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Heather Monahan
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to let go of? Because you are meant for more. The sooner you let go of mediocre, the faster you're gonna be able to grab great, right? If there was something broken in it and it inherently wasn't gonna work, you've gotta let that go. You have to cut those ties so that you can move on to what you're really meant for. And you're never gonna find what you're really meant for until you let go. Surrender. Let it go. Close the doors to the things that are no longer meant for you and ask God to open those doors to what actually is and show you the way There, living in that uncertainty is living in all possibility. Make the decision that you were meant for more, because I truly know that you are. Come on this journey with me each week when you join me, you're 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
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much as I do. Hi and welcome back. I'm so glad you're back here with me this week. I hope your week is off to a strong start. This past week I gave a keynote for the girls club who I've been, they've been bringing me back the past couple of years. I'm super grateful to deliver keynotes for them. I love the group of fantastic ladies and gentlemen. I wanted to share some of what I talked about this week in my speech with you because I thought maybe it could add some value to your week. Okay, so one of the things I think that people get caught up with is when times get tough, right? Because I get it. When everything hits the fan, it can be very trying to stay positive. It can be trying to find out what that opportunity is, right. To look and shift your perspective when you're really overtaken by negativity. My moment with that for sure. Two big ones that stand out. One was when I got fired. I went into total panic. I couldn't think clearly. I was not looking for opportunity. I was like, how am I going to survive this? How am I going to pay my bills? I mean, total panic. Okay, so I get it. The other one was when the pandemic hit. That was another big moment in my life where I thought, oh my gosh, I just built everything up on my own company and my speaking business disappeared overnight and I had to pay my mortgage and take care of my son. And I and my son didn't leave the house anymore and we were stuck inside. So that was another big moment. I broke out in a rash, right? Like I, I freaked out. I panicked. And that never helps me, by the way, but I'm sharing that with you. So, you know, if you panic and freak out, totally normal, it will pass. It's not going to solve any problems. The more we can learn to acknowledge, huh? I'm acting a little crazy right here. This is not gonna help. I have some grace for myself. I get why I'm doing it. But I know as I look towards other challenging times I've gone through my life, these aren't the things that help me get over it. But there are some things that I can do differently that will help me get through these tough times faster. Which, that's kind of what it's all about, Right. As you start to move through it, you start to figure out the opportunity and then you start to build momentum, and then you start to get excited and then you this amazing new path ahead. That's the ultimate goal. Right? And then you're excited about what you're working towards. And then new doors start opening. And then there was no way before and a way is made. And then miracles start happening. Yes, this is legit. Okay. So I want to get you there faster. Maybe you're going through a tough time right now, maybe you're not. But as we know for sure, change is inevitable. And no matter where you are, if it's good or bad, it will change over time, it will evolve and there will be challenges again. Right. That we know for sure. Okay, so one of the things, this is like a long intro to tell you that one of the things that I talked about in my keynote this week was things don't always go as planned because you deserve so much better. And I know that's hard to understand, right? Whether it be you're in a relationship. I remember when I was engaged, you know, a couple years ago, and I thought I was getting married and we were moving into house together and I was. So this is what was supposed to be for me in my mind, you know, I thought that. And then it didn't work out and I ended the engagement and I wasn't happy anymore. And now here I am a couple years later and I'm so grateful. I didn't go down that path. It wasn't meant for me. I was meant for something better than that. Right. But in the moment, sometimes you don't fully know that. And some things have to play out so that you can ultimately get to where you're supposed to be. So don't forget that things don't always go as you have planned because you deserve better. And God has a bigger plan for you. You just don't know it yet. Okay? So I have so many examples of this in my life and I wanna share a few of em with you. Cause it's funny now, it wasn't funny at the time, but it is pretty funny now. When I look back on these different times that I saw as super dark, super challenging, and now, you know, I have this grace to look back on my life and see how all the dots connected and how they were all leading me somewhere incredible and purely magical. Just incredible. But you can't see the dots connect when you're in it. You can only see it when you reflect back. So you have to give yourself that faith that things will turn for you, that you are being led to something bigger and that you are certainly meant for more than where you are right now. Meet a different guest each week.
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All right, the first one. When I was younger, I grew up poor. And I. And I know I've shared that with you before, and I struggled. I had a lot of shame around that. I never thought there was any gift in growing up poor. I felt bad for myself. I thought this was terrible. Poor me. Why do other people have such easy lives? And I don't come to find out as an adult. Now, when I look back, part of what's made me so successful in business has been my drive, my willingness to never give up, no matter what. I mean, I am not a quitter. I outwork 99% of the people I know, always have, always will. And. And that drive and that intensity, it came from growing up poor. So the funny thing is, what I thought was this challenge, what I didn't like, I was angry about it. I was ashamed about it. Now I have this totally different perspective that I'm so grateful that instilled this crazy work ethic and drive in me that anytime things get tough, I can always lean into that grit that is just omnipresent within me because I've used it my entire life. And that gift came as a result of growing up poor. Again, I didn't know it at the time, but now, in hindsight, when I look back, I can see the blessing that growing up poor was. What challenge in your childhood can you look at and say, wait a minute. I didn't realize it at the time, but this challenge or this headache or this thing I thought was so awful ended up being this incredible blessing. And I want you to reflect on that, too. So again, remember, things don't always go as planned because you deserve better. Had I grown up really wealthy and this amazing life, I would never have this grit and desire to get ahead, to make it to the C suite as a female, to do things that I had to push myself through that hopefully opened A lot of doors for other people that came after me. Okay? So that's the beauty in it. All right? Another big one for me. And this is so funny is I graduated college and through college, I'd had a very serious boyfriend. And we moved in together. And again, I was in my early 20s. I thought I was going to marry him. I thought he was the one. And my family had moved away. And really his family had become like my alternate family. And, you know, we did everything together. We lived together, we did everything with his family. And one day, I'll never forget, I had heard rumors from people. Just FYI, people always say, you must have known. I had heard rumors that, you know, he might be cheating on me. And we've been together for years. But I didn't want to believe it, right? Because I thought, no, this is my guy, and he's like my family, and we're getting married and blah, blah, blah, whatever story I was telling myself. And I got home from a girls weekend. I went away with my girlfriends. We used to go to Newport a lot. Newport, Rhode island, back then with my friends. And I went away for the weekend with my girlfriends. I got home and he had cheated on me in our house. He had this girl over our home. I found her clothes with lipstick. I mean, the whole thing. Literally. Devastated. When I tell you I was so devastated, and I'm laughing right now. Cause it's so funny. Cause it's so long ago. P.S. if you, like, think about the first time you got your heart broken when you were a kid, whether as a teen or in your 20s, it's devastating in the moment, right? And my little boy had his heart broken a couple years ago. And it was so hard to watch him go through it, but I was so grateful he was going through it. Because, as you know, once you go through it and get through it once, you're like, okay, that stunk. I didn't love it, but I lived. I'm okay. And I learned from it. And I wasn't meant to be with that person. And wow, like, there is life on the other side of these challenging moments, right? It's like this amazing life lesson that we're given. Okay? So I was devastated. I just started working in the radio business. I was working for this independent owner who owns one radio station in Worcester, Massachusetts, and I was killing it. I was the number one seller my first year on the job. And I went to work the next day after I caught my boyfriend cheating. And I moved out immediately. I was driving one of his cars at the time. So I had to take his car, which I gave back right away. But other than that, I had to leave our dog. I mean, it was so sad. I went and moved in with one of my girlfriends in Boston. Devastated. Complete disaster. Went to work the next day, no makeup on, looking, like, horrible, you know, still crying at work. And the owner, my boss, came up to me and said, let's go talk. What is going on with you? Like, who are you? What happened to my all star? I told him everything. And he looked at me and he said, would you be willing to get on a plane with me? Don't ask me where we're going. I'm going to drop you off somewhere. You're going to be my partner. You're going to run a company. You're going to blow this company up, and I'm going to make you a very wealthy, very successful young woman. And I thought about it for maybe two seconds, and I was so driven to get away from this man who had just broken my heart into 9 million pieces that I said yes. I had no idea where I was gonna move to. All I knew is it would get me away and out of the same city that this man who devastated my life was living in. And I knew I didn't wanna run into him. So it was so funny, because in this moment, I didn't realize that this man cheating on me was the greatest gift. I'd still be living in Worcester, Massachusetts, if this guy had never cheated on me or I possibly could have, right? So what a blessing. What a gift. I was not meant to live in Worcester, Mass. Forever. I was meant to board a plane with my partner and get dropped off in Saginaw, Michigan, which I would have never agreed to move to if conditions had been different, right? But we bought a $25 million company. He dropped me off. I ran that company seven days a week, 24 hours a day, took zero vacations. And my number one job was to accelerate revenue, which I did aggressively. And in under three years, I sold that company for $55 million, netting me and my partners $30 million. And that really put my name on the map. Not only did it put my name on the map right, in business and in media, the industry I was in, but it showed me what I was capable of. And I would have never taken that leap of faith and jumped on a plane not knowing where I was going if that guy hadn't cheated on me. So yet again, things don't always go the way that you have them planned because you're meant for something bigger and better. And you have to trust that in those moments. Okay, so that was a really big one that completely changed the trajectory of my life. Then the company that bought us, they had a non compete on the deal, which meant they were trying to force me to stay and work for them, which I was never going to do. Right. I knew I was leaving, so I couldn't work for my partner anymore. That's who I wanted to work for, that's who I trusted. And we had just done a great job together. I wanted to stay partnered with him. They put an end to that in the clause when we sold them the company. So I, I'm like, oh my gosh, who am I gonna work for now? I never thought about working for myself back then, by the way, which is so bizarre and funny now. So I said to my old partner, who should I work for? He said, jump on a plane, go to Florida, meet my friend George. I want you to go work for him. He has a bigger company. Go there for a couple years, turn their company around. You' run the entire company, you'll kill it. And then once the non compete for you and I expires, we'll do another big deal. And so that was my plan. Things did not go as planned, by the way. Shocker. I was meant for more, just like you are. I jumped on a plane, I came down, I met with George's son, I pitched him for a position that didn't exist. VP of sales of the entire country. He said no. But they gave me a very small job in their Naples operation. I took it. I took a big step back. I took a huge pay cut. I took a huge, huge. Nothing went as planned. And within the first year, I became the number one revenue generator in the company. And I said, okay, I've proven enough. I'm gonna go back and pitch myself for the VP position I know this company needs. And I know I'm the person. I had so much conviction within me that I could do it. So I called a meeting face to face. Always meet face to face anytime you really wanna get something done. And I sat across from the same gentleman that hired me, the president of the company. And I said, listen, I built up major equity here with you. I've done an incredible job. I'm number one in the company. I turned your weakest operation into the top operation. I can extrapolate this and go ahead and implement the same strategies I've done here across the entire country and make you a very wealthy man and your shareholders Very happy with you. And he smiled and nodded, and he said, you know what? You're doing a great job where you are. Stay where you are. I wasn't married back then. I didn't have a child. So I said, okay, I'm gonna move and take another job. You know, create my own future. And I started dialing other companies, pitching myself for bigger jobs. I found one back in Boston. So now this is years later, right? I had been in Michigan for three years. I had then, at this point, been in Naples, Florida, for a year and a half. So I felt fine going back to Boston because that guy who had cheated on me was like, you know, way in my rear view now. By the way, I did run into him at a wedding a couple of years ago. And karma is a bitch. I'm just gonna leave it at that. Okay, Moving on. So, so grateful that that did not work out for me. Blessing. Okay, Hashtag. Hashtag blessed. So then I found another job, called the president again, said, hey, let's meet for lunch. It was a week later. And I said, I'm here today to resign, unless you're gonna offer me the position VP of Sales. And he said, what do you mean? I said, well, you know, if you don't see the value in me, I do. And I know I'm meant for more. So I'm going bigger. I'm gonna go big market, big company, big money. I'm out. And he walked out of that restaurant and came back in 10 minutes later and said, I'd like to award you the VP of Sales position. It's just been created now. And I said, where did you go? And he said, I went to call my father. I couldn't approve of this without his approval and support. And I learned a really important lesson that day. Never take a no from someone who can't tell you yes. I hadn't qualified if he was the ultimate decision maker or not, and he wasn't. So I had almost walked away from this huge opportunity I ended up being given. And so I became the VP of Sales for a publicly traded company nationally, and I started traveling all over the country to elevate revenues for this. At the time, we were doing 100 million annually. Over the next decade, I was promoted three times, became the Chief Revenue officer. And when I got fired, we were doing in excess of 200 million annually in an industry in decline. I was killing it. And I was named one of the most influential women in radio at the end of 2017. And three weeks later, I was fired. When that Woman was promoted from CFO to CEO because her father became ill. So, again, things did not go as planned as any of this. None of this has gone as planned because it truly is. Because I'm meant for more, and so are you. So as you look back and start connecting these dots, I can see where all of these different big pivots were leading me to where I was meant to be. And during this time, I started asking myself, what is it that I'm really meant to do? Like, why am I really here? Right? And you can start pondering big questions like this, not knowing what the answer is, not having any idea. I had no clue. But that led me to charity work, you know, a decade ago. And I was on the City Year Miami board of directors for a decade, and I did massive amounts of charity work. And leaning into charity work is what really opened my eyes to. I love helping people. I like making people better. I like investing in people. I like investing myself, but I like investing in others. And then the charity work led me to bigger speaking opportunities. I had always spoken in my own industry, in the media business, and I'd taken massive stages there and spoken, you know, at every company event and every sales event, and so I was speaking all the time. But when I started leaning into charity events, people responded differently to me. People in the media business had known me forever. I had been there for over 20 years. When I started speaking at charity events, people started going crazy, and it made me start thinking, maybe there's something to this speaking thing. I wonder what it could be. So just asking yourself these questions that you don't necessarily have the answers to and allowing it to unfold, sitting in what those questions are, are the way that you will eventually figure out where it is that you're supposed to go. And then for me, obviously, another big moment was the moment I got fired, right? I felt devastated. I thought I had lost everything. I started having panic attacks. I went under a weighted blanket, right? I lost my mfing mind. But it turns out that that whole thing was this gift, this butterfly effect that I had to go through in order to come out the other end and realize I was meant to write books. I was meant to speak life into others. I was meant to teach the things that I've learned. I was meant to be here with you right now on this podcast, right? I was meant to do so many different things that I had never thought about. No one handed me a blueprint and said, hey, this is what you're meant to do. Just like no one handed it to you. We've got to figure it out through stumbling and making mistakes and trusting ourselves and failing and getting back up and taking a wrong turn and going the other way. But for me, it's really been about accepting that things don't go the way that I have plans. Because I deserve better. I deserve more. And God's plan is bigger than mine. Meet a different guest each week.
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confidence I asked you to try to find your passion and as you start to surrender to that which I'm not saying any of this is easy. P.S. it's not. And for any of you that have gone through some of these low moments with me, you know, geez, it's not like I had mentioned before just a couple years ago, ending my engagement was hard, right? That was sad. Letting go of things that you had all these high hopes for and wanted to pan out a certain way. It's sad, it's heartbreaking. But the sooner you let go of mediocre, the faster you're gonna be able to grab. Great, right? If there was something broken in it and it inherently wasn't gonna work, you've gotta let that go. You have to cut those ties so that you can move on to what you're really meant for. And you're never gonna find what you're really meant for until you let go. Super challenging in the moment. Super scary, that whole idea of letting go. But I see so many people, so many people I care about, so many people I love settling and hanging on for dear life to something that they should have let go of a long time ago. So I'm asking you this question today. What is it that you need to let go of? Because you are meant for more. And I promise you this, you're not going to find out what it is until you let go. So surrender. Let it go. Close the doors to the things that are no longer meant for you and ask God to open those doors to what actually is and show you the way there. It's a lot of faith. It's a lot of moving forward, not knowing where you're going, but living in that uncertainty is living in all possibility. I promise you. And I'm so grateful now today for all of These low moments for all of these challenges that I thought were gonna go a different way that completely blew up and turned out so different than I could have ever imagined. I see it all now as fate and me living out my life's purpose and being presented with true miracles. It's such a blessing. And as you start letting go of the resentment and anger and start forgiving and truly letting go at peace and with ease, doors just start opening for you where previously there weren't any. This I know for sure. This I know is a truth for you. Whatever you're hanging onto today that you know you need to let go of, I'm challenging you. Make it today the day that you let go. Make the decision that you are meant for more. Because I truly know that you are. Okay. Things don't always go as planned because you deserve better. Know that I'm cheering you on. Know that I want you to be your biggest cheerleader because there are going to be moments where you're going to have people like me right there with you, cheering you on. So proud of you. And I am so proud of you. I'm proud of you for investing in yourself. I'm proud of you for listening to this podcast today and doing something good for you. But know that there's gonna be moments you're gonna be alone and you gotta be the one to look in the mirror and remind yourself that you can do all things and that you are meant for more and that this is your moment to go for it. Okay, if you like the show, please pound share. Share it with somebody that you love. Please leave a review of the show. It helps so much. And when you tag me on social media and share this episode, it's a way for you to tell me, hey, Heather, I liked that episode. It was cool. Create more content like that and I will do just that. So if you could please share the episode, it means the world to me. No one succeeds alone, and that includes your girl. So I need your help. Please share the episode, tag me, leave a review and subscribe. If you haven't hit that subscribe button yet, oh, my gosh, what are we waiting for? Like, let's do this life thing together. I'm coming at you twice a week with new content, and I hope you're subscribed. I hope you're sharing the show. And if you want me to answer any questions, send me a DM on social media. Go to my website, heathermonahan.com. you can find me everywhere. Shoot me a note. I will always answer your questions each week until next week. Keep creating your confidence. You know I will be. 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.
Episode: Confidence Classic: You’re Meant for More Than What’s Holding You Back
Host: Heather Monahan
Date: June 2, 2026
In this highly personal and motivating solo episode, Heather Monahan shares pivotal moments from her journey—from climbing out of poverty to breaking the corporate glass ceiling to building her own brand. Through candid stories, she reminds listeners that life’s detours and hardships often set us up for greater success and fulfillment. The core theme: You are meant for more, and letting go of what holds you back is crucial to stepping into your true purpose. Heather encourages the audience to reflect, surrender the past, and trust that setbacks are setups for something bigger.
[02:08] Heather Monahan: Urges listeners to let go of mediocrity and the things that aren’t working, so they can reach their true potential. Surrendering and closing doors to what’s not meant for you opens new, better paths.
“The sooner you let go of mediocre, the faster you're gonna be able to grab great.”
“Living in that uncertainty is living in all possibility.”
Emphasizes faith: Trust that what lies on the other side of letting go is better, even though uncertainty feels scary.
“If you panic and freak out, totally normal, it will pass... The more we can learn to acknowledge, huh? I'm acting a little crazy right here. This is not gonna help. I have some grace for myself. I get why I'm doing it.”
Childhood Poverty [10:53]:
“What I thought was this challenge... I was ashamed about it. Now I have this totally different perspective... I'm so grateful that instilled this crazy work ethic and drive in me.”
Heartbreak and Betrayal [12:25]:
“I would have never taken that leap of faith... if that guy hadn't cheated on me. So yet again, things don't always go the way that you have them planned because you're meant for something bigger and better.”
Setbacks in Corporate Advancement [15:50]:
“Never take a no from someone who can't tell you yes.”
Getting Fired [21:46]:
“The sooner you let go of mediocre, the faster you're gonna be able to grab great.”
"Know that I want you to be your biggest cheerleader because there are going to be moments where... you gotta be the one to look in the mirror and remind yourself that you can do all things and that you are meant for more and that this is your moment to go for it."
Heather’s delivery is empathetic, candid, and relentlessly optimistic. She balances vulnerability (sharing panic, shame, heartbreak) with practical wisdom and a confident, encouraging energy. The episode’s tone is empowering and compassionate, urging listeners to trust in the process, forgive themselves, and boldly step into the unknown for the sake of greater purpose.
For more confidence-building episodes and interactive support, Heather encourages connecting via her website and social channels.