We Wear The Masks
We Wear The Masks, Hosted by Michelle Singh
We Wear The Masks
Breaking Through the Mask of Identity An Uncomfortable Duality: My Indian Family and My Blackness
The moments that shape us are not always loud. Sometimes it’s a quiet look in a crowded room, a careless joke in the back of a Jeep, or the way a family talks about people who look like you.
Michelle opens up about growing up half Black and half Indian in Jamaica—immersed in Indian culture, carrying the family name, and still absorbing messages that her features and Blackness made her lesser. That gap between outward pride and inner doubt became the fuel for relentless performance: the grades, the scholarships, the accolades. Impressive on paper, exhausting in the soul.
We dig into how identity confusion hides beneath success and how early narratives become the script behind our masks. Michelle traces her first memories about her body—big lips, broad nose, thick thighs—and examines how those impressions hardened into insecurity. She names the internalized bias she heard as a child and shows how it bled into adult spaces, leading to overcompensation and perfectionism.
Instead of staying stuck in shame, she offers a practical identity audit: track the earliest feelings about yourself, identify the words you heard around your identity, and notice where you still shrink or strive for conditional acceptance.
This conversation is for anyone who has ever felt like an outsider in their own life while trying to meet someone else’s standard. We talk about turning survival masks into mirrors, integrating the parts of your story that hurt, and choosing rooms that welcome your full self. By reframing painful memories and honoring both lessons and blessings, you can shift from proving your worth to living from it.
Subscribe, share with a friend who needs it, and leave a review to help more women unmask the stories beneath their success.
Message from Dr. Michelle Chanda Singh
I’m Dr. Michelle Chanda Singh, born in Jamaica, raised in a traditional Indian household where I never quite fit the mold. For over 40 years, I chased every expectation family, culture, society, collecting degrees, titles, and accolades. I had purpose and security, yet something was missing. I was achieving, not thriving.
As an award-winning global educator, Michelle finally realized that fulfillment doesn’t come from perfection, it comes from alignment. Today, she help high-achieving, culturally diverse women educators recognize how disengagement quietly steals their joy. Together, we break those patterns so you can redefine success on your own terms and lead with purpose, from fulfillment, not sacrifice.
That’s why I created this podcast, to tell my story honestly and unfiltered. The truths I buried, the patterns I tolerated, the lessons that set me free. But this isn’t just about me, it’s about you. Through these stories, you’ll see reflections of your own journey and uncover what’s been holding you back.
Join me as I disrupts disengagement, break the cycle of busyness, and learn to lead and live from a place of true joy and wholeness. It’s time to reclaim your power and thrive, not just survive.
Welcome to We Wear the Masks. This is a podcast for high-achieving women who check all the boxes, got all of the degrees and the accolades, and you have it all together, but you still feel empty and disconnected inside. I am Michelle Singh, and I've been there and I'm still there in some cases. So I created this space to tell my story, all of the truths that has trapped me, the secrets that have held me captive, and the people and situations that I endured for far too long. So, as you listen, I invite you to uncover your lessons and your blessings from my story. I invite you to reflect on your own journey because we have to break this cycle of disengagement and disconnect and unmask what is holding you back so that you can find your fulfillment and your joy. Let's dive in. Half black, half Indian, born in Jamaica, and I grew up with my Indian side of the family, my mom's side of the family. I even carried the Indian last name. My father was out of the picture for the majority of my life growing up in Jamaica. So I didn't get to be around too many of the family members who were black. So I spent a lot of time. I remember specific memories in Jamaica going to parties and Indian sessions with my grandmother. I remember my grandmother teaching me to dance to Indian music. I remember listening to a lot of Indian music and just being in that culture. I remember my grandmother teaching me how to make roti and dal roti. So I have those fond memories, but I also have feelings of insecurity and feelings of not belonging that comes from those experiences as well. So in my family, my brother and I at the time were really the only black kids, black people, everybody in the family was full Indian. And we didn't really know what that meant. We just knew that we were different. I knew that I was different. I was always told that I had these big lips and this broad nose and the this bushy hair and these, you know, fat thighs. My my shape was different from the people that I saw every day. Um my physical appearance was different from everybody. I was bigger, big, big boned than the tiny Indian people in my family. And although I didn't know it then, it created uh this this these insecurities in me and that that I, you know, wasn't pretty enough or wasn't especially wasn't skinny enough because Lord knows I've struggled with my weight my almost my entire life, right? The times where I was skinny, I wished I was uh I wished I was skinnier. And the times where um, you know, I of course gained weight after childbirth and all those things, wishing I was skinnier. I wished I was the size I was back when I actually thought that I needed to be skinnier because I would actually be skinny, but that's another story. Um, but yeah, I was very self-conscious and didn't even know it until diving, you know, diving into what were what were the feelings and what were the experiences from my past that really impacted how I navigated my entire life. And that feeling of insecurity and not feeling like I belonged was definitely one of them. I remember I had an uncle, a great uncle, who I have this, this memory is so vivid in my mind. We were in the back of um, we were in the back of a Jeep, and I don't remember where we were going, but I remember him looking at me and him telling me, I would like you more if you were full Indian. Now, of course, you know, he laughed at, he laughed at what he said, and I didn't really know how to respond to it. So I really didn't say anything. And I'm like probably about six, seven years old at the time. So how could I respond to that? I don't know what how to respond to that when you have this older, um, you know, elder in the family telling you something like that. But all I know is I remember it. All these years later, I remember it. So imagine what that does to you subconsciously when you're told that you're not good enough. Right? You're basically not good enough how you are. And so I also remember, you know, being in those settings that I talked about earlier, where I would go to these different Indian parties and sessions with my grandmother. I remember feeling very uncomfortable. And I remember feeling judged a lot. And a lot of the times I was likely one of the only mixed kids or black kids there. And I wondered, you know, I wondered why did I feel uncomfortable? Why did I feel some type of way when I was there in those settings with all those Indian people? And it was because subconsciously, I felt like those people were actually looking down on me. Now, how did I even get there? How did I get to the conclusion that they were looking down on me? Well, as I began to dig deeper, I realized that the people who I saw around me that were black, these were people that helped to take care of me and my brother. These were people who were help that we call helpers. They helped in our home, they cooked. These were, you know, people like the barmaids that were in the bar that we owned. These are people, you know, people on the the street who came in and did stuff in the yards. I mean, these were the black people that we saw. And all I remember are these people being called thiefs and liars by certain people in my family, particularly my grandmother. And as a child, if you grow up hearing that, being assigned to the people that you look like the most, what do you think about yourself? So as I dig deep into my story, I realize that my sense of belonging or lack thereof and my insecurities, that's the root of it. It comes from me being in a family that maybe they knew, maybe they didn't. I don't know, but culturally, um in my family, they looked down on black people. Now, maybe not all the people in my family did, obviously, not all of them, because all of my cousins, pretty much for the most part, are mixed, just like me. So none of my grandparents' children, all the children that they had, actually have full Indian kids. They all ended up with black or Hispanic or even white. There's no full Indian grandkids in my generation or even the generation after me. So my Jamaican, my Indian family, the family whose name I still bear, uh, had a lot to do with the beginning part of how I started to view myself as a as a as a girl, as as a as a person, as a human being. And a lot of that unfortunately is negative because that's where that identity crisis that I experienced growing up even further uh you know stemmed from me trying to find the right spaces and the right people to fit into, and I couldn't, and and trying to fit into boxes and trying to um, you know, wearing different masks to just fit in because I longed for that sense of belonging. The root of all that came from what I felt growing up that was subconsciously hidden, that just impacted the way that I navigated life. Instead of being, just being, I was trying to fit into someone else's boxes or expectation of who I should be. Being confused about your identity, it really is a problem where you don't truly know who you are, you don't know where you belong. You are trying to belong in spaces and places that don't feel right and don't sit right with you, but you you are still there. You are still there because you are trying to fit into a standard or your your your culture, culture or family or society is telling you that that's where you should be. So the not not truly understanding your identity can really affect how you live your life. And so the woman who feels like she is lost, like she just does not fit where she is, that she is not fulfilled in what she's doing. I want to encourage you to think about what is your what makes you you, what is your identity, what makes you you? How do you feel about being from the place that you're from, in the family you're from? What makes you you and how does it make you feel? Whether it's good or bad, you have to confront it, you have to face it, you have to accept it, you have to forgive yourself for it. Whatever that looks like for you, you have to just be able to embrace it and either move from it or allow it to just be part of who you are. So for me, I navigated this identity thing until just recently, uh, to be quite honest, because I didn't know I had an identity problem. I didn't know I was confused about my identity. I was very proud to be uh in my family and and and proud, I am super proud to be a Jamaican person, okay? And so I never thought that I would have an identity problem because I know where I'm from. I'm from Jamaica, right? I know what my family looks like, I know who my family is. I wear my last name very proudly. Um, but my issue, my confusion about identity, it has nothing to do with those things. It has nothing to do with where, you know, me being from where I'm from, um, and me having this last name. It has to do with how I felt with the people who I grew up with, right? So having an uncle tell me that the that that I'm basically not good enough being a half Indian and half black person, going to family events where they're all the Indian people, and I feel judged and looked down upon, that is part of what formed my identity. And unfortunately, it formed an identity that was rooted in being self-conscious and being not feeling value in the blackness that I am, and so really understanding the feelings behind the things is what helped me to face the identity issues that I have lived with my entire life. So, like me, if you feel like you may be trying to figure out is identity really a problem for me? Is it am I really confused about my identity? How do I even know if I'm confused about my identity? You have to really think about the first memories that you have that relate to how you felt about yourself. Because for me, my first memories of how I felt about myself was my bushy hair, my big lips, which by the way are of high value now. So I love my plump lips now, you know, my broad nose and my thick thighs, right? Those were things that made me super self-conscious. I was not confident about those things at all. And those were some of the first memories that I have of really looking at myself and not loving myself, right? So, what are your feelings of yourself and what are the memories that those feelings stem from? That's where you begin your journey to your identity and figuring out what really is your identity in doing the hard work and retrospection and reflection and going deep into my past and my feelings, I've come to realize that when I don't feel safe, when I feel like I'm not good enough, when I try to fit in to groups or spaces or places because I want to be accepted, I know that those feelings come from what I experienced with my confusion about my identity. When my uncle told me that he would like me better if I was full Indian, I look back at that, and there's there's no difference between that and someone saying that, oh, you'd be better if you were white. Literally, if you were to take, you know, take me, the Jamaican person in Jamaica and put me in America. That's what I was being told ultimately. So imagine, imagine what that does to the the mind and the subconscious of this little six, seven-year-old girl now her entire life thinking she's not good enough because of who she really is, like who she looks like, and something that she cannot change about herself when I hear in my head liars and thieves being associated with people who are black and look like me. What does that tell me about me, the black girl? What does that tell me about the way that the people who are in my family that's supposed to love me no matter what actually really truly feel about me because I am black? I am a black girl in an Indian family. So I spent my entire life trying to be better and outdo everybody. Got it, getting all the degrees, being on top of my class while I was in school, getting all the awards, first in the in my family to go to college on scholarship. I mean, when you talk about overcompensating, you'd see my picture in the dictionary. But I did all of those things because I was trying to be better than the person I thought the people in my family saw me as. And that's the identity. That's the problem with not being clear and being confused about your identity. So you have to do the work, you have to figure out what those things are that happened to you early in your life, good or bad, because it could have been good and you are very confident and proud of who you are. But it could also be very detrimental and affect you in the way that it affected me. And so you have to find those pieces and put those things together and make those part of your story so that you can understand the real you, so that you can live a life that fulfills the real you. Thank you for diving deep in my story with me. Thank you for listening to We Wear the Masks and for walking with me through my story. Know that this podcast is more than just a chronicle of my life. It really is a mirror for yours, and it reflects the masks that you wear, that I wear, that we all wear, and those truths, whether or not we like them, that are hidden beneath those masks. So I hope it sparked a reflection for you about your own journey, those lessons and those blessings that are part of your experiences, as well as the masks that you are ready to remove. I would love to stay connected with you on your journey. Visit me at immichellesing.com or you can reach me on my social media platforms. And finally, if this episode resonated with you, please subscribe, leave a review, and share it with someone you know who needs to hear it because I know you know someone just like you. And remember that this journey to unmasking and uncovering your true self is ongoing. So keep pushing and moving toward that fulfillment that you have worked your entire life for because you deserve it.