Midlife Women's Makeover: Radiate Confidence. Reclaim Your Power.
21 May 2025 · 36 min
In this Flipping 50 episode, host Debra Atkinson opens with a sponsored endorsement for Blue Sky CBD sleep gels, highlighting their non‑THC, anti‑inflammatory benefits for sleep, especially during perimenopause and post‑menopause. She then introduces makeup artist Jennifer Kaiser, who brings over 30 years of experience in TV, print, fashion, and film. The conversation explores Jennifer’s early inspiration—watching her mother’s transformations in the 1960s—and her path from fashion merchandising to beauty school and a career behind the camera. They discuss how makeup serves as a confidence‑building tool for midlife women, detailing strategies for first‑time makeup users, camera‑ready adjustments, and the philosophy of “less is more.” The dialogue shifts to broader topics of aging, gendered beauty standards, and the evolving self‑perception of women over 50, with Jennifer noting a growing movement toward embracing gray hair and authentic style. Jennifer announces her first virtual summit, “The Midlife Women’s Makeover: Radiating Confidence, Reclaiming Your Power, and Feeling Amazing,” aimed at creating a supportive community, offering virtual consultations, and empowering women to rewrite their beauty narratives. The episode concludes with calls to action: links to the summit (flipping50.com/jennifer), the Flipping 50 Insiders Facebook group, and the podcast’s archive, reinforcing the mission to help midlife women optimize health, mindset, and confidence.
Chapters
Real quick, before we dive into this episode, I have a little sleep secret I want to tell you about. Look, sleep is crucial for your fitness, but it's crucial for just plain old everyday life and function. And I find I sleep great unless I have a migraine. And I've had more than my fair share since perimenopause all the way through postmenopause. My secret weapon was Blue Sky CBD sleep gels. Each gel contains 25 milligrams of CBD and 25 milligrams CBN for deep restorative sleep. Something about it helps to reduce inflammation, which I believe for me was key in helping me get to sleep. But the biggest thing is so many of the over-the-counter solutions, whether for sleep or migraines, can ruin gut health, and liver health. Neither one of those did I want to be problematic for me. So this option is recommended by healthcare providers worldwide and backed by thousands of happy customers, many of whom come from our Flipping 50 community. There is zero THC, so it's non-habit-forming. It's made by a trusted family-owned company that we all can feel good about. Third-party tested for purity and potency. And if you're interested, you too can try a sample for just $6. But even better, you can get 30% off forever with discount code FLIPPING50. That's FLIPPING50. Just go to flipping50.com/blueskycbd. We'll put that link in the show notes and you'll find it everywhere on Flipping 50 at My Favorites. What are you waiting for? Good night. How would you like a makeover? And no, there's not a drawing, but I have something even better, juicier if you will. So we're gonna go behind the scenes with a 30-year makeup artist who's had some really important people in her chair and look at what has she learned about the confidence that comes from the outside when you actually put on makeup, and what has she learned about women and our need for looking good in order to feel good. I am talking with Jennifer Kaiser. She's a makeup artist. I ran into her and I want to share her with you. I'm Debra Atkinson and you're listening to Flipping 50. I started this podcast over a decade ago to answer questions about fitness and menopause and beyond before you know to ask them. The goal to help accelerate your results with the science and the practical application of proven protocols while living your best life. There's no more powerful health influencer in the world than a midlife woman. It's not just you, but it's the 3 generations that you influence. My unique 40-year career, including being a university senior lecturer in kinesiology, an industry subject matter expert, an international speaker, to founder of the first and the only exclusively made-for-menopause-and-beyond fitness membership in the world. Every week I interview experts behind the science of optimal hormone-balancing fitness and longevity and share answers to our community's questions so you can have the vitality and the energy you want, need, and deserve. My guest today is Jennifer Kaiser. Now, this is unusual, so I can't tell you if ever I've had a makeup artist on the show, but here's a first. So Jennifer Kaiser has over 30 years in the beauty industry. She's passionate about helping women, especially especially in midlife, look and feel radiant. Known for her work in TV, print, fashion, and an occasional movie, she blends expert techniques with heart, empowering women to embrace their beauty, reclaim their power, and shine from the inside out. And you'll hear me talk about how I met Jennifer myself and how she's actually working behind the scenes, helping a lot of people get a lot of very important messages out to the public. But her real passion is helping you. And we may hint at her age, but you won't believe it until she drops that bomb. So I'm going to have you guess when you see her, if you're watching this on video. Jennifer Kaiser, thank you so much for being in the house.
Debra, thank you so much for having me.
Well, and I'm so wishing that you had been able to come over and help me get ready. Actually, no pressure, because I'm in the bathroom getting ready, having just come out of the pool, goggle eyes, and I'm thinking, and I'm meeting a makeup artist. And you look amazing.
Sure.
I know. No, no pressure whatsoever. So first of all, it pays to advertise. So the backstory for listeners, the docuseries Shield about the health of a woman from the moment she's born until the moment she dies will be out soon. And Jennifer has had the pleasure of working behind the scenes with many of the experts who will go in front of the camera. She's the get it— get you ready to look good on camera gal. And she's been doing this for 30 years. First of all, how did you get into it? Did you grow up knowing— I mean, you were playing with makeup and Barbies way back then, or what happened?
Kind of. I have 3 sisters, and I have a mother who was a very Southern mom, and she would be getting ready to go out to a function, and we'd all kind of gather around her vanity and just sit there like this while she got ready. And this was back in the '60s. So she would get her hair done and put her makeup on and put on this beautiful dress and these gorgeous shoes. And at the end, she would look like Elizabeth Taylor. And it was just such a magical transformation that I always just thought, wow, there's a lot of power in that transformation. And I just love that. And I think as a child, I was a very creative child, but also I was a very shy child, so I loved to be in plays and theater and ballet and all of those things, but I was really, really shy. And so I always gravitated to the back. So I would do set design and costumes and makeup. And that's really how it kind of started. So when I decided like, oh, what am I gonna be in life and where am I gonna go to school? I thought, what do I love to do? And I thought about theater and clothes hair and all those things. And I ended up initially going to school for fashion merchandising and design. And while I was there, uh, we did a lot of fashion shows, which I love because that's theater. I mean, it's just chaos and running around in the back and getting everybody ready, and then all of a sudden the doors open, it's like, you know, and I just realized how important it is that if you're going to present something, that it needs to be from the head to toe, right? Really, to sell the look of the clothes, the hair has to be right and the makeup has to be right. It's kind of all one. And so that's when I decided to go to beauty school and learned about hair. And I was working in a salon— long story— but I was working in a salon as an assistant, and they were a very popular salon at the time. And someone called and said, hey, we're doing a fashion segment for Christmas. Do you have a hair and makeup artist who can come and do the hair and makeup artist for the catalog? And they didn't have anybody to do makeup. And I said, oh, I'll do makeup. I'd love to do makeup. And so that was my very first job. I had no idea what I was doing, but I absolutely fell in love with it. And I thought, this is— I love this. This is, this is where I'm meant to be. And that's kind of how it all started and just continued from there.
This is so interesting. So I really— in what you're doing, I want to liken this. So right now, you know, let's go back to the SHIELD event and the docu-series where so many health and wellness experts, functional doctors, health coaches, people in biohacking, you know, myself as a fitness and functional health expert, you know, we are not— many of us don't think of ourselves as sellers or marketers. And yet I would say that right now it's what has had to happen over the last 30 years. We've had to make health and fitness sexy. We have to because we compete with Doritos and Lay's and Pepsi-Cola that are trying to do it. You know, I mean, what do we got, right? So in that way, when you're getting, say, experts ready to go and deliver a message, you know, you are really setting them up for success too in doing that. Who— a doctor who may be used to being in a white lab coat, you're putting them in a— is that hard? Because are you selling something to them so that they can do it?
No, I don't think so at all. I think I'm selling myself. I just want them to feel comfortable, to feel— I mean, I think that's my job, is because they see me before they go on set. Yeah, I want them to feel as beautiful and as confident and as radiant and just— and comfortable, you know, relaxed, so that when they go out on stage, they know that they look their best. They can look in the mirror and say, damn, I look good. I, you know, I feel confident and I feel empowered and I feel radiant. And, and I feel that's my job, right? I mean, I talk to you and say, how much makeup do you normally wear? What is your usual routine? Because I want you to be the best version of you. I don't want to make you look look like me or Kim Kardashian or anything like that. I want Debra to look like Debra, but the most polished, best version of that. So when you step out, that you feel confident and radiant and sexy.
I so love that. Talk a little bit more about— is there anything you do strategy-wise to— when someone's in your chair and say they're somebody not used to wearing makeup, Is there, is there a method to the madness, say, in the conversation that you're having with somebody to put them at ease?
You know, I think it's, it's, um, I want to come with good loving energy, you know, and I want you to know that I'm— when I ask the questions that I ask, what do you normally wear? Maybe even have them show a picture so I can kind of see exactly what makes them feel beautiful. And I want them to know that I see them and I hear them and that I am— I usually start with less and then we can kind of build up from there. But I always try to let them know that the camera sees things differently than you and I see things. And that sometimes we need a little extra because the camera can kind of wash you out depending on the lighting. And that's why I always start with a little less because we can always build up. It's easier. And I always go out on set with you and I look and see how you look in the camera, what their lighting is, because a lot of times it's very different from what the lighting I have in my green room, right? So I want to make sure that you look beautiful on camera so that what the camera sees is, is correct. So I might have to add a little more blush or add a little more color in your lip or fix your hair a little different way because I thought you were going to be sitting this way. So I kind of did it for this way. Now all of a sudden you're over here and it's like, okay, well, we can't see your face, so we're going to have to adjust this. So, you know, that's, that's usually how I go about it. And it's having a conversation, like a real authentic conversation with you so that you're comfortable with me and you trust me to do what makes you feel good.
Talk a little bit about this because I think it's hard for women going through a lot of changes, maybe not in love with the body and maybe feeling not completely in control of the body that they've got showing up right now. And changes in hair— it's interesting, in the green room we were talking about how my hair color has recently changed. You saw me as a brunette, I think, in December or January. And, you know, it's all very different. And even my own love affair or not, you know, with the transition, but it changes everything. What if you could tell a woman or give her some advice in order to— not one woman I know likes herself in pictures— in order to like herself in pictures with the family? Because I think she wants to be in them. She wants to have those memories. But often women, that's, that's the first thing they go to is, oh, I look big or I don't, you know, my hair or my face or she doesn't like the way she looks. What would you give as tips so that somebody at home could just feel a little bit better about herself?
I would say, you know, a lot of that does come from within. I mean, you know, it is a matter of feeling confident inside and feeling empowered. I mean, I think a lot of that comes from within and kind of shines out. So if you're not feeling good about who and what you are, I think a lot of that will show, no matter how beautiful I may think you look. And I've seen that many times, that I say, you look beautiful, what are you talking about? And women will say, but you know, they pick out their little flaws and I think you've got so much beauty going on here. Nobody sees that but you. But I certainly think with women over 50 that less is more, that you want to use products that radiate your skin, illuminate your skin, And I think too, if you really don't know much about it or you feel like, oh my God, I've been wearing this makeup since the '60s or '70s or '80s even, and it's heavy and it's thick and I know it's probably not the best, go and search out a makeup artist. Find somebody in your area or somebody online that you think, I really like the way she looks. I, you know, maybe that's who I need to talk to. Maybe have a consultation with that person or a makeup lesson with that person. You know, that, that's really, I think, what I would advise. But I think less, less is better.
Less is better. Yes. You know, and I think the whole thing is, yeah, all the rules have changed. And women, well, of course, many are here saying the rules have changed about exercise or what we eat, but also the skin texture has changed. And they're like, like a change in your hair color. If you've embraced gray or if you're just playing with some other color, that also changes your skin tone. And so, right, so first of all, you got to go buy a new wardrobe. There's that. And you know, your, your makeup doesn't sit the same, doesn't look the same. So many things there. Of all the people that you have had sit in your chair, quote unquote, what percent is men versus women?
I would say it's probably 80% women, 20% men, maybe 70/30. It depends. I mean, I do do a lot of commercials. That is something that I do a lot of. So, you know, it just depends on, on what the commercials are. But generally, ladies more than men. Men don't require a whole lot.
What are our deepest secrets? Are women sitting in that chair revealing them? Oh, I don't like this, or I don't like that, or This is my good side. This is not my— this is my bad side. Can you hide that? What are we sharing with you? Do you have a question for a podcast? A question you'd love to ask, or maybe a story you want to tell? Did you know we have a special group just for podcast question roundups and the answers? My community coaches and I provide answers daily inside of this group, but it's also where I go when I occasionally say, Okay, open call for podcast questions or tell your story. Would you like to be a guest? So if you're looking for a community of women who are also interested in optimizing their health, strengthening their mindset, and looking forward to every new year, join the Flipping 50 Insiders group. That's Flipping 50 Insiders on Facebook.
I mean, I think that they do, you know, certain— like I said, everybody, no matter how beautiful they are, sees a flaw in themselves. Hmm. And it's different for every single person. Some people don't like their eyebrows, some people don't like their lips, or, you know, that the fact that their, you know, eyes are now like their lids are heavier than they used to be, or, you know, you've got this action happening under their neck. I mean, everybody's got their own thing, but I will say everybody's got something. Everybody's got their own thing. Yeah, everybody's got something. I mean, it's very rare. And especially some of the women who are younger and are just beautiful, you know, I mean, they are just beautiful and they still are like, do you see this little tiny teeny mole? Can you cover that for me? And I'm thinking, No, I can't even see that little teeny tiny dot. Like, what are you talking about? And they're like, will you cover that for me? You know, it's kind of crazy sometimes because I'm like, really? With all that you've got going on, you're concerned about this little dot on your face?
You know, so interesting. Yeah. Wow. Wow. Yeah, that's so true. Is there any— is there anything that you— do you see us evolve? I mean, and I say us, I mean collectively, you know, from the younger women to as we mature, 50s, 60s, you know, and 70s. Is there a difference when somebody sits down? Are, are we getting more relaxed about our looks? Are we getting— are we getting more self-conscious? That would be— that would be depressing.
I think that most women that I I see are more confident. And there— I think there's, um, a movement happening where women— and I think maybe because it's the baby boomers and there's so many of us and, and times have changed, but right, that you feel comfortable changing your hair color. I mean, there's a lot of women out there that after COVID decided, to heck with that, I'm going gray, and really embracing it and look beautiful. So I'm seeing more and more women in their 50s and up that are really embracing their power. And that— I just love that because it really— I mean, I'm going to be 65. I got my Medicare card.
It's like a transition, right? That's the next step, right?
I don't want that. You know, if I cut my hair off and I let it just go natural because it's really curly and gray and wore no makeup and frumpy clothes, I mean, I could look 65 to 70, but I choose not to, right? Because of my attitude and my confidence and the fact that I want to express myself how I feel, and I don't feel that age. And so I'm going to be true to myself and be authentic to myself. And I see a lot of women really stepping into that, and I want more women to step into that because you don't have to look— I don't even want to say old, but you don't, you know? I mean, my mom is 92 and she is beautiful, beautiful. But, you know, she wears her makeup, does her hair, she dresses cute. You know, and some of her friends, it's like, wow, she's 30 years older than some of them and she looks younger. But it's an attitude and it's the way you dress and the way you carry yourself. It really makes a difference.
I do too. I want to go back though, and I want to pick something. I want to talk about this a little bit. So you said that don't look 65 or 75, but what if we're redefining that? What if this you are the look of 65. I mean, it's— you're raising the bar out there. But, um, there's that. But, you know, it's funny that I think we still, even as we get to it, we're like, but I don't want to look my age. Essentially, we're almost saying, I don't want to look my age. And, and yet it's like, well, why not if we're just changing the way that looks, or our expectations about it. It's still funny how we're having a hard time embracing and navigating that, don't you think?
Yeah, it's—
I'm not sure we figured out what our feelings are about that yet.
I don't think I, I embrace my age, I guess, but I don't want the, the stereotypical or society's thoughts on aging. I don't— it's anti-aging. And oh, you get the birthday cards at 50 that you're over the hill. And, you know, that's the messaging out there. And men have always been able to age, you know, and they get more handsome with their gray hair and they're— they get more debonair. And you don't usually hear things like that about women. You know, women, you know, it's a totally different thing. And I want to say You know, whether I'm 65 or 85, this is who I am, and I'm gonna express myself the way I want to express myself and the way it makes me feel good. And that's it.
Yeah, yeah, a lot of good said right there, and I think so true. I do think there still is that, you know, big gap gender-wise between, you know, distinguished or not distinguished. And I also think we're seeing more— I don't know if this is true or not, or I'm just— my antenna is up and so I see more because I'm thinking more. But I feel like there are more like men who are in their 40s and 50s who are actually graying early, and yet I find it very distinguished. I mean, it's funny, but we would not say the same thing about a female.
No, we wouldn't.
Yeah.
And it's been that way for a long time. I mean, you can look at movies, you know, you know, the James Bonds and all those, and they, they could have gray hair. Sean Connery, I mean, you know, he was such a sex symbol for years and he was not only gray but kind of losing his hair and still was considered, you know, this handsome man. And he was a handsome man. I mean, I'm not denying that at all. But, you know, women in Hollywood after 40, they have to really work hard. It's a different game for them. And, and I just think that that's what you are doing, right? Flipping 50 is that the same thing that I'm doing and saying, like, you know, this is how 65 looks and I'm proud, right? This is what it looks like, you know, and, and, and, and where it was pride.
I love that. And so speaking of that, so we're, we're on this tandem path. You are hosting your summit, and this is a first for you. So although you're so used to being behind, behind the scenes, you're a little bit more in front of the scenes yet. So title of this, by the way, so kind of hand in hand with Flipping 50 and that whole idea of flipping the concept of what you think about it as and that being the thing that empowers you, listeners. But the title is Radiating Confidence, Reclaiming Your Power, Feeling Amazing. What does that mean to you? What is it that you hope that you're going to inspire someone who attends to do or think or feel differently?
Well, I— there is a panel of women, yourself included, that have 20 women, various, from a divorce coach to fitness to fashion, um, you know, just a wide range of women who are all in their midlife and, um, just brilliant and are teaching you ways from, you know, all these different let me start that over, but that they are bringing their expertise and telling you that you are not alone in how you feel. And there are tools and there are ways and, and communities who will support you and empower you and help you rise. And whether it's to change your hair to gray or change your makeup or your clothing or start meditating whatever it is that you need to have that support and get that confidence and start radiating from the inside out. That's what I want women to do, because I think that if you are— I really think that's where the magic is. Like, I love making women up, but I really get lit up when I see them look in the mirror and I can almost tear up because— and they look at themselves and they've never seen themselves look before.
Beautiful.
Yeah, never felt beautiful. And they get up out of that chair and they, they kind of stand different and they have a little bit more confidence. And, and I think that when you feel good inside like that, that radiates outside, and that's sexy as hell.
It is. It so is.
And it's our sexy back.
Yes, yes. You know, it's so serendipitous, but we have done this at a Flipping 50 retreat. So notoriously, we are, we are all about hiking and reaching and training to get here. We have a big movement weekend, but, you know, I can't move them all day, you know. So I let them shower, I let them rest, and we brought in, you know, a photographer who also kind of doubled as a makeup artist because she'd been a beauty pageant gal. And she made everybody up, gave them a snapshot. And my goal was I want them to have a picture of themselves that they love. That, that was all I wanted, so that they see themselves the way the world sees them. And, and so I said, whatever you need to do, do that. I want them to go home with a picture they love. And You know, this last retreat we did, we did something different. I had somebody there the entire time. So she didn't really get anybody glamorous, but she got them like in their element, strong, pardon me, as fuck, riding mountain bikes, you know, down a scary mountain, you know, and doing things that were hard and different. And so we got a different side of them, giving them that perspective of this is who we are today. And you can rewrite that story anytime you want to.
Anytime you— every day is a brand new day.
Yeah. Yeah.
Every day you have that opportunity.
So tease a little bit more. First of all, what, what inspired you to host this virtual summit? And I want everybody to Pay attention here because this is actually meta meta, right? We're talking to a woman who's 65 doing something outside of her comfort zone, probably for the first time. I mean, this couldn't be any better example of the opportunities we have at our hands right now. What inspired you to do this, to step out from behind the scenes and be in front?
Well, I just felt that it was time for me to pivot. I love, love, love doing makeup, and I will never stop until I can no longer do it. But it's long days. I mean, it's 10, 12-hour days, and it is— it can be tiring for me. And so I just feel like I can't do it as many days. And I thought, okay, things are changing. Things started changing after COVID, you know, and now we've got all the AI and all this stuff. And I thought, you know, I really need to start looking into something that I can still do what I love, but maybe pivot in a way that I could do more things online and kind of from anywhere so that I can travel and do all those kind of things. And that's where I met someone who is a coach that teaches these things. And I thought, you know, this is a great opportunity for me to step outside my box, learn something new, challenge myself. And I, and I'm really proud of what I've accomplished so far. You know, it's been really tough, and, but I've met some amazing women in the process that will hopefully be in communication with for the rest of my life. And my goal is to build a community Right. I want a community of like-minded women where we can come together and talk about these things and lift each other up and share tools and tricks and help each other out. And that's really what I wanted to do with this. And, and, and come to me and we can do a consultation on your— what you have in your makeup bag and what shouldn't be there. And, you know, teach you a few makeup tricks, right, and tips. And, and we can now do that virtually where we couldn't before. And it just seemed exciting to me and just something new and different. And so here I am.
I love it. Absolutely love it. And that whole train of thought, I, I am going to challenge everybody who's listening to raise the bar for themselves and just looking at, you know, well, I like this and I love this this, and, you know, I am evolving in my career to what I can do or want to do and want to plan ahead for what's next for me. And it's just exploring— if you got only that far, what would be on that paper? What are the things you love? What would you love more of in your life, in your day? I so love it. Okay, so give us the title again.
The title is The Midlife Women's Makeover: Radiating Confidence, Reclaiming Your Power, and Feeling Amazing.
Absolutely marvelous. Okay, so everybody, that was a lot of words we just threw at you. You are walking, you're lifting, or maybe you're commuting, but we've got it in the show notes. It'll be flipping50.com/jennifer. So we're just going to use Jennifer's name, the common spelling, two N's and an F. Okay, nothing crazy. So, so that's where you'll get in if you want to join us at the summit. I of course will be there too, but you hear me all the time. I'm always thinking the asset is you get more of Jennifer, you get more of the people that she's pulling in. So if you're looking for a level up, not just to make over in terms of makeup, but all of the things that it is from the inside out as well as the, the outside in, I think it goes both ways. Jennifer, thank you so much for sharing. It's been super fun.
Oh, Debra, thank you so much. I just can't say how much I appreciate your having me here. It was a pleasure.
We'll see you all at the summit. Yeah. Thank you so much for listening. To listen and access a decade of episodes and the show notes, visit Flipping50.com, where you'll be able to find all of our prior episodes. And I made it easy for you to make the most of your listening time by selecting 5 specific areas most commonly high priorities for our community and giving you a top 10 list if you let me know you'd love them. If you know a midlife woman or a soon-to-be one who wants to optimize her midlife energy and time with the right exercise and lifestyle changes and a mindset shift, if about just what is possible, share this podcast with her, and I thank you. There is no more powerful health influencer in the world than you, midlife woman.
