210 | The Tao of Self-Confidence & Money with Sheena Yap Chan

Sheena Yap Chan - Love, your Money



Welcome to episode 210 of Love, your Money! In this episode, I’m joined by Sheena Yap Chan to discuss how to infuse your personal and professional life with self-confidence. 


Sheena Yap Chan is a Wall Street Journal Bestselling author, speaker and podcaster on the topic of leadership and self-confidence. She is the host of the award winning podcast The Tao of Self-Confidence (1M+ downloads) where she interviews Asian women about their inner journey to self confidence. 


Today, we’re talking about her bestselling book, The Tao of Self-Confidence: A Guide to Moving Beyond Trauma and Awakening the Leader Within. You’ll hear about the unfortunate stereotypes Asian women face, how to build self-confidence, and action steps for women who want to do it all but feel overwhelmed.

Here’s what you’ll find out in this week’s episode of Love, your Money:

  • The story behind “The Tao of Self-Confidence”
  • The leadership challenges Asian women face
  • Finding cultural pride instead of embarrassment
  • Stereotypes and barriers in professional settings
  • How history plays into stereotypes
  • Battling discomfort when promoting yourself
  • An argument for ditching the word “minority”
  • The value in asking for help as a woman

Inspiring Quotes

“It's always the small, actionable, daily steps that yield the big results.”

“Seeking help was the biggest boost of confidence for me because I realized I didn't have to do everything myself.”

Enjoy the Show?​

Hilary Hendershott: Welcome back to Love, your Money. I’m your host, Hillary Hendershott. I have with me today the amazing Sheena Yap Chan. She is a Wall Street Journal bestselling author, speaker, and podcaster on the topic of leadership and self-confidence. She’s the host of the award-winning podcast, The Tao of Self-confidence, with over 1 million downloads where she interviews Asian women about their journey to self-confidence. Sheena has been featured on Fox, NBC News, Business Insider, Manila Times, and more. She’s also the co-author of two international bestselling books. And today, we’re talking about her debut solo book, The Tao of Self-confidence: A Guide to Moving Beyond Trauma and Awakening the Leader Within. Welcome to the show, Sheena. 


Sheena Yap Chan: Hey, Hilary, It’s such an honor to be here. It’s so great to reconnect with you. I know we’ve seen each other do stuff on social media and we go way back, so I’m just really honored to be here today. 


Hilary Hendershott: It’s so cool. It’s just so amazing. I mean, I give a lot of lip service to the idea of watching women rise up and being part of the rising tide of all boats, and just watching your success has been so inspiring. So, thank you for being here. Let’s start with a cultural ignorance question. Tell me, what’s the difference between Tao and Dao and what does that mean? 


Sheena Yap Chan: So, I’m probably the wrong person. So, back then it was pronounced as Dao but now it’s more accepted to say either/or. And when I was searching through my podcast, I’ll share a little background story of when I first started my podcast. So, the Tao of Self-confidence wasn’t the original title for my podcast. I don’t know if you ever saw it in our podcast paradises a group but I actually had a different title. I was going to call it The Stripper and have a tagline: To Strip Your Limiting Beliefs Away. 


Hilary Hendershott: No, I never saw that. 


Sheena Yap Chan: Yeah. So, I had a graphic artist literally have a podcast art with a silhouette of a stripper with a whip and then I shared it there. And of course, everyone was like, “I think you’re going to give the wrong idea. I don’t think you’ll have the right audience.” And so, I had to step back and get clear instead of getting clever. And so, I was looking at iTunes back then. Apple Podcasts was in iTunes, right? I saw a lot of people saying The Art of, The Art of. And I was like, “Okay. This is great,” but I didn’t want to be another person that said The Art of. So, I wanted to start looking for different things. And I saw the word Tao and what it meant and it meant the way. And so, it made a lot of sense. And then I had a friend who’s a spiritual healer tell me that she helped me get clear and she’s like, “Your podcast title will have a word that starts with C,” and I saw Confidence, and then we just came up with the Tao of Self-Confidence, went back and got my graphic designer to redo the art with the new name. And then it’s a silhouette. It’s an Asian woman in a professional outfit but her shadow is a woman with a cape. And that’s how I got the name, The Tao of Self-confidence.


And so, the way can be any way because we’re all different people, we’re going to do things differently. We’re going to have different ways to build confidence, different ways to overcome some of the things we go through. And that’s why interviewing all these amazing Asian women was so important because culturally we’re not told to share what we’re feeling, how we’re going through. And it’s important to be more open, to share that sometimes we struggle, sometimes we have bad days, sometimes we’re in a funk like I mentioned to you before the call I was going through a funk and I think we need to share that because in entrepreneurship, it’s not always rainbows and butterflies. It’s not always about fancy cars and first-class seats in business. 


Hilary Hendershott: No, ma’am. It is not. 


Sheena Yap Chan: Yeah. Sometimes it’s maybe you have to eat ramen noodles for a month just to get by. 


Hilary Hendershott: Oh, my goodness. Okay. And so, this book, I mean, it seems to me like it’s the culmination of these 800 interviews that you did with women about their journies to success and self-confidence and power. Is that how you would say it? 


Sheena Yap Chan: I think, for me, it’s really about not sharing their stories but it’s more about some of the commonalities that they went through and kind of put a book together, right? Like, some of the commonalities is like trauma is something that’s prevalent in our community, especially recently with what’s been going on with anti-Asian hate. I mean, I just read in the newspaper that two elderly Asian people were attacked in San Francisco just like maybe half an hour ago before we got into this interview. Yeah. And then just the representation of Asian women in leadership alone, we have one of the lowest in the U.S. So, part of the reason why I wrote this was because there was a report by Catalyst.org that mentioned that in 2021, Asian women only made up 2.7% in high corporate and leadership roles in America. And then I think there is a report from McKinsey that mentioned it fell down 80%. So, we’re literally left with nothing. And I was wondering, why do we have one of the lowest leaderships in America? Yeah. And so, I had to figure out why and it was really the catalyst that helped me write this book, really figure out what is it? Because there’s a lot of leadership books out there, of course, right?


Hilary Hendershott: Right.


Sheena Yap Chan: But a lot of them are how-to manuals but if we don’t figure out what’s holding us back to move forward, we’re going to be stuck. And so, I literally had to go and dig deep, talk about the different things we go through like the model minority myth, the traumas we face, just the things that Asian women face alone, being seen as quiet, submissive, and obedient. People don’t realize we’re not only carrying the traumas of like our own traumas, we’re carrying the traumas of our ancestors, our parents, grandparents, great-grandparents, and so on. I feel like in our culture it’s longer because of just the history and the traditions we do that really affect Asian women. Like, one of the things that Chinese culture, a sign of beauty back then was having your feet binded. It was all status. Yeah, it was considered a status symbol. It was considered a thing. It was a sign that you were taken or married or something like that. And earlier this year, I found out my great-grandmother had her feet binded. 


Hilary Hendershott: To make you not be able to walk? Literally, you can’t leave. 


Sheena Yap Chan: It’s painful, right? Like, if you see photos of feet being binded…


Hilary Hendershott: It’s torture. 


Sheena Yap Chan: It’s torture. Yeah. And so, sometimes we don’t question the things that we do. It’s like, well, why did they do that? Was that just like a way to bring them down and give them less power? I don’t know. These are just guesses. But we have to learn to question these things so we can figure out the root cause and be like, “Well, should we really follow this or should we let it go?” And so, I really had to dig deep to talk about these things that we don’t normally talk about, the taboos. I mean, mental health is a huge taboo in our community like any other community, and then finding ways to heal from it, and so that we can go out there and be the best version of ourselves, be the highest version of ourselves to show up more authentic and realize we all go through something, right? Especially after the pandemic, I feel like the world is in the stage where we’re just a hot mess, and I think we just need healing but healing doesn’t mean it’s pretty. It could be the ugliest thing in the world, right? You’re ugly crying, you’re feeling depressed, you’re feeling uncomfortable. And I think sometimes we feel like there’s always one way of doing things when there’s different ways of doing things. 


Hilary Hendershott: Well, and unraveling years and years and years of cultural expectation, cultural habit. I mean, I’m as emancipated and free as I know how to be but I was still raised Protestant and there’s still some of that in me, some of that be good, be quiet, that kind of stuff. So, your story really starts with you landing in Toronto as an Asian-American woman. And you shared how hard it was for you. You actually said at times you wanted to say change your name to Heather. 


Sheena Yap Chan: Yeah. I mean, I never saw anybody on TV that looked like me. And Toronto is a very multicultural city, right? It’s one of the most diverse cities in the world. But back in the 90s, there’s no one on TV or on media that looked like me. So, I was always ashamed of being Asian. I want to have blond hair and blue eyes. I like denounce being Chinese and Filipino. I was embarrassed, to be honest, even going back home to the Philippines. I would look down on everybody that wasn’t from America or was just straight up from the Philippines. And this was actually just a realization that I had maybe last week. I was like, “Oh my God, I was terrible.” Like, I literally was ashamed of my own culture, not realizing I should be really proud of where I’m from, where I came from, the achievements we had. And so, sometimes when you look back and you do the horrible things you did back then, you’re like, “What was I thinking?” Because I was really bad when I look back and just kind of think about it, I was like, “Oh my God, this is crazy. Like, why was I so embarrassed of being Chinese and Filipino? Why did I not want to be Asian? You know, why do I want to assimilate to a different culture when I am more than enough just as myself?”


And so, this is why having representation is so important. We need to show others what’s possible. We need to show them there’s Asian women out there who are doing amazing things. Like, yesterday, I just found out there’s a 75-year-old woman who broke three marathon records, I think, in Europe. Yes.


Hilary Hendershott: Are you kidding?


Sheena Yap Chan: And she’s super fit like she’s my new fitspiration. 


Hilary Hendershott: Oh, is this the woman you posted this morning? 


Sheena Yap Chan: Yes. 


Hilary Hendershott: She’s 75? She looks like a fitness model. 


Sheena Yap Chan: I know. And then I just found out like the women’s soccer team in the Philippines competed in the FIFA Women’s World Cup for the first time ever and won their first game against New Zealand. I mean, these are the stories you want to hear. These are the stories that we want to share and showcase and say, “Look, here are some amazing women who are defying the odds, breaking the mold, breaking barriers, breaking glass ceilings, showing the impossible, what is possible.” And stories like that, get me fired up, get me motivated because it’s like, especially the 75-year-old marathoner, I’m like, okay, I got to get back into jogging again because it just goes to show that doesn’t matter how old you are, what situation you’re in, of course, everyone’s situation is different. I’m not saying we all have the same situation but within the capacity that you have, you can find ways to change things, right? You know, like you can go out there and start doing little things to yield the big results. 


Hilary Hendershott: Well, I think it’s really insightful and actually brave of you to admit that you had insights last week about looking down on where you geographically came from or your ethnic culture. And now I notice you’re almost always wearing red. Is that about what I think it’s about? 


Sheena Yap Chan: So, for me, red is my confidence color. And I’m a little bit quirky. I try to live as like minimal as possible because that’s just me, right? So, when it comes to wardrobe, I only actually wear three colors. And people think I’m just the weirdest person in the world and I’m okay with that. You know sometimes as women, we love to buy everything in the same color, right? Especially if there is a dress I like, I would buy in every other color. And so, I have eight dresses, eight of the same dresses in different colors or three of the same boots in different colors. So, I realize I’m like, I’m not going to wear all these clothes at all, right? So, I had to like figure out, okay, I’m going to minimize the number of colors I’m going to wear and then have a color that really stands out. And so, red for me symbolizes courage and confidence. And then at the same time, it also represents my culture. In Chinese culture, red is a lucky color. We celebrate it during birthdays. So, if someone’s birthday, we wear red as a happy occasion to celebrate. And then Chinese New Year, we get a lucky red envelope with money in it. So, it also symbolizes abundance. So, you’ll see me in red 99% of the time. 


Hilary Hendershott: I’ll take the abundance. 


Sheena Yap Chan: Yeah. When people don’t see me in the red, they’re like shocked. They’re like, “Are you okay?” I was like, “Yeah.” 


Hilary Hendershott: All your red’s at the dry cleaner. Okay, good. Yeah, I thought so. And so, obviously, one of the things the book really tries to do is address head-on, which I have not seen before, the stereotypes about Asian women. Of course, I’ve heard the stereotypes. And so, I’m just wondering, did that come from your growing up in Toronto? Did people have those same common stereotypes about you? 


Sheena Yap Chan: Oh, yeah. I mean, there was always these commonalities especially in the workplace, right? It’s like if you speak up, people get shocked. Like, I thought, you’re just supposed to be quiet. You’re not supposed to make any noise, make any trouble, or it’s like you meet someone, you tell them who you are and they look at you and they’re like, “Well, I’ve been to China before,” and it’s like, “That’s great. I’ve never been to China in my whole life.” All these like weird assumptions. It’s like I don’t look at you and say, “I’ve been to England before,” because that doesn’t make sense, right? But this happens to us all the time. Not that, you know, I apologize if that may have sounded weird but like, you know what I mean? 


Hilary Hendershott: I don’t know how you knew I was English?


Sheena Yap Chan: I don’t know. I just guessed but it’s just like little things like that. And then especially as a woman, it’s worse, right? It’s like I remember working at my job and I wanted to actually change positions or change into a new job or a different company. And I had an old coworker at the time tell me like, “Why are you going to change your job? You make more than enough as a woman.” And back then I actually believed him and so I stayed at my job for so long because of that. I thought, “Well, as a woman I made more than enough so I guess I don’t need to go look for anything else.” 


Hilary Hendershott: I should just stay here and wait for my husband. 


Sheena Yap Chan: Yeah. And be miserable, right? It’s insane like what we go through and just the different things. And then also being seen as a sex object, right? I mean, you think a social media platform like LinkedIn is where people are professional because it’s a professional website but you’d be surprised some of the people you encounter just like because I do a lot of outreach, right? And so, sometimes I would reach out to people and be like, “Hey, I would love for you to support me to buy a copy of the book.” And one guy was like, “I’ll buy a copy if you send me some pretty photos.” And I’m like, “Are you serious right now? Like, you’re really going to say that?” And I’m like, “Where am I? Am I on Facebook or am I on LinkedIn?” But it happens, right? Or you get marriage proposals and you’re thinking this is a professional website but because they look at me, I’m Asian, they think I’m probably a mail-order bride or something, right? 


Hilary Hendershott: Oh, my goodness.


Sheena Yap Chan: Last year on the day Roe versus Wade was overturned, I mean, I saw a sponsored article. This is a sponsored article which was a manual on how to land an Asian mail-order bride. And so, they have like a step by…


Hilary Hendershott: No.


Sheena Yap Chan: Yeah. They had a step-by-step manual of it. They chose the five top countries in Asia to look for an Asian mail-order bride and what to look for and the profile of each country like they put Vietnam loves male leadership. And just the wording was just disgusting. And I called it out and they took it down and had like a lame apology because they were like, “Oh, we didn’t know this was happening,” even though they had articles since like September of 2021. But if nobody called it out, everyone thought it would be okay. And you’d be surprised how many people were telling me, “But it’s a sponsored article.” Like, I’m thinking, “What is that supposed to mean? Because if someone paid to have it promoted, it should be okay?” And when it comes to journalism, you still have to live by a code of ethics. And Asian mail-order brides or mail-order brides in general is human trafficking. So, you want to support human trafficking because someone paid to promote it? You know, it’s just… 


Hilary Hendershott: I feel like that’s a whole podcast in and of itself, the whole idea because those poor women grow up in this environment where they think that’s the best they can do is land an American husband. 


Sheena Yap Chan: And it’s not just in America, right? They go to Korea. They go to different countries thinking they have a better life, not realizing they’re pimped out, they’re trafficked themselves. They get beaten up emotionally and physically. And they don’t know the story behind it. And so, this is why it’s so important to call out these things. If not, they think it’s okay and then we get walked all over on. So, yeah, it was crazy to see that. And that was in 20… That was last year. 


Hilary Hendershott: That is wild. 


Sheena Yap Chan: We still have a lot of work to do. 


Hilary Hendershott: And I had one of those. You know when a good comic is on stage and they say something and it’s really funny and you realize, “I didn’t realize other people have that experience.” And so, part of the breath of fresh air that you take is about, “Oh, that happens to other people, too.” And I was reading this section of your book on calling out the stereotypes about Asian women and honestly, Sheena, I feel regretful, I feel sad that I’m going to say this but I didn’t realize Asian women were in protest of those stereotypes. I honestly thought they were interested in perpetrating them that it worked for them. I mean, I had a breakup 15 years ago and the man said to me, and I mean, you can tell I’m outspoken, he said, “I think in the future I’m going to date Asian women. They don’t talk back.” 


Sheena Yap Chan: Yeah. I mean, we’re seen as emotionless or robots. And because of that, we’re targets for being like Asian mail-order brides, being in the sex industry, and also being easy targets for anti-Asian hate. They think if we target them, they’re not going to say anything. They’re quiet. They’re not going to talk back. You know, they think Asian women just love to serve men. 


Hilary Hendershott: Where did that quiet stereotype come from? 


Sheena Yap Chan: You know, to be honest, it’s probably just since history, right? Like, if you look at China, Chinese men were allowed to have multiple wives and concubines. But if women did that, they’d have the scarlet letter all over them because it’s like, “How dare you?” But that was prevalent also in Korea. If you look at India like child marriages are prevalent. If you’re a widow in India, you’re considered an outcast to society. And I don’t know if you ever saw the movie, Water, but it’s basically a story about that. Yeah. So, that was the first time I actually heard about widows being outcast from India. But there’s just so many things that each country in Asia go through, especially when it comes to human trafficking like it’s prevalent because…


Hilary Hendershott: Let alone putting little baby girls on the river to die. 


Sheena Yap Chan: Yeah. I mean, when you look at the cost of living, they don’t make as much as like here in North America so, of course, it’s not easier. And then back in the day, if a family had to choose between a son and a daughter to go to school, they would choose the son over the daughter because it’s all about the male carrying the family name, the male being higher than the woman. And so, it’s just history dating back to history where men were preferred over women. And it’s like that’s the reason why they want multiple wives and concubines. It’s just greater chances of a man having a son. That was it, right? There’s nothing else to it. I remember like my grandma, the highest level of school she was able to go to was grade 6. And then after that, she had to leave school to take care of her siblings. And my grandma had 11 siblings. 


Hilary Hendershott: Oh, my goodness. 


Sheena Yap Chan: Yeah. We’re a big family. If you see like our family Christmas photo, it’s like you’re trying to search for me, it’s like a Where’s Waldo moment. 


Hilary Hendershott: It’s like the high school graduating class. 


Sheena Yap Chan: Yeah. 


Hilary Hendershott: Okay. So, here you are, you’re an Asian woman raised in the Philippines, growing up in Toronto, subject to, and sort of fighting off all these stereotypes. How did or was there a moment when you decided to take this on that this was going to be your cause? Did you have kind of a turnaround moment? 


Sheena Yap Chan: I mean, I’ve always wanted to do something to help women. And then as I kept thinking about it, I really wanted something that helped Asian women because of just my own experiences. I mean, it was one of the reasons why I started my podcast. You know, back then in 2015, I was looking for resources that really cater to Asian women’s confidence because I was dealing with my own. I couldn’t find any. There was nothing out there. And so, part of me thought something was wrong with me or, yes, I just thought it was crazy. I was the only one dealing with this, not realizing that everyone was dealing with this. It’s just nobody ever talked about it. And so, I started the podcast, didn’t really know what I was doing. In fact, like I just mentioned, the name of my podcast was wrong to begin with so I thought I was already a failure from the beginning. And even in the beginning, I just started interviewing every woman, right? Not just Asian women, every woman, because I still wasn’t really clear.


And I think sometimes as women, we think we need to perfect every single thing, not realizing you can always change the course at any given moment. So, as I was doing the podcast, I realize I think I’m ready now to just reach out to Asian women and really create a platform for it. And so, I did, right? And it was okay like nobody’s going to notice it. And if they do, who cares? It’s not the end of the world. At least you’re out there doing something, creating something, creating a platform. And as women, we face such a huge confidence gap over men, right? If a man and a woman went out to get a promotion, as a woman, we’re 110% ready. We know everything and everything from the back of our hand, yet there’s still something that holds us back, which is really how we perceive ourselves. We think we’re not good enough. We think there’s someone better out there. While a man is probably about 30% ready and he’ll go out there and just do it regardless if he gets a yes or no. For him, it’s like, “I went for it. I know my result. I can move on to the next step.” And imagine if women did that, how much results we could get? How much more action we can take? 


Hilary Hendershott: I talk about this all the time is that women don’t get as much but they also struggle to ask. 


Sheena Yap Chan: Yeah. And I mean, I always tell people, “Don’t be afraid to ask. The worst they could say is no.” I mean, I get rejected all the time. 


Hilary Hendershott: Oh sure, if you’re LinkedIn messaging people to ask them to buy a copy of the book, I imagine you get rejected more than you get accepted, just by the nature of the request. But how cool is it when people do it? 


Sheena Yap Chan: Yeah. And you’d be surprised, like where it could lead to, right? Just being out there promoting yourself, being your biggest cheerleader. I know as women we’re afraid to promote ourselves out there because of the double standards we go through. But if you have a product and a service that you know is going to change the world, go out there and share it. You’d be surprised how many women constantly ask me, like, “How do you know if you’re doing too much self-promotion?” I’m like, “I don’t know. I mean, are you sick of looking at your face? Because if not, then you’re not doing enough.” That’s how I see it. And people don’t understand that. Back in the day, pre-social media, a person needs to see the product at least seven times before they make a buying decision.


Hilary Hendershott: That’s right.


Sheena Yap Chan: Well, now with LinkedIn, TikTok, and now even Threads and Twitter, it’s going to take at least over 25 or 26 times before a person makes a buying decision. So, promoting it just once is not going to cut it. Like, you have to do things differently. Be okay to promote yourself, be okay to showcase it out there, be okay to be on podcasts, and on stages and on different forms of media to share your message, your story, your product, your service, because you know it’s going to help somebody out there. Guys don’t care. They’ll be in your face. They’ll be in your face telling you, “Hey, buy my stuff. Hey, buy my stuff. Hey, I can help you.” And as women, if we did that, guess who shames us the most? Women, right? Unfortunately.


Hilary Hendershott: Correct.


Sheena Yap Chan: And this is probably a topic that’s never talked about but I know that part of the reason why we don’t advance as fast is because as women, we can be catty. And I dealt with it in the office, I’ve dealt with it even in this journey and realizing we just need to find ways to get out of that and learn to collaborate because it’s through collaboration where we can create actual change and not trying to be the superwomen and shaming other people that we’re not taking care of our kids or going out to work. Everyone’s in their own stage. 


Hilary Hendershott: I feel like that catty energy is just sort of misogyny and patriarchy that we’re perpetrating on each other. It’s so heinous. And so, you’re now one of the only resources for Asian women’s confidence. So, what’s been the reaction from the community of Asian women? 


Sheena Yap Chan: I mean it’s not just Asian women. Actually, I’ve gotten a lot of great feedback from every person regardless of whether they’re Asian or not, how they love the book, how it could relate to them. And I was really grateful for that because for the longest time, I would always get questioned like, “Do you think this can relate to people who aren’t Asian?” And at first, I was like, yeah, I mean, everyone goes through trauma, everyone goes through confidence issues but I kept getting it a lot and I was like, “Am I like stupid? I don’t know how to relate to other people?” I don’t know, right? But you would never ask like Jack Canfield or Tony Robbins the same question. So, why am I getting constantly asked about this? It’s just it’s insane, it’s crazy that this still happens. But it’s been a really great journey just to see the people, readers telling me that they’re having the hard conversations with their kids. Because having those hard conversations isn’t easy, right? If it was easy, everybody would be doing it, being able to walk through their own traumas.


And of course, I’m not a licensed mental health therapist so, of course, this book is based on my observations, research, my own experiences. I mean, I tell people, if you need a mental health therapist, go out there and search for one because I’m not a licensed mental health therapist but I’ve been through enough to understand like these are some of the commonalities. These are things we go through. Here’s some of the research that’s backed by it, and it’s all packaged into this book. So, yeah, I’ve just been grateful for the whole experience. And I just love when people take selfies with a book or share out they have the book in their hands. Like this?


Hilary Hendershott: I love the shameless, not self-promotion but I love it. I love it. I feel like you embody so much of what I talk about, which is like, no one’s going to advocate for you except you, right? Sit back like the community is going to isolate you as their hero and then exalt you up on a pedestal. No, that’s not how it goes, you know? And so, you have to really be willing to step out and promote for yourself. And so, thank you for doing that. One of the things you say in the book that I thought was very interesting is about doing away with the word minority. Talk about that. 


Sheena Yap Chan: Yeah. I mean, for the longest time we’ve been seen as a minority, any person of color. And I was like, “Why are we called that?” Like, I don’t understand when you think about it, there’s nothing minor about us, right? 


Hilary Hendershott: Right. 


Sheena Yap Chan: So, why do we keep using this word? Like, can’t we just use another word like underrepresented or just like we’re all people in the end?


Hilary Hendershott: How about just Asian, you know? 


Sheena Yap Chan: We’re all humans, right? 


Hilary Hendershott: Right. 


Sheena Yap Chan: We need to get away from language that really just brings people down to another level.


Hilary Hendershott: Separates.


Sheena Yap Chan: Yeah. And it’s language like this that really hurts us, right? And so, for me, I don’t like that word at all. I don’t like being called that. I would never call other people that. And so, I just replace it with underrepresented. That’s it. Because sometimes you just sit back and you wonder like why do we use this? Like, what’s the meaning behind it? And then when you think, do I really want to be called that? No, not really. So, we need to stop using this word. So, that’s just me. I mean, everyone’s different, of course, but like when you sometimes sit down and just dig deep, you’re like thinking, “Why?” And then you get curious and then you start like just thinking to yourself and thinking like we could do something better. So, yeah. 


Hilary Hendershott: You know, as a white woman in Silicon Valley, I often wonder what side of that line I’m supposed to straddle because I’m supposed to be humble because of my privilege but also when I look around me, I’m actually the ethnic minority. There are more Asian and Indian people here than white people, honestly, because Silicon Valley engineers. And so, I never know how to grapple with that term. Like, maybe not here. So, thank you for calling that out. And so, I will just use the term underrepresented. So, what do you think as you interviewed people and clearly your book really attempts to synthesize the core of what it takes to be and build confidence, I know it’s a super big question if you want to take it apart in sections but clearly that’s what the book is about. And so, what’s your core message to women and what action steps would you recommend? 


Sheena Yap Chan: I think for women especially, the biggest thing is being okay to ask for help. We’re always seen as the superwoman who does it all but that doesn’t help us. I mean, it’s exhausting trying to do everything yourself. I mean, especially if you’re a mother like you’re doing like ten jobs plus your business or your work and then taking care of your other family members. So, we have to learn to seek help from one another. In fact, seeking help was the biggest boost of confidence for me because I realized I didn’t have to do everything myself. I realize there’s other people who are better at what they do than I would, and so I would just do that. Having support is so important. As women, we want that support but we’re so afraid to ask for that support. So, it would be okay to join a women’s group, hire a coach, hire a mental health therapist. You don’t have to do everything alone, even reading a book or listening to a podcast. Start small. You don’t have to make big leaps to create big results. I say it’s always the small, actionable daily steps is what yield the big results. Because for me, doing the big like trying to make the leap actually brought my confidence down because I wasn’t able to hit that goal. And so, I felt bad and I thought, “Oh man, I’m the biggest loser. I need to like not do this.” So, taking small steps is really important.


Hilary Hendershott: The biggest loser. 


Sheena Yap Chan: Yeah. So, like a lot of people want to write a book, right? They want to write a book. They think it’s the most daunting thing in the world. I mean, if you broke it up in sections, it’s not that bad. Like, say you wanted to write a page a day and you did that for 100 days straight. You just wrote a book. 


Hilary Hendershott: Then all you have to do is sell it. 


Sheena Yap Chan: Yeah. Put it together or hire someone to put it together. You know, hire a copy editor or a proofreader, and then you’re done. I know it’s easier said than done but, I mean, think about it. One page a day for 100 days straight, you’ve got a full book right there. Or let’s say you need to write 50,000 words divided by 100, that’s like what, 500 words a day? If you wrote 500 words a day, you got a 50,000-word book. You got a book. 


Hilary Hendershott: So, the easiest way to eat an elephant is one bite at a time, that old saying?


Sheena Yap Chan: Yeah. You know, Rome wasn’t built in a day. You know, everything starts with your first step. So, just take it one step at a time and you’d be surprised how much you can accomplish. 


Hilary Hendershott: Amazing. Well, Sheena, I don’t know if you know the power of your voice but you’re such a powerhouse too. I mean, I don’t know if people reflect that to you often enough. You have such clarity and such great thinking. I mean, just so many ideas. In this interview, you basically covered most of the questions I wanted to ask you in the first 6 minutes. So, then I had to go back and pull it apart. But I thoroughly, thoroughly enjoyed the book and just want to thank you for being here. We will make copies of this book available to folks who are listening. For those of you who are listening, we’ll put a link underneath the show. Go buy the book today, buy it for your female friends, buy it for your Asian female friends. And let’s make sure that Sheena’s work gets spread around the community. Sheena, anything you want to say before we close up today? 


Sheena Yap Chan: I just want to say thank you again for having me. It was such a fun conversation. Appreciate your support. You know, it just means a lot. And I know for everyone out there who’s been supporting me along the way, I just want to say thank you because without you, I wouldn’t be here today. 


Hilary Hendershott: Yeah. Amazing. Thank you so much. 




Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.


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