challenge you, get online, join the community. www.curated living by yh.com. All the information you need is there. I'm not going to push it anymore because that's not what this podcast is about. But I do want to give you an opportunity to go see what I'm talking about. While we're at it, let's talk about what's new. What's new is we've started releasing our newsletter. We release a newsletter every Tuesday that will discuss the podcast. It will give you a preview of what to expect even before you listen. It will feature whatever our line pairing is of the week. It will give you some pairing suggestions. And then we send one out on Friday, and it's a reflection. It is encouragement to take into your weekend. We have completed the week. No matter how that week was, we're going to carry nothing but positive energy into our weekend. And that is what our Reflection Friday newsletter is about. In addition, I briefly mentioned we are working on our community. The Curated Circle. There will be more information that will be released leading up to the September 1st launch. We're active on Instagram. I ask that you follow us at Curated Living Circle. We are active on Facebook. Same name, the Curated Living Circle. The links will be in the description. It is a lot happening on this end. There is so much that I want to implement in the community. I can't wait until we're a year in and we can just go back and talk about all the things that we've done. Not that I've done, but that we've done as a community. This is important to me, and I hope that you see the need for it, and it is important to you as well. I want to hear from you. Share with me. Tell me what your thoughts are. If you want to be a guest, this is a podcast for everyday black women over 40, and we all have a story to tell. If you want to be a guest, if you have a question, if you want to share some insights, some feedback, just make a comment. Email me at questions at winewisdomwhatnow.com. I greatly appreciate you for joining me. Without you, there be no me. I hope that this is feeding you. I wanted to give you the feeling that you're not alone. We're all experiencing life at this age. So with that, I thank you for joining. Until next week, we release every Tuesday at 6 a.m. Until next week. I hope you have an amazing week on purpose. Thank you.