We Wear The Masks
We Wear The Masks, Hosted by Michelle Singh
We Wear The Masks
Stripping Away the Mask of Expectation Balancing Dreams and Expectations While Pregnant in College
The world loves a tidy story: first-gen student, full scholarship, senior year, future secured. Then the plot twists, pregnancy upends the script, and the “golden child” glow collides with cultural, family, and personal expectations. Michelle opens the door to the moment everything changed and the long stretch after, where shame tried to set the tempo and achievement became a mask that looked like success but felt like distance.
We walk through the rationalizations, the late-night plans, and the sprint to over perform, internships, multiple degrees, classroom excellence, community accolades. On paper, it’s a climb. In the heart, it’s a numb march away from presence.
The story shifts when “fixing a failure” gives way to receiving a blessing: a daughter who becomes a source of joy, a bridge back to family, and the center of a bond with a grandfather whose everyday love—rides to appointments, gentle watchfulness, reframes what support truly looks like. That tenderness lives alongside vigilance, as Michelle names the boundaries required when returning to a home with unresolved harm. It’s complicated, honest, and deeply human.
The core question emerges: whose standard are you living by? We explore the danger of inherited rules that define worth by sequence and optics, and the freedom of redefining success as alignment, choosing presence over performance, values over validation, and self-trust over scripted milestones. Michelle shares regrets about moments missed and the practice of repair: more affection now, slower attention, fewer masks.
If you’ve ever felt like you did life “out of order,” this conversation offers language, perspective, and a path to set your own order.
If the story sparks reflection, subscribe, share it with someone who needs it, and leave a review to help others find the show. Then tell us: what standard are you ready to rewrite?
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 it's senior year of college. I made it the senior year, got to college on a full scholarship. First in my family to go off to college. So I'm so close to that career path and you know, bringing it home and being the golden child, I guess you could say, in the family, right? The one, the one kid who went off to school and and is is gonna be the example and the one that they talk about and they they brag about to everybody else. So that that that's how I felt um going to school, going to college and getting to senior year. I was the golden child, right? And so senior year also shook me up a bit because I found out that I was pregnant. Now it was this and it was senior year, so practically I was finished with all my coursework and everything like that. And at least that's what I told myself in my head. I'm like, oh yeah, I'm good. I'm still gonna, you know, graduate and I'm I'm gonna be able to do what I need to do. And and those were the thoughts that were going through my head when I found out I was pregnant. I just wanted to make sure that being pregnant did not thwart my plans of success or of what family culture and society showed me that success was. Those expectations that were ingrained in me of what success looks like that I was trying to meet. That's what I see now in retrospect, right? But I didn't know that back then. And so I'm trying to reason with myself when I found out that I was pregnant, that it was gonna be okay. And that, oh yes, we, you know, my my me and my husband at the time, we were like, okay, we're seniors, you know, we could get a place. We we'll be good. We'll but you know, we're gonna be working, we'll be, we'll be fine. In our minds, we're trying to rationalize that this is gonna be okay. And then the true feelings that were deep, deep down inside was there is no way in hell that I'm gonna call these people in my family and tell them I'm pregnant because they sent me off and I'm supposed to bring back the the you know the golden trophy, right? At least in my mind, that's what I'm thinking. And instead, I'm coming home pregnant. That's the worst that could happen. So I'm not coming home with a degree, but I'm coming home with a baby, and so I thought of myself as a complete failure, complete failure, and I held on to that feeling of failure for such a long time without actually seeing that being pregnant and having my daughter was such a blessing. I tried to fix the failure of getting pregnant in college instead of embracing the moments and the memories of the blessing that is my daughter. And when I say I tried to fix the failure, I started to do everything that I thought I was supposed to do to continue to be successful. So I did the internship, I got the degree, I went and got a master's degree while working full-time as a teacher, got the career, got another master's degree, got another degree, you know, became earned all these accolades, teacher of the year, rookie teacher of the year, all of these wins. And I just stacked up on all of these things in my career and also in the community, because I did lots of things in the community too, because I was trying to fix what I thought was a failure and what I should have appreciated as being a blessing. I remember making the phone call home to let my family know that I was pregnant. Now, this came about because initially I wanted and we had decided that, and when I say we, that was me and my um husband, not my husband at the time, but my husband now, we had decided that we were gonna stay where we were in the city that we were in school, and you know, work it out there. But then things changed, plans changed when other people started to get involved. And I'll talk more about that in another episode, but that is ultimately what happened. And so I felt like I needed to fix things myself because the plans that I had and the person I was somewhat depending on, or felt like I was in it with you know, with him was not what was gonna happen. And so I had no choice but to call home and tell them that I was pregnant. And so when I made that phone call, I remember asking to speak to my aunt because I was not gonna tell my mother. And so I when I did tell my aunt, my aunt was very like she she was very nurturing, but this aunt, particular aunt, has that nurturing nature. Uh, and she she was excited and she reminded me that, hey, you know, you're you're you're 22 and you almost finished with school, and you know, she she made it feel right. She she tried to make it feel right, but her her position um was not necessarily the same position as everybody else, right? And so I did end up going back home to uh have my daughter and ultimately to to live after after um graduating school. And I will say that having my daughter at the time that I had her was nothing but God's design, obviously. I believe that wholeheartedly, because had it been another time, I would not have gone back home. When I left for college, I left for good. I was not going back to Miami, Florida at all. In fact, that same senior year of college, I was um slated to do an internship in England the following semester, which would have been the January, and Chanda was born the February, so I couldn't I couldn't do the internship because obviously I was having Chanda. And for me, I had this plan of how things was gonna work out and happen. Um and I had no intention at all of going back home at all. I wanted to get the hell out of there, and I did when I went to college, and I just wanted to keep it moving. But I ended up back home when I got pregnant with Shanda. And so uh once I finished that uh semester, that fall semester, I did go back home and had Shanda in February. So I went back home in December and had her in February. And one of the things that I did that I do regret is when I left Tallahassee because I felt like a failure and I did feel the shame because you know, I'm a college kid getting pregnant. Like I felt shame about that. I really did. And although the, you know, the friends that we had rallied around us, they threw us baby showers, they, you know, they really loved on us. I didn't embrace the love because I was so focused on the failure. And so when I left school, I pretty much ghosted everybody. I disconnected myself and disengaged from everything that was, except for obviously my relationship with uh my now husband. But I didn't call nobody, I ain't talked to nobody. Uh at that time, um, MySpace was just now coming out. And I may I created a MySpace profile and started to add little, you know, people here and there, but I didn't want anybody to know what was happening to me or even where I was because I felt so ashamed. I felt like such a failure. And I just held on to those feelings because I did not meet society's expectations of where my life should have gone, the cultural expectations of where my life should have gone, and the family expectations of where my life should have gone. I didn't, I didn't do the things in the order that it was supposed to be done. And I beat myself up for that and felt shame and didn't forgive myself for that for a very long time. And as a result, I isolated myself from people who loved me, from friends who loved me and who were there for me. I isolated myself from them. And when I did end up having Shanda, I started to see how much of a joy she was and is as a kid, and how she was able to bring family together. And so I said I didn't realize how important um how important me being, you know, getting pregnant at the time was until looking at it from this perspective, because having Shanda at that time brought me back to Miami. It brought me back to spend more time with my grandfather. It brought me, and and and that's really important for me because my grandfather passed away a couple of years ago. And when I tell you Shanda was the apple of his eye, Shanda was the apple of his eye. There is not one thing that he would, he would have not done for Shanda, because he raised Shanda from the time she was in my belly to the time that she turned um, well, almost 18 when he passed away right before she turned 18. But when I came home from college and I was pregnant, my grandfather didn't want me to drive anywhere. He drove me to all of my doctors' appointments and to the store because he wanted, he was concerned about Shanda in my belly. And so he was that kind of loving um, you know, to her before she even got here. So you can imagine the love that he showed when she got here. And I really believe that uh having Shanda at the time that I did and having her where I did, although I was very um on edge, I will say, because I was coming back into the family where certain people lived in that home, like the person who molested me. Okay. And so I was very on edge and I was very guarded, and I was so protective. Um, but I am glad that she was able to be a part and see the love in the family that I just never saw, to be quite honest. I didn't see that. I didn't see the the coming together in the loving way that they did when Shanda was around. Like the joy that she had as a as a kid, and she it's like she brought things out, and I was glad that she was able to to to to be a part of that and and to do that, and and I saw the family in a different light. And so me getting pregnant in college did not check any of the boxes on my list, but it was definitely something that I am glad and I am thankful to God and I am blessed with the result because Shanda is an incredible human being. She's 20 now, but she's incredible, and there's no other word but proud and and and and and glad and happy that she is a part of this world. And so I say all of that because even the thing that you might think is your biggest failure can be the biggest blessing if you just shift your perspective on it. I was so focused on fixing the failure that I missed out on moments with Shanda where I could have been more affectionate and I could have been more loving instead of so numb trying to get the degrees and do all the things that was right to fix this thing that I screwed up, right? And had I just embraced, I feel like I would have been a better mom to her. And if you are trying to fix something that you think you did wrong, reevaluate it. Did you really do something wrong? Or are you just trying to live up to a standard that you were told is the standard for you to live up to by society, by your culture, by your family? Is that your standard of success? What is your standard of success? Because my standard of success now has no alignment with what cultural or society standards of success is. I don't have a nine-to-five job, and that's definitely not a standard of success. And so there are other things that I'm putting myself first. I'm selfish for me. That is definitely not on society's standard of success or my cultural standards of success or my family's standard of success. So reevaluate what your standards of success look like so that you can be in the moment and embrace the moment and love the thing that you're supposed to love the right way. 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 iammishellesing.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.