Why You Keep Doubting Yourself and How to Rebuild Your Confidence | Heather Monahan - EP 836

Heather Monahan, bestselling author, speaker, and former chief revenue officer, joins Passion Struck to explain how self-doubt, toxic environments, and other people’s opinions can undermine our confidence and limit what we believe is possible.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

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• 1:00John R. Miles?

  Coming up next on Passion Struck. What happens when a toxic environment slowly changes the way you see yourself? Heather Monahan experienced it firsthand. As harmful behavior went unchecked, she watched her confidence and the way others treated her begin to change. Her story reveals how to recognize when an environment is holding you back and what it takes to reclaim your confidence. Take a listen.

• 1:31Speaker 02

  The problem is, bad behavior doesn't go away. When you ignore it, you amplify it. And that's what I was doing. So over time, I was becoming a B-rate version of myself. She was growing in power because people were seeing how she treated me. And then they started treating me not as nicely, without as much respect. They weren't giving me the accolades anymore because they were seeing what she got away with me, and it changed the way others around me treated me. And again, I take full responsibility for that.

• 1:57John R. Miles?

  Hey, it's your friend John, and welcome to Passion Struck. I'm so glad you're here. Whether you're a longtime listener or someone who just discovered the show, thank you for pressing play today. Maybe you've built the life you were supposed to want, but you've quietly wondered why it still doesn't feel like enough. If that's you, you're in the right place. Every week, I sit down with the world's top scientists, researchers, and thinkers to uncover what it actually takes to build an intentional life that matters. Thanks for joining me. Let's get into it.

• 2:38John R. Miles?

  Hey friends, welcome to episode 836 of Passion Struck. Earlier this week, in my conversation with Nir Hellevy, we explored how hierarchies, competition, and workplace cultures influence the way people treat one another. Today, we're taking that conversation one step further by looking at what happens when those environments begin to shape how we see ourselves. My guest is Heather Monahan, a bestselling author, renowned speaker, podcast host, and confidence expert known for her work on building self-belief and overcoming the people and circumstances that hold us back. She's the author of Confidence Creator and Overcome Your Villains. Heather's

• 3:23John R. Miles?

  career has taken her from the media business to executive leadership and entrepreneurship. Along the way, she's experienced extraordinary professional success, difficult setbacks, and moments that forced her to rebuild her confidence. One of the most revealing parts of her story involves a workplace where she allowed harmful behavior to continue for too long. As she described it, she gradually became a lesser version of herself. The behavior went unchecked. The way people treated her began to change, and she eventually realized that something had to change in how she responded. That experience became a turning

• 4:05John R. Miles?

  point. Heather developed a deliberate plan to rebuild her confidence, speak up for herself, and regain the ability to show up as the person she knew she could be. In our conversation, we explore how self-belief influences achievement, why the people and environments around us can either elevate us or hold us back, and how to keep someone else's opinion from becoming our identity. We also discuss boundaries, professional loyalty, and the courage it takes to pursue a different path when the circumstances around you no longer support your growth. Heather shares practical lessons on building confidence through action, recognizing your value, and taking the next step even when the outcome is uncertain. This conversation

• 4:50John R. Miles?

  is part of our October series, The Architecture of Agency, which explores the forces that shape how we see ourselves, make choices, and build our lives. If today's episode resonates with you, please share it with a friend or family member who needs to hear today's message. Also, don't forget to subscribe to the podcast on Apple Podcasts, Spotify, or on YouTube. Now, here's my conversation with Heather Monahan. Thank you for choosing Passion Struck and choosing me to be your hosting guide on your journey to creating an intentional life that matters. Now, let that journey begin.

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• 6:08John R. Miles?

  I am absolutely thrilled today to welcome Heather Monahan to Passion Struck. Heather, it is so great to finally get you on the podcast.

• 6:15Speaker 02

  John, thanks so much for having me. I'm so excited to be here.

• 6:18John R. Miles?

  As I was researching you, I was surprised at how many people we both know and have been on each other's podcasts. It was pretty much uncanny. Before we came on, we were talking about Gary Vaynerchuk, but there's also my good friend Matt Higgins, John Gordon, Jess Ekstrom, Jeremy Utley, Mark Manson, who I just had on, our mutual friend Hala, Jason Pfeiffer, Colin O'Brien. So there were a ton of them. When you look at the kinds of people you've been drawn to interview and learn from, what do you think you're trying to ultimately understand about the people?

• 6:56Speaker 02

  For me, I'm so curious about the way success looks like on the outside, which I know for myself when I was coming up, I just thought some people were born smarter or luckier or came from money or whatever, whatever it might be. And now that I've gone through my own life journey, I love getting to identify successful people and then learn what it really was like for them to get to the bottom of what was it, was it actually easy coming up? Because what I've found thus far is no, I haven't found anyone that had some really simple journey of success after success. In fact, what I keep finding is these people learn different ways to reinvent themselves, to build confidence in difficult

• 7:41Speaker 02

  moments, to bounce back from failure, to never give up despite what other people were telling them. And I love sharing those stories with my audience so that not only do we all build resilience, but we all realize that we can create the life that we want.

• 7:55John R. Miles?

  I think Matt Higgins is a great example of that. I love his story. If people aren't familiar with him, he wrote the book Burn the Boats. But he was also an EVP for one football team, the Jets, if I have my memory correct. And then he was the vice chairman for the Dolphins down where you live. But people don't realize the struggle that he had even to get to the path where he went to law school, long before he did any of these amazing accomplishments. And I think a lot of it has to start with the belief that you have in yourself that you're deserving to do these things with your life. Do you think any of that factors into it?

• 8:32Speaker 02

  Without a doubt, self-belief is such a huge part of holdbacks for so many people, whether they realize it or not. And no matter how successful you are, you still see those self-doubt moments creep back in anytime you're going bigger, anytime you're going for something new, anytime you're about to burn the boats again. That's why I love Matt's book as well.

• 8:56John R. Miles?

  Heather, before we get into any of the work that you're doing today, I want to take the audience on a journey back to the beginning. As I've read and listened to you talk, you've said that you grew up with really humble beginnings and you struggled to find confidence early in life. And I think it's always interesting because I remember Rory Baden telling me one time, "We're best positioned to help the person we once were." And I think that's definitely the case with you. What do you remember about that young version of Heather who didn't yet believe in herself?

• 9:29Speaker 02

  Oh, my gosh. So a funny and timely question. As we were just discussing off camera, my son just started college freshman year in Boston a week ago. And so I just took him, I'm from, originally from Worcester, Massachusetts, right outside of Boston. I lived in Boston in my early twenties. And so for me, it's going home to that version of me back from childhood to early twenties, when I was full of self doubt, full of imposter syndrome, not realizing what was possible, not confident at all. And my strategy back then was to fake confidence, which I'm going to tell everybody this, and it's, I wrote a chapter of it in my first book. A lot of people don't like it. It worked, right? I'm not saying it's

• 10:12Speaker 02

  a strategy that I would deploy today. I don't need to, because I've seen enough proof along the way that I can't, I know other ways to build confidence in myself. But when you don't, just that sheer brute force, that was the only lever I had to pull, and it worked for me. But the funny thing is now, going back to the high school that I went to, my son was playing basketball there, training for, to start school. I hadn't been back to my high school in so many years. And I don't know, John, if you have been back to your high school recently, but going back, it's really interesting, environment impacts us immensely, right? I was a psych major in college, and I am so interested and

• 10:51Speaker 02

  curious about psychology. Well, I lived it two weeks ago, going back to my high school, where I was full of self doubt, full of imposter syndrome, and full of this concept of, I wonder if people are going to know that I'm really not confident at all, and I don't feel like I'm worthy to be at this school. I had a full scholarship to go to a school named Worcester Academy. It was very prestigious. My sister and I were there, and we were work-study students. And I'll never forget the shame that I carried around me. I didn't want other people to know. Very privileged children went to the school, and very wealthy. And so I remember that, in my mind, I had to show that I was worthy to be there, that

• 11:33Speaker 02

  I was smart enough, that I was good enough. So it probably isn't surprising that the things that I leaned into were sports, leadership, speaking, whatever they were, and I wanted to be the best. And I would push myself to any limit to achieve that. And it's just wild today, or two weeks ago, to go back there and see, wow, how much smaller everything looked, how in my mind, I created this image of where, how scary it was, and how hard it was to be successful there. And then to arrive there two weeks ago, after I've been to Saudi Arabia, Dubai, I've spoken all around the world, and it was so small. And I was explaining to my son, wow, your mind plays such tricks on you, when you allow it to,

• 12:13Speaker 02

  that I was so taken down by my own thought process, by my own shame, my own imposter syndrome, that I was shrinking myself, so that I felt small in a large place, when the reality is, I'm large in a smaller place. And it took all of these years of being away from that version of me, is the best way I could put it, to understand, wow, I created that jail that I was in there. Nobody else saw me that way. And I actually saw my old softball coach, and I was the MVP and captain of our softball team. And when I saw her, she said, "Oh, my gosh, it's so exciting to see you back here. This is amazing," and whatnot. We had this great conversation. I said to her, "Do you realize how insecure I was back then?" And she gave me a little wink. She really took me under her wing, and

• 12:58Speaker 02

  it matters so much, the people that you surround yourself with, as we know. And she was great to me and developing me. But I still don't even think she grasped how much insecurity I had back then. And I don't even know that I realized it until two weeks ago, when I walked back in there. But it was an incredible moment for me to realize how far I've come. But also to remind myself that no matter what environment you walk into, whether it's a million people on an event that you're doing, you are the only one that can shrink yourself. You are the only one that can put that limitation on you. And that's going to be a great reflection point for me, that I will leverage as I go into other bigger opportunities, to remember that difference. It was only, it's only me that's changed.

• 13:40Speaker 02

  That school has not changed at all. And that goes the same for everybody listening right now.

• 13:45John R. Miles?

  Heather, I love that answer. And I'm going to just digress here for a second. This week, I had two great interviews, episode 817 and 818, if people want to go check them out. One was with Angela Duckworth, and the other one was with Jared Diamond. And they both happened to be on exactly what you're talking about, the environments that we live in. And it's interesting, when I was talking to Angela, we started out talking about her book, Grit. And then I said, "What made you write this other book?" And she said, "Well, what I realized was that grit is necessary, having passion and perseverance. But there's another dimension of this that's equally as important, and that's the environment

• 14:26John R. Miles?

  that you deploy your grit in." And we were talking about West Point, I happen to be a Naval Academy grad, so it's near and dear to my heart. What she was explaining is that there was a period in time in West Point's history, where the number of cadets who were completing beast barracks, the basically equivalent of plebe summer, was going down. But now they've had decades and decades where the number of people who are completing beast barracks has been rising. And she asked the superintendent at the time, "What's the difference? Is it the cadets?" And he said, "No, it's the environment." Because there was a point in time where West Point was trying to weed cadets out, and now they're,

• 15:08John R. Miles?

  they put in a developmental program where they're trying to build them up. And just that example shows you exactly what you were talking about, our environments, and how much it can shape who we become and what is output from them.

• 15:24Speaker 02

  The best analogy I can give people that relates to my life and to me today, literally to me this week, is if I'm on a treadmill, running in my building downstairs at the gym, and I get tired, and I see a text, and there's distraction, and I say, "You know what? This is a wrap. Forget it. I'm just, I'm not going to do the full hour, or I'm not going to run seven miles," or whatever the mini goal I had in my mind. I just hang it up and come back upstairs, versus, I happen to live in Miami, as there are professional athletes all around here, there, University of Miami athletes are everywhere where I live, and I happen to live where a run team runs every evening. If I want to push myself

• 16:06Speaker 02

  and not let myself down, all I do is I go outside and I start running, because I know this, I will see a major athlete, I will see someone running three times the speed I'm running, I will see someone that I know has been running 10 miles longer than I've been running. And when you start running with a crew of people, or even in proximity to people training in that level, you hold yourself to a higher standard. And it rings true every single time, because last night, I chose to run outside, which I typically try to do, and halfway through my run, it started raining sideways, because it is not, it's not the ideal climate right now in Miami, and it can happen. But it was so cool, because the people who were running out in the same situation I was in, were waving to me, high-fiving

• 16:51Speaker 02

  me, running by, and you felt, hey, I'm part of this. They're not quitting, I'm not going to quit either. And when you surround yourself with like-minded people who not only run with you in the pace you run at, but run ahead of you, you're going to push yourself to go for more.

• 17:04John R. Miles?

  Man, I can so relate to that. We started this talking about our high schools. I haven't been back to my high school in decades. But while I was there, we won the state championship in cross country. And my teammate, Keith Dallin, went on to become the top US finisher in the cross country championships, when he was a collegiate athlete, and went on to just missing the Olympics by a fraction of a second. But having Keith on the team elevated all of us to be so much better, because we examined his work ethic, and what he put into it, and it made all of us want to be like Michael Jordan, be like Keith.

• 17:45John R. Miles?

  So do you think having the extraordinary career that you've had in the competitive industry, that you spent so much of your career in, had a lot to do with what we were just talking about, that you understood that modeling yourself

• 18:01John R. Miles?

  Around people who you aspired to be at the same playing field helped you keep moving forward, or were there other things that helped you achieve it?

• 18:11Speaker 02

  I'll tell you, it's an interesting question. I don't know that anyone's asked me that before. It's making me really reflect. And the first thing that came into my mind is what I deemed a negative, the fact that I grew up poor, turned out to be a huge advantage over everybody else in business. I had a paper route since I was 10 years old, bus tables since I was 13, waitress since I was 14, bartender since I was 18. So I had this, ultimately, this series of jobs that was teaching me sales. And everybody's in sales, as we all know, right? In any exchange, somebody sold and the other person is being sold. And so I learned selling, I learned referrals, I learned how to close people, I learned

• 18:52Speaker 02

  how to follow up, I learned how to deliver outcomes, I learned how your name and your reputation would drive referrals. I'd learned so much at such a young age that I had this huge advantage over everybody when I actually graduated college and started my career, which was with the Gala Winery initially. I was one of three women on a team of 100 men. And so the odds were stacked against me. And because I had played sports my entire life, I just thought, you know what, if these guys can do it, why can't I? And what I ended up doing is leveraging the fact that I was different, and I saw things differently. And everyone on the team did it a certain way, and they would tell me, this is the way you do it. And I thought, well, I could do it a different way, too, and we could

• 19:36Speaker 02

  try this. And what's funny is that's been, that way of looking at things differently has been what's a differentiator for me in everything I've done in my entire career to this day. I think that's one of the things that has driven my success. So, one, the fact that I grew up poor was an advantage. Two, the fact that I saw things differently, that I wasn't like everyone else, gave me a leg up, even though it didn't always feel that way, even though it didn't look that way on the outside. And the other thing that I think of is, I ended up being sexually harassed at that company, and I left back then, I didn't even think to get an attorney or anything. I thought, just get out of this horrible situation. I left that situation, went to an event, and met a gentleman who just started chatting me up. We had a great dialogue. Halfway through the conversation,

• 20:20Speaker 02

  he says, you should work for me. I said, you can't afford me. Mind you, I was 21 at the time. And he said, give me a number. By the way, Google didn't exist back then, much less AI. And so I said, $8,000. Little did I know, this man was worth hundreds of millions. And he said, good, you start tomorrow. And I went to work for him the next day, and that brought me into the radio business. So again, a negative situation, seemingly, a door closed, I showed up at an event, started talking to people, a new door opened. I had no idea what I was walking into, but I just walked into it. And that turned out to be an incredible opportunity for me. That, he was the owner of a radio station, which he had purchased himself. He took me under his wing. And then another negative situation,

• 21:03Speaker 02

  my boyfriend cheated on me a year later. It devastated me. I thought I was marrying this man. But what was interesting is, that seemingly negative situation turned out to be this incredible positive situation. I went to work upset. My boss, the same man that had hired me, said, what's wrong with my number one rep? What's happening? And I told him, and he said, hey, do you want to get on a plane with me, move away from here, and become a really rich young lady? I said, if it means I never have to see this guy again, yeah, let's do it. So I would have never taken that leap, because I was staying for a relationship. I ended the relationship when he cheated on me. That opened a door for me to become an equity partner. We bought a company in Saginaw, Michigan for $25 million.

• 21:45Speaker 02

  My partner dropped me off to run that company. And the whole goal was to accelerate revenue as quickly as possible, so that we could flip the property. And we did that. We sold that company in under three years for $55 million. And that really put me on the map in business as a revenue generator, and someone in media who could deliver big results.

• 22:04John R. Miles?

  Let's take a moment to share a resource that connects with much of what Heather and I are discussing. In my new book, The Mattering Effect, Creating a Life of Meaning and Worth, I explore how our relationships, workplaces, and communities shape our sense of significance, and what happens when those environments leave us feeling invisible or replaceable. The book, which was just named a USA Today Bestseller, also offers the Matter Framework, a practical way to think about meaning, autonomy, time, trust, energy, and reciprocity in our lives. If those ideas resonate with you, The Mattering Effect is available wherever books are sold. Now, a quick break for our sponsors. Thank you for supporting those who support the show.

• 22:52John R. Miles?

  You're listening to Passion Start right here on the Passion Start Network. Now, let's return to my conversation with Heather Monahan. What an amazing story. I'm gonna, again, go off my track. I was gonna take you on for just a second, because I can't tell you how many successful people I've had on this show who started off with a paper route. And ironically, I started my route when I was 10 or 11 as well, and did it till, I think I was halfway through my junior year in high school, because I was also working in grocery stores and other things. Did you have a morning route, or an afternoon route?

• 23:29Speaker 02

  Morning, it was, gosh, it was dark out. So I don't know what time that was, 4:30, 5:00 in the morning, but it was really early, yes.

• 23:36John R. Miles?

  Mine was an afternoon route to the York Dispatch. And I learned so many important lessons. One, I'm not sure if you ever went through this, I had customers who never wanted to pay. In fact, I think they saw me coming up to the door, and before you had ring, and they purposely wouldn't answer it. And for the longest time, I didn't have the confidence to go up there and keep knocking on it to get their payment. I was eating their papers for a little bit, until I finally was like, I can't keep doing this. And it made me confront them. And that was a very powerful lesson for me, because it taught me, I wasn't going to allow myself to be bullied, I wasn't going to allow myself later in life to be in that

• 24:19John R. Miles?

  type of position. And I learned that they're either gonna pay, or I'm not gonna deliver the paper. Did you ever have any lessons like that?

• 24:28Speaker 02

  Oh my, that exact one, right? Learning how to have a difficult conversation without feeling guilty or bad about it. When someone, it's so interesting, and you see this in business, I see it to this day, where I have clients that their companies, you'll look at how much good they do, and how great their work is, but they will have monies owed, or payments owed, and they're struggling so much, well, I don't want to hurt the relationship. When the reality is, when agreement has been made, an agreement has been made. That is on between two parties, and two parties enter into it equally, the same way in a paper route, right? That they signed up for wanting this, they knew you were upfront about what the cost was, and what the deliverable was. Same way in business today, whether

• 25:11Speaker 02

  it be for millions of dollars, or hundreds of millions of dollars. And having that conversation, I love this now, and I share this with all of my clients and people I work with. My first thing to say is, I'm confused. I'm confused. Help me to understand why you haven't been able to pay on the terms that we agreed to. And when you don't have to fight with somebody, you don't have to argue with someone. I used to think you had to fight with people, that it had to be a difficult conversation. It doesn't have to be. You can actually ask people for their help, share with them that you're confused, because you're at a loss of, why wouldn't you deliver on your end, when I've been delivering on my end? And it can be a very simple conversation.

• 25:47John R. Miles?

  Heather, I want to talk about what happened in your career next. So you end up going to Beasley Media Group. You were there, if my numbers are correct, about 14 years. And you end up rising from Director of Sales to EVP, ultimately, you're in the C-suite, Chief Revenue Officer. And as I connect the dots, it seemed to me that the long-term CEO, George Beasley, had become an important mentor to you in your journey, and a big supporter of Heather. What did those years and that relationship with George teach you about leadership, believing you belonged in rooms that you might not initially have imagined yourself being in?

• 26:28Speaker 02

  I go back to that, the deal prior to that, which was with Wilkes Broadcasting, and the PE that we worked with. That was such a mind-blowing opportunity for me to be exposed to that level of what could happen with multiples, what could happen when you get investors, and going through that entire process, and then seeing I was the one leading that entire organization. Granted, I would call Jeff, he was back in Boston, and I would call him on the phone at night, and we'd discuss things, so he could help develop me. But I was the one, you know, boots on the ground, leading that team. Realizing what I had accomplished, that shifted the level of confidence in me. At that point, when I made that move to Beasley,

• 27:11Speaker 02

  I knew my worth from a business standpoint. And I hope people understand this. You can have confidence, massive confidence in business and have zero confidence in your personal relationships. You can have massive confidence in your sales ability and zero confidence in your workout routine and health. Right? So confidence can ebb and flow in different parts of your life and different times of your life as well. When I got fired, I had a low level of confidence in me in business and I had to reengage with who I really was. So at that moment, entering that organization, I knew my worth and I actually took a step back in order to get into the organization because I could see on the outside looking in, there was a massive opportunity. And so I took a step back.

• 27:56Speaker 02

  I took a small, a much smaller role than I had just had as an equity partner. And I came in and I said, let my results speak for themselves. I'll show you what I can do in a finite window. And within six months, I drove massive results for the position they put me in. And then I called a meeting with the president of the company, George's son, Bruce. And I asked him to meet me in person because if you really want something, you better show up in person and ask for it directly. And I sat with him and I said, listen, I see a bigger opportunity here. I pitched him for a job that didn't exist. And he said, no. He said, you're doing a great job in this local opportunity. We have you and we're so impressed with you. Please keep up the good work, but we don't need change.

• 28:40Speaker 02

  And I left that day and I was younger and I didn't have a child and I didn't own a home at that point in time. I was renting and I thought, you know what? If they don't see my value, I know my value. I'm better poised to take a much bigger opportunity than they've given me. It's time for me to go. And I still believe that to this day. If other people don't see your value and you're willing to settle for that, they're never going to see it. And so I started dialing different companies. I found a much bigger opportunity with a much larger broadcaster. And I thought I'll give him one more chance before I resign. So I asked, and it was two weeks later, I asked, can we have lunch again? I sat down in front of him and I said, have you thought anymore about the concept and idea of creating this VP for the entire company?

• 29:25Speaker 02

  And he said, no, not really. And I said, great, then I'm giving my resignation right now. And he said, give me five minutes. And he walked out of the restaurant and he came back five minutes later and he said, I'd like to announce that you have been chosen the new VP of Sales for the entire company. And I was so confused and I said, well, then just tell me, where did you go for the last five minutes? And he said, I had to call my father, George. I wasn't in a position to make that decision on my own. And that day taught me a lesson I will never forget that I really want to share with your audience. Never take a no from someone who can't give you a yes. And that was on me. I should have qualified that meeting before I even asked him to come to lunch.

• 30:08Speaker 02

  I should have said, if I have an incredible idea that can change the trajectory of this company and make our shareholders so happy, who would need to be in the room in order to make that decision? Is it just you? And I didn't do that. So I almost walked away from an opportunity that ended up being a fantastic opportunity for many years. And so Bruce and I worked side by side. He was the COO, president of the company at the time. And ultimately I was the VP of Sales, then the EVP, and then the CRO, all under George's leadership as the CEO. And we were a publicly traded company, but obviously very heavy with the actual family and family members at the top of the company, which is an interesting dynamic. If anybody's worked in a situation like that, I'm sure you understand.

• 30:53Speaker 02

  And so I had a great run there. I was named one of the most influential women in radio. And four weeks later, I was terminated. When George stepped down, surprisingly, out of nowhere, he became ill. And his daughter was elevated to replace him as the CEO. And she had been the one person on the executive team that never liked me.

• 31:17John R. Miles?

  Well, an incredible journey that you just discussed. And there's something in that story that I can relate to personally. At Dell, I was Chief Information Officer. And the way that Dell worked at the time is you had Michael and then you had four or five SVPs that had the title of president who ran divisions underneath him. And those guys were competing like crazy. And all it took was one of them to not like you for whatever reason. And they could take your career and put it down the trash. And that's exactly what happened to me.

• 32:00John R. Miles?

  There was a divisional president who seemed determined to find fault with me. No matter what I accomplished, no matter how much work I did, it never felt like enough. And it seemed to me like even though George was the head of the company, his daughter was similar to this divisional president, trying to figure out, no matter what you did, to enough for her to feel like you've accomplished enough to stay in that role. Is that kind of how you felt? And how do you deal with situations like that? Because what I found, there was nothing I could do to change his mind. So I tried to influence the other people in the room and sway their votes because I knew, no matter what I did, it was never going to change his.

• 32:45Speaker 02

  John, that's such an interesting question. And when I look back and reflect on it, and I actually did a TED Talk about this because I think, number one, I think this happens very often in business, specific to this women against women in business, in corporate America specifically. I think it happens very often where another more senior woman is trying to sabotage a younger female. I've seen it across my career.

• 33:08John R. Miles?

  I've seen it a bunch myself.

• 33:10Speaker 02

  But nobody talks about it, right? It's that elephant in the room, nobody wants to talk about. And so to me, that was a big part of it. My male peers were great to work with. They weren't perfect, right? Nobody's perfect. And we all had our own faults and strengths and weaknesses, but there was no one maliciously trying to sabotage me but her. And the games that would go on, not responding to emails, not acknowledging me in meetings, setting meetings for the C-suite, not inviting me, right? Trying to do, when I would be invited to speak on behalf of the company and she would find out about it, calling and having them resend the offer and put her, the game that would go on back and forth was crazy.

• 33:53Speaker 02

  And you start to feel crazy because I wasn't in the position of power. She obviously had the name that I did not have, as I mentioned before, right? So one, two, three, four of the people in the C-suite, all the same last name. I was the odd guy out. And so you knew that there was a power play there. And people would say to me, Heather, play nice. Heather, you can get along with anyone. Find a way to make it work with her, maybe similar to what you were dealing with. And I tried at first. I tried for a while, but then suddenly my hair started falling out. Suddenly I couldn't go to sleep at night. Suddenly it was like God, the universe, however you want to see it, was saying to me, this isn't work, the math isn't mathing, kid. This doesn't work, right?

• 34:34Speaker 02

  So my, your attention will be grabbed if you ignore bad behavior. And that's what I had been doing. I had been ignoring bad behavior in hopes that if I focused on my lane, my business, sales, revenue generation, which we were doing an incredible job, that everything else would be okay. The problem is, bad behavior doesn't go away when you ignore it, you amplify it. And that's what I was doing. So over time, I was becoming a B-rate version of myself. She was growing in power because people were seeing how she treated me. And then they started treating me not as nicely, without as much respect. They weren't giving me the accolades anymore because they were seeing what she got away with me and it changed the way others around me treated me. And again, I take full responsibility for that.

• 35:19Speaker 02

  At some point during that journey, and this is near the end, this is in that last year, right before I got fired, I remember going home one day and I said, this is enough. I don't like going to work anymore. This is crazy. I've allowed for an environment to change and become toxic around me very quietly. And I didn't notice what was happening, but I'm clear where it is now. And I thought, I can't change that, but I can change me. And so I created a 30-day plan to build confidence in myself. I took out an image of myself when I was super confident. I created daily action steps. I created a playlist that I would use to hype myself up before meetings with her. I did so many different, unique, intentional things to get me back to who I really was. It worked.

• 36:04Speaker 02

  It worked really, it worked so well that I believe that's why I got fired at the end. And I became that really powerful, confident version of myself again, who stood up for myself in meetings, who acknowledged when someone didn't acknowledge me and did it with class and grace. And that changed everything. And in the end, obviously, we know she got the CEO title, which that was surprising. I didn't know that was going to happen. Her brother didn't know that was going to happen. She had not been marked for that person to get elevated, but it did. You never know what's going on behind closed doors, by the way, which is an interesting thing. And I encourage people, don't put your loyalty all into one boss, one company, one industry. It can change drastically overnight, having nothing to do with you or them. And that's really what happened when he became ill.

• 36:47Speaker 02

  Going through that whole situation taught me that you're not in charge of how other people treat you, but you're actually teaching people how to treat you by what you allow to happen and how you allow other people to respond and react to you.

• 37:03John R. Miles?

  Thank you for sharing that Heather. And I think there's an important follow-up question that is important for the listeners to understand here. I have listeners who are earlier in their career, later in their career. But one thing I have known from my own career is that eventually, if you're doing it for long enough, someone with the power over your career is going to repeatedly make you feel like you're not enough. And what I wanted to ask you, since we've both been through this, is, what does that do to your confidence? And how do you keep their opinion from becoming your identity?

• 37:37Speaker 02

  First of all, I'd highly suggest not keeping yourself in that environment. You are going to make it much tougher on you than you need to. And I remember when I used to be in that situation, the younger me, I used to say, I have golden handcuffs. I would literally walk around like this with holding my hands. I have golden handcuffs. I can't leave because I had decided to put myself in that cage. I could have busted those golden handcuffs off at any point in time and gone out and figured something out differently outside of media. I had an 18-month non-compete, non-solicit, which meant I had to leave the industry I was an expert in if I wanted to leave. So that, in my mind, kept me there. But I wasn't thinking big enough. And so I would just challenge you, think bigger.

• 38:18Speaker 02

  Think beyond your non-compete. Think beyond your situation or whatever it may be that's golden handcuffs are keeping you somewhere. There's an opportunity somewhere else. If you set the intention and start taking the action to elevate you and put belief in you, remove yourself from that situation. Because I call it overcoming your villains. If you are going to work side by side with somebody trying to hold you down, you're never going to run at the highest level that you can. You're never going to reach your potential. So start taking action today to get yourself out. I see so many, and I've had so many people in my programs, C-suite executives making tons of money. So smart and miserable in their job. And they're only a fraction of what they could actually be because they're settling for what's around them. So change that environment. Get out of there. There is somewhere that wants to have you,

• 39:00Speaker 02

  that will challenge you to get better, that will be a team member with you for your growth. So get away from that person first and foremost, and that will really change the trajectory of your life.

• 39:12John R. Miles?

  Heather, one thing about me, and we're getting to know each other, is I have a terrible time asking for help. And so what you did after your experience with that media company, really to me, is something I would have never done. You could have disappeared and quietly started to look for another job. Instead, you go on LinkedIn and you publicly post that you've been fired and need help. Something I would never in a million years do myself, but you had the courage to do it. Why did you choose visibility when most people like myself would have chosen to hide?

• 39:50Speaker 02

  It's a great question, and I truly believe you need to listen to your own intuition. But the way I was reasoning it, I knew, I had been in that career for 20-something years. I knew everybody in media. I just did. And I had done favors for thousands of people. And so I found it odd that 24 hours after I'd been fired as a chief revenue officer and one of the only females in the C-suite in all of media, that no one was going to send me a note and say, hey, how are you doing? Are you okay? Can I help you? I found that odd. So I remember thinking, okay, what would I liken this to? And I remember thinking, I'm going to liken this to when I got divorced. If no one knew I was single, how could anyone ask you out?

• 40:33Speaker 02

  They wouldn't because they would think, she's married. I should respect that. Right? So I remember thinking, I had to tell people, oh, gosh, I'm single. If you know anyone that's single that I should be dating, introduce me. I had to let people know my situation. Otherwise, people will default to what they used to know. So I thought, okay, well, if that worked with getting divorced, I bet it will work with this. And so I just immediately went and posted, I've just been fired. If I've ever done anything to help you, I need to hear from you now. And it's funny, I got phone calls from friends saying, take that down. It looks really pathetic. And again, I had to check in with the one voice and opinion that matters, your own. And I remember thinking, I don't feel pathetic. A lady I don't fired me. I didn't do anything wrong. I did a great job for that company.

• 41:18Speaker 02

  She just doesn't like me, and I don't really like her. So I'm not a fit for her team. And the more I thought about it objectively, how, why would I feel badly about that? I feel great about that. I don't want her to like me. I don't want to be on her team. I want to go for more. I want to go bigger. And I want to be around people that want to elevate me and help me on that path. Let her find her people. I'm going to go find mine. And so when I started to think about like that, I got excited about, wait a minute. I remember saying this, let me Google, has anyone successful ever been fired? And then I saw Steve Jobs and J.K. Rowling and Oprah Winfrey, and the list goes on and on. It turns out getting fired was their jump-off point to massive success and to what they were really called to do.

• 42:02Speaker 02

  So I remember thinking, okay, this is my jump-off point. This I need to get excited about. The one thing that happened that I didn't know was going to happen was that post went viral. It reached millions of people and the amount and influx of opportunities and help that I received as a result. Heather, how can I help with this? The piece of advice I give others, when people are reaching out to wanting to help you, convert in the moment because life moves fast. And a week later, no one's going to remember what's going on in your life. Even though you think they will, they're not going to. That one day, they thought about it, but they won't think about it again. So every single message I could respond to, and it's so sad, AI wasn't available back then, I would respond right away, yes, can you leave me a testimonial?

• 42:45Speaker 02

  Can you connect me to so-and-so at your company? Can you get me on the Elvis Duran Show? Which ultimately I landed on the Elvis Duran Show, and that completely changed the trajectory of my business, my career, and turning into an author, basically over a month period, which was wild.

• 43:03John R. Miles?

  I was going to go into the Elvis Duran story, but you just covered it. So I'm going to jump to this. Your experience ultimately became the foundation for confidence creator. And you argue that confidence isn't something that we wait for or something that we're born with. I think it's like courage. It's something we create. Can you unpack what you mean by that and how a listener could do this in their own life?

• 43:31Speaker 02

  Oh, my gosh. So confidence is not something with a magic wand that's just waved over certain people. People believe that. It is so not true. But in fact, it's something you're either creating or chipping away at in any moment. And what I mean by that is, and I've learned this initially through business, I guess probably first through sports, then through business. And then I apply it now to my entire life, whether it be dating, working out. It could be anything, writing, deciding to go on Substack or not, deciding to take a speaking engagement or not. You, in any moment, you're creating confidence or chipping away at it. And when you start approaching things with that intentionality, you will start understanding how simplistic this is. It's simple. I'm not saying it's easy, but it's very simple.

• 44:16Speaker 02

  And so when you're building a muscle the same way you do in the gym, but this muscle is confidence, and when you become confident in business, you become more successful, you take bigger risks. When you take bigger risks, there's larger gains. There's bigger opportunity, right? You build momentum and you start having fun with it because it isn't so scary. But you have to start somewhere. So for a lot of people, they'll say, well, that's easy for you to say. You had confidence in business at a young age, right? But everyone has to remember, it's because I jumped on a plane not knowing where I was going and having no idea if I'd fail and living in Saginaw, Michigan after I grew up in Boston. Right? So there was tons of risks that I took and tons of opportunity for failure.

• 44:59Speaker 02

  But that big moment for me, which spanned three years, I say it as a moment, but there was a lot of highs and lows, and there was a lot of crying nights and wondering if I had made terrible mistakes. Turns out I didn't. I made a great decision, but I didn't know it at the time. And so when you create these, and most people have a moment like that in their career that you can look back to, oh, I doubted this, or I didn't know how this was going to go, or I thought I was going to have a panic attack at that presentation. I made it and I got great feedback after, right? Those mini-wins are confidence-building moments. Track those things. Create a journal all around your success moments with confidence. And success means you didn't die. You were scared to do something. You got up and did it anyhow, and it all worked out okay.

• 45:40Speaker 02

  So that starts reframing the way that your mind works over time. You can rewire your own brain. Again, this is all psychology. You can start taking action steps that are building that confidence muscle for you. And then suddenly you start doing it more and more. It becomes natural for you. I'll give you an example. I was building this confidence muscle all through my career in media and then taking that leap and going out to try to reinvent myself. Because remember, I had to leave the media business. I had an 18-month non-compete. And I was a single mother and I didn't know how I was going to do it. And everyone says, oh, we knew you'd figure it out. I didn't know I was going to figure it out. Right? So those little micro-moments going on the Elvis Duran Show, that built confidence in me.

• 46:23Speaker 02

  I was scared to do it. But when those scary moments come, lower the expectation on yourself. I remember thinking, okay, as long as I don't fall and have that get caught on a Getty image, it's a win, Heather. So that was my whole goal. I just don't want to fall walking out with all the cameras out there. And I didn't. And so I was already winning when I sat down. Did I make some mistakes? Yes. I left my phone on vibrate on his show with millions of listeners. And all of a sudden, in the middle of the show, he said, who's the rookie that left their phone on? And I had to raise my hand as the guest, and we all started laughing. Things don't go perfectly, but the fact that I took the step, showed up and did it, even though I was scared, made it a win for me. That went in my confidence-building journal. Then to the next thing, then to the next thing. Right? So all these scary moments have taught me

• 47:07Speaker 02

  that every time you step back from something and say, is this going to build confidence in me? Or if I walk away from it, will it chip away at it? You'll know the answer. And then it's on you to say, I'm going to move forward and build the confidence, or I'm going to take a different route and shrink back. But I promise you, the harder route is to shrink back from it. The easier route is to take the hit that moment, overcome the fear, choose to see fear as a green light that means go and go faster. And the more you lean into that, the faster the confidence muscle builds, and then the faster you step into the life that you're really looking for.

• 47:41John R. Miles?

  I'm so glad you just gave that advice because I think what you just talked about is one of the biggest misconceptions a lot of successful people have about confidence. I often talk about this is people will see Heather speaking on a stage in front of 20,000 people, and they'll think that is the defining moment. And what they don't realize is the defining moment is really the micro-choices, micro-moments that build up to reaching that point where you built that confidence muscle again and again, so that by the time you got on that stage, it was just natural for you. And people think that you just go from point A to point B without Taking so many of those steps that you need to along the way, would you agree?

• 48:27Speaker 02

  Oh, my gosh. It's funny. People will say, oh, it's easy for you to say because of, as you just explained, for whatever reason, they think that why you have success. And again, no one truly knows unless you live in a house with somebody. You don't really know what's going on in someone's life. My son will be the first one to tell people, oh, she could be a disaster. I was a disaster before I went to Saudi Arabia for the first time. I was crying. I was freaking out. I was scared. They don't know that when they see me on the stage. So everyone needs to know. People show their highlight reel on social, but you don't have the whole story. My whole story, especially around speaking, because I know so many people are afraid of speaking. I started speaking when I was 21, when I worked at the Gala Winery and I was promoted to brand manager

• 49:10Speaker 02

  for Cask and Cream. I'll never forget. That was my first sales management job and I had to stand in front of 100 people in front of the team and speak. So that at 21, I started my public speaking career, even though I didn't know that's what it was called, but I chose to build confidence in that moment. And I'm sure I was not good, but I did it anyhow. And so over the next whatever two decades as a sales leader, I was speaking every single week in front of my teams, in front of different marketplaces, in front of different events, and the events got larger and larger, and the stages got bigger and bigger. But it started with those micro moments along the way, putting the reps in. That's how you change what next stage you can go to. I didn't start one day

• 49:53Speaker 02

  in front of a small audience and then jump to the leap audience of 250,000 people. Heck, no, I would have had a panic attack and passed out, right? It doesn't work like that. But in our minds, we see other people and we believe it does. And it's really about putting those reps and creating that momentum and creating that belief that we can take that next step and that next leap, and then you will.

• 50:14John R. Miles?

  Heather, I haven't, as of late, done as much public speaking as you have. I did a lot more earlier in my career, but a couple of years ago, I was the emcee for the Podcast Hall of Fame Ceremony. And I get up there and as the emcee, you've got to introduce all these different people who are getting the awards. It's like the Academy Awards for podcasting, plus all the sponsors, everything else. So I get up on stage and of course, my teleprompter is not working. So there's this thing that you're usually counting on to be your guide is completely black. And to me, it really goes into what you're saying, because if I were at the beginning of my career, I would

• 50:52John R. Miles?

  have leaned into that and not have had two or three backup plans from previous experiences when shit goes to hell. And so I had memorized all the guest names, et cetera, anyhow. But I think for a lot of us, we get in that situation, teleprompter isn't there. And what do you do? You go into panic mode. But because of the preparations and doing Toastmasters and improv and other things, I was confident in myself in that situation. But is that a good analogy for what this confidence allows you to do?

• 51:30Speaker 02

  Absolutely. The fact that you memorize their names, that's wild. You know what's interesting? And I have mad respect for that because that is major prep. And just guys, everyone listening right now, no one does that. So that's incredible that you did that. And thank goodness that you did, because you were able to deliver for these people and people love hearing their own names, right? So that was so important, given this audience and the gravitas of it. But it's so funny, I'm very different. And this is where I think everyone, you need to lean into what's unique and different about you, whoever you are. For me, I lean into humor, which is my personality. And so when you were talking about that, it was reminding me of I was the emcee giving an award for the National Association of Broadcasters for the radio stations across the country. So

• 52:15Speaker 02

  it was all thousands of the biggest personalities since probably 10 years ago. And I'm up on stage and it's this huge venue. Everybody's there. Everyone wants to hear their name. Everyone wants the win. And I announced the winner. And at the time, it was Clear Channel, which is now iHeartRadio. And at the time, it was Clear Channel. I announced Clear Channel and everyone starts booing John. And I have no context as to why. I'm standing up there on the stage and there's bright lights everywhere. I can't see anything, but I hear everyone's booing. And I just thought, that's rude. And so I have no idea why. So I just decided to make a joke about it. And I said, whoa, all right, everybody. Sounds like people are a little testy. I don't

• 52:58Speaker 02

  know if anyone needs to run to the bar or grab another bite of food. But if you didn't see the Dallas airport this afternoon, I think you understand why people probably aren't here. Who's with me on that one? And so people started laughing. I was just trying to get out of this situation, because obviously you don't want to just stand there and say nothing when, but it's public speaking is so interesting to the point of both of our stories. Something unpredictable will always happen. And the key is for the people that make through those moments are the confidence you have in yourself and how you can get yourself in and out of situations. And that's all about really owning who you are. And in that moment, it highlighted how disciplined you are and the

• 53:41Speaker 02

  work that you put in. For me, it highlighted, like you with improv, I have leaned on humor and that was able to get me out of a tough situation. Funny enough, when I got off the stage, someone came up backstage and he said, great job finding your way out of that one. And I said, well, I said, what was that one? They said, oh, they boycotted. There was some boycott going on that I knew nothing about. And so it worked. I'd rather not get into something like that on stage, right? That's not going to be a win for anyone. So I don't know. Things are funny, but you have to be ready in life for the unpredictable. Life never goes the way you think it's going to. But the more confidently you can show up to those moments and the more real you can be, the better it's going to go.

• 54:21John R. Miles?

  Heather, I want to close out by talking about your second book, Overcome Your Villains. And it's interesting. My lead into this is my first book was called Passion Struck. And I think it's interesting that oftentimes as an author, what you think is going to be the most popular aspect of your book doesn't become it. And the thing that you think is going to be the least likely thing to take off becomes the thing everyone wants to talk about. And I had this concept in my book called the mosquito principle. And it overlaps your idea of overcome your villain, villains. And what I meant by mosquitoes is that oftentimes the environment that we put

• 55:01John R. Miles?

  ourselves in, we're surrounded by lots of invisible and visible influences all the time. And to me, the mosquitoes represented the invisible influencers, and I call them the bloodsuckers, the peters, the invisible suffocators, that really derail us from the goals in life that we want to have. They keep us playing small and staying, playing big. Can you talk about how to know from your concept when the villain is genuinely outside of us and when the real obstacle is something happening inside of us?

• 55:36Speaker 02

  That's such an interesting question. It's funny. Our books are talking about similar things in different ways. And this is why, for everyone listening, everyone's voice matters and counts, because some people are really going to resonate with that idea of the mosquitoes, where some people wouldn't and will resonate with the idea of villains, right? And it's so important that people find their voice and share it with the world, in my belief. I love that idea. I also believe there hasn't been an original piece of content created since the Bible, that ultimately we're all reimagining everything through the lessons we've learned through scripture. It's kind of cool through the lens of your own experience, how you can reimagine things. I love that idea. For me, one of the ways that I was able to differentiate, is this negativity coming

• 56:20Speaker 02

  from outside of me or is it within me, is journaling. And the more you journal and get real with yourself, because that's the space nobody else is going to have access to, you're going to be more real. You're going to take off the mask that you're wearing at work, where instead you're just pointing fingers at other people and you're going to start being real with yourself. And that was how I got to that moment of, wait a minute, I'm the one choosing to put my head down and let someone treat me poorly. That's on me. Why am I allowing that to happen? That I wouldn't give a young child that advice. I wouldn't give my son that advice if he's being bullied at school. I wouldn't say, oh, put your head down and keep your day going. No, I told him, you go out there at the schoolyard and you tell that boy he will not speak to you like that again.

• 57:03Speaker 02

  And listen, if he punches you, you can hit back. I'll never forget, that was an actual conversation that happened. Stand up for yourself. I don't want you to be the person to go out swinging at other people, but if people are coming for you, you will stand up for yourself with class and grace. And if somebody hits you, you will protect yourself. And so I thought to myself, am I handling myself in that same regard? I'm not. And so I realized I was the problem, right? I was the villain. As soon as I changed that and decided to fire that villain, the one in my mind, and rewrite that narrative for myself, everything changed around me. Granted, it got much more intense. It definitely took a turn, but I felt better about who I was. And then I could realize, oh,

• 57:44Speaker 02

  now I see these are villains outside of me. And again, villains outside of me doesn't mean they're bad people. It means they're not my people. And some people confuse that. I talk also about frenemies. Sometimes people have friends that are putting them down quietly, giving them disparaging looks. They're not champions to you. They're not encouraging. They're not challenging you to get better. Creating boundaries around people like that, places like that, it's so key. But for me, it all started with journaling first to get real with me and then make the changes I needed to make so that I can fire the villain inside my own two ears. And then once you do that, you see the external completely different. And then you can make bigger changes there.

• 58:23John R. Miles?

  Heather, it has been such an honor to have you on the show. I can see why so many thousands of people listen weekly to your podcast and why so many companies and associations and conferences hire you to get on stage, because your message is just incredible. And the impact it's had on so many is a testament to what you've accomplished since you left Beasley and took the leap to do what you're doing now. So thank you so much for joining us on Passion Struck, because you are absolutely a passion-struck person in everything that you're doing with your career.

• 58:58Speaker 02

  Well, thank you so much for having me, John. I appreciate you.

• 59:01John R. Miles?

  Nearest research reveals something important about the environments we create. The rules, incentives, and hierarchies around us can influence whether we see other people as partners in our success or threats to it. And that influence can reach deeper than our behavior. It can shape our confidence, our sense of possibility in the way we see ourselves, which raises another question. What happens when the environment you're in begins to change the way that you see your own worth? That's where we're going in our next conversation. My next guest is Heather Monahan, bestselling author, amazing keynote speaker, and confidence expert. Heather has built an extraordinary career, but her path has also included self doubt, professional setbacks,

• 59:46John R. Miles?

  and the challenge of finding her confidence again, when the people around her stopped recognizing her value. Heather and I talk about the environments that help us grow, the ones that slowly diminish our confidence, and what it takes to stand up for yourself when someone else's opinion starts influencing how you see yourself. It's a conversation about self-belief, resilience, and recognizing when it's time to change the circumstances around you. I hope you'll join me.

• 1:00:14Speaker 04

  We thought that what we would hear is how different young people today were from the students in our classrooms, in our advising groups on our campus. And then we pressed play. And what we heard was this deeply resonant story that echoes exactly what our students talk about today.

• 1:00:33John R. Miles?

  Until next time, I'm John Miles. Stay curious, stay intentional, and stay passion-struck.