Creating Confidence On Stage, with Heather Monahan

March 20, 2024
Today we explore what many of us struggle with - the power of confidence and self-belief. The trick is that confidence is a muscle we can work on every day, and we can create a strong foundation from within.
Creating Confidence On Stage, with Heather Monahan
March 20, 2024
Today we explore what many of us struggle with - the power of confidence and self-belief. The trick is that confidence is a muscle we can work on every day, and we can create a strong foundation from within.



Today we explore what many of us struggle with – the power of confidence and self-belief. The trick is that confidence is a muscle we can work on every day, and we can create a strong foundation from within.

Join us as Jess chats with Heather Monahan, who shares her transformation story from sales manager to successful keynote speaker, while emphasizing the value of authenticity and aligning personal stories with industry problems.

She also shares her tips on visualization and positive affirmations for public speaking success.

Heather Monahan is a Top 50 Keynote Speaker in the World 2022, TedX Speaker, Podcast Host of Creating Confidence, 2X Best-Selling Author (Confidence Creator and Overcome Your Villains) and the CEO of Boss in Heels.


Heather Monahan

Heather Monahan is a Top 50 Keynote Speaker in the World 2022, TedX Speaker, Podcast Host of Creating Confidence, 2X Best-Selling Author (Confidence Creator and Overcome Your Villains) and the CEO of Boss in Heels.

FOLLOW Heather


Today we explore what many of us struggle with – the power of confidence and self-belief. The trick is that confidence is a muscle we can work on every day, and we can create a strong foundation from within.

Join us as Jess chats with Heather Monahan, who shares her transformation story from sales manager to successful keynote speaker, while emphasizing the value of authenticity and aligning personal stories with industry problems.

She also shares her tips on visualization and positive affirmations for public speaking success.

Heather Monahan is a Top 50 Keynote Speaker in the World 2022, TedX Speaker, Podcast Host of Creating Confidence, 2X Best-Selling Author (Confidence Creator and Overcome Your Villains) and the CEO of Boss in Heels.

[02:53] Confidence is the key to speaking success.
[05:48] How a lost job led to intrinsic confidence.
[10:56] Caring enough or caring too much?
[17:26] How research, asking questions, and solving problems leads to increased revenue.
[23:29] Investing in yourself and declaring your worth.

Amplify with Jess is produced by Earfluence, and brought to you by Mic Drop Workshop.


Heather Monahan – 00:00:01:

And then I just let go. And I did this when I gave my TEDx Talk. I closed my eyes and I said. If you don’t walk out there, you’re never going to forgive yourself. If you walk out there right now and you blow it, I’m going to be so proud of you. Like I just take all the pressure off of me and I’m like, I’m going like this. If I’m not doing it for me, I’m going to do it for that girl coming after me. I’m going to do it for that person coming after me. I’m going. And then I just let go and let God and it works out.

Jess Ekstrom – 00:00:33:

Welcome to Amplify with Jess Ekstrom, a show designed to help women get out of their head and into their zone of influence. A recent study at Cornell found that men overestimate their abilities and performance, and women underestimate them. Sounds pretty on par to me, which is why we were talking to my dear friend today, Heather Monahan. Heather is a top 50 speaker, two-time bestselling author, and host of Creating Confidence podcast. A lot of times, speakers are looking for the tactical things. What do I charge? Who do I speak to? What should I say? But my experience at Mic Drop Workshop is most of the time, we need the tactics later and the confidence first, which is why I’m bringing in Heather today. Let’s find out how to boost our confidence with Heather Monahan.

Heather – 00:01:21:

Like anyone, I’ve struggled with my confidence all throughout my life because confidence isn’t something that’s static, right? Like you could be, I’m super confident in my workout that I just came from, right? I crush it when I’m running or I’m at spin and I’m super confident in that. Doesn’t mean I’m always confident in my romantic relationships. Doesn’t, I’m super confident on a stage. Doesn’t mean that when I take the biggest stage of my life, I’m not going to have a dip in that moment, right? So, there’s ebbs and flows through life. And as people grow and change and take on new opportunities, your confidence is not going to remain the same. So the important thing that I share with anyone I work with in regards to speaking is looking across your life and identifying, like me, working out. That’s like something that I own. I think I’ve pretty much always been confident in that other than when I got injured, right? So I look at moments like that. I remember when I was going into this race and I crushed it. And I came out on top and I was nervous going in. And then I hold that visual as, wait a minute, I know what confidence looks like. Now, yes, I’m taking a stage in front of thousands of people, but I’m parlaying that past confidence from this moment of this marathon and we’re running this or whatever, whatever that moment is in your life and use that as proof that you’re going to be able to find that confidence in this other moment that you’re stepping into.

Jess – 00:02:43:

Now, do you think that… Like, I guess for you growing up, because like anyone who sees you right now, I mean, sees that you are like top of the world. Best-selling author, really sought-after keynote speaker. I mean, I was like, the first time we met, I was like, oh my gosh, you know, feeling some imposter syndrome. What came first? Did you become confident because of your success? Or did you have to be confident in order to get your success? Like, and tell us, kind of take us back to the beginning, because I know your story is a bit untraditional.

Heather – 00:03:20:

No, I mean. You don’t need to be confident to be successful, right? I mean, there’s so many times in my life I haven’t been confident, but I figured it out along the way. I think that’s more the reality. Because if you’re constantly stepping into unknowns, stepping into fear, stepping into growth, you’re not gonna be confident all the time. I certainly have not been, but that’s sort of, that’s like the magic is that once you do that repeatedly enough. That becomes your normal. So for me, I have this incredible opportunity that coming up and insane, I’m so excited for it. And it’s going to be the biggest speaking opportunity in my entire life. It’s crazy. And I was on a Zoom with the person the other day. And he says to me, I mean, I don’t know if you’re going to be able to handle this. You know, you’ve never spoken to an audience of this size before. And I haven’t. And I said, you’re right. I spoke for 80,000 people for Amazon International Women’s Day. And I was thinking that was the biggest audience I was ever going to speak to. And I was nervous when I did it. He said, but you did it. Can you pull this one off? And I said, Oh heck, yeah. The reason why I know I can is because for so many other times, I’ve stepped into fear so many other times, I didn’t want to get on that TEDx circle. Oh, that red circle, I was scared to death. Right. But the more you step into fear, the more you step into these moments, the more it becomes normal that of course, it’s going to go amazing. But I also know the things to do. I have a routine and a process that I put into place that’s like, you know, pushing a button at this point, I’m conditioned, and I’ve conditioned myself, I know the things that I need to do, I know what to do when I feel nervous, I know how to override these things and actually put them to work for me to propel me forward into the fear.

Jess – 00:05:01:

What’s interesting is that you’re talking about how you just came from a workout, which is like your sacred thing that you do in the morning, and how your approach to confidence is very similar. You know, it’s a muscle group that’s trained. There’s a routine. You know what you have to do. The more you do it, the better it becomes. So is confidence a muscle group? Is that like how you approach it?

Heather – 00:05:24:

Yeah, I liken it. It’s very similar. It’s totally like a muscle. If you work it out every day, you’re going to get stronger and stronger and better and better. If you don’t and ignore it, it’s going to atrophy, right? It’s going to lock up on you. It’s not going to be a go-to for you. It’s not going to work. So yeah, I definitely, I liken it the same way, but I learned that not intentionally. I learned it through mistakes, right? I learned it because I felt like life was leading me there. Meaning when I was in corporate and I was getting advanced and getting promoted, I kept stepping into fear because I felt like it was what I had to do for work. And then I ended up getting fired when I was 43. And that was the first real intentional moment. I remember thinking, okay, wait, I’ve lost everything. My confidence is gone. Where do I go from here? And that’s when I got really intentional about, you know what? I’m going to create confidence within myself. I’m going to make that my intention. I’m going to make that my goal. And I’m going to make it a goal to have that confidence be from within me intrinsically, not externally, which I had been doing for years.

Jess – 00:06:27:

Yeah, it’s definitely, I’m guilty of that, of like trying to find the confidence from the accomplishments rather than the intrinsic motivation. Like it’s like, well, if I can just get this or if I can land on this stage or if I can get this accolade, then that will fuel my confidence. But there was like this interesting study, and I’ve probably talked about it on here before because, I’ve been kind of obsessed with research around imposter syndrome lately and how men and women approach. Like for a while they thought women experienced feelings of imposter syndrome more than men, but they realized that both genders experience it equally. It just manifests differently in like how we go about it. Whereas men, if they feel unqualified, they like, you know. Try to step into the role, fake it until you make it. Whereas women, and I know I’m generalizing here, but this is just what the research showed. Women try to overachieve in order to, like feel qualified, which leads to intense burnout. They’re like, if I can just keep achieving, then maybe I’ll feel confident and qualified to do the thing that I want to do, which is not the way to go about it. But it’s really tough to get out of that cycle. So what is, you said that you have a routine and kind of like something that you step into for your confidence. For those listening and watching, can you give us some steps of that routine that maybe we could try to emulate?

Heather – 00:08:00:

Yeah, so I was a psych major in college and I remember this. This scientists there that was called Pavlov’s Law, right? And so if you haven’t heard of it before, I’ll give you the short overview of it. Basically it was these researchers were training dogs that when they would ring a bell, they would feed them immediately thereafter. And what they ended up learning through this repeated process was they could ring the bell. The dog didn’t even have to see the food and the dog would start salivating as if he’d already, you know, he’s about to consume food. So it was a conditioning through the brain to teach them to actually have a body bodily response to something that hadn’t even happened. So I learned about that in college. And I remember as I grew up and, you know, was going into different situations that might be scary or whatever, intimidating in business. That I would, hey, I should condition myself to overcome fear, to overcome, you know, this feeling of doubt or lack of self-worth. And so essentially that’s what I’ve done is I, and I recommend this for anyone. It’s science, it’s fact, it’s neuroscience actually, and it works. So I have a playlist that I only use right before I’m going to take major stages. And I love it so much. And everyone always says, what’s the songs? It doesn’t matter what the songs are. You should pick whatever your songs are people. But I mean, mine is like Drake, it’s Jay-Z, it’s all thug life hip hop, and I worship it. And I only let myself listen to this playlist right before I’m going to take a massive stage, right before I’m going to do something super scary, because what happens is I’ve done it that way. I’ll use this one example, it’s popped into my head. I was going on the Steve Harvey show and I was super intimidated. I was the only person that didn’t know him out of everybody that was going on that day, really intimidating. And I used my playlist that day. And I was like, to condition my mind. And I was in the green room with my AirPods playing, locked in. I start visualizing everything going well. I always write on the bottom of my shoes. I can, and I will. Like I have this, I wear my power colors. Like if I’m super nervous, I’m always going to be in blue or I’m going to be in red. Like there’s certain colors. I’m very thoughtful and intentional about what I’m about to do. I lock in with my music. I remind myself of three other times in my life that I was nervous and I faced the fear and I came out on top. And then I use that as proof that I’m about to go do it again. And then I just let go. And I did this one, I gave my TEDx talk. I closed my eyes and I said, If you don’t walk out there, you’re never going to forgive yourself. If you walk out there right now and you blow it, I’m going to be so proud of you. Like, I just take all the pressure off of me. And I’m like, I’m going like this. If I’m not doing it for me, I’m going to do it for that girl coming after me. I’m going to do it for that person coming after me. I’m going. And then I just let go and let God. And it works out.

Jess – 00:10:56:

And I think that one of the things that you said that I think is like a really important dance that can be tough to strike is like caring enough versus caring too much. You know, it’s like before you have an opportunity, of course you care about it. But sometimes when we like grip things too tightly, like this has to go well or this is my make or break, it can be suffocating to the experience. Would you agree?

Heather – 00:11:22:

Oh yeah. I felt like that about my TEDx because you know, when you give a TEDx, it’s more like of a legacy piece. It’s, you know, it lives forever on the site. If you bomb your school, like there’s no do over, but then, you know, it’s funny here I am years later. It was, I gave it in 2019 and I realized Mel Robbins has done hers over. Like there’s other, actually people do do them over, but I had all this pressure on me that this is your once in a lifetime, you have to nail it. And gosh, I almost crushed myself. It was ridiculous. I’ll never forget that day. And I’m so grateful that I put that pressure on me because I learned to your point, I will never do that again. Like it’s comical now to look back. Instead, I had another moment that was intimidating. I was interviewing Sara Blakely live on a stage in front of thousands of people. My feet sweat when I get nervous, I was walking out on the stage. And my foot came out of my Louboutin, which has happened before when I get super nervous and I almost felt like I almost face planted in front of Sara Blakely in front of thousands of people. But luckily for me, I was at a point in my life where I was like, oh, well, I almost fell on my face. I might as well lean into who I am and make a joke about it. Right. So I just owned it. And I was like, who wants to shout out for the hometown girl that almost face planted? And people went crazy. Like it was you think I was like a full blown comedian. And so I’m experiences like that teach me like step into your quirkiness, step into what makes you funny. I wish when I gave my TEDx, I stepped out there and said, anybody else nervous or is it just me? Like, own who you are and whatever is going on in your life in that moment. And that attracts people towards you and makes you more relatable and you connect more and it puts you at ease.

Jess – 00:13:08:

Totally. I think that when we’re trying to be perfect and when we’re on stage thinking like, I have to get everything right. I have to hit every mark. I can’t stumble at all. It, it, it feels like suffocating. And then it also like, to your point, isn’t relatable to the audience. I listened to this podcast episode of like Amy Schumer and all these like comedians, and it was a time that they bombed. It was like, talk about a time that you bombed and how you handle it. Like, you know, not every joke is going to land. Not every line is going to be a life-changing line that people are going to take with them. So what do you do after that? And one of the things that one of the comedians said is like, anytime something goes wrong on stage, you know, someone is talking or there’s a, you know, noise or I bomb a joke. I always ask myself, what’s the most honest thing I can say right now. And usually whatever that thing is that I say gets like 10 times the laughs than whatever I was going to say before. So being able to be truthful and still be yourself on stage, instead of almost feeling like you have to step into a role can be really empowering of like the only role that I need to do is myself. So what was your, I’m curious, like, I actually have never asked you this before. What was your first gig? You know, you’re the first time that you were asked to speak. Do you remember?

Heather – 00:14:36:

Well, I mean, I’ve been speaking. I was a sales manager in corporate America when I was 23. So the first time I spoke publicly was when I was 23 and I addressed a team. And I stood up in front of a team and spoke to a team. And then those audiences grew as I became a VP of sales and EVP. And then I started speaking for the industry. And I was speaking in front of thousands of people. But it wasn’t called keynote speaker or paid. It was you’re an executive and that’s part of your job. So I didn’t even know the speaking business was a business until I got fired. I posted I had been fired. That post landed me in the Elvis Duran show. Halfway through that interview. He’s like, you’re writing a book. I said, oh, I am, okay. So I wrote a book. You know, thank you, Elvis Duran. And then I Googled, how do you sell books? And it said speak. So I thought, oh, I’m a great speaker. That’s easy. I speak all the time. I didn’t even know. I’m like, I’ll just call people and ask if I can speak. So I started cold calling businesses like, oh, hey, I want to come in and speak about innovation and business. Blah, blah, blah. And so all of a sudden, one day someone said, what’s your speaker fee? I’m like, hold, please. And I Googled speaker fees. And I saw Gary Vaynerchuk was getting at the time. I think this was 2019. He was getting $300,000 for a 60 minute keynote. And I was like, what? Hold the press. What is this? And I went down the rabbit hole. And then I really immersed myself in understanding. I didn’t have any grasp that there was this multibillion dollar industry. And so I started researching bureaus and agents and keynote topics and who pays for speakers. And I guess during that time, one of those people I’d cold called had offered me money when I called. I don’t know. I think I just said like, oh, $5,000. I just said like a random number. And maybe that was Royal Caribbean. It was one of the companies local in Miami. That gave or paid me for coming in, which I’ve been doing for free for about a year. And that was like, you know, like anything, once you see money for something, you’re like, oh wow, there’s probably more of that out there, right? Like I could probably keep building on this and growing this. And that’s when I just really leaned into it.

Jess – 00:16:47:

And when you were cold calling these places, which is a total baller move, I love that. What were you saying? Like, do you need a speaker? Did you even have like a keynote of like what you speak on? You were just going for it.

Heather – 00:17:02:

Well, don’t forget, I had for 25 years, I had led sales teams in corporate America. So that’s what I’m an expert in, right, is leading sales teams. And so what I would do, what company, anytime you’re going to ask for something, put your, immerse yourself in that person’s shoes, right? So if I’m calling a company, let’s use Royal Caribbean, for example, I’m thinking to myself, are they happy with their sales? Typically, any organization wants, you know.

Jess – 00:17:28:

Wants more sales,

Heather – 00:17:28:

Increased revenue, right? Right. So and I know that because that was my job for 25 years. So when I would approach somebody, I would do some homework on them, first and foremost, you know, just do a random cold call. Like I’d research the company trying to understand, you know, if they’re publicly traded, where are they last quarter? What are their forecasts? You know, what’s happening in their industry? Immerse yourself in their world. Then I would call and get them to empty their glass to me, right? Call and ask great open ended questions. And so, hey, it’s so great to be connected with you. I’m reaching out today. I heard in your industry, business was. Slowing down a little bit. What are you guys currently running into? I’d love to be able to help you solve problems and get things back on track. Have them empty their glass once you understand what they’re specifically dealing with. And then you see a pain point that you can solve for them. That’s where you jump on to say, I’m so glad that you brought that up. Actually, for 25 years, I was leading sales teams addressing this issue and fixing them readily. I’d love to have the opportunity to come in, address your team and help you solve that problem at scale.

Jess – 00:18:29:

Love it. Love it. I mean, that is one of the things that, you know, we teach in Mic Drop Workshop is like, you can’t just pitch a story. You can’t just pitch like, hey, I’m Heather. And this is my story. Or hey, I’m Jess, this is my story. That’s how I got started. And I was like, why is no one? Why is no one biting? You have to look at the industry. Yeah, no one cares. You got to look at the industry, see what the problem is, and then how can your story solve that problem? So I love that approach. And like, I’m sure that Royal Caribbean, you were not batting a thousand. Royal Caribbean, you know, converted, but I’m sure there was many people that you called that didn’t. And that’s just the name of the game is putting yourself out there. And in like each time learning, okay, that didn’t work. Let’s figure out the next one. One of the things that I love, I think this is in your book and you also posted it on your LinkedIn recently, is like life is a constant tug of war between two forces. Actions that elevate your confidence and then actions that erode your self-belief. And I was like, yep. And especially this year, you know, after having Ellie and just like trying to figure out who I am, realizing that my actions that I take are basically like a. Scoreboard for who I want to be in that confidence. And some actions can also take those points away. So I’d love if you could elaborate on this, like how can we use, instead of just forcing ourselves to be confident, how do we use our actions to do that?

Heather – 00:20:10:

Oh my gosh. It’s such a, well, first of all, being a new mother is you’re starting over as a rookie at something totally new. You have no expertise, no experience. It’s that is a, I’ll never forget when I started out as a new mother. It’s so intimidating. It’s imposter syndrome. It’s all the self-doubt, all the lack of confidence. So normal. Like you’re in such a good company. Right. And it’s like, it’s like anything. It’s like the first time you take the big stage. Oh, you have no idea what’s going to happen. But to me, that’s even harder being a first time mom, because someone’s life is like, you’re responsible to keep them alive. I remember I used to say that to myself, like, this is fast. Yeah, yeah. Like it’s mad I like anything over time you’re gonna be like I know I already see you traveling with her and like you’re seeing like oh my gosh she’s still alive it’s working out like wait a smile are you freaking kidding me I’m killing this game and suddenly it’s so funny this morning my son like was running so late and didn’t say I love you and whatever and then I, I got a text like 30 minutes later, sorry mom I love you have a great day. And I’m like boom, I’m killing this game, right? Like you have these moments later on that you’re like, oh boy, I’m really good at this I think because it’s really working out. So have faith that like the confidence is going to keep continue to come it’s going to get easier and easier just like everything but you know in any day this is a great example had I not gone for my workout this morning? That would have shift away at my confidence during the day, because it would have been a way for me even though my morning was crazy and chaotic it would have been a way for me to say i’m not that important. I need to put other people ahead of me even though like, I was a little panicked about being late like or whatever I’d rather show up a couple minutes late, and do the right thing because I’m proud of me and like I own that and rock that all day long and also showing up for friends that I love like that makes me proud of me right like doing to me it’s all about like doing that next right thing and the only person you need to ask that question to is yourself like, in this moment, if I show up and do this, am I going to feel better about who I am or worse. And like if you start looking at things through that lens on a continuous basis it makes making decisions very easy.

Jess – 00:22:32:

One of the things I pulled out of that is follow through, I think has a lot to do with our confidence level. Like when we think like, I’m going to work out or I am going to write a book or I am going to do this thing. And it’s like, we’re setting the tone and the longer we sit with that and don’t do it, I feel like the more it erodes our confidence. Like I know that I’m almost having, like when I wrote Chasing the Bright Side, like my confidence was going because I was like, this is the thing I want to do. And I, here I am doing it. And now I’m writing my next book and I realize like, oh, I, the longer I sit with this, like the more I’ll start to get in my head and I just need to put the pen to paper and do it because that cognitive dissonance is like. Can really do some damage to your confidence level. So as we close, for those who are listening, who are like, either speaking, wanting to speak, really wanting to just kind of step into their confidence, own their presence, what are some words of advice that you have for those people looking to become speakers and present with confidence?

Heather – 00:23:49:

Oh my gosh. Invest in yourself. Like first of all, the act of investing in yourself, hire someone that’s already done what you’re doing, right? Like, because here’s the things there’s someone out there, Jess, who has the roadmap for you. She’s already done it. She already put the pain and years into figure it out. You don’t need to reinvent the wheel and stumble around and get lost and get discouraged. She’s already got it figured out. When you actually invest in yourself, you’re saying that you’re worth it. You’re saying that you’re worthy. It’s like me going to my workout this morning. It just reminds me I am worth it. Make yourself your number one priority. Show up and invest in yourself. And by even making that declaration to the world, to the universe, to yourself, you’re going to see doors start opening. People in my communities, I know you’ve seen this too, Jess, and they’re like, you’re not going to believe what just happened. This came out of nowhere. No, it didn’t. It’s because you made the intention, like you decided you were going to start showing up for you. You decided to start investing in you. You decided to say, I’m going to raise my hand and take this action now and declare this. And watch, when you’re meant to be doing something like that and you take that leap of faith, great things just start happening.

Jess – 00:24:56:

It’s so true. And I know that maybe some people like listening that are like, yeah, okay, no. Like one of the things that we do first thing in Mic Drop Workshop or Mic Drop Academy, before you even have your website, your demo, any of that, just put the word speaker in your bio, put it on your LinkedIn, put it in your email signature, just by naming and declaring that this is what I want to do. You have no idea the opportunities that come from that. Like we have people message us that are like, I literally changed the word speaker of my LinkedIn header and I got an inquiry three days later. And like that kind of stuff can just happen in the small changes and those small declarations that we make. And it also impacts our confidence, which you know better than anyone. Anyone who is watching or listening, definitely go follow Heather on LinkedIn, order her book, Overcome Your Villains, listen to her podcast. I believe I have two episodes on creating confidence now. So definitely listen to those. But Heather, thank you so much for being here. Where else can we find you? What’s going on in your world right now that we can be a part of?

Heather – 00:26:04:

Oh my gosh, just stay tuned. Major, major announcements coming in September. I’m so grateful. I’m so thankful. I can’t wait to share it with everybody. And thank you so much, Jess. You’re the best.

Jess – 00:26:15:

Yes. Okay. Give Heather a follow. Thanks everyone for listening. Bye everyone. Thanks for listening to Amplify. If you are a fan of the show, show us some podcast love by giving us a rating and review. And give us a follow at Mic Drop Workshop and @jessekstrom. This episode was edited and produced by Earfluence and I’m Jess Ekstrom, your host. Remember that you deserve the biggest stage. So let’s find out how to get you there. I’ll see you again soon.


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