Creating Confidence with Heather Monahan
Confidence Classic: Where True Confidence Really Comes From with Nicole Kalil
27 Jan 2026
Chapter 1: What is the main topic discussed in this episode?
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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.
Chapter 2: What is the biggest misconception about confidence?
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. Tell me, have you been enjoying these new bonus confidence classics episodes we've been dropping on you every week? We've literally hundreds of episodes for you to listen to.
So these bonuses are a great way to help you find the ones you may have already missed. I hope you love this one as much as I do. Hi, and welcome back. I'm so excited for you to meet my guest today. Nicole Khalil is an in-demand speaker and a 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 100 C-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 fangirl moment. So I could not be any more honored to be here today.
Isn't it funny? That is so funny.
But you know, it's funny. I have a fangirl moment over my pastor lately. Like I'm obsessed with him.
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Chapter 3: How does inauthenticity affect self-belief?
And when I, I haven't met him yet, but I keep telling my friends 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...
Chapter 4: What role do commitments play in building confidence?
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, ballsy response. 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 SoulCycle 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 diehard 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.
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Chapter 5: How can mistakes and failures enhance self-confidence?
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 and a very male dominated industry. So as often one of the only women in the room.
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 it 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 and 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's still some insecurities at play 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 is the confidence that I want?
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Chapter 6: What are the five biggest confidence derailers for women?
What is it 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 and 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 the story in my new book, Overcome Your 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, 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.
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Chapter 7: How does perfectionism undermine our confidence?
And I had 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 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 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.
Meet a different guest each week. Confidence Queen.
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Chapter 8: Why is comparison considered poison for confidence?
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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 was a leadership in finance to coaching women and coaching executives, where did you and why did you decide to write this book?
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