We Wear The Masks
We Wear The Masks, Hosted by Michelle Singh
We Wear The Masks
Confronting the Mask of Compromise The Truths in Marriage I Did Not Want to Admit Existed
What happens when the checklist is complete but your heart goes quiet?
Michelle tells a story many high-achieving women will recognize: a college romance that felt safe and whole, a pregnancy that drew in outside voices, and a split-second of silence that echoed like a choice. That moment nudged her into survival mode, degrees, accolades, relentless productivity and a life that looked perfect while feeling numb.
We walk through the years where achievement became armor: early alarms, packed classrooms, validation on repeat, and a home that ran on logistics instead of presence. Michelle names the trade-offs with care, not blame. She chose the image of a two-parent household and the comfort of social approval over her own happiness, not because love was missing, but because numbness made it hard to be honest. Gratitude turned into a script that kept the truth offstage: if you have a career, a house, and a family, how dare you want more?
The turning point is both tender and practical. With time, support, and hard conversations, she learned to see her patterns, guarding, over-functioning, letting silence decide and to rebuild trust from the inside out. Intuition becomes the throughline: a quiet guide she once ignored, now a daily compass.
If you’ve ever felt “fine” but frozen, you’ll hear steps you can try today: notice where your energy drains, name one real feeling, keep one honest boundary, and let small truths shift your choices.
This is a story about reclaiming joy without abandoning responsibility, about loving your people while also choosing yourself, and about how curiosity can thaw years of numbness. Press play for a grounded, compassionate take on relationships, identity, and the courage to feel again.
If it resonates, follow the show, leave a review, and share it with a friend who needs a gentle nudge toward their own voice.
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. So when I was a sophomore in college, I met this guy, and he was a cutie pie, and he was super tall as well as very outspoken. I immediately thought, oh yeah, he checks all the boxes. And so we became friends, we talked, we we got to know each other, we fell in love, we were we were together the the entire you know time from we from the time we met. And one of the biggest things for me was that that he that he met. One of the biggest things for me that he met was he made me feel safe. And he also made me feel loved and he also made me feel accepted. And those were things that I did not have growing up, I would say, because of my confusion with my identity, because of the things that I experienced with the result of sharing about my sexual abuse, and I felt those things that in in what we had developed, and I mean I went all in with this relationship, and so if you listen to another episode, you'll hear about me getting pregnant with our daughter senior year of college. But the relationship that we had before getting pregnant was a dream for me. It really was. You know, we spent all the time together. I mean, it was magic. And then when I did get pregnant with our daughter, things started to change, but it started to change only when other people started inserting themselves in it. And so we were both seniors in college. I was 22. Uh, so you know, it this wasn't like a teenage pregnancy or anything like that, where we were too young to make decisions. I mean, we were in our 20s, we were grown. And so things that we had planned to do, like staying where we were, getting, you know, getting a place together and having Shanda there and being together there, these were things that we had talked about and we had decided that we were gonna do. And all of that changed when his parents got involved. And all I remember is I remember having sit uh sit-down with his parents, and I remember them saying that I should go back home and he can finish up school, you know, up there. Now, granted, I was pretty much done with my coursework. I didn't need to still be in that town. I could have gone home because I was practically finished, but he still needed to take classes. But the fact that that decision was made by them and he accepted it. And when I say he accepted it, he didn't say yes, let's do it. He didn't say anything. And him not saying anything meant that he accepted it. And so when that happened, I guess a survival instinct kicked in with me because now I was taken back to this feeling of my family didn't choose me when I told them about what my uncle did. And so now I'm experiencing, you know, this uh life-changing event, and this person that I love and felt so safe with didn't choose me either. He chose what his parents told him to do, and he chose them over me. And so that put me in survival mode. I don't know how else to say it, but I got my guards up and I got my independence up, I guess you could say, because I was like, okay, that's how we're gonna roll. That's how I'm thinking in my head. Okay, this is what we're gonna do. And so I did the thing that, I mean, the only thing that I could do, which was call home and let them know what was happening, because I at that point had to go home. I was not yet graduated. I did not yet have a full-time job. I only needed a few months before I was able to do those things, which I did in the few months that that um I needed to get it done. But I needed, I wasn't gonna, I was not going to go against what had already been decided because he chose them and not me. Right. And so for me, that did put um it, it did change things for me in the relationship. But because I got into that that mode of survival and that mode of fixing the thing, if you listen to another episode, I talk about fixing the failure. I got into that mode of fixing the failure and proving everybody wrong. I'm gonna show you, I'm gonna show you that I'm not you know a failure, I'm not a this, I'm not a that. And so I just got on this path where it was just winning in the way that I knew how to win. And winning in the way that I knew how to win was intellectually. I was always a smart kid. I was all I always did well in school. And so I could continue to do that. And so I got lots of degrees. I am multiple degreed, right? Got lots of degrees. I, in my role, um, in my job when I became a teacher, I got all the awards and all the accolades, and I overcompensated so much so that it turned into numbness. It turned into burnout, and I didn't even know it because I was in such a like that that that survival um mindset that I was just like, I have to do this, I have to get this done. I cannot be a failure, I cannot let them win. I cannot, I cannot, I cannot, I cannot. And so that's how I lived through that time frame and how I operated and how I also dealt with my husband during that time frame. I was numb, y'all. I really was. I was numb in emotions, I was numb in actions, and uh we lived together. Um, we bought a house, we lived together, but we were not like we were just ships passing through the night. He would go to work, I would get up real early. I taught high school at the time, so I had to be at school at like 7, 7:30, 720. And so I would leave super early. His, you know, in in those beginning years, his job was in a whole nother city, so it was like an hour plus drive. And so he would get home very late. And I would leave super early. And so our our our schedules were off. And so we never really like saw each other, like really, really saw each other. We were just doing the thing that we knew that we had to do to survive and to also not be considered, at least for me, not be considered a failure. That was my biggest thing. I I could not be a failure. And for the people who do think that I'm a failure, I'm gonna show you that I'm not, right? And so one of the the things that I realized that I did was in my numbness, in my desire to meet someone else's standards and not my own, because I didn't have any. I was just going by society, culture, you know, family. I chose all of these things over myself. I never wanted my daughter to not have a two-parent household because I didn't have a two-parent household. I never wanted her to be deprived of having a relationship with her father. And so although I felt numb and although I felt like things were just going through the motions, they there was there was nothing attached, right? We were just doing the thing that we thought was right to do. I chose family, I chose that two-parent household over any kind of happiness. Because truth be told, I really wasn't happy. But I didn't allow myself to believe that I wasn't happy. Like I didn't even know what happiness was supposed to look like. Because how dare I be ungrateful if I got a career and I got a good, you know, I got a house. I got, I got a husband, I got a child. I I have so much to be grateful for and to be thankful for. So how dare I not be, you know, not be happy, right? And so I did choose those things over really and truly being happy. And the reason that now I know that I wasn't happy is because I was operating in numbness. I was not feeling, I was just doing. I was just doing, I did the things. I went up, got dressed, went to work, taught the kids, felt so validated in my role as a teacher, got so much recognition as a teacher, felt so useful in my duties as a teacher. Went to go pick up my daughter, took her to all her activities, came home, did homework, got online, probably was working on another degree, ate, you know, had dinner or something, and went to sleep. By the time I did that, he probably was coming home because he worked, you know, so far and he got home late. And so we did it all over again. And that was life. That was life. And I accepted and I chose that life because I wanted my daughter to not be in a household where she didn't have two parents. And I don't know what kind of impact her seeing or if she even saw any of that had on her. Like I don't know if she could, she's very intuitive, though, by the way, because she she could pick up on things. But I don't know what impact that had on her. Seeing me that way, seeing him that way, just seeing that disconnect that we didn't realize was there. I'm not sure how that may have played a role in her life now, but I what I want her to know is that she doesn't have to choose because society tells her so, or because the family tells her so, or because she thinks that she's doing the right thing by choosing. I want her to choose her happiness over anything else. And I want her to know that she cannot live her life feeling disconnected, and she can't live her life feeling a void and not even realizing that that that void is there because you're just doing the thing and doing the action and not actually feeling the feelings. You gotta feel, and you gotta feel what's right, and you gotta feel what's wrong. And so I know she'll listen to this. I I want her to know that it wasn't that there wasn't any love there. Her dad and I love each other dearly. Um, we've been through so much together. It's been over 22 years. We've both grown in so many different directions apart and together. We are at a place now where I adore him. Um, he is so supportive and truly accepting of my journey and even this phase of my life where I'm diving deeper into the things that are not so nice and not so, you know, not and not so happy. Uh, but it's part of me discovering who I am, rediscovering who I am, so that I can be a better person, a better human being, and have a better human connection with the people that I love. And so he has really truly been one of the greatest, the greatest supporter, him and my daughter in this journey for me. So our relationship has definitely been um a journey as well. And I'm I am honored and happy to say that at the end, here where we, well, at least where we are now, not at the end, but where we are now, it is better than it's better for us than before. Um, because we've, you know, we've gone through our fair share of frustrations and joys as well. And we've had to, we've had to do a lot of things differently, and we've had to put in work for us to even get to this point. Uh, but part of that work is allowing, at least for me, allowing myself to accept and see who I was in the relationship so that I know how to be better for the future of our relationship, right? And so living in that zombie numb land is not where I ever want to go back to. I never want to just do the action to check off the checklist, to have the routine, to be in control because I feel so guarded and I can't trust him because of what he did and because of what he may have subconsciously done. And I never said anything to even make him realize that he did it. Right. And so I don't want to get back there. But in order for me to realize that that's not a place where I want to be again, I had to face it. I had to face that this was me. This was me, you know, um, doing all the things that I thought was aligned with someone else's um, someone else's ideas of what should be done in a marriage or what should be done in a relationship or in a family. And not really thinking about or choosing what I wanted to do. So if you're in a relationship and just you're going through the motions, it's really important for you to take a step back and pay attention to the feelings. It may be hard because you haven't allowed yourself to feel for a long time because you've been so guarded and you've been protecting your feelings from everybody around you. But what I had to do was I had to lean into a strength that I had that was starting to dissipate because I was not feeling the feelings. I had to lean into my intuition. My intuition is one of my strongest strengths, and I was ignoring my spirit when my spirit would tell me something don't feel right. In Jamaica, we have this phrase that's my spirit don't text somebody. And I started to ignore my spirit when it told me not to, you know, be around this kind of energy or this kind of person or in this kind of space, and that really affected me because it was almost like I was lying to myself by ignoring my own intuition. And so I will say that one of the first things that you can do, because listen, as a woman, you got intuition. Lean into your intuition and start to trust it again and start to let it um guide you again. And that's when you can start to feel the feelings and get out of that numbness that you may be experiencing that you don't even know you have. 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 iammichellesing.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.