Peeling Off the Mask of Quick Fixes Why Real Healing Began When I Stopped Applying Quick Fixes

The smile, the accolades, the calendar packed with purpose on paper it looks like fulfillment. 

Michelle opens up about choosing a “safe” career in teaching for the security and steady validation it promised, only to discover that safety without self-connection can turn into a quiet numbness. 

We explore how routine, compliance, and external praise can mask deeper wounds, and why so many high-achieving women mistake being needed for being known.

Together we walk through the hidden costs of autopilot in education: policies that push us to betray our values, the exhaustion of always performing “put together,” and the way unprocessed trauma reappears as overwork, rigidity, or disengagement. Michelle shares the pivotal question that changed everything, "What am I unwilling to feel" and offers a path back to presence through self-inquiry, boundaries, and compassion. 

This is practical, honest talk about how to see students clearly by first seeing ourselves.

We honor the teachers who saw Michelle when home felt unsafe, and we translate their quiet genius into everyday moves: naming strengths precisely, being curious about behavior, and creating classrooms where dignity leads. If you’re an educator, leader, or high achiever who feels strangely empty despite all the gold stars, this conversation is a mirror and a map. 

Subscribe, share with a friend who needs it, and leave a review to help more educators find their way back to connected, values-aligned work.

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.

Transcript

Welcome And Purpose Of The Show

SPEAKER_00 0:05

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 well, you know, put together. And of course, those were things that I valued and things that I wanted to be. I wanted to be well put together, also, right? Because that's what society was telling me was the right thing to be, right? And so I wanted to just be her. I wanted to be a school principal. And then I went to college and found out, oh, you can't be a principal, you got to be a teacher first. And so I chose a major, chose English as my major because I had another teacher who told me, Michelle, you're a good writer. So I was like, okay, let me lean into that a little bit. Since I'm a good writer, let me just go ahead and be uh an English teacher. And so I became a secondary English teacher and I taught high school students English language arts. So I chose to be a teacher. I remember thinking in college, I need to do something that is gonna. I didn't, I didn't quite put these words to it, but this is what I was feeling. I wanted to do something that was safe, that I knew I was gonna get a job right out of college, and I knew I was gonna have a paycheck, and I knew I was gonna have a career that was honorable, a career that was valued, right? And so teaching, and there there had my my mother actually um was a teacher in a preschool, and so I would volunteer with her preschool and her kids all the time. And so I thought that was safe. Being a teacher was safe, being a teacher was security, and I leaned into that and I became a teacher. One of the reasons I became a teacher uh was because of that feeling of safety and security that it promised. A lot of women educators go into teaching without knowing that they chose it because of that sense of safety and security. I'm one of them. But I also chose it because being a teacher gives me value. It validates me. I have students, I have colleagues, administrators, parents, family members who value the work that I do on a daily basis. And for me, in those phases of my life, I needed that validation because I wasn't getting that in any other space. I wasn't getting it in my family, I wasn't getting it at home. And I needed to have that validation. And so going to school every day and teaching the kids and doing the things and earning, you know, the the accolades and and and the the awards and all of those things gave me value that I lacked in a lot of the areas. And so it caused me to just kind of be on this robotic, this robotic um routine that I was in control of, right? So woke up, got my stuff together, went to school, did the teaching thing, did you know, after school stuff, picked up my daughter, went home, got dinner, did homework, did studying, planned for the next day, and did it all over again. And I began to be in this everyday routine that was the same thing over and over and over again. And what I didn't realize is that I was be I was numbing myself. I was numbing myself because I was feeling the validation, I was feeling the appreciation while I was at work, but I wasn't feeling it anywhere else. And I really gave all of my energy into my work. That was the area I could control, but I was numb everywhere else. I wasn't feeling anything at home, I damn sure wasn't feeling anything in my family. And I only allowed myself to feel and feel for the students I taught and the families I served. But how long can you do that for? And it's not gonna be all roses and you know, butterflies in teaching either, because you might end up getting a leader or a legislator that just shakes things up for you. And now what you've been doing has to change, and it causes friction with even your beliefs and your values, and so because you've been operating in validation, being, you know, getting being valued and being seen as the person who checks all the boxes and does all the things, you're not gonna ever think to go against what someone says you're supposed to do, what the legislator says you're supposed to do, no matter how much you are even uh not aligned with it, right? And so you're gonna continue just to do the things day to day, day to day, and that is a form of numbness too. Just doing the motions, doing the actions day to day and not feeling it. And that can get exhausting, that can get overwhelming. And when you're operating in that kind of automated mode, that's not living, that's not being, that's not being a connected teacher, a teacher who is serving the students the way that you know you're supposed to serve them, the way that they deserve. And I'll tell you this if you're if you're a teacher, if you're an educator, and your students, or even if you're an administrator and your teachers are experiencing anything that affects them. So I was that teenage student in a classroom, in several classrooms, who felt rejected by her family after telling her family that she was molested by her uncle and her family swept it under the rug. How are you supposed to see that disengagement if you're not connected to your own self? How do you see that student? As an adult, as a teacher with that same trauma from childhood, that manifested itself in many ways in the teacher me, in the adult me. As a leader, how are you gonna see how that affects the teacher, leader, adult me if you're not connected to your own self as an educational leader? You have to have that human connection to self before you can humanly connect to others. And that's the only way that you can see and serve the the students and the teachers that we are blessed to have in our in our in our hands on a daily basis. And so I leave this with you. As a teacher, as an educator, we want to serve, we want to help, we want to cultivate, we want to create, we want to empower, but we also need to feel appreciated, we also need to feel loved, we also need to feel accepted, we also need to feel valued. And if we cut off those feelings for ourselves because we are not getting them met at home or wherever. And so we are guarded and we try to protect ourselves by becoming numb and disengaged and disconnected, we are never going to be able to see those students and those teachers in the way that they truly need us to see them and serve them. So we have to be connected self first so that we can connect with those that we serve. When I think back on my own educational journey as a student, as that student who experienced the shame and the pain and the traumas, I think back on teachers who really saw me. I remember my sixth-grade teacher, who I still talk to today. She saw me exactly for who I was, the little Caribbean girl. She made me feel smart. She made me feel like I had a place in her classroom. I remember my middle school math teacher, who I still talk to today. She made me feel like the one subject that I thought I was a failure in, I just needed to work a little bit harder than the other subjects. She gave me tools to help me to see my own strength in math. And she still to this day will tell you that I should have been a math teacher and not an English teacher. But teachers like that have confidence. Those women had a level of confidence that you can't have if you don't know yourself. And because they knew themselves, they were able to see me and see past the insecurities and see past my struggles with identity and see me for someone who I didn't even know I was. They saw value in me, they saw beauty in me, they saw intelligence in me, they saw a future in me that I didn't even know I had. And it's something that you can do too, because the students who are sitting in those classrooms that are disengaged themselves, they may not raise their hand or you know, they may do just enough to get by. They may be the ones who talk a lot because they don't get no attention at home. Whatever that, whatever that disengagement looks like, or whatever the behaviors look like, there's something deeper that those children need. And you have to be able to see it, but you cannot begin to see it until you explore your own self, until you dive deeper into your own story, until you look at the things in your past that have impacted you and you begin to accept them. You begin to forgive yourself for the things that uh you need to forgive yourself for, and you begin to put the pieces together so that you can have a better connection with yourself as a human being. But those students they need teachers to see them because at home their families don't see them. At home, their families reject them. They have the father who didn't choose show up for them to save them from the family. They have the mother who didn't choose them. And it's in the classroom where they spend all those hours of the day where they really need, really truly need for us as educators to see them and see their strengths and not see their deficits, but shine a light on the strengths that they 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 iammichelle Sing.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.