Women & Money: The Shit We Don't Talk About!
Women & Money: The Shit We Don't Talk About!
Confidence and Money with Sheena Yap Chan
Money and confidence go hand in hand, but too often, women are expected to do it all without being paid what they’re worth.
In this episode, we’re focused on embracing who you are, inspired by our reflections and the incredible story of our guest today, Sheena Yap Chan. Sheena is a Wall Street Journal bestselling author, keynote speaker, strategist, and award-winning podcaster, renowned for her expertise in elevating leadership and self-confidence through media. She is the founder and host of the acclaimed podcast, The Tao of Self-Confidence, where she interviews women about their journeys to self-confidence.
Sheena shares her personal journey of moving from the Philippines to Toronto, her struggles with identity, and how she ultimately found confidence to embrace her Asian heritage. We talk about the insecurities many face, and the vital role of self-acceptance and self-promotion, particularly for women in leadership roles. Sheena also talks about her successful podcast, 'The Tao of Self-Confidence', and her bestselling books that aim to empower women all over the world.
Listen to this episode to learn how to build confidence, the importance of financial independence, and hear Sheena's inspiring advice on setting and achieving big money goals. Tune in for a conversation that's sure to leave you feeling more empowered and ready to tackle your own dreams.
01:56 Embracing Authenticity and Confidence
04:13 Introducing Sheena
04:36 Sheena's Story: Overcoming Identity Struggles
11:07 Launching the Tao of Self-Confidence Podcast
14:49 Addressing Financial and Cultural Challenges
22:49 Empowering Women Through Financial Independence
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Barb: Maggie, do you remember the time I said to you? Gosh, when I went to high school, there were always like the group of super talented women. 'cause I went to all girls school and there was this one girl that I went to school with, she was always so popular, lead in the play, top basketball player, really funny.
And I was like, wow. She just has it all, and I just thought, she is gonna go a long way. I mean, I just couldn't believe, like, I would always think, wow, I wish I could be like her as talented. I wish I could sing like her. I wish I could play basketball like her. I wish I could be as smart as her, valedictorian, I mean somebody who has it all.
Maggie: In high school.
Barb: you know who that is? Have you seen that same person?
Maggie: Yeah, a hundred percent.
Barb: Yeah. And I thought. Wow. I'll never add up to anything like that. I'll never be as popular. I'll never be as smart. I'll never be as this or that. And really high school is just a blip, right. And you said to me, mom, you don't wanna peek in high school.
Maggie: I know those people who've peaked in high school and they're still in the same hometown, still raving about how they were on the team. I'm like, if you're still living on this high, like yikes
Barb: Yeah. But at that time it was so important to kind of wanna be those people, right? Like our own self-confidence was so suppressed because we didn't feel like we had any of those skills or those talents or those brain cells. I think many of us suffer with an identity crisis at some point in time. I don't think it's just high school, but I think it's a big time, probably college as well. And people go off and they try to get into sororities or whatever and they rush. I've never done any of that, but I've heard about it.
It sounds uncomfortable to me, but I think we all at some point in time think we wanna be somebody else. Right.
Maggie: Oh yeah, I've had that thought for sure.
Barb: yeah. That's not uncommon. I think a lot of people suffer from. Not feeling good in your own skin, not embracing who you are authentically, not cherishing your own talents and skills.
Having confidence in what you can do and what your unique value is that you bring and confidence that you can do whatever you wanna do and move forward. That's what I loved about the conversation that we had with Sheena.
Maggie: Yeah, I mean it definitely took her a while. Like it does all of us to really find who we are and that our identity is unique and individualistic and there's nothing wrong with it, it's just who we are. We can't be the other person 'cause they are who they are and we are who we are. But it takes a while to get into that groove and to feel comfortable and to feel confident and, to have that almost just belief in yourself.
Barb: Yeah, and she even took it to an extreme. I mean, she, as an Asian woman, dy her hair blonde
Maggie: It sounds like So much upkeep. As someone who doesn't even dye their hair, I'm like I couldn't imagine.
Barb: I mean, she really wanted to be somebody else, and I think we can all relate to that, right? You're trying on something that looks like would be more acceptable in society and trying to be somebody that you're not. And like she said, it was upkeep that made her go back to her own color of her
Maggie: Roots. Her own roots.
Barb: definitely went back to her roots and. That's when she looked in the mirror and said, this is who I am.
Maggie: I feel like there's a song for this. I'm thinking of like this Disney song right now. Like This is Me, I think is what it's called.
Barb: Oh, from The Greatest Showman.
Maggie: Yeah.
Barb: Yeah. I love that song too. It's so inspiring. Because. It's all about acceptance. All those people who were in the circus and how people looked at them, side eyed, and they were the odd people out, but really they stood in their confidence and said, this is me. So I think that would be a perfect song to align with this discussion.
Maggie: Yeah, I'm excited for everyone else to tune into this one and learn a little bit more about Sheena and her story and what it really took for her to be herself.
Barb: Yeah. And now she's a bestselling author.
Maggie: I think twice.
Barb: Yeah, twice, and she's sharing how she overcame all of that, and she's talked to hundreds of women about confidence. She shared her tips and tricks with us, so I can't wait for people to jump in and give this a listen.
Maggie: Sheena, we are so glad you are here on our podcast today. Before we dive in, could you introduce yourself to the audience, share about who you are and what you do.
Sheena: Yeah. First off, thank you so much for having me on the podcast. For those of you who may or may not know me, my name is Sheena AP Chan. I am a Wall Street Journal bestselling author, keynote speaker. Podcaster and strategist on building confidence and leadership, especially for women. Everything really stemmed from my upbringing, moving from the Philippines to Toronto when I was seven.
And as much as I love Toronto and it's a. Very multicultural city. There wasn't anyone in the media that looked like me, so I was always ashamed of who I was, what I looked like, felt like I had to look a certain way to feel beautiful and accepted. And it wasn't until my twenties when I my hair back from blonde to my original hair color where I finally embraced my culture.
And in 2015 when I was dealing with my own confidence issues, I was looking for resources on the internet. That specifically also catered to Asian women, just because I'm Asian
And I couldn't find anything. So part of me thought maybe something was wrong with me because I was the only one feeling this way.
And I realized in our culture, we don't talk about the things we go through. And also. Representation was still very important for me because there was very minimal representation in the media. And so I started my podcast, the Tell of Self-Confidence, where I've interviewed over 800 women on the subject of confidence, mostly Asian women.
And as much as I love podcasting and, podcasting's a labor of love it's still a very small media platform compared to others. And so I realized in order for me to create the visibility and representation that I wanted, I had to venture into different media platforms. So, I ventured into books.
My first book is a co-authored book called Asian Women Who Boss Up. Which is an anthology series, and it led me to writing my first book with Wiley called The Tao of Self-Confidence, A Guide to Moving Beyond Trauma and Awakening the Leader Within, which became a Wall Street Journal bestselling book.
This year, this May, my next book with Wiley is called Bridging the Confidence Gap, how Empowered Women Changed the World Is Coming Out. So I'm super excited about that. Never in a million years, I think I would get one book from a traditional publisher, but two is really wild.
Then I also do workshops and talks on confidence in leaderships for organizations and corporations that are seeking more, especially for women, just because I believe having more women in leadership really is a win-win situation for the world. So yeah, that's a little bit about me.
Barb: I love it. I'm so glad we're having this conversation today. To dive into kind of your transition from having all of this concern about yourself and your identity to really being a powerhouse that you are in speaking on this exact topic. You mentioned that, it was really hard for you to embrace your Asian identity, but what was that moment that you decided to really fully accept who you are?
Sheena: Yeah. As I mentioned, in my twenties I did dye my hair blonde, right? And retouching your roots is not cheap. Sometimes it's actually more expensive than dyeing your hair. So I realized this is not part of my lifestyle. I cannot afford this every three months. Like it was ridiculous. That was in like 2003 or or 4. So I said, you know what? I'm gonna dye my hair back to my original hair color and I asked my hairdresser to do it. When the final product came out, I looked in the mirror and that's when I realized, oh my God, this is who I really am. This is my actual self.
This is how I'm supposed to look. I'm Asian. This is my heritage, this is my culture. I'm gonna embrace it. So it took from me being let's just say financially savvy to recognizing my culture.
Maggie: Yeah, that's not an easy upkeep, especially just having like drastic hair, color differences. I know that can be expensive. And so you didn't only dye your hair blonde, but you also went by the name Heather, right?
Sheena: Yeah. When I was young, I wanted to have blonde hair and blue eyes to feel accepted and also to have a name that was more acceptable. And, I thought Heather was very acceptable because I saw that in movies. So I wanted to change my name to Heather, but
I didn't. still have my
Maggie: No, I love Sheena. So how do you think today's society beauty standards affect women and their cultural authenticity when it comes to their leadership?
Sheena: Yeah, I mean as women, we always have to show up a certain way, and especially in leadership, we have to dress a certain way, unfortunately, to be taken seriously. When you look at like, let's say the VC world, like men in Hawaiian shirts and shorts, and some of them look like hippies, and yet they can still get funding.
Imagine if women were to dress like that, like we wouldn't be able to get a dollar, right? So unfortunately we have to dress the part in order to be taken seriously. Like I remember talking to this girl who's also in the VC industry, she's asking me.
Just like these little tips as to like, how does she present herself? What can she do to get more funding? And yes, unfortunately, the way she was dressed, she was dressed like she looked really young, and I told her, you need to upkeep, like, invest in your wardrobe a little bit more, right?
Like instead of jeans, wear khaki pants or some nice dress pants. Have a nice dress shirt because we have to look the part that we're serious about what we do. There's been studies where if you upgrade your clothes, your style, your income also grows. I think a well-known marketer did that, and he said that his investment led him to like five times more his revenue or five times more his investment on his wardrobe.
So it does play a part, unfortunately. And I know sometimes we're like, no, you gotta be authentic. But of course there's this like tug of war, like yes, being authentic, but we also wanna be taken seriously. Men and women are different, right? When it comes to leadership, men have been more accepted because that's how it's been.
So for us, we have to work a little bit harder. We're gonna have to get back up a lot more than men. We're gonna have to do things differently to be taken seriously so that we can break through these barriers and be able to achieve gender parity at a faster rate. 'cause they said it's gonna take the earliest, the year 2158 to achieve it.
So I don't think anyone wants to wait over five generations to see that happen.
Barb: Yeah. And let's face it, it's a man's world. Even in the VC world women don't get funding really, no matter how you look. It's very difficult for women to get funding in the VC world, but I totally understand what you're saying about that. I mean, we have to really check ourselves and we preach a lot about the cost of that, right?
Like you were saying, with your hair, for any of us to keep the maintenance up and the hair and the nails and the wardrobe. I mean, it is an investment and it's necessary unfortunately, to really step into that person that you're pledging to be if you're looking for monies and things like that.
So, very interesting. I love how you started the Tao of self-confidence podcast to help Asian women dealing with self-confidence issues. Tell us a little bit more about that step into that moment in 2015 when you decided to launch that.
Sheena: Yeah. I've always wanted to create a platform and I didn't know what that platform looked like, and that's when podcasting, I heard about it. Back then it was on iTunes. There was no Apple Podcasts I just invested in a course to learn more about it, and I love the concept where people can download the episodes anytime and listen to it at any given moment, whether they're stuck in traffic, jogging, doing chores, taking care of their kids.
I just loved that concept. I didn't have to be on video. I can just talk. I thought it'd be easy because I was already doing videos, so talking was like not a big deal. But then I realized. The self-doubt creeps up the imposter syndrome. Then you being your biggest critic comes up.
You're like, oh, your voice sounds weird. Are people gonna like your voice? Just little things like that, right? Like, I'm sure we've all been through that. But yeah, if it wasn't for me investing in the course to learn how to set up a podcast and things like that, the podcast wouldn't even be here today because I remember my original title for my podcast was gonna be called The Stripper with a tagline to Strip Your Limiting Beliefs
away. And I hired someone to do the graphic, and it was literally a silhouette of a stripper with a whip. And so when I shared that with the group that I was in for that course, nine out of 10 were like, I think you're gonna have the wrong idea, or you're gonna give the wrong idea, or I don't think that's gonna fly.
So part of me was like, oh my God, if I can't get the title right, how am I gonna get the show, right? So, because I made that mistake, it led me to having the right title, being clear instead of being clever. Then we're here today. So, yes the biggest lesson is be okay to make mistakes. I always say, your mistakes will lead you to your greatest opportunities.
Maggie: I mean they definitely will, but I'm sure after having, seven, 800 guests on your show. It gives you a lot of confidence to hear from these women that we all struggle with the same things. We all have those same limiting beliefs, these sound like a lot of women who've, been there, you know where you wanna be.
And so they have probably great words of inspiration or motivation to keep you going and to keep podcasting 'cause I mean, to get 700 episodes under your belt, you stuck with it right?
Sheena: Yeah. I mean, it didn't happen overnight and I've had this podcast for almost 10 years, and even though I've mostly interviewed Asian women, I mean this is stuff that all women can relate, even men, right. Being able to know that you're not the only one dealing with these issues, you don't feel so alone in this world, and you realize it's just part of the process.
Sometimes when we don't talk about what we feel, we think we're the only ones feeling it, then we think we're crazy. Something's wrong with us because we're feeling a certain way, not realizing a lot of us feel this way. Just by hearing the stories, all you need is one person's story to realize
if she was able to come out of a similar situation that I'm in, then it's possible for me as well. And this is why for me creating better representation is so important because it leads to other possibilities. One of the things I'd love to do is dismantle the negative stereotypes we go through, right? Especially as women, being an Asian woman, we're always constantly seen as quiet and submissive and obedient. I want to dismantle that. 'cause sometimes that doesn't help us, right? They just think that we're not leadership material because of that negative stereotype.
Barb: Yeah, and I think it's so important, like you said, stories, you know what people have gone through and nobody's getting through life without being unscathed by something that has happened to us, right. In your book you talk about, moving past tough experiences so that you can feel more confident. Let's talk about how money might play a role in that, and how can women start feeling more in control.
Sheena: Yeah. I talk about money in the book. Money trauma is a big thing, especially, in our culture we've always been told like just these little things that really hurt us. Like if I went to babysit my aunt's kids and my dad would be like, don't take her money.
That's really shameful of you, even though she offered it to me and I'm doing a service for her, right. So even just that little thing, it feels like if we take money, we're being greedy. Even though it has nothing to do with that. It's just sometimes pride is a big thing.
It's like you don't wanna take people's money because you're too prideful, but being too prideful is a bad thing, right, because then you just think you just can't take people's money because you don't wanna be seen as shameful or greedy and things like that. So these little things do make a difference.
Even just your upbringing, right? Like, my parents, when they came here, they had to save up. They had to penny pinch, make sure they had enough money to cover expenses and things like that. Like, I remember we would always go to Burger King and just eat Whoppers because my dad would clip out 99 cent whopper coupons.
And so till this day I'm very traumatized by the whoppers. But these little things, right? We think like, oh, we have to penny pinch, we have to save every single cent. Because if we don't, we feel like we're gonna run out of money, right? And then there's the opposite, because your trauma could be like, well, I don't wanna go through where I had to penny pinch everything.
I'm gonna spend whatever money I have to the point that you're in debt, right. I'm not an expert and these are all just observations. So, this is what I've observed, especially for women, right? Like, we tend to discount our prices, right? We tend to lower our prices because that's due to our worth, right?
And our worth is due to outside forces, whether it's cultural upbringing, society, it all is a factor of that. Especially when as women we're told, self-promotion is tacky. Like, who said that? Definitely a man probably said that, right? But yet you see men constantly promote themselves all the time.
So for me, something as small as self-promotion is so needed. For me, it's empowering. It's not tacky because that builds confidence, it builds leadership. It also teaches us how to promote, how to show our products and services. Sometimes we're told if we show it, we're being too braggy. According to who, right? According to one person's opinion. Like, we don't even know, like someone just made this up and decided, let's place this on women. It is tough sometimes, right? Because when you're out there doing things there's also outside forces that also diminishes your worth, right?
In the speaking realm, generally men get paid more than women for the same exact thing, same exact talk. Or sometimes women don't even get paid at all, right? Because they think, well, we're doing a favor for you. You get to be on our stage.
Meanwhile, you hear the man who talks the same exact topic will get paid four figures, five figures. It's very frustrating. Don't get me wrong, it's so frustrating because it's like, you know your worth, but yet there's so many outside forces that bring you down that tell you're worth is like down here when it's like up here.
So that all does tie up to money and trauma and how you see yourself and how your perception affects the prices you charge to your clients.
Maggie: Yeah, we see this so often of people wanting to offer visibility instead of getting paid, where a lot of men get paid and they get the visibility. It's hard when you are fighting kind of your own demons of what your self worth is and trying to boost that up enough to charge those prices and then have these people come and diminish that, and say, you're really not worth anything more than visibility.
it can be hard to overcome. And so I'm glad you're having those conversations and we can share about that because if anyone is struggling with that, they're not the only ones out there. It's not just happening to them, but we do need to put our stake in the ground and say, no, this is what we're charging.
I'm not just getting paid for visibility. I have this skill and this expertise that I'm coming to the table with.
Sheena: Yeah, and we're bringing value to the audience. This is not only happening in finance and vc, even in Hollywood, right? Like women with big names who've won prestigious awards also still get paid less, right? Like I remember Viola Davis doing an interview. She's won all the awards.
She has the Emmys, the golden Globes, the Oscars,
Maggie: The to Tony.
Sheena: the Tonys, Yes. So, I mean, that's huge, right? When you win all four, so you think your income's gonna go way up, right? And then people tell her, she's known as like the black Meryl Streep, but she only gets paid a 10th of Meryl Streep's salary, right?
Then Meryl Streep still gets paid half of like, I don't know, let's say like Robert De Niro's salary. Even though she's won all those awards, she still gets a small pay compared to everybody else. Then she mentioned that she's number one on the call sheet. So if she is already a prestigious actress who's won and only gets a 10th of, let's say, what Meryl Streep gets paid, what more for the other women of color actresses out there who are still fighting tooth and nail to get seen, to get paid for what they deserve?
So, it is a battle till this day, I'm not gonna say it's roses and butterflies. This is why it's so important for us to show up, to keep showing up, to fight for what we deserve. Is it easy? Of course not. If it was easy, everybody would be doing it right?
Barb: Exactly. Everything you say is so true. We see it every day. I mean, people come to us and ask us for our services for free, it's just crazy. But Sheena, you believe in setting big money goals. So can you share a time when you took a risk with money that paid off?
Sheena: Yeah, I think everyone's biggest investment is property. I remember investing in my first condo which was really like nerve wracking because that was the biggest purchase of my life. I mean, with real estate, either it goes up or it goes down, right? So I was able to make a profit out of that.
So that was probably my biggest risk that had a positive return.
Maggie: And so are you still investing in real estate? Is this a big portion that you are a part of?
Sheena: Oh no, that was just a one-time thing. So I haven't delved into it since.
Maggie: Yeah.
Barb: But as they say, more women are investing in real estate than ever before. They're owning more homes, especially single women, so fantastic.
Sheena: For sure. I love that. I mean, especially like countries, like in China, where there's laws that even if you're married the wife's name doesn't need to be on the deeds. So, that's really bad, right, because when something happens when you're divorced, the man gets everything while the woman is left with nothing.
And so it's the same trend in China. A lot of women don't wanna get married. They'd rather be single, buy their own homes, because if they get married, they end up being broke or being in debt because, they put in money to this property and then they get nothing out of it because they don't have to put their name on the deed.
So it's unfortunate that things like this still happen.
Maggie: And we still tell women today, I mean in America, like you've gotta get your name on the house as well if you're paying those bills. So many partners do say, oh, it's not necessary though. No it is actually necessary. Let's go to the bank, let's get that done. And so if they're saying it's not necessary, let's dive into that.
Let's have some conversations, because otherwise there could be some major red flags there.
Sheena: Yeah. And it's not even just married couples, even just common law, right? Like, if you are putting in money and you're not getting anything for it, it's unfair, right? Because you've also put your money into it. I mean, at least get back the money that you've put in versus not getting anything at all.
So, yes, having that, or even just having a stipulation or contract or something just to protect yourself, it's so important. This is the problem, right, as women. Financial literacy is not something that's taught, especially in business. Most women wanna have a business just to provide more things for their kids.
A little bit of shopping money, more money for expenses or groceries. They don't talk about, well, what's the exit strategy? How are we gonna scale? That's how men think most of the time, right? But as women, we're not educated with those tools.
And so it's important to have shows like yours to educate women on money. Why it's so important, why financial independence is so important for women. You look at countries like Afghanistan, where women's basic human rights have been stripped away from them. They're not allowed to have a job, not allowed to go to school.
They're not even allowed to sing in their own homes, can't show their faces in public. Like, can you imagine if that happened in other countries? This is a big issue because if one country can do this, it can still create a domino effect. It's 2025 and we're still dealing with this and it's just really unfortunate that places like Afghanistan, women have to literally fight tooth and nail just to be heard and seen, or even be able to sing a song in their own home.
Like, what kind of a rule is that you're not allowed to sing in your own home? Like what does that do?
Barb: Yeah, it's suppression right? Even in the United States, we're dealing with that every single day. The pay gap, the pink tax, caretaking, our rights are still being suppressed and that's why we need to come together all of our brilliance, all of our information, share with other women, lift them up, give them confidence, give them the tools and resources that they need to move ahead.
And really be financially independent and on their own, because I know, you know that, financial independence, it's tied to self-worth. So are there ways that you share with your community or with all of the women that you've interviewed on how women can start taking control of their finances and feel more confident about it?
Sheena: Yeah, I think the biggest important thing is just start small, right? Like you don't have to make big leap to create some income into your life, right? Just start really small. Whether it's saving $5 a day or $10 a month, at least you're doing something versus nothing. And as you slowly build your confidence up, you can add a little bit more.
Like, let's say I wanna save $5 a week, like something small. And then once you make a a little bit more, you're like, well, I'm gonna add another dollar to that, right? So then you have $6 a week. So just adding it little by little trying to find ways to create income. Now with ai, there's so many opportunities for women to really create a business that can help them. As women, we tend to do a lot more things than men, right? We're not just a business woman. We're the caretaker. We're the babysitter.
we're taking care of our kids, we're doing chores, taking care of our parents, like we're doing a million things at once and we can't do it all, right? There's also this notion that we have to be the superwoman of everything, which really we don't have to be.
Being the superwoman of everything is really exhausting and it's energy draining. And then because of that, we don't have enough confidence because we feel like, if we can't do everything, something's wrong with us and then our worth again goes down. So, that perception of yourself is really important because if you don't see your own value, you're not gonna go out there and do those things.
You're not gonna go out there and charge the prices you're worth or even find ways to start creating an income. So, yeah.
Maggie: Yeah, that's it, I feel that definitely and that independence really helps you then have that more opportunity to do whatever you wanna do and feeling like you can really do whatever you wanna do. So I think this has been a great conversation and I'm so glad we have your voice to share.
All the accomplishments that you've done, and I know people then can tune into your podcast and grab your book and your new book coming out, which is super exciting. But there is a question we like to ask everybody who's on the show, and that is, what is your definition of financial freedom?
Sheena: For me, it's just having enough funds to live life on your own terms, and everyone's life looks different. Like if you just wanna live in a hut in a beach in the middle of nowhere, then that's fine. Not everyone wants to have the fancy cars or a big fancy house. Some people just wanna live very simple where they just, get to do their own thing.
And so it all depends on how you wanna live your life. Like I mentioned, if you want the fancy cars, then great. If you just want the little hut on the beach, that's awesome as well. So that to me is what financial freedom is really having that choice on how you want to live, right?
Because not everybody gets to choose how they wanna live depending on the circumstances.
Barb: Fantastic. I love how you said start small because I think what that means is you're strengthening that muscle. You're opening that account, you're making those contributions, and you continue to add to those, and that adds up over time. Thank goodness for compound interest and just getting started.
I think that's the hardest part for most women is just to get started, but starting small, adding to it, you're strengthening that muscle. You're seeing all the profits grow. You're seeing your own investment grow that's giving you financial freedom, and I love that you've come on here and really shared your own story.
And the wisdom that you've gotten from all of the other women that you've talked to as well, it's fantastic. So thank you so much, Sheena, for being on our podcast today.
Sheena: Yeah. Thank you so much for having me. I've really enjoyed this conversation. I think this is a topic that's so needed to be addressed to all women. So appreciate it.
Maggie: Thank you, Sheena. You can check out all of Sheena's social media links, her podcast and her books, all in the show notes. Until then, we'll talk to everyone soon.
