#263: Discover The Root Of Your Confidence, With Nicole Kalil Author & Host Of This Is Women’s Work Podcast
4 Nov 2025 · 38 min
This is a transcript of episode #263 of Heather Monahan’s podcast featuring guest Nicole Khalil (October 2022). The conversation centers on redefining confidence as internal self-trust (the "confidence con" is the mistaken belief that confidence comes from external achievements or appearance). Nicole, a former Fortune 100 finance executive turned leadership coach and host of This Is Women’s Work, describes her path to studying confidence, tactical practices to build self-trust (keeping commitments, boundaries, owning voice), and five key "confidence derailers": perfectionism, head-trash (negative self-talk), comparison, overthinking, and seeking confidence externally. The episode includes personal anecdotes, advice for women in male-dominated fields about authentic voice, sponsor ad reads, and information about Nicole’s book and online presence.
Questions this episode answers
#263
October 2022
nicolekhalil.com
@nicolemkhalil
Validation is for Parking: How Women Can Beat the Confidence Con
Chapters
When I get this promotion, I'll feel confident. When I make this level of income, then I'll feel confident. When my children are perfectly behaved, then I'll feel confident. When the scale says a certain number, then I'll feel confident. And the reality is that's just not how confidence works. And so the con is that it's something outside of us. This idea that so much of us have bought into is that confidence is related to how we look and how we feel. The root of the word confidence is trust. So confidence is when we trust ourselves.
Come on this journey with me each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow.
I'm ready for my close up.
Hi, and welcome back. I'm so excited for you to meet my guest today. Nicole Khalil is an in demand speaker and the dynamic host of this is Women's Work podcast. Known as the Confidence Sherpa, Nicole reveals strategies that set her apart from other self help experts. Previously a Fortune 100C suite executive, she's helped thousands of women reclaim their confidence so they can live authentically, both personally and professionally. Nicole lives with her husband and daughter in Andover, Mass. My old stomping ground. Nicole, thanks for being here today.
Heather, thank you so much for having me. This is like a surreal moment because I followed you for years and then of course, we have a shared passion around confidence. So I read your book many years ago and so when we were connected earlier this year, I felt like I was, you know, meeting a celebrity and Total had a fan girl moment. So I could not be any more honored to be here today. Isn't it funny?
That is so funny. But you know what's funny? I have a fangirl moment over my pastor lately. Like, I'm obsessed with him and when I. I haven't met him yet, but I keep telling my that know him, I'm like, introduce me. I need to hug this man. Like, I'm so excited, I freak out. So I totally. I get it. I'm with you and thank you for that compliment. However, you know what's interesting, and guys, I want to give you a little backstory is Nicole and I were connected through our mutual amazing friend, Jordan Montgomery. And if you guys haven't heard that episode, go back and check it out. Jordan is the ultimate connector, and his whole episode is about how to network, how to connect with other business people and really take advantage of those opportunities. And so Jordan's introduced me to so many people Jordan introduced Nicole and I. And Nicole had me on her podcast, which was great. Definitely go back and check out that episode as well. We'll link that in the show notes. But what was funny is that we connected on the computer, of course, you know, post pandemic Internet zoom and did our interview there like we're doing today. But an opportunity arose for you to come to Miami to meet me and Gina, which it's so funny to me because my experience in corporate America was women backstabbing women, women not supporting women. And definitely different than what it is like with you and with a lot of the people that I know today. And you were so quick to say, oh, guys, I'll jump on a flight, come right down to Miami, I'll stay in town, we'll get together, we'll meet, we'll work out together, we'll hang out together and see how we can support each other. And I just thought that was such a confident ball. So it just. Massive credit to your confidence Sherpa title.
Well, it could be confidence. It could be a touch of just, you know, tenacity to get what I want. But I was getting on that plane and I was going to follow you to Soul Cycle or wherever you would have me so that I could pick your brain. And they often say, don't meet your heroes or don't meet the people that you admire from afar. And one of the things that I will say in meeting you is I just like you more. And I just. You're about as real as they get. And everything you're listening to and hearing from Heather, it is who she is times 10. And yeah, you're just a gift. It's one of those things when you make a fast friend, which I don't do often because I'm a die hard introvert. So it's been fun.
It's been so fun. And what Nicole is alluding to is that my life is a shit show right now. I'm literally falling apart. The seams. I'm in the process of moving. I'm closing on my condo today. I'm getting my house packed to move into my new condo. I can't find anything. Everything is disorganized. I couldn't even get my AirPods to work today. I couldn't find my glasses. I mean, I am a complete disaster. But we are finding ways to make this work today so we can bring you some value. All right, so back to Nicole. I want to get into Nicole. How did you stumble upon the whole topic of confidence? Why was that an important topic for you to start digging into.
Yeah. The honest answer is because I'd completely disconnected from my own. So many people thought I was uber confident. In fact, people would comment on it all the time. Being at an executive level at a Fortune 100 company in a very male dominated industry, so is often one of the only women in the room. What there is what industry?
For those that don't know you, what were you in?
Yeah, Finance. Yeah. So still very male dominated. So there was an implied confidence. Right. Because was one of the only or because I had progressed and got promoted and things like that. But the reality is I was living so inauthentically. I was trying so hard to be like everyone else around me and I completely lost any confidence I might have had anywhere along the way. And so I think as is true for so many of us, the pain and the discomfort led me to what has become a passion, a mission, a purpose. The lack of confidence is what had me focus on it. And then being surrounded by people telling us to be confident, but very rarely telling us how you actually become confident. Like I'm like a how to girl. Give me the step by step, tell me what to do and I'll do it. So I really wanted to dig into the more tactical side of confidence.
So self awareness and becoming aware that you were lacking confidence was sort of the starting point. Where did you take it from there? What were those steps that you went through for your own journey?
First I would say observation. I started paying attention to the people around me and who was confident, what were they doing and why were they doing it. And then beginning to recognize that sometimes people who appeared confident were not. And recognizing that there are still some insecurities at play in with people who are achieving at the highest levels or have success or the highest income. And so it just was a paying attention to things that were going on around me and starting to define what. What is the confidence that I want? What is the life that I want? And a parsing of that. And then of course, like anybody would, I started reading anything I could get my hands on as it related to confidence and then digging from there, listening to podcasts, listening to TED talks, anything that was confident adjacent I was all over then. Which is kind of a funny way to do it. I started teaching it. As a woman in a male dominated field, I was often being asked to do women's events or and I had avoided those like the plague. I didn't want to be a great woman leader. I wanted to be a great leader, but the universe has a way of. Or God has a way of driving you in a certain direction. And so I found myself working with a lot of women, coaching a lot of women, mentoring a lot of women. And I was passing down what I was learning. And what's interesting in my experience with leadership is often when I teach something or I suggest something to someone else, it makes me model it more, right? Like, then I want to be more of the example. I want to take my own advice. And so it was experience and then witnessing the effects in other people, and then just. It became this lifelong journey.
I love that you bring up that teaching, puts that pressure back on you to model it more, because I feel the exact same way. I'll never forget. And this just reminded me of a story. I think I share this story in my new book, Overcome youe Villains. It's one of the chapters. But I was speaking for the WNBA in Las Vegas, and I had packed and I had just gotten home from one trip, and I was like, unloading and repacking and jumping on a flight and moving really fast and made a mistake. Didn't know that I had made a mistake, landed in Vegas, you know, got checked into the hotel, and I had to go get ready and go give the speech. And so I opened up my suitcase and I pulled out my regular standard programming only to find out that the jeans that I had were ripped jeans. These were like jeans I would wear if I was going to a club in Miami or something, right? Not jeans I would wear to go give a speech. They were shredded like Justin Bieber style or something. And so suddenly I found myself to your point. I'm looking at these jeans and I'm saying, oh, my gosh, wait a minute. I can't get on a stage and give a speech like this. And I have to pause and say, wait a minute. You always talk about show up as your most authentic real self. These are still my jeans. Maybe not the ones that I would choose to wear to a speaking engagement, but they're mine. So if I'm going to rock my own look, I'll be more confident. I need to wear this with confidence. And I will never forget. I showed up, I gave the speech, and so many people after came up to me and were saying, I love your outfit. I love that you have the confidence to rock an outfit like this. So it ended up just furthering my message, even though I was struggling with it. So I'm so with you that it's almost like reverse pressure on yourself to remind yourself, hey, Wait a minute, I'm teaching this stuff. I better be living it.
Yeah. Also added that one of the most surprising things that I uncovered covered in like my journey to understand what builds confidence and what derails it is that mistakes, failure, losses, missteps. Those things actually build our confidence, not derail it. So like your example right there is like, obviously you felt at the moment that was a mistake, but the byproduct of it was people perceived you as confident you were being authentic. There's so many things that come on the other side that build and reinforce our confidence from those failures and those mistakes. So that's been an interesting discovery.
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You've really gone down this confidence journey at a whole other level. Even now writing a book about it, which I have to say where did the idea from someone who's a leadership in finance to coaching women and coaching executives. Where did you and why did you decide to write this book?
Yeah, so writing a book has always been on my bucket list. Like, from a very, very young age. I'm an avid reader, typically read like 60 books a year. So, you know, I wanted to write a book for as long as I can remember. Ironically, once I committed to doing it and started putting one foot in front of the other and getting into action towards writing the book, I had originally had a different book in mind. I was going to write a book debunking some of the success principles or some of the advice we get about being successful. Things like the morning routine or the kind of hard work, grit and grind things that come at us from a little bit more of a masculine lens. I am not anti men. I do not advocate for women at the expense of men. But I do think there's an opportunity for us to balance out some of the advice that we're getting. So it's not always in the hard work. Get up early. Whoever gets in first, leaves last is going to win, that type of thing. So anyway, I had gone down the road of writing that book, and it was really hard, and I kept running into obstacles, and it was just difficult. And I at one point was like, why am I doing this? I already have half a book written on confidence already, given my speaking engagements and what I talk about on a regular basis. And so I was like, you know what? I'm just going to test out writing a book about confidence and see where it goes. And it was so much easier and so much more. It felt like everything opened up. It felt like I was doing what I was supposed to be doing. So that other book idea may be the second book or another book in the future, but it was one of those moments where I recognized I was making it harder for myself than it needed to be. And again, the universe or God or whoever, it just redirected me to where I was supposed to be.
Oh, my gosh. This message is hitting me right between the eyes right now because I've been living this. And for everyone listening, hear what Nicole is saying, sometimes when things are tough, it's because you're going that wrong way. You're knocking on that wrong door. I just had an experience like this. I was trying to find a place to live. I had gone and looked at a lot of different properties, and I made an offer on a property. I wasn't in love with it, but it was fine. And I thought, you know what? Pull the trigger, Heather. Like, hit the easy button. Let's make this work. And the realtor starts fighting with me on text that night, saying, you need to up your offer. You're going to be out bid. I need to hear from you in the next 10 minutes. And I was getting so frustrated, and I thought it was so inappropriate the way the realtor was behaving. My son saw my face and said to me, what's going on, Mom? You look really angry. And I said, I don't like how this person's doing business. It just doesn't feel good. And he said, then you know what? It's not our place. If it was our place, it would move through with ease and grace, Mom. It would happen easily. This is not meant for us. He spoke to me in such a way that I thought, you know what? I think he's right. And I put the phone down. I did not look at the phone again. That night in the morning, when I woke up, there was a text that said, you've lost the property. Somebody else got it. And I thought, great, because that wasn't meant for ours. That wasn't ours. And then when we ended up finding the one that we're moving into now, everything happened seamlessly. It was so easy. It was just right. So, you know, things don't have to be hard just because you're in a situation where you've allowed it to be hard. Maybe start looking for what is that, that easier, more organic option, like Nicole did in going back and saying, you know what? I'm writing a book, but it doesn't have to be this book. Let's test and try this other one. I'm so grateful that you shared that.
Yeah. I found, you know, everything requires a measure of hard work, for sure, and tenacity and risk and anything worth doing, I think does. Having said that, in my experience, the things that are meant for me, the things that are right, somehow have a way of becoming obvious. They might not be easy, but it's obvious or simple. Right. Like, it just. It's that feeling of, like, when you're working against something versus when you're moving through or toward something. I have to remind myself, and I'm grateful for people like your son that remind us, like, hey, maybe this is not for us. Right.
I'm grateful for him, too. Nicole. Let me tell you, next time you're running into a challenge, wondering if you're on the right path, feel free to give us a call and he'll advise you as well. He's very good at that. I love it. So you started stepping into the confidence topic, and it was much easier to write. It was much easier to flow. How did you come up with the concept Was this based off of your speeches and the feedback that you had gotten from people in real time?
Yeah, so definitely. So much of the content is the stuff I share from the stage. So there's a lot that was, again, really easy and sort of already written from all the work that I'd done preparing to do speaking engagements. Interestingly enough, the first three chapters were the hardest because it was more the sharing of the why and the personal stories and the things that I don't talk about a lot from the stage. The other thing that is important is the subtitle of the book is How Women Can Beat the Confidence Con. And it went back and forth in my mind of whether to write this book with women in mind for women as opposed to more of a general audience. One of the reasons I wanted to write a book and one of the reasons I ended up going in that direction is because I'd read a stat that 92% of business books are written by men. And I just had this, like, moment of like, okay, we need to, as women, be adding our voices into this conversation about what it is to create success, what it is to build a business, what it is to be confident as a professional. And so that was really important to me. I do hope anyone of any gender would read my book and get a ton out of it. But I did want to write something very specifically with women in mind. And I don't know if you'd agree with this or not, Heather. I find that there are nuances as it relates to building confidence for women and men. Some of the things that are chipping away at women's confidence is different than what's chipping away at men's. And some of the ways that we might build confidence might be different or nuanced compared to our male counterparts. So I just wanted to be relevant in that space and be able to dig deep in that.
Yeah, I couldn't agree more with you. There's definitely different tactics and strategies when you're dealing with a man and his confidence issues versus with a woman. And there are some shared get into what is the confidence con?
I call the confidence con. This lie that I believe we've all been told and frankly, mostly have bought into that confidence is something that comes to us from an external source so that we gain confidence from someone or something outside of it, us. Something like, when I get this promotion, I'll feel confident when I make this level of income, then I'll feel confident when my children are perfectly behaved, then I'll feel confident when the Scale says a certain number, then I'll feel confident. And the reality is that's just not how confidence works. And so the con is that it's something outside of us, like some weird game of Where's Waldo? Someone or something out there has our confidence and we just need to find it. Right. But on top of that, this idea that so much of us have bought into is that confidence is related to how we look and how we feel. Right? Like we throw the word confidence around when we really mean happy or attractive or successful. In the word confidence, the root of the word confidence is trust. So confidence is when we trust ourselves. And so, yes, if we get dressed to the nines, we might feel attractive and it might help us do things or show up in a way we wouldn't normally. But unless it's impacting our trust in ourselves, it's not confidence, it's something else. And so I just wanted to really clarify what confidence is that it's firm and bold trust in ourselves. What it isn't the way we look or feeling happy all the time and identify that con of that, it's going to come to us from some external source as opposed to the way that it's built, which is from the inside.
And how do you help people to begin trusting themselves?
Yeah, so I always say, you know, this isn't a one size fits all, one answer, works for everybody equation. So I would start by asking you how you build trust with other people. How do people build trust with you? Therein typically lies the answer of how you would build trust for yourself. So I'll give a few examples that I think are fairly universal. Example number one, keeping your commitments. We trust people who do what they say they're gonna do. We don't trust people who flake on us all the time. And so the same thing is true about building our internal trust. If we can keep the commitments we make to others, but also to ourselves. And I find we are typically better at keeping the commitments we make to our children, our spouse, our boss, our friends, family, than we are the ones that we make to ourselves. And they're equally important as it relates to the trust we have in ourselves. So if we say we're going to work out consistently and then we don't, we're chipping away at trust that we have in ourselves. So keeping commitments is pretty universal. A component of that that I often talk about with women is don't over commit. Make sure when you say you're going to do something, you follow through because it is important. As it relates to our confidence. Another example would be boundaries. Saying no when it should be no, saying yes when it's a firm yes. Standing up for yourself, using your voice, being your own hype person, being your own cheerleader. There are a lot of things that we do and can do that build trust. But I would again go back to what matters most to you. If you think about the trust you have with a best friend or you know, with your significant other or whoever it might be, what is it about that relationship that makes you trust or where they trust you and then begin to apply that to yourself.
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You brought up owning your voice, standing up for yourself. And I know, I'm certain in business, in the finance world, you definitely were in situations where maybe you jumped in and did that or maybe didn't. You know based upon how intimidating it can be at times? How have you learned to advocate for yourself in those heavily male dominated meetings that are really tense and I so feel the pressure and I've been there too, wanting to speak up and many times I haven't. And then there are examples and times where I haven't. How have you been able to thrust yourself into that to actually elevate your voice?
I'll be curious if you feel this way too. Me using my voice has never been a challenge for me. Like I've never had a hard time saying this is my opinion or these are my thoughts. So isn't now wasn't then a big struggle for me? Like I'D be in meetings, only woman, you know, people way ahead of me, never had a hard time saying what I thought. Where I struggled was being authentic in that. So I would share my opinion, I would speak up, but I did it very much in the way I observed it being done around me. And so I did it a little bit more aggressively, a little more bluntly, a little bit more boldly, a little bit from a more masculine lens. I. I sort of put on the armor of the masculine in those meetings. And so I'm not saying there's anything wrong with that. And I might have had to in some cases, but what I didn't bring to the table was some of my other authentic qualities, like empathy, like listening, being transparent and vulnerable. Like, I didn't bring any of those things that, oh, now I have naturally in me. But I was so afraid of what would happen, what people would think if I would be not invited to any other feature meeting, if I showed up as my full self. And so that's really been the opportunity is not to. Using my voice was never the challenge, but showing up as my true self was the problem or what was the challenge. And that's been very much a work in progress. And I think people like you are a good example, somebody who just shows up as themselves and you can feel it, like you can experience it and how refreshing that is and how it does build trust when you're around a person like that. And so, you know, again, work in progress. But to me that's been the opportunity is, yes, to use my voice, but more to be authentic in doing so.
Well, just to be fair, Nicole, so you do understand, I have not always been this way, you know, for sure. When I worked side by side in corporate America next to a woman who appeared perfect and wanted everyone to believe she was perfect and was trying to sell that she was perfect. I definitely emulated that for a while. I went down that road for a couple of years trying to, you know, not show who I really was, trying to, you know, sit a certain way, dress a certain way that wasn't in alignment with who I am. And I'll tell you, I became a B rate target version of myself, which I am never going back to. So I can't encourage people listening. It is so important to show up as that authentic, true version of you. I talk about it all the time, my speeches, I've got smelly feet, and I frickin own it and rock it, people. Because you know what? It makes me feel good that I'm different and I'm unique and you know, own who you are and do it with pride, even if it is different than what's popular opinion. And even more important because it's different than what popular opinion that just makes you instead of feeling shame about who you are or embarrassed about who you are, you start stepping into that powerful, competent version. And I just had Molly Fletcher, who's an incredible negotiation expert and sports agent on the show and she was talking about she was one of the only women in that industry negotiating $500 million in deals and the differentiator for her why she was so successful is because she's so empathetic and cares so much. The thing that made her different was the thing that why people don't get into that business when they're women, when they're female. So she leaned into that unique element that was different about her instead of trying to hide it. So I couldn't agree more with you that lean into who you really are and when you start owning it and rocking it, that's when you're going to be the most powerful, confident version of yourself.
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Free okay, so let's get into what are some of the things that derail people's confidence?
Identified five confidence derailers again with the lens of women in mind. So Confidence Derailer number one is perfectionism, this idea that we're supposed to do it all, have it all, be it all, and look good while doing it. And, you know, God forbid we should ever make any sort of mistake, right? So perfectionism is the number one confidence derailer. I've heard it called the enemy of confidence. And I couldn't agree more. Confidence derailer number two is what I call head trash. These are the things we say in our own minds to ourselves, about ourselves. Things like, you're not good enough, you'll never measure up, or nobody will love you. It's just mean, right? The stuff that we say in our own minds that are very rarely true and never kind, and we would never actually say to somebody that we love, yet we say it to ourselves. So head trash is the second confidence derailer. And I consider it the bully of confidence. The third confidence derailer, and we kind of talked about this already, is comparison. Comparison and judgment. Specifically, when we compare ourselves to others and basically feel bad about something about ourselves, we fall short. We don't measure up. Why isn't my life or my career or my whatever as good as this other person? I think it's fairly obvious to see why that would chip away and do damage to our confidence. The thing that's unfortunate about it is we're very rarely comparing like with like. We're typically comparing our behind the scenes to somebody else's highlight reel, right? So we are seeing their best moments, their achievements, the things that they really want us to see. And then we're comparing our everyday, normal lives. And of course, then it would feel like we're falling short. The fourth confidence derailer is overthinking. Thinking is not a problem. Overthinking is a problem because overthinking leads to inaction and inaction leads to regret. If you talk to the most confident people, the most successful people, about their biggest regrets, more often than not they will tell you about the things they didn't do, not the things that they did. And so it's so important that we don't get stuck overthinking because then we're not doing anything. And then finally, the fifth confidence derailer is seeking confidence externally. It's that if X happens, then I'll feel confident. If, you know, I get that promotion or if I fit into a certain size, or if I find the person in my dreams, then I'll feel confident. And it's a false equation. It doesn't work. In fact, what ends up happening more Often than not is we become addicted to the thing and it's never enough. Right. So like for me early on it was if I get that promotion, then I'll feel confident. Well, then I got the promotion. It was like I felt confident for about 30 seconds until I started freaking out about whether or not I could do the job or if I was ready or if people would respect me or whatever. And then it was like, oh, the next promotion, then I'll feel confident. And it just, you know, it's always something else if you choose to try to build your confidence in that way. So seeking it outside of us is a confidence derailer. Now I'm not saying that those things don't feel good or that validation doesn't feel good or it's not not a good thing. I'm not saying. I just think it should be the icing on the confidence cake, not the cake itself. The cake itself is the internal work, the trusting ourselves that we all get to do.
Oh, that's so good. I definitely put a lot of value on my paycheck, my title, my team, when I was back in corporate America and then when I got fired and it was taken away, it was one of those moments that you feel like you lose everything when you have real confidence internally in yourself. No one can ever take that stuff from you. And so it's so much more powerful. Even though it appears sometimes on the outside that people think you're confident when you are getting it externally, that is going to be short lived. I love all of these tips. I love the tactical nature of this book. Tell us, where can everybody find the book? You know, how can people get a hold of you?
Yeah. So nicolecalil.com is my website that's probably the best place for all things. You know, you can get the book there and find all, all the good stuff. Of course the book will be available on Amazon and Barnes and Noble or wherever you for books, but the website's probably the best. One stop shop and the book is.
Validation is for Parking. How Women can Beat the Confidence Con. Thank you so much, Nicole for writing it. Thank you for all the work you're doing supporting other women. You are so my people. Where can people find you on social media?
So Instagram is probably the best or at least the realest @nicolemkhalil. I'm also on LinkedIn. I always say if you want to follow me professionally, follow me on LinkedIn. If you want to follow me with cursing, follow me on Instagram.
I love that clarification and thank you for being that real version of you. All right, go to the show notes, guys. We've got all the links that you need. Until next week. Keep creating your confidence. I decided to change that dynamic. I couldn't be more excited for what you're going to hear. Start learning and growing. Inevitably something will happen. No one succeeds alone. You don't stop and look around once in a while. You could miss it. Come on this journey with me.
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