Anastacia – All My Songs Have Been Good Therapy

1 Jul 2026 · 54 min · 22 chapters

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In short

Anastasia discusses “failing better” through personal setbacks and identity—using music as therapy, rejecting being packaged as a pinup, navigating industry rejection, coping with breast cancer, and reframing fear/anger into advocacy. She also reflects on technology’s impact on music, her “glasses deal” and body-image choices, and the idea of “mothering” beyond having biological children.

Guests

Anastasia (singer-songwriter; 8 albums; 50M+ records; 227 gold/platinum certifications; born in Chicago; breakthrough via MTV’s The Cut finals in 1998; debut single “I’m Out of Love” in 2000; 25th-anniversary arena tour; breast cancer survivor with double mastectomy in 2013; founded the Anastasia Fund; Humanitarian Award at GQ Men of the Year). Brody, her Yorkie, appears in-studio.

Key claims

“All my songs have been good therapy.” Authenticity wasn’t “signable” early on. Cancer stigma can be countered with education and earlier screening. Technology/streaming shifts money away from artists. Anger can be used for good (e.g., reframing “cancer” by “looking at the first three letters”).

Notable examples

singing at Steven Spielberg’s wedding; Arnold Schwarzenegger’s birthday party where he requested an En Vogue song 12 times; “Left Outside Alone” as a song about her father; tinting her glasses to avoid being labeled a “sexy librarian.”

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Songs as Therapy

0:00 to 0:19

Anastasia discusses how her music has been a therapeutic outlet.

“All my songs have been a very good step into therapy.”

Songs as Therapy

0:45 to 1:46

Anastasia discusses how her music has been a therapeutic outlet.

“people are talking about America's 250th anniversary.”

Anastasia's Journey

2:35 to 4:49

Anastasia shares her musical journey and early career struggles.

“Just a little quick safety note about Upneq.”

Reflecting on Early Jobs

4:49 to 6:36

Anastasia talks about various jobs she held before her music career took off.

“Well, Anastasia and Brody, I should say.”

The Evolution of My Music

6:36 to 10:46

Exploration of Anastasia's unique style and the challenges she faced in the industry.

“Once I was, let's just see, in the 24th year and thinking, let's plan a 25th year anniversary, I then was actually sinking in the number and going, that's kind of epic.”

Performing for Icons

10:46 to 13:00

Anastasia recounts memorable performances, including weddings for celebrities.

“Is it true that you sang at Steven Spielberg's wedding?”

Technology and Creativity

13:00 to 14:01

Discussion on the challenges of adapting to technology as an artist.

“And I'm looking at all the rest of the people that are there to sing their songs and I'm like, do I get extra?”

Navigating Childhood and Creativity

14:01 to 21:30

Anastacia reflects on her childhood in Chicago and New York, revealing how they shaped her creativity.

“It's like the phone already knows it doesn't want to do it.”

The Impact of Family on Music

21:31 to 23:06

Anastacia discusses her relationship with her father and how it influenced her songwriting.

“Well, I don't have a relationship with my dad.”

Reflections on Technology and the Music Industry

23:07 to 26:56

Anastacia shares her mixed feelings about technology's impact on music and artists today.

“However, writing about it made me feel really good to share it, but not have to go deep.”
Show all 22 chapters

Reflections on Technology and the Music Industry

28:40 to 29:23

Anastacia shares her mixed feelings about technology's impact on music and artists today.

“There are those weeks when everything lands at once and it feels overwhelming.”

Understanding OCD: Myths and Realities

29:51 to 31:06

Explore the realities of OCD and treatment options to manage it effectively.

“A lot of people listening to this show have sat with something they've never told anyone.”

Glasses and Identity: A Personal Journey

31:06 to 31:21

Anastacia shares her experience with glasses and how it relates to body image.

“and will help you learn to take the power away from intrusive thoughts in live, face-to-face virtual sessions.”

Glasses and Identity: A Personal Journey

31:27 to 33:00

Anastacia shares her experience with glasses and how it relates to body image.

“Your second failure, and you mentioned how important it was for you to get glasses at that young age because it made you feel closer to Elton John.”

Navigating Sexism in the Music Industry

33:00 to 36:29

Discussing the challenges of sexism faced in the music industry and personal experiences.

“Talk to me more broadly about glasses, though, and what they represented.”

Breast Cancer Awareness and Advocacy

36:29 to 42:00

Anastacia opens up about her breast cancer diagnosis and her advocacy for awareness.

“I mean, that strength of character from that early in age is rare, I think.”

Addressing Cancer Stigma and Self-Care

42:00 to 46:05

Learn about the importance of discussing cancer openly and the concept of self-care birthdays.

“Like I told the doctor I was going to do it and he was like, I don't know if you should do that.”

Harnessing Anger for Positive Change

46:05 to 47:36

Discover how anger can be transformed into a tool for empowerment and change.

“And thank goodness, Anastasia, that you got loud.”

Harnessing Anger for Positive Change

47:54 to 49:03

Discover how anger can be transformed into a tool for empowerment and change.

“That's the sound of zero sugar, 200 milligrams of caffeine and the power to burn body fat.”

The Complexity of Songwriting

49:08 to 53:26

Explore the intricacies of songwriting and the challenges of balancing creativity with simplicity.

“It is the most thought of way that I think every time I go in, I'm writing songs right now in my life.”

Motherhood Beyond Biology

53:26 to 56:00

Engage in a heartfelt discussion about the various forms of motherhood and personal fulfillment.

“brother who's disabled and her and I are kind of like mom and dad.”

Embracing Failure as Growth

56:00 to 57:42

Learn about the positive perspective on failure and personal growth.

“Because I think when you do something, you're like, oh, I could have done it.”
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Transcript

Automatic transcript. May contain errors.

0:00All my songs have been a very good step into therapy. Not trying to please the man who needs me to look like a pinup doll. If a guy approached me, I'd be like, what do you have to say? So the word cancer, I didn't like it, but I looked at the first three letters and I was like, oh my God. This episode of How to Fail is brought to you by Dove Whole Body Deodorant. Welcome to How to Fail. This is the podcast that believes failing better is living better. Before we get cracking on this episode, please do remember to like, follow, and subscribe so that you never miss a single conversation.

0:40Hey everyone, it's Jonathan Van Ness from Getting Better with Jonathan Van Ness. Everywhere you look right now, people are talking about America's 250th anniversary. And while a lot of folks are celebrating, there are also people trying to use this moment to rewrite history. Christian nationalists are pushing the idea that America was founded to be a Christian nation where one religious movement gets to decide who belongs. But that's not what this country was founded on. America was founded as a democracy committed to liberty and justice for all. That's why I want to tell you about Americans United for Separation of Church and State.

1:13They work every day to protect church-state separation and defend everyone's right to live as themselves and believe as they choose so long as they don't harm others. The stakes are real. These attacks show up in censorship efforts, attacks on public schools, restrictions on reproductive freedom, assaults on LGBTQ plus rights, and attempts to give government favoritism to one version of religion. If you're looking for a way to stand up for freedom this summer, consider supporting Americans United. Americans United, supporting everyone's right to live as they choose, so long as they don't harm others.

1:46Learn more at au.org slash better. Hey guys, this is Molly Sims, host of Lipstick on the Rim. So I have a little bit of a pet peeve that I think you're going to relate to this. I'll be having a great day, feeling good, and someone will say to me, you look tired. And I'm like, I promise you, I'm not really tired. But here's what I've learned. My eyelids, they do sit a little low. And once my doctor explained that to me, it actually kind of made a lot of sense. She prescribed me Upneak, the first and only FDA-approved prescription eye drop for adults with low-lying eyelids. One drop per eye in the morning, and I noticed my eyes look more open, awake within minutes.

2:23And it's like just one simple step, that's it. And the results, guess what? They last up to eight hours. Learn more about upneq.com. That's U-P-N-E-E-Q.com or talk to your doctor. Just a little quick safety note about Upneq. Oxymetazolene hydrochloride ophthalmic solution, 0.1%. Tell your doctor your symptoms and medical history, including blood pressure, blood flow issues in heart, brain, or eye disease. Drooping eyelids can be caused by other more serious conditions such as a stroke. Do not touch the tip of the upnick vial to your eye or any other surface. This is not a complete list of risks.

3:00My guest today is a singer-songwriter who has released eight albums and sold over 50 million records worldwide. She has collected a total of 227 gold and platinum certifications and counts Elson John as one of her biggest fans. Named Anastasia by a mother who loved Russian literature, she was born in Chicago. By 15, she was working as a dancer, later singing backing vocals for Jamie Foxx, Tiffany and Paula Abdul. Her breakthrough came in 1998 when she reached the finals of MTV's talent contest, The Cut. At 30, she'd had to lie about her age to get in. She claimed to be 24 and her undeniable vocal talent landed her a record deal.

3:49In 2000, she released I'm Out of Love, her debut single, which quickly topped charts worldwide and paved the way for her first album, Not That Kind. This year sees her embark on a major arena tour to celebrate that album's 25th anniversary. Alongside her music career, Anastasia's own experience with breast cancer, she underwent a double mastectomy in 2013 after being diagnosed for the second time, led her to establish the Anastasia Fund to promote awareness of breast cancer among younger women. That same year, she became only the second woman to be presented with the Humanitarian Award at the GQ Men of the Year Awards.

4:32I was in my 30s when I had my first hit, she says. Being that little bit older makes a difference. I'd done real jobs, waitressing, shop assistant, receptionist. That reminds me not to take things for granted. Anastasia, welcome to How to Fail. What an intro. Well, Anastasia and Brody, I should say. Yes, Brody is here with me today. He has decided to be the Brody on the roadie. So he, and apparently he is smelling something amazing in the studio. So he's very nose up right now. He's usually not that snooty. Hopefully he'll just sit down and become a little comfy once we get to talking. For anyone listening to this podcast rather than watching it, Brody is the most beautiful chocolate Yorkie who has the wisdom of the ages in his face.

5:26He does. He's a little old soul in there. I love him. And I love you. Thank you so much. Thank you. We're a good duo together, aren't we? You are. Okay, down. There we go. So talk to me about all of those other jobs that you've ever had. Which one was the worst? You know, I don't think I've had a worst. I think they were just jobs so that I could pay bills. So I never really looked at it. It really needed to happen. So, I mean, I sold sunglasses. I was a hostess. I, very small time, I was a waitress. I think that probably was where I was least effective because I really did enjoy talking to people.

6:06So I'd be like, okay, what was your order? You know, I don't think I really remembered orders when I was a waitress that well. Loved working in a hair salon as a receptionist. I thought that was very fun. And then did some gymnastics, well, not gymnastics, but it was called Jamnastics. It was kind of like a step class and aerobic class for a while at Jackal Lane. but they were really to make a difference in paying the bills. Sin. Not that kind. I can't believe it's been 25 years. Can you? Once I was, let's just see, in the 24th year and thinking, let's plan a 25th year anniversary, I then was actually sinking in the number and going, that's kind of epic.

6:58That's kind of a big number. and I was still able to perform and I still had people wanting to see me. And it's, you know, and then all of a sudden, like this whole Y2K comes around and now my fashion is, you know, spot on right now. Yes. I had a lot of fun looking at Anastasia Images as a research for this podcast. Your midriff is like the eighth wonder of the world. It was. It was the eighth wonder of the world and I never worked out. I never did sit-ups. It was just part of just me. And I was very okay to show it because I was trying to distract from the top, which I was very top heavy in my chest area.

7:47So I felt like if I showed my midriff, like the attention could go there. That idea of wanting to be seen as a musical artist rather than as an easily pigeonholed female. Can you talk to me a little bit about that? Because you have such a specific style. And I know that you were rejected a lot in the early years in the music industry. What do you think was going on there? Well, I didn't fit into any of what was happening in music then. If I was looking at the artist that I was looking at to see if I could find a me in there or am I on the right path? Celine, Mariah, Janet Jackson, Madonna. I was definitely not in the sexy category of being that.

8:40And they didn't sound like me. I, the more I continued to try to have a career in my 20s, it just seemed futile because I didn't fit the mold and I also didn't sound the mold. And I would try to work with producers and sing a little different. but I do say that when I was doing like in the last three years before I got the deal I was doing a lot more weddings and I mean that was another way to make money was work with different bands and be a you know a band singer so that you could still do what you love doing but I think that's where I learned my voice. So when I wrote Not That Kind, to me, that was normal.

9:34But when I played it for people, they were like, well, what genre is this? What are you? Like, where would you fit? And I'm like, oh my God, I don't even know it. Like I didn't know I had to figure that out to be a singer. It just seemed I had to be like this business. And I didn't have that sense. I just had an artist sense. It's so brilliant that Not That Kind is an anthem for not fitting in. Right. And that's the thing that... Well, that was an easy song to write for me because I was just not the typical girl. Same with the title of my second album, which was Freak of Nature. You know, it's just I'm a little bit different, you know, but freak isn't a bad thing.

10:16You know, you could freak in your own little way. And that's why I ended up calling my fans my freaks. You know, They beat to their own drum. They're just their own unique selves. And I encouraged that. So I really did try to be my authentic self. When I did get my deal, that was lovely that they felt that way. But prior to being on that show, my authentic self was not signable at all. Is it true that you sang at Steven Spielberg's wedding? Yes. What was that wedding like? Well, I mean, it's like every wedding you're at. It's unbelievable and fabulous and everybody's there. And the only reason that that has come up in my conversation is because I was shooting one day in your life video and we all went to dinner.

11:07We were at an Italian restaurant and there is Steven Spielberg, his wife, Tom Cruise and Penelope Cruz. Wow. Let's just say the table of four that you're like, oh. And I said to people at the table, oh my god I sang at their wedding and they're like no go up to him and I was like I'm not gonna go up to him and so then I just okay whatever so I went up to him and I'm like I'm so sorry of course they thought you know I want an autograph and I was like uh I don't mean to be rude but I thought it was ironic that I'm here uh my name is Anastasia uh I actually sang at your wedding and I now am a singer and I just shot my video and I just think it's, you know, ironic.

11:55We're in the same restaurant together. And Stephen goes, what is your name? Anastasia. And he said, you know, I think the most ironic part is that we're still married. And I was like, and granted, I'm totally like so nervous at the same time. I was like, oh, okay. Nice meeting you. Bye. Well done you for going up. Also Arnold Schwarzenegger's birthday party. Yeah. Okay. Where he requested the same song 12 times. The number is more than more than four, but maybe no more than seven. Let's just say, but it it's his theme, like his, his really cool song that he thought was fun and he liked to play it, but it was what a man.

12:42It was an En Vogue song and I was singing it and just over and over. But he was just so sweet, like with it. He wasn't like, it's all about me. He was like a little kid in a candy store when it would come. And I just thought it was very sweet, but I was like, okay, dude, like, is there another song? And I'm looking at all the rest of the people that are there to sing their songs and I'm like, do I get extra? No, just kidding. But it was quite wild to perform in front of all these amazing stars and just wonder, not kind of, but like, will I ever be there? But probably not. You know, I didn't really dream dream about things, but I always did wonder what it would be like to be on the other side.

13:32Does it feel like you thought it might being on the other side and being the star that you are now? I just never thought it was possible. But looking at it, it just looked inconceivable. Even though I could see what was happening. I just I don't think I ever saw someone that seemed like they could be a me that it could be possible. Let's get on to your failures and the being you of it. Your first failure is technology, and that came accompanied by a triple exclamation mark. it's so true it is an absolute tragedy I if I did not have people that could facilitate my online life I probably wouldn't be able to do what I do it just breaks it just doesn't work like they're why is your phone not and I'm like see like you can't download this why isn't she able to do that?

14:33What's wrong with her phone? Everybody. And I'm like, it's not just me. It's like the phone already knows it doesn't want to do it. It already knows that I'm not into it. So they're like, I'm not working. I wonder how much of it, because you, like me, grew up analog and then transitioned into digital. Yeah. Let's talk about childhood and what that was like for you, where you got your creativity from. You grew up in Chicago. Yes. I grew up in Chicago and definitely a kid's kid. We're outside a lot, riding bikes, roller skating, but Chicago also has snow. So we were outside in the snow and ice skating.

15:19And it was all about going outside and playing or locked to the television. So that was like the way that life worked in our bubble of us three, which was my sister, me and my brother. And can you remember the first piece of music that you heard that really spoke to you or the first person you were obsessed with? Well, when I was young, my mom had a lot of Barbra Streisand albums and Elton John, And Billy Joel, too, and a lot of other Chicago and tons of Eagles. But for some reason, Barbara and Elton albums, the covers, and maybe Barbara because she could sing so pretty. And maybe I thought that was kind of like my mom, you know, as a pretty voice.

16:10And Elton was, I think I gravitated to him because at six years old, I got glasses. and I kind of remember that being a defining moment of when my mom said I needed glasses she said I did like yes and I did the whole like my life is good she was quite surprised at that but I think because I was visually stimulated by his records having different glasses and And I think that I was cool like him. Talking about this transition from analog to digital, you were in New York in the 90s. What an era. What are your memories of New York in the 90s? I grew up in New York in some of the 80s because I was quite still young and still in high school when we moved from Chicago to New York.

17:08and the move was hoping my mom could get on some more Broadway. She was an actress. Yeah, she was a musical actress, my mom. And I think that was the purpose. Once we did move there, it was very, very apparent that my brother, who is cognitive brain dysfunction, it was not a city for him. We were in Manhattan. It definitely was not a thriving place for Brian. So they only stayed for about three years and then moved to California. I immediately was like, I love New York. And I stayed after high school and just decided to stay in New York. So for me, my growth as like young, late teens and 20s manifested its life in New York.

18:04And I realized I became me. And also the people I ended up hanging with, like had their own identities and they were quite sure of who they were, but also really OK that I was kind of wide eyed and innocent. but they kind of just took me in and a lot of the families were different people were Ecuadorian family and a Puerto Rican family and a Dominican they were all like Latin and um and like Haitian so they all were family oriented but not white and so for me I think I learned different cultures being around New York and learning that different cultures were fun and exciting. And I adopted different energies from the cultures and I just loved it.

19:02Prior being in Chicago, my mom being a thespian, everything was at my house. There were gays and drags and, you know, black, white, brown, everything. So it was all accepted from my childhood. But I'd never adulthood it. You know, I never went out there myself and met friends. You know, I was kind of like a little bit of a shy kid. My mom was like, don't lie. Don't wear makeup. You know, I was very, very more on the sheltered side. And she instilled fear in a good way, my mom. So it was kind of like when I went to places and my dancing didn't start till about 18, by the way. And I went to clubs because my mom knew the guy that owned the club.

19:55And so I go to the club and I get, I get to dance all night and then take a cab there, take a cab back. But my mom said, here's money for a soda or an orange juice. But her whole story was like, you take that, the minute he pours it, you keep your eyes on it, you put it in your hand, and you go into the bathroom, and you go into a stall, and you drink that. And unless you drink the whole thing, you put it down, you can't drink it anymore. Someone will spike it and kill you. Like, it literally had me terrified. But at the same time, rightly so, I was single-focused on dancing, single-focused on, I'll just have a little soda and everything's good.

20:40And my life was easy. You know, come and kiss me when you get home. All her reason for it was she wanted to smell that I didn't drink alcohol. I was like, are you kidding? I wouldn't lie to her. It's like my biggest fear. Smart, smart woman. She was a very, very, she had her techniques going on. Yes. Fear never hit us. The fear of hitting was probably the bigger fear because nothing was ever done to us she was like if like teeth clench don't you you know so we were like okay you know you're just sort of like these kids that did what she said for us to do all the more impressive because she was a single parent and you've written so movingly about your dad and one of your biggest hits yeah how are you feeling about that relationship now?

21:32Well, I don't have a relationship with my dad. And so that was pretty much what the song was about. And I sort of left it as I'm able to say, don't have a relationship with you. And I leave it at the door. I don't talk about it, but it was enough for me to be able to get out a song that allowed me to write Left Outside Alone with a theme going, yeah, this is, believe it or not, this is becoming about my dad. Didn't mean to write that, but okay, that's good. That's out. You know, all my songs have been a very good step into therapy and not all of them have been told what they're about, but I did feel quite surprised that I had written one sort of, and it, it helps, I think everything like that, therapy or whatever can help your closure in your own spirit about how something made you feel, um, whatever that may be.

22:33And, um, I really enjoyed that song because it had such power in the words, you know, the words actually, and the song itself is powerful. It's a, it's a very big song and became one, if not my biggest song in my career and how ironic it was about something so sensitive or something so close to, you know, nobody, I don't talk about my, my father. I don't talk about my past because it is what it is. You know, it's just my, my part of my life that, that I, I have. However, writing about it made me feel really good to share it, but not have to go deep. Yes. Well, I know so many people who've been helped by that song.

23:24So thank you. And sometimes it could be about a boyfriend. That is how I first heard it. I'm just thinking. I know most people did think it was about that, but I was like, well, I don't want to lie, but it just happened to be in there like, oh, wow. So it definitely keeps something honest and something to be mine. Totally understood. Technology. How do you feel? Okay, aside from your own personal failure with it, how do you feel about its impact on music? I'm sad and happy. I'm sad that musical artists, writers, and people that work so hard on their music are not making the money that they should make because now all these new platforms are streaming their music and they are making more money than the artist is making because they own the platform and you're just lucky enough to be on it.

24:26It's definitely not what you would be making if you sold physical copies. So that's the unfortunate part. The thing that I think is also positive is that people that do have talent have a way to facilitate and get their music out to so many places, not just where they live and go on the corner of the street and try to sell, you know, a CD or, you know, try to just have one little place that people go to. Then there is the amount of music out there is super saturated. So the great music can get lost because everybody wants to be a musician, like everybody. And really, you can, you know, and you really can be a musician and you can actually make yourself sound better than you are.

25:22And now that once again, technology is technology, AI are writing songs and AI are singing similarly to an artist. When I was young, it was about standing outside and waiting for the release date. And that release date meant you waited outside the store and hoped they didn't sell out before your three hours or 10 hours or 24 hours of waiting in line for your product, your favorite artist. And now it is, you know, like one song off the album you'll take. You know, it just doesn't get the whole vibe of what it was to create a whole album. It was like a story arc of the way you used to write before.

26:12And now it's super singles and EPs. And it's just changed a lot. And if you don't know it and never experienced it, I think it's OK for the younger audience. So they don't really get the uniqueness of what it was like. But I'm glad I experienced that. Because if I didn't, obviously I would have as much sympathy as I do for even musicians today. I have tremendous amount of sympathy. I don't know what to tell musicians today, to be fair. Good luck. Yeah. Like, just get another vocation in case, you know, this becomes hard. Because it doesn't mean you're not talented these days. That was an amazing answer.

26:58Thank you so much. probably 12 of your questions just and I feel exactly the same and I feel so grateful to have had that experience right of saving up my money for a Madonna album that came in like a little cassette and literally opening up the cassette yeah and looking at all the words and looking at the pictures and look who did sing backgrounds like you end up kind of going oh my god you know what this person is saying backgrounds on this person's like you start to love your artists enough to see that you go, oh my God, Michael Jackson had the same singers as Luce the Vandross. You're like, you just really got to be musey.

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29:47TaskRabbit.co.uk and the code FAIL. Terms and conditions apply. A lot of people listening to this show have sat with something they've never told anyone. Not a mistake, not a bad decision, a thought that arrived uninvited and just kept coming back that made them feel like there was something deeply wrong with them. And because it didn't look like a failure they could talk about, they just carried it in silence. For millions of people, that's not a character flaw. It's OCD. Not the organising stereotype. real OCD is persistent, unwanted, intrusive thoughts that latch onto the things you care about most your relationships, your values, your sense of who you are and bring enormous guilt and shame with them and the more you fight the thoughts, the louder they get The good news is that OCD is highly treatable with the right kind of specialised therapy OCD needs ERP or exposure and response prevention therapy which has proven to be the most effective treatment Regular talk therapy isn't recommended for OCD and can actually make it worse.

30:52And that's where NoCD comes in. NoCD is the world's leading provider of OCD treatment, and it's covered by insurance for over 138 million Americans. All their licensed therapists specialize in ERP therapy and will help you learn to take the power away from intrusive thoughts in live, face-to-face virtual sessions. They also provide support between sessions when you need it most, so you're never facing OCD alone. If any of this sounds familiar, visit nocd.com to book a free 15-minute call with their team. That's nocd.com. Your second failure, and you mentioned how important it was for you to get glasses at that young age because it made you feel closer to Elton John.

31:37Your second failure made me laugh. Not securing the world's biggest glasses deal, dot, dot, dot, yet. Yet. Still out here, folks. still out here, still wearing glasses, still have a great, great eye for glasses. Half the time, everyone's like, oh, my God, I love your glasses. I wear so many different shapes that it's not about one shape suits one face. I think people now are really into wearing glasses with the tint. So I think if now it's not even like the second thought is there, Like I would love to have like a spec savers type of situation because it's not about paying a lot for glasses. The fun part is if you need them to see, you could put a little tint in your glasses and they could always be there.

Read the full transcript

32:26And you can also get the transition glasses. And I just know so much about glasses that I think I would add so much. You would. And have you ever been offered a deal? Ever? I've had little special collaborations with different companies, but never a thing that I think would be, I'd love to be able to long haul it. Not major, but just like this little niche that I am. It doesn't always have to be like just my little niche with your big old company. My little niche that works for me will always kind of work for people that like a tent, you know. Talk to me more broadly about glasses, though, and what they represented.

33:10So when you were told you needed them, as we've heard, you fist bumped the air and you were thrilled. But is there something deeper here about kind of body image and how you wanted to present yourself when you get older as a female artist? I decided to put a tint in my glasses primarily because when I wore glasses and they were uniquely shaped, they didn't have a tint. And guys, more than I want to care for, would always call me a sexy librarian. Emoji throwing up. So really, dude, bye. It was just a big, big, terrible, didn't work for me. So then I was like, what if I put like a tint, like a little tint in them and sort of create them to sort of feel like they're not like library glasses and they're, you know, kind of like cool glasses.

34:06So then that's where the tint came from. And so probably mid-20s, I started doing that. And then it was cool. But then at night, people would be like, why are you wearing your sunglasses at night? And I'd be like, would you like to try them on? Would you like to have your eyeball separate from its aura? You know, like, they were very necessary. And then they're like, oh, you need them. I'm like, do. Yeah. Yeah. Yeah. They're purposeful. Talk to me more generally about the sexism that you experienced when you started out in the industry. In what way? Did you have record bosses wanting to package you a certain way because you looked a certain way?

34:53Well, when I got my deal, no, I did not have anyone wanting to package me differently than what I had performed on stage with. They really understood everything that I was. Prior to that, I don't think anyone knew what to do with me, so it wasn't like they wanted to put me in a dress, they just didn't understand my rock meets blonde girl sounding completely Tina Turner, soulful, and a little bit of a town boy. But everything I did was a contradiction of everything I did. Yes. You know, and I think that was their reason to not understand it, you know. and even on the show The Cut, Drew Hill said, well, you know, I think if you take off that hat and, you know, we could see what's underneath all that, I think you look like you kind of cute underneath that.

35:59And I was like, well, that's why you're not what I'm doing it for. Not trying to please the man who needs me to look like a pinup doll. I wasn't that kind of girl to be your trophy. And I was very like that my whole life. I didn't want to be seen as an object. And so maybe it was part of my way of dressing and stuff so that it avoided that. Good for you. I mean, that strength of character from that early in age is rare, I think. I really just feel like it was what made me happy. and I also liked not being like picked up by guys because I just I don't know I just thought guys were so corny in that way because they would pick you up the same way like there was nothing unique and I was like you know also I was really shy so I didn't probably want to be picked up and so I probably made it really easy for them not to if a guy approached me I'd be like what do you have to say?

37:07Like, I wouldn't be like, oh, what do you like? I didn't know how to use that femininity. Like, I always think that women that do that, you go girl. I had no, no girl game inside my soul. It was definitely, I think I was way more wanting to make somebody laugh. You know, I always called myself, I have a great personality. I never saw myself as the pretty girl, you know, getting all the guys. I was like, the guys like me because I'm one of the dudes and the girls like me because I'm not intimidating. So I always felt like that was a great mix for me because I could hang with the guys and I could hang with the girls.

37:46And that was comfortable to be able to be that part of being a teenager into 20s. How do you feel about femininity now? Oh, I love all of it. Well, I'm definitely a lot more comfortable in my skin as a human that I still don't do the know how to get what I want by turning on a girl thing. I still feel quite guilty to do. I don't know. It's just not in my nature to be like, oh, my God, I'd really love that purse. You know, but if some woman does that, I'm like, you go, girl. I am not mad at your game. Like, I am not a hater with that. I just have never been able to do that. I think I'd probably laugh in mid-sentence.

38:33I love how pro-women you are. Yeah. And you have done so much for women over the course of your life. I mean, I mentioned you are a survivor of breast cancer. You set up this extraordinary fund for younger women. How important has that been for you? When I got cancer, it was not the typical way. I went in for breast reduction. So then I found out I had cancer. And then the whole purpose of finding out that the higher number of all women that get cancer is like 75%, but not genetic. And then I'm kind of like, wait, I thought it was probably the opposite. And I'm okay, mind blown. Wait a minute.

39:18Let's have a discussion. So what doctors are saying, we don't know scientifically everything thing to tell you you can't, you shouldn't do to not get this type of cancer, which is, there's a big, environmental, stress-related, food-related, you know, da-da-da-da. So what are you going to just not do everything? No, you have to sort of just hope that you don't get it. That really is the bottom line. And so knowing that truth, I felt, oh, I need to tell people because I had no clue. And I really feel more jazzed to want and almost because when I found out I had cancer, not knowing anything about stage or anything, I found out on a Friday and Saturday night, my press record people said, the world news knows you.

40:21They want a statement. And I was like, are these statement things real? Like you really just, I never made a statement. I don't know. And so, you know, I just had them write something. And I just felt like, dude, I haven't even told my friends and family members. Like I'm just trying to be like, I'm dying. So that built up like a little bit of a rage, some anger. also kind of, I don't want to use all the anger, but it was like, didn't know this answer, didn't know the percentage. Now they've taken away the ability of me being able to say my truth. Oh, I'm going to be loud. I'm going to tell people.

41:10Cancer gave the wrong girl cancer. And I have a platform, so I'm going to use it. And if it's my only platform that I have for a short period of time, I'm going to go there because I don't know how long I have this and I don't know how deep it's going to go. But if I can save lives by telling them what this actual truth is, then I'm going to do it. And then I just continued doing it. And I didn't expect it to turn out to be me actually saving lives, me actually being the advocate, me actually being what people call a role model. Like that was not, it was purely survival mode of how dare you take away my ability to tell people it, which I was going to do anyway.

42:00Like I told the doctor I was going to do it and he was like, I don't know if you should do that. And I was so like, wait. So all of a sudden I'm hearing it's 75%. Then he tells me, I don't know if you should tell people. And I'm like, wait, why? And he said, well, a lot of women are they they just get so ashamed and they they feel like less of a woman and they don't want that to be their defining moment. And I'm like, but it's not their fault. Like literally, I'm telling him, I'm like, but did they go? OK, I'd like a tuna sandwich, some cancer and a Diet Coke. Like they're not asking for it. So why?

42:40Oh, now they now it's their fault. Oh, no, we need to talk about this. It's not your fault. It's not period point blank. Husbands support your wives. But, you know, sons support your moms like everybody support the women. You know, this is a family disease. Now, when a woman gets it, everyone's affected and we need to like be smarter about it. So that's sort of what it did for me, which is just put a fire underneath my soul to want to get the stats out there and then tell women it's earlier now and things are getting better with research. so check it out earlier and early stage is a really great way to find it look at Jessie J you know you find it early and you do have a lot of ways to facilitate doing things and having your hair or just getting monitored from them on also they have ways for you to keep your hair where 25 years ago it really wasn't as easy so times have changed with the stigma of the word cancer.

43:53So I do try to tell people to advise earlier, mid-30s, go get a checkup. And young women are like, yeah, but it's expensive. I can't get it on my, you know, insurance. And I'm like, okay, this is my perfect idea that I thought in my head if I was not able to afford it, this is what I would have done. like this is called self-care. So you have a self-care birthday and the self-care birthday is telling people, sending an email out, this is my self-care year birthday and I'm going to go and get a mammogram, but I have to pay for it. And I don't want presents. If you can give me five pound note, like help me try to self-care myself.

44:43I'm scared. I'm this, I'm that. But But Anastasia told me that I've got to go get it. And at least if I'm 35 and I'm in a good place, you know, we're then another like four years, do it. And then eventually you're going to you're going to kind of know where you are and and what's happening in your your cancer possibilities in breast cancer. And so what ends up happening, ironically, is that people really appreciate that you're self-caring and you also send the message to them. to self-care. And so it's like a double-edged sword. So you're also helping somebody else. Not only are you taking care of yourself, but by saying that, you put something in somebody else's head.

45:26And I said, and then they, maybe they don't give you five pounds. Maybe they give you 25 pounds. I said, and then most of the time, you can get a mammogram, you can get a pair of shoes, maybe a purse. Like you do realize that self-care birthdays are really self-caring. So you actually do get a present out of it. And one is probably early stage cancer or which most likely is a situation. You're fine. Peace of mind. But it's peace of mind to your friends, to yourself. And then hopefully you've inspired somebody else to do it. I think that's brilliant. Self-care birthdays. Right. And thank goodness, Anastasia, that you got loud.

46:08I think that that story is such a great example of a woman using her rage for good. And we as women have been told for so long that our anger is unhinged in some way or quote unquote hysterical. Right. Whereas men are allowed to be righteously angry. Oh, gosh, yeah. And I love that that story shows you how anger can be such a radical tool for change. Right. And what you do is the anger. I can always deliver anger with humor. I call my titties toxic titties, you know. They're my ta-tas. So it's a good way to try and make something negative positive. So the word cancer, I didn't like it. But I looked at the first three letters.

46:57And I was like, oh my God. I was like, can. Okay, I can deal with this. There's like another thing in this word that now just takes out. There's no way it has no power over me. So you have to find the little bit of positivity in something that you know is not great. But to look at it and be able to look at it in some kind of perspective of better, it loses negativity. It loses its power of taking you down. It just does. Anything you do. Divorce everything. Sometimes the negative is there to take you down, but you have to find some way to make a negative situation positive. Everything that this podcast stands for.

47:46Thank you so much for talking about that. Love it.

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49:03Learn more at AmericanExpress.com slash business dash platinum. Your final failure, not writing a less complicated song to sing on days when your vocals are a bit tired. It is the most thought of way that I think every time I go in, I'm writing songs right now in my life. and I always say I mean Sade she's like unique fabulous but this is no ordinary love I mean and I wonder if you know like what what am I doing like what but I don't know how to do that The cleverness of her, the brilliance. There's only one Sade. But I guess because I like to make everything colorful and I like to write the passionate and thought provoking and I write very complicatedly vocal songs.

50:04and maybe it's because I can and I choose to, but if I have my easiest song I think I've ever written is Sick and Tired. Like super, there's no real high notes in there and everything. And I find that that song is the least complicated vocal song I've ever done, but it's still quite, you know. It's quite meaty. It's still meaty. I'm still hopeful. I'm still hopeful for that song that has possibly five notes in it that'd be awesome but I think also because you write about so much that is meaningful and so much of the life that you've lived that maybe there is no way no it's just me like it's just me and maybe the drama I like to bring to my vocal and that it's just been what ends up happening and maybe working with the producers.

51:04I mean, I wrote Not That Kind. I don't know. I was like 26 years old or something. And I wrote like like a bluesy, you know, talky, singy thing that was kind of, you know, it was it was we can call it it was a ballsy girl song I wrote it where I'm just coming out all the time you know just coming out with the thing coming out with the the way I am you know from the jump and not much music you know just coming out almost acapella like oh wow all right she's going there I'd like to draw this to a close by talking about something that I believe has connected all of these failures and everything that you have discussed so eloquently.

51:55And it's mothering. And you and I have something else in common. I tried and failed to be a mother in the biological sense. But the word failure, I know we didn't mean to say it. I know you didn't mean to say it. It's not a failure. Just wasn't in the cards. And I want to thank you for that because you are one of the only people who I can remember talking about this when I was going through it and facing the prospect that I would be on the other side of it. Exactly. Exactly. Yeah. You were clutching at your stomach and it was exactly that. There was so much sadness attached to it. It did feel like my failure at the time, even though it doesn't now.

52:35And I'm so at peace with it. And I'm so passionate about saying there's creativity and fulfillment on the other side. Yeah, and I want women to know we're more than the capability that our body can produce life. We're more than that because inside of us, we have all that. Even if you don't have a child, you are mothering to friends. You are mothering to your job. You are mothering to a dog. You are mothering to your friend's friends. so you can do all the things that come naturally to our absolute makeup as women and I did think I would have loads of kids my sister and I were the two sisters that she said she would be the auntie and I would be the mommy and then she is now kind of uh taken over um guardianship of our brother who's disabled and her and I are kind of like mom and dad.

53:38So I kind of go out and do more of the work. She's kind of has to stay at home a little bit, but now she can come on the road and do the tour part. But she used to travel all the time with me. And once my mom got to a certain age where we really just felt like Brian probably just needed a little bit more focused assistance And my mom was willing to let us take over that. It was more, I think, just her level as a woman, having children in the mid-60s, having a disabled child as her third child. She didn't want to face that. she was more, he's just a late bloomer. He's okay. Don't worry about Brian.

54:27He's fine. He's going to be fine. You're going to get married. You're going to have your own place. You're going to do this. She had really, you know, pink rosy glasses in an optimistic way. And I have to understand that because I am not a mother. I have to understand the feeling that it would feel because in my mom's time when she was young, they went to a separate facility and you never saw those children. So I have compassion for the fact that she didn't want him diagnosed in that way. But Sean and I knew he was just, he's like caps out at second grade maths and everything. You know, he's not, he's just, he's like the person who's taken the most advantage of because he doesn't have that filter of, you know, get over.

55:24He did learn how to lie. And then that's been the worst thing because he's a terrible liar. When he learned how to lie, we had to kind of let him know that it's not a bad thing it's a bad thing but when we realized how his brain is brian is kind of like a 24-hour guy not officially but the way that you almost have to keep reminding him because if you think of an eight-year-old kid when they turn nine and they kind of learn that facility it's like that when you say you want to bottle up your kids we got like win-win chicken dinner you know we got brian that you sort of have to just go we're gonna have to have a maid come and clean when sean goes out of town because we know yeah he's gonna clean his toilet but is he gonna clean his toilet we'll have to count how many underwears he has in the laundry to know did he wear it three days in a row but that's there's so much love there yeah and i really appreciate how much you show up as a mother for so many people that you haven't even met like beyond your family through your work yeah thank you so so much thank you for coming on this mad cat little podcast i love it i love it and it was like you know and i it was kind of wild because when of course i heard how to fail i was just like no but this is how i look at failure are all the things that you're like, you know, I don't look at my life as what could I done better?

57:06Because I think when you do something, you're like, oh, I could have done it. You do it better. And that is not, you know, I don't want to be the repeat offender. I want to be the one that goes, hmm, I could have thought of a better way to facilitate that. But you have to go through these things as a human to, and have a lot of bumps in the road to go, yeah, I got that. And so I love this whole philosophy of learn. Yes. It's all a lesson from the universe. It's all lessons. It's all lessons. Anastasia, thank you so much for coming on How to Failure. Thank you for having me. Thank you so much for listening and watching.

57:49This episode has been brought to you by Dove whole body deodorant. Please do follow How to Fail to get new episodes as they land on Apple Podcasts, Spotify, Amazon Music, or wherever you get your podcasts. Please tell all your friends. This is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening. Refresh the rooms you love for spring with Pura. Our collection of floral, citrus, and fresh scents brings a light, airy feel to every space, like opening the windows on the first warm day of the season. From soft blooms to bright citrus, each scent is designed to capture the energy of spring and make your home feel renewed, effortless, and alive.

58:28Learn more at pura.com.

From the publisher

Anastacia has released eight albums and sold over 50 million records worldwide. She has collected a total of 227 gold and platinum certifications and counts Elton John as one of her biggest fans.

In 2000, she released "I'm Outta Love", her debut single, which quickly topped charts worldwide and paved the way for her first album, Not That Kind. This year sees her embark on a major arena tour to celebrate that album’s 25th anniversary.

In this episode we talk about her experience with breast cancer - she underwent a double mastectomy in 2013 after being diagnosed for the second time, dealing with sexism in the music industry and being a mother beyond the traditional sense.

✨ IN THIS EPISODE:

00:00 Intro

02:32 Brodie Joins the Studio

03:15 Day Jobs Before Fame

04:16 Not That Kind at 25

05:31 Finding Her Sound

08:25 Celebrity Gig Stories

11:34 Failures Tech and Glasses

26:04 Dream Glasses Partnership

26:57 Tinted Lenses Origin Story

28:31 Sexism and Image Pressure

31:45 Redefining Femininity

32:32 Cancer Advocacy Fire

37:40 Self Care Birthday Hack

41:44 Writing Singable Songs

44:22 Mothering Beyond Biology

💬 QUOTES TO REMEMBER:

Give yourself a self-care birthday - go and get a mammogram

There are so many different ways to be a mother

 So the word cancer, I didn't like it, but I looked at the first three letters

🔗 LINKS + MENTIONS:

Anastacia is celebrating 25 years since the release of her debut album ‘Not That Kind’ and is taking her #NTK2026 on the road

Join the How To Fail community: www.howtofail.supportingcast.fm/#content

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Shania Twain - took us back to her childhood, where she felt she grew up too fast, singing in smoke-filled bars at a young age. There are some real similarities between these two episodes - see what you think: swap.fm/l/JyU54nvq2muyBpNFq3B9

💌 LOVE THIS EPISODE?

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👋 Follow How To Fail & Elizabeth:

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Website: www.elizabethday.org

Guest bookings for How To Fail only come from official @sonymusic.com emails

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Production & Post Production Coordinator: Eric Ryan

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