#194: Just Think BIGGER With Heather!
4 Nov 2025 · 32 min
Heather Monahan went from corporate jobs to a Top 40 female keynote speaker in 2020. She talks about the moment she decided to think bigger, how self-doubt crept in after early success, and why surrounding yourself with supportive people matters more than you think.
Chapters
Come on this journey with me each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. Fasten your seatbelt. I'm ready for my close up. Hi, and welcome back. I'm so glad you're back here with me today. Thanks for being here. Okay, so I'm working on a post right now. It'll already be live by the time you hear this, but I'm working on a post around. I've seen a lot of posts where it says I am a female, blah, you know, female CEO, I'm a female executive, I am a female author, I'm a female negotiator, whatever it is. And then they put a line through the word female and then the post goes on to talk about that. They don't wanna. They're not finding success because they're a woman. That's just part of who they are and they don't wanna be put in that labeled that way. So it's interesting because I'm constantly looking at trends, I'm constantly looking at what's working outside of my own work. If you're not doing that, oh my gosh, please do. Not that I'm not saying everyone's your competitor, but I'm saying there's information accessible to you, all around you. For example, I noticed on LinkedIn posts that were quote cards that had no text in the actual post, just the only text was on the quote card, did incredibly well. So of course I said, let's test this guys, to my team, let's create a quote card and not put anything in the actual comment area where I typically would write text. And it did. Unbelievable, right? So trends and what other people are doing can open your eyes to what's responding well. You know, what people are connecting with. And again, I'm not saying steal somebody else's, but make it your own, right? Use your quote and your words in that text post. Okay? So that's just giving you a little bit of insight into how I create content, especially for LinkedIn, which is where I double down. It's where 90% of my business comes from, 90% of my speaking engagements, everything really comes from LinkedIn. So it's super important to me. So I'm always looking at this stuff. Well, I start seeing that these female with the word female crossed out posts are doing really, really well. So I thought to myself, you know, I want to do one, but I like to do things a little differently, like with my own spin. I don't want to make it about, you know, being called female. And that's when it hit me is in 2020, I was named top 40 female keynote speaker, right? By Real Leaders. First of all, let me just tell you that two years before that, I wasn't a professional speaker, which is so ridiculous, by the way, because I'd spoken for 20 years publicly, but I just wasn't named a keynote speaker back then. I was named a C suite executive, so. So they don't count that. Whatever. That's when I just called BS to everybody. But, okay, that's Heather's opinion. You can have your own. But I just kind of dismiss those people saying, well, you're new to this industry. Well, so what? I've been doing it for 20 years. I have some expertise in this arena. I feel really confident when I'm on a stage and when I'm speaking. Luckily, that came through. I ended up, two years later, I was named Top 40 Female Keynote Speaker 2020. And to say that was shocking and surprising. Of course, I didn't even know these lists existed. I didn't even know about Real Leaders. And when it happened, somebody just tagged me in a post congratulating me. They had been checking the list and saw. And it was just super exciting, right? It's like one of those moments where you say, oh, my. Like, this is so unexpected. I had no idea this was happening. I'm so excited and randomly. It was on my birthday that the list came out in August 2020. So it was just. It was so cool. I was super proud. You know, when you put a lot of work into something and you just don't know if you're making progress, right? You're like, is this worth it? Am I connecting the dots here at all, or am I spinning my flipping wheels? You know? And anytime you enter a new arena, a new business, a new product launch, anything, you don't really know how you're doing until you start seeing some results. And sometimes that can take a while. So I was super proud, so, so excited and. And really honored. But of course, you know, 24 hours later, I'm sitting by myself, and I remember thinking, okay, I'm super proud. I'm super grateful, and I don't want to dismiss that. But inside of me, something inside me was saying, well, how do I get to become a top 40 keynote speaker, you know, and compete with men and women? Not just women. Again, still an honor to be on the top 40 female list, but how do I get onto the just overall top list? And that was the first thing that, you know, when I kind of grounded myself, I thought of was, okay, well, how do I go to that? How do I get bigger? Like, how do I get to that next, like the ultimate level? That's to me, the ultimate competition with men and women in it, right? And again, and not about saying I'm better than anyone, but saying that I'm at the highest level that I'm at. You know, I'm in their league. That's I want to charge the same things they're charging. You know, I deliver great results. I see, see the responses, right? I wanna go to that next level. And I remember thinking, okay, if I'm at the top 40 female now, after two years doing this, how long will it take to get to the highest level, the top 40 keynote speaker level? But then wouldn't, you know, immediately after that thought came into my mind, just go bigger, right? Turn up your light, shine brighter, go to the next level. Another thought came in my mind. Am I really qualified to go to that level? Right? That doubt. And I know this is funny, I have a new one. On one client, I just started working with a woman, and she was so funny. Our first meeting, she said, I just can't believe you were never not confident, Heather. I don't believe it. And I said to her, listen, and I'm saying this to you too, I swear to you, if people had seen how upset and mind blown I was when I got fired and had no idea what I was gonna do. Let me tell you, those were lowest of the low moments, right? Very similar to when the pandemic hit and my speaking business disappeared. Right? I've taken some big hits in the past few years, and what I've learned from them is it's really the only thing that will ever hold me back is going to be me. And I know that you know this in theory, but our confidence will get wrecked in these moments. It's happened to me a number of times, but the more my confidence gets wrecked, the more I say, okay, wait a minute. I know other times this has happened. I know I have the possibility and potential within me to rebuild this.
And.
And I know the steps I need to take. That's why I wrote my first book, Confidence Creator. And that's ultimately an extension of why I wrote my new book, Overcome youe Villains, is I wanted to share that game plan, roadmap and insights with anyone who would read one of my books and help them. So, yeah, I was completely lacking confidence in many different moments in my life. And I Just found out ways to rebuild it. So just letting you know that's true, because it just reminded me when this woman said this to me, people might actually think that I just always was confident. That's not true. And P.S. there's no one out there in the world that is just always confident. And if they act like that, they are arrogant, which is a difference, which means they're ultimately insecure. Okay, Just behind the scenes for you. Okay. So anyway, so I'm named top 40 female keynote speaker. I have the thought, how do I get to become a top 40 keynote speaker and get to the highest level, competing with men and women? And then immediately thereafter, I have the thought, am I really qualified to be at that level? Right. So it was great that I won something I was recognized for something super cool, super grateful. Even greater that immediately, within 24 hours, I started thinking, how do I go bigger and get to the next level? Right? Let's keep going. Let's realize our potential and go for it. But bummer that right after I did that, I kind of dismantled myself and said, wait a minute, am I qualified? So I'm sharing that with you. So, you know, if you go through this, right, you start to question, oh, wait, hang on a second. Who am I kidding? You know, can I do this? Those are the moments that we're chipping away at our confidence. Those are the moments that we're telling the universe, hold back. I'm not ready to go to the next level. Which is so weird because we were just trying to get to the next level, and now we're ultimately the ones holding ourselves back. So I didn't realize it at the time. Like most of us, right, when we're in it, we don't necessarily see it, But I remember, okay, am I really qualified? And I remember thinking, I don't really know. I don't know. Maybe time will tell, right? I just kind of. I left it there. So yet again, that's just a bummer. As I moved forward with my speaking career. So this is back in 2020. Everything's virtual. I start getting added to some major lineups and getting hired by some major companies. Google hired me, which was insane and super exciting. And. And then I headlined a conference, a virtual conference with Jamie Kern Lima and Daymond John. And there was my face on the COVID of the promo sheet next to Damon John, like they were saying, these are the two top speakers of our event. The event was incredible. It was a huge event. And that was in the end of 2020. And so I remember seeing that picture and that's sort of the moment where I said, oh, maybe this is proof to me, really, it's just for me, but prove to me that I am ready to go to that next level. So in that moment when I saw that, it was like a sign to me, you are ready to go to the next level, to be at that highest level.
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Okay, maybe this is possible. So this was months later, probably like, I don't know, five months after I was named top 40 female keynote speaker. Maybe five months later, I'm headlining this event with Daymond John. My picture's everywhere with his was crazy, surreal, so exciting. And that somebody else putting that image together, somebody else picking me to headline the event with him, allowed me to say, wait a minute, I guess I am ready to go to the next level. And that's when I decided it was possible. So here's the thing. I was never going to go to the next level until I decided it was possible. Do you hear that? This is what I want you to know. No matter where you are in your journey, no matter if you're in corporate America and you want to get to the next level, no matter if you started your own business and you wanna go bigger, no matter if you're in a job you can't stand and you wanna make a leap and go to work for yourself or do something totally different, you have to decide first. This is the most important thing, that it is possible and available to you. And until you make that differentiation, it's not going to be. It's going to be out of your reach. And thankfully for me, I had that moment. But I shouldn't have had to wait for that. Do you know what I mean? I shouldn't have had to wait for someone else to show me the high sign. I shouldn't have had to wait for someone to put that marketing material together and choose me and Daymond John to be featured. I should have chose it for myself. I should have chose it for myself. Back in August 2020, when I saw the top 40 female keynote speaker list come out, I should have said, that's great, super grateful for this, and I'm ready to go to that next level now. I'm good enough. I pick me. But I didn't. I waited five months, right? So, okay, I don't want you to wait. I want you to change your beliefs today. I want you to change what's possible for you today. Once you change that, everything ahead of you will change. And that's what happened for me. So I made that decision. Maybe it was December 2020 now. That's when the virtual conference was with Dame and John, and it went really well, and I killed it. And I was super proud and the feedback was great. And I realized, I'm here, this is my time. And wouldn't you know, nothing happened immediately, but it was December of 2021, a year later, and the top 50 keynote speaker list for 2022 came out, and I was on it. So it was Tony Robbins, Daymond, John, right? All these incredible. John Gordon, Ed Mylett, all these amazing speakers, and Heather Monahan. And it was one of those moments that I just. Wow. I couldn't believe it. I was so grateful. So, two things. Number one, go bigger, right? No matter where you are right now, just go bigger. And number two, believe it's possible for you, because if you don't, you will be the thing standing in the way of you going to that next level. And that is what I realized today. Also, surround yourself with people that are there to challenge you and support you to go even bigger. And. And I don't know if I mentioned this to you last week, but I had a meeting with. I'm on a content creation program with LinkedIn, and my manager met with me. He was in town and was leaving and wanted to see me before he left. And we're sitting down, speaking, and he said, talk to me about some goals, like, what can I support you on? What are you looking to do, Heather? And I said, you know what? We're moving into March. It's Women's Month. I really think that LinkedIn should be supporting and recognizing female leaders that are giving back and creating content to support others and recognizing women that are creating content on LinkedIn for business and shine a light on them. I'd like to be featured in something like that. And this was so great. You know, I thought that was a big ask. There's 400 million people on LinkedIn, right? Like, I think that's a big deal. And he looked at me and he said, why don't you think bigger? And I said, what are you talking about, think bigger? I thought, that's a pretty big ask I'm putting out there. And he said, hang on. And he pulled his phone out and he showed me a global TV commercial that LinkedIn just launched, which has content creators on it. I'm not currently on it, but others are. And he said, why don't you ask me to get you featured in this commercial? And it was one of these light bulb moments. I had never thought of that. It didn't even cross my mind. And I was so grateful to be sitting with someone that wasn't just going to cheer me on for my idea that I came up with and say, great idea, Heather. Let me see what I can do and walk away. But instead was gonna challenge me to say, why aren't you thinking bigger? So surround yourself with those people, and if you're not with them, pick your head up and find these people. Right? But first, here's the thing. You've gotta overcome the villains around you in order to go and find the ones that are there to stretch and grow you so they're never gonna show up, those people that you need to be surrounding yourself with. If you're around negative people or energy suckers or people who are holding you back in the past, the number one thing you need to do first is overcome your villains so you can set yourself up to take off. Okay, so to that end, today I wanted to read a chapter of my new book to you. This is from Overcome youe Villains, my newest book, chapter 23. The title of this chapter is Just Think Bigger. And I thought it was appropriate considering the story that I shared with you today.
Okay.
A true teacher would never tell you what to do, but he would give you the knowledge with which you could decide what would be best for you to do. Christopher pike, who are the people you spend your time with? Have you done an audit of these coworkers, friends and family? Are they holding you back, getting in the way of you achieving your goals, or catapulting you forward? What would it take for you to leave behind the people who are standing in your way and get you to go bigger? Okay, pause for a second. That's exactly what I was just telling you about. My LinkedIn manager, you know, he's pushing me to go bigger. These are the people I'm picking to hang with. Okay, back to the story. In the old days when I worked for a large corporation, my friends and I would regularly take vacations to the Keys or Palm Beach. We could easily reach either by car, and there were fabulous places to stay that made you feel like you were on your own personal island. We would usually go somewhere amazing during the major breaks when the kids were off school, Labor Day, President's Day, spring break, and the rest. That all changed when I became my own boss. As an entrepreneur with unpredictable and erratic income my first year, this didn't seem to be the way I could live any longer. I had a talk with my son and let him know we wouldn't be going on as many trips as I focused on building my company, which would take some time. I believe he understood, as this was our new life. But I wonder if I really did. Each time I would be asked to go on the next trip with my friends, I would politely decline and feel bummed out that Dylan and I were missing out on amazing trips. While I realized these are first world problems, they are when your life has been one way for 20 years, it takes a bit of adjusting. I also realized I didn't want to adjust. I needed to find a way to accelerate revenue faster and I hadn't been able to find that solution quite yet. I knew it would be there. I just had to be patient, persistent and find it. Revenue fixes all problems On Labor Day, I received the same ask to go to the breakers in Palm beach for the weekend with my friends and their families. I automatically declined as I had been doing for some time when I suddenly remembered my son was going on a trip with his father over that weekend so I would be able to stay in my girlfriend's room instead of having to pay for my own. The cost would be minimal and I would have a much needed opportunity to get out of the house and have a fun day and night with my friends. I was in I drove to Palm beach and was blown away by the massive hotel and all of the activities. It had been over a year since I had last been there. While I never missed my old job, I sure missed my old guaranteed paycheck. I met up with my friends. We all headed to the pool so their kids could swim and we could eat lunch. Janine and Bobby had been married for the past decade and had helped see me through all of my highs and lows. And they had two little kids who were adorable and consumed with the pool. When your kids are young, you have to play the divide and conquer game to ensure that one adult is always on watch, keeping your little ones from slipping underwater. Janine and I have been talking for a while when her husband Bobby asked for her to switch. That's when Bobby asked me to go sit with him and get some lunch. As soon as we sat down, he started with the questions. Bobby has been an entrepreneur forever. He gets excited talking about it and has enjoyed tremendous financial success. So for me, he is a great person to speak with and learn from. Anytime I can talk to someone who has been where I am and has broken through, it inspires me to do the same.
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Questions about what I had been doing and how it was going. I shared everything about my business. But then I added, I just don't know if this is really gonna work. I'm definitely keeping the door open that I just might go back to media and take a similar job to my old one, but with a better company. Those last couple of sentences were part of my standard script. I had told only a few close friends and colleagues that I was starting my own company. Because I was so afraid I would fail. I figured it was better that I kept it quiet. Bobby was floored. What did you say? Did you just say that you came all of this way but you may still go back to a career you outgrew years ago? No, I'm not letting you speak like that. In fact, you need to turn this around. You don't need to think smaller to keep yourself safe. You need to think bigger to make it work. Holy cow. I had never thought of it this way. I hadn't thought that the problem might be that I was trying to straddle my past in a train that was trying to leave the station. I had one leg anchored behind me and one trying to find a foothold ahead of me. There was no Way I could stay in that place anymore. It wasn't physically possible. I realized in that moment that if I was going to make this work, I had to go all in. Yes, I had written my book and I was building my business, but I still wasn't all in. I still had my eye on the dusty little path that would take me back to my old comfort zone in case things got too tough. I was still keeping a door open for a career that I should have closed the door on a decade earlier. Yet again, fear had snuck into my mind and worked its dark magic on me. And the whole time, I hadn't even realized it. Bobby sat with me for more than an hour, giving me ideas on how I could go bigger. I would say, I'm booking some good shows and promoting the book. He would counter with Fox News. Now that's big. Think bigger. Only the biggest is what you should focus on. No excuses. Well, I would, but I don't have an agent or a PR person and I don't know anyone there.
Ha.
When you were in sales and you needed to get to a client, what would you do? Well, I would send them a life size cutout of myself and I would show up and ask to see them. I would find someone we knew in common on social media. I'd ask for an intro. Bottom line, I would always find a way. Then Bobby went on to tell me that he had worked for Evel Knievel years ago. The lesson he learned from Evil was to never let any roadblocks stop you. Evil's personal roadblock was that no one knew who he was. Early in his career, he didn't have a big name and he did not command a big audience. He decided the solution was to make himself seem as though he had a huge audience and bring that audience to Caesar's palace in Las Vegas when they booked the date. So Evil marched right into Caesar's palace with no following, and he told them he would sell the hotel out with his show. He never even implied that it might not happen. He went all in on his vision, and guess what? He got the show. Had he said, listen, I'm not really sure how many people will show up or how the show's gonna go. We would have never, ever heard about IPL Knievel. Everyone starts as a beginner. Some stay there, some retreat. But others, the successful ones, they lean into the fear and claim their greatness. Hearing all of this made me extremely excited and very optimistic. I had been feeling down that I didn't have my old paycheck and within an hour I was raring to get back to work. Go bigger and bolder. Bobby asked me why I didn't have my books for sale in Costco. When I told him that it doesn't work like that because I was a self published author, he laughed. Excuse. He exclaimed. Let's do this. Get a stack of your books and you and I, we will head to Costco. I'll film everything, we will cover one of their giant end caps with your book and we will record what other people say when they pick it up and look at it. What's the worst that can happen? What will happen is we will get footage of people loving your book and then trying to buy it. Costco is going to have to bring it in. How about that? Well, I hadn't thought of that kind of approach before. I had been brainwashed in the conventional way of thinking, which was that self published books are sold only on Amazon.
No more.
No way. I am bigger than this. Bobby wrapped up our chat with a great analogy. It's like you're sitting on the side of a river looking in and saying, I know if I jump in I can swim hard enough and fast enough to make it. But for some reason I haven't jumped in. Realize this is the time to jump. Not next week, next month or a year from now. A year from now the current may pick up and you will not be able to make it jump. Bobby knew I could do it and I knew I could too. No more excuses or waiting for someone else to do it for me. I am jumping in now. I left the breakers that day overjoyed and anxious to go big and make major things happen in my business and in my life. I was so excited. As soon as I got home I put together an action plan. The steps I would take the very next morning, the emails I would send, the people I would call, the pitches I would send out, the meetings I was going to set up that next morning. I was ready to go big as an entrepreneur. No going back. No path to my old job. I closed the door once and for all on the past and stepped through the door to my new future. This was a game changer. After I finished my plan, I sent a thank you email to Bobbi and sat down to watch TV and rest up for the next day. When I would put the plan into action. I turned on Netflix and the movie the Secret caught my attention. I had heard of it before, but I had never seen it. So I sat down and watched. When it ended, I wrote down My main impressions from the film on a piece of paper. I still revisit it every day 9 to 18. What you focus on is what you attract. The secret? The creative process. Number one. Ask for what you want. Let the universe know what you want. Number two. Believe that it is already yours and have unwavering faith in what you cannot see. People don't know how they are going to do something. They just know they will. There is zero room for doubt. Number three.
Receive.
Begin to feel the way you will feel once it arrives.
Feeling good.
Putting out that frequency of what you are wanting. You have to feel it to make it real. Test drive the car you want. Go tour the house you want to buy. Create the real feeling so it will be the universe like speed. When you feel it act. Focus on what you do want, not on what you don't want. Visualize it. Feel what it feels like and stay in that space. Feeling. Here is my new manifesting statement that I am making real. I'm so happy and grateful that I've sold over a million books and helped so many people. Now money flows freely and easily to me. I create and enjoy my life by shining my light. Your wish is my command. What will you manifest for yourself? Key Takeaway it is essential to have people in your life who are ahead of you. When you surround yourself with successful people, they will inspire you to push past your current limitations and allow you to see something so much bigger in yourself that you hadn't previously thought of. Accessing knowledge from those who are light years ahead of us is priceless. Okay, so I just thought that that chapter really followed nicely to the story I was telling you earlier. I hope that you take this as a sign for you to just go bigger and go all in. Cut the excuses, cut the doubt and have unwavering faith that this is your time. If you like this episode, please share it and tag me. I will always repost Reshare on any and every platform. I am so grateful for you. Until next week. Keep creating your confidence. I'm gonna make it my own for again. I decided to change that dynamic and you like their map. I couldn't be more excited for what you're going to hear. Start learning and growing. Inevitably something will happen. No one succeeds alone. You don't stop and look around once in a while. You could miss it. Come on this journey with me.
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