Building Your Confidence with Heather Monahan- CR49

Sometimes, getting fired from your job can be a blessing in disguise. This was true for Chief Revenue Officer turned professional speaker and author of "Confidence Creator" Heather Monahan. In this episode of Career Relaunch, Heather shares her thoughts on the power of revealing your vulnerabilities, asking for assistance when you need it most, and taking steps to become more confident in your career. In the Mental Fuel segment, I also share some thoughts on how simply asking for help made my transition from the US to the UK much smoother.

Sometimes, getting fired from your job can be a blessing in disguise. This was true for Chief Revenue Officer turned professional speaker and author Heather Monahan. In this episode of Career Relaunch, Heather will share her thoughts on the power of sharing your vulnerabilities, asking for assistance when you need it most, and the steps she’s taken in her career to become more confident. In the Mental Fuel segment, I also share some thoughts on how asking for help made my transition from the US to the UK much smoother.

Key Career Insights

Journaling allows you to look back and gain strength from seeing how far you’ve come
Getting rid of negative people in your life opens up opportunity for positive people to come into your life.
Allowing yourself to be vulnerable and being very transparent with the kind of help you need gives you an opportunity to receive that help.
Done is better than perfect.

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Done is better than perfect.


Heather Monahan


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You gain strength from seeing how far you've already come.


Heather Monahan


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Resources Mentioned

Check out Heather’s book Confidence Creator, filled with her personal stories of her own career turning points and how she built her own confidence along the way.

Listener Challenge

During this episode’s Mental Fuel segment, I asked you to consider one area in your career where you could really use some help. Then, once you’ve identified that area, to let people know you’re looking for help in this area. You might just get that nudge in the right direction, the introduction to someone who can make a difference, or an idea you hadn’t thought of that helps you turn a corner.

About Heather Monahan, speaker & author

Heather Monahan is a best-selling author, keynote speaker with the Harry Walker Agency, brand ambassador for Perry Ellis International, entrepreneur, and founder of Boss In Heels. Having worked nearly 20 years in Corporate America, Heather’s been named a Glass Ceiling Award winner, one of the most Influential Women in Radio in 2017, and a Limit Breaking Female Founder in 2018 by Thrive Global. She’s also a member of Florida International University’s Advisory Council, serving as a mentor and leader in the South Florida Community. Most importantly Heather is Dylan’s Mom.

Be sure to check out Heather’s Creating Confidence podcast where she provides techniques and strategies to create your confidence, pursue your dreams and leapfrog the villains you’ll meet along the way.

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Episode Interview Transcript

Teaser (first ~15s): I had been putting myself in a box my whole life, and that was wrong. I realized that my strengths, my skills, just like anyone’s, can apply to any lane or any career. It doesn’t have to be just the one you have experience in.

Joseph: Hello, Heather. Welcome to Career Relaunch.

Heather: Hi, Joseph. Thanks for having me.

Joseph: Thanks so much for making time out of your busy schedule to join me here today, Heather. I know that you’ve had a really busy few weeks recently. We’ve got a lot to cover today, because I want to talk about your former life in radio, your career transitions, your current book, and some of the career lesson you go through in your book. I was wondering if you could just start us off by telling me what you’re focused on right now in your career and your life.

Heather: Sure. Since my book dropped May 22nd, I was picked up by the Harry Walker Speaker Agency. I’ve been speaking somewhere different every single week. It’s really been intense. From New York City to heading to Las Vegas in two weeks to speak to the WNBA. That’s been taking up a lot of my time. I just finished editing the video version of my book, which will be dropping in the next couple of weeks. It’s been pretty exciting.

Joseph: Wow, very cool. I just wanted to thank you for sending me a copy of your book. I want to definitely come back to that, because there are some really great points that you make.

I was wondering, Heather, if we could just go back in time, first of all, because you’ve had a very interesting career. I know you haven’t been an author or professional speaker. I was wondering if you could take us back to your time at the Beasley Broadcast Group, when you used to work in radio, and then maybe we can move forward from there. Can you just tell me what you were doing there, and then we can talk about some of your transitions afterwards.

Heather: Fourteen years ago, I started a publicly traded radio company as a director of sales. I saw an opportunity in the company that there was no leader for the sales organization. I pitched myself for that job, for VP in sales. I got that job. I was in that job for a few years, and I saw the opportunity for advancement. I pitched myself for executive vice president and then, ultimately, chief revenue officer. I was promoted time and time again.

In July 27 of last year, 2017, I was fired. That’s really the moment where I made the decision to go out on my own and start a completely new career at 43 years old.

Joseph: When we spoke before, I know that one of the things that you did, which is something that is quite common for a listener on this show, Heather, is that you started to work on some side projects. Can you just give us a glimpse into what you were working on and how that was coordinated with your day job prior to you departing from that company?

Heather: A couple of years before I was fired, I decided I wanted a little bit more purpose in my day-to-day life. I tried creating a women’s group within my division at the company to really unite women to support one another, and ultimately I was shut down when the founder’s daughter found out what I was doing. Her brother said to me, ‘Why don’t you just do this in your own personal life so no one can shut you down?’

At that time, I decided to launch my own website, HeatherMonahan.com, and a tribe called Boss In Heels, which is all about being a leader in your own right, whether you’re a man, woman, no matter what your background. I created a community where I could share all of the things that I didn’t know when I was a young person – basically, what it takes to get ahead. I really wanted to give back and be that person and mentor for me that I didn’t have when I was a younger person.

I created that community. I started writing at night and creating blog posts and social media posts on all the different platforms. When I was challenged that it was possibly taking away from my work, my day-to-day job, I hired to people to manage it for me, and then I would just evaluate it at nights and on the weekends to ensure that it was really my voice and my message that was getting out there.

Joseph: You mentioned that you tried to do this within your company, something similar, and that your employer also didn’t react that well to you doing this on the side. Can you just share with me what that was like for you to have your current employer basically dissuading you from doing something that you were so passionate about?

Heather: Ultimately, it became harassing. It was just a horrible time for me, personally and professionally. It was one of those moments in my life where I decided, ‘I’m so sick of being bullied and intimidated because of a paycheck and a job,’ that I decided I’m going to stand up for myself anyways.

When I got the phone call and was told to shut it down, I said, ‘I’m not going to shut it down. This is a positive message. This is something I am passionate about. This has nothing to do with work. I hear your concerns, but they are not valid. I’m going to move forward.’

I ultimately put disclaimers on everything so that people would know this wasn’t the voice of my employer. This was my personal voice. I really started building my confidence during that whole time by standing up for myself, but it definitely was not easy.

Joseph: Was this ultimately what got you fired, or was it something else, and how did you react to being fired?

Heather:  This was definitely the catalyst. This initiated the drama for me at work. When I didn’t back down and do what this woman wanted, that’s when things got very difficult and tumultuous. This started me down a path that… I still didn’t think I’d be fired, because I’ve been in the company so long – I had just been voted one of the most influential women in radio in 2017. I was on so many different boards, and I had so many great relationships. I couldn’t imagine that I’d be fired.

However, I knew she didn’t like me. I knew she didn’t like what I was doing, but I knew what I was doing was positive and it was within my rights. At the end of the day, she fired me saying that my position, Chief Revenue Officer, was no longer needed and therefore I wasn’t needed either.

It is what it is, and I got fired. I felt terrible. The whole meeting after 14 years lasted about three minutes. I drove home my three-hour ride home crying and basically sat on my couch for 24 hours under a weighted blanket, wondering what I was going to do with my life, because I was under a non-compete, so I couldn’t go back to my same industry for months. I really didn’t know what to do, so I was really devastated.

Joseph: How do you bounce back from devastation, because I know that it sounds like you’re doing really great right now, but what I want to make sure that we talk about today is how you ended up digging yourself out of that hole and finding your way forward. Could you just walk us through what you did after those 24 hours?

Heather: Luckily, I’ve been journaling my entire life, and I recommend that to everyone, because journaling allows you to look back at different moments in your life and gain strength from seeing how far you’ve come.

I’ve been divorced. I made it through the recession. I’ve been cheated on. I’ve been sexually harassed at work. I look back at all of these moments, these low moments in my life, and they gave me courage in that low moment that I was faced with yet again.

Through all this adversity over the past 43 years, I started to learn a solid plan that can allow me to get out of trouble. What I did 24 hours after getting fired was I created a 30-day plan which was finite. It’s not too big. It’s palatable, and I crossed off the days. I wrote down specific things that I wanted to accomplish each day, so I could feel proud about myself.

I also realized that getting rid of negative people in your life, like that person I was working for, opened up so much opportunity for positive people to start coming into my life, which wasn’t happening before. I recorded all of those things in that 30-day plan. I started creating a vision for where I wanted to go.

Each day and each step that I took brought me closer. I didn’t know where I was going. I just knew I was moving forward. That brought me to the day—within one week after being fired, no one knew I was fired—I decided I’m going to take control of this. I’m going to post social media that I’ve been fired, I am devastated, and I need help.

People thought I was crazy for doing that, but that ended up being the single game-changer for me in those low moments and low times. I had thousands of people reach out to me trying to help me, offering me connections, offering to put me on different shows and to help me and hire me. That was a real catalyst for change for me that first week.

Joseph: That’s a great lesson. I know that you and I first crossed paths when you shared that tip for a Forbes article I wrote about, LinkedIn and how important it is for you to be transparent about what you’re going through. I think that that’s a really great tip for people who are going through a transition to actually let people know about it. Is that how you eventually landed your gig as a brand ambassador? How did you become a brand ambassador, which I know is something that you started doing late last year?

Heather: No. That, actually, was very separate from this initiative. I had realized that, when I was fired, I wanted to really align myself with the Marquee Brand, because I knew that, going out on my own, I was going to be a one-man show, and there’s not a lot of credibility at first until you start creating some success on your own. If I could partner and align myself with a successful proven major brand, that was really going to elevate the perception of me.

I targeted a local company which a multibillion dollar company, Perry Ellis International, and I was relentless in pursuing that CEO. I did not stop. For 45 days, I pursued him every way that I could. I had come up with a great idea that was going to bring him value, and I just wanted a meeting. Eventually, after many dark nights of no response, he responded, took the meeting, and he loved my idea. We started working together.

Joseph: Very cool. I want to switch gears, and I definitely want to make sure we spend a good chunk of time talking about your book, Confidence Creator. Before I do, Heather, I just want to go back to something you said earlier, because this is something that’s been on my mind which you mentioned something about getting rid of the negative people in your life.

I’m just curious. How do you go about doing that? I guess what’s behind my question is this is something I’ve been think about recently also. If you’ve got people in your life who just make you feel either bad about yourself or you just don’t feel very good around them and yet they’ve been a part of your life for a long time—I don’t know if that was your situation—I’m just curious how you managed that, I guess what I’m going to call, like a purging process of getting rid of negative people in your life.

Heather: It’s huge. That’s the single thing I point to for anyone that can be the greatest catalyst for change and really help you in a very quick time period. It doesn’t need to be some long, drawn-out thing.

It’s a discussion, first with yourself, that you’re deciding to remove negative people from your life. I call it firing negative people, and then it’s just a simple conversation with them, which can literally be, ‘This isn’t working for me right now. I don’t feel great when I’m around you, and I’m going to give myself some space. Thank you for understanding,’ and then you move on.

You’ll see over time, that person will stop calling you, stop contacting you, because you’re not going to respond anymore. Now, it becomes more challenging when that person is a member of your family. There’s a lot of people that have relatives that might not lift them up. They may be trying to drag you down.

That’s a different conversation, but still taking emotion out of it and saying, ‘Mom, I love you very much. However, when you speak to me like this, I don’t feel great about myself, so when we get to a point in the conversation where we’re going to end up here, I’m going to have to disconnect the call and go on my way.’

When you do that repeatedly, that person will learn that if they speak to you that way, you’re going to be gone. They’ll either change their ways, or they’re going to respect you and give you a little bit more space which is going to help you.

Joseph: Very good advice there. That’s a good segue way into your book Confidence Creator, Heather, because it sounds like that act in and on itself does takes some confidence. I want to, first of all, talk about your process of writing the book and then a few of the points you make in the book which I feel are especially relevant to career changers.

First of all, I got to thank you for sending me a copy, Heather, because I get sent a lot of books these day. I don’t always get around to reading them, but I decided to read yours because I just really appreciated how honest and simple your messages are. It’s also kind of a page turner. I was wondering if you could start by just telling me how you came up with the idea that you even wanted to write a book.

Heather: When I asked for help and I put it out online, the Elvis Duran Show reached out to me and said, ‘Hey, if we can help you, let us know.’ I said, ‘Sure, I’d love to be on your show.’ They have 10 million listeners every day.

I went to New York. I went on their show. By the middle of the interview, Elvis asked me, ‘Well obviously, you’re writing a book, Heather, aren’t you?’ I wasn’t sure at that point if I was or if I wasn’t, but I realized in that moment, I was going to make a commitment to 10 million people that I was going to create a book. That moment where you hold yourself accountable to other people really allows you to move forward. I made that decision. In the next second I said, ‘Yes, I am writing a book.’

When I got home—I had been writing every day—I mocked up a book with a fake cover. I gave myself a deadline. I wanted it done within one year. I really fast-tracked my progress. I started looking for an editor.

Once you start pulling in a mentor, like an editor, someone that can help you leapfrog through the challenges that you have because they’ve seen that movie before and they know how to get you where you need to go, you really start moving quickly.

Joseph: It sounds like you actually gained some leverage on yourself, which is something we talk about on this show. It’s like you’re making a public commitment to do something, and that forces you into action, which is really interesting.

What was the process like for you of writing the book? I know you mentioned you got an editor to help guide you through the steps of it, but what was the day-to-day like for you to get your thoughts down on paper?

Heather: I think everyone overcomplicates this. I just sat down and wrote. Really, the day I started which was earlier on, I just Googled, ‘How do you write a book?’ It’s about making the time commitment. It’s nothing more than that.

When I started, I didn’t know I was writing a book about confidence. I didn’t know I was writing a book about my lowest moments. I just simply sat down each day and wrote whatever was in my mind. Within a few weeks, I started seeing that there’s a pattern about challenges and overcoming challenges, and I started to realize, I was writing about building confidence.

Joseph: Interesting. I’d always just presumed that you had set out to write about confidence, because it is such a strong theme in the book. That’s really interesting that that came to you more organically.

What about the publishing process? How did you go about actually creating the physical book once you had it written?

Heather: That, I found to be much more challenging. Self-publishing is hard. I looked at the potential of going the traditional publishing route, but the problem is it takes months to pitch yourself and present yourselves to sell a publisher onto you, which I really don’t want to wait that amount of time.

When I found out, to get in their queue, it’s usually 12 to 18 months from that date that you signed with them that your book will come out, when I heard that timeline, I said, ‘No way. I don’t have a year or a year and a half or two years to wait. I need traction and action now.’

I decided to self-publish. Again, I Googled, ‘How do you self-publish a book?’ I just piecemealed them together. The reality is if you are committed to finding ways through the obstacles and finding solutions, you’ll find them.

I asked for help, and I was relentless in my pursuit of researching who could help me design the cover, who could help me with the layout, and I ended up finding a company that had an a la carte service that really allows you to pick. If you want someone to edit your book, they have someone for a fee for that. If you want someone to design the layout, they have someone for a fee for that. I decided to go that one-stop shop and then just pick the pieces that I needed, so that I didn’t have to go running around dealing with a lot of different vendors.

Joseph: Through the process of writing and eventually publishing this book, I’m curious, Heather, was there something that you learned about yourself?

Heather: I learned that I had been putting myself in a box my whole life, and that was wrong. I believe that my box and my lane was sales. It was leadership and it was business. That’s where I belonged because that’s what I knew.

I was so scared the day that I decided to jump out of that lane and jump into this author lane, entrepreneur lane. I was petrified, and so many times, I nearly gave up and just started applying to old media companies and trying to get back to what I knew I was good at.

By getting rid of the lanes, blowing up the box, I realized that my strengths, my skills, just like anyone’s, can apply to any lane or any career. It doesn’t have to be just the one you have experience in.

Joseph: I know you were also recently featured in Thrive Global, which is very cool. Congratulations on that. One of the questions that they asked you was about some of the lessons you learned or some of the things you might do differently. I’m just wondering what relation to the book… It sounds like it’s going really well. If you could do it over, what would you do differently, if anything?

Heather: I believe done is better than perfect. You can drive yourself crazy over moving the title up a quarter, a centimeter or the color shift, but one thing that I would’ve done was I would have read through my book in completion again. There’s a couple of small errors I would have tweaked. Same thing with my audiobook. I decided to narrate that on my own which I was so scared of, but it’s really meaningful now when people hear it, because it’s me and my emotion coming through the stories, which is really powerful.

However, there are a couple of errors in the audio book as well, but I was so fixated on getting the book to market that I said, ‘You know what? Done is better than perfect.’ I got to pull the ripcord and go. I’ve had a couple of people reach out to me and say, ‘Did you know there’s an error in the audiobook?’ I said, ‘Well actually, there’s two. Go back and listen again, and try to find it.’

Joseph: That’s a great segue way, Heather, into the last thing that I was hoping to talk with you about before we wrap up with some of the work you’re doing right now for the Harry Walker Agency, which is this point you made about done is better than perfect. In your book, in chapter 10, you say something around not feeling like you have to have everything be perfect. This is something that I continue to work on myself. How do you go about letting go of perfection?

Heather: Well, perfection doesn’t exist for no one. There is no such thing as perfect. The more that I come to the realization that people that try to pretend they’re perfect are the most insecure people out there and my whole goal is to be the most confident me I can be, that means shining my flaws, really shining a light on everything that could potentially be wrong allows me to be my strongest self, my most confident self.

I really step into that as a power. That makes me feel strong and phenomenal versus when I wanted to try to make everything perfect, I never felt so good. I felt badly. I couldn’t achieve perfect. It just doesn’t exist. It was elusive to me.

For me, letting go of that idea of perfection and instead embracing that perfect means that’s the low moment, the insecure moment where you’re trying to hide what’s underneath, when I remind myself of that, I allow myself to shine that light on my mistakes and my imperfections, which draws people closer to me because that’s the real me.

Joseph: Another thing you say in the book is that we all need people who pick us up when we’re down, but sometimes, it’s a job we can do ourselves. For those listeners out there who struggle to do this, what’s worked well for you when it comes to trying to pick yourself back up without having to rely on other people to do this for you?

Heather: I leave reminders for myself everywhere. I read about this in a book, whether it be little notes I put in my suitcase. I’m going to New York to speak tomorrow, so I’ll have a really positive note in my suitcase tomorrow when I get there to remind myself, ‘You can do this. You’re going to be phenomenal.’ I write notes on the bottom of my heels. I put them in my phone, in my calendar, so that if there is a potential low moment that I wasn’t prepared for, I’m going to be able to pick myself right back up in it.

I also hold on to three accomplishments that really help me realize I was scared going into this situation, it turned out okay. Let’s tap into this for the strength I need for right now, wherever I’m walking into.

Joseph: The other question I wanted to ask you was you’re recently on headline news. You talked about finding your superpower. I’m wondering. What is your superpower, and how did you go about finding it?

Heather: I actually have a lot of superpowers. I believe everybody does. For me, I have really, in the past couple of years, come to grips with speaking, public speaking as a superpower of mine. Really, that is about storytelling and feeling comfortable sharing your own stories publicly.

I’ve learned about that through a challenge a friend gave me when I said, ‘I feel like I’m going through life, and I don’t really know what the purpose is.’ He said, ‘You need to put yourself in an uncomfortable situation, so I’m going to challenge you to a standup comedy class.’

I gave him every reason why I couldn’t do it. I’m a single mom. I run a publicly traded company – at that time I was. I don’t have time. He said, ‘Give yourself more excuses or find a way to do it, but I’m telling you this is going to help you really get yourself out of your comfort zone.’ It did. Taking that class allowed me to see what was different about me.

Another recommendation I made to people is to ask those in your circle, peers at work, friends and family, ask them, ‘What’s different about me? What is that special unique quality that you really think I should step into to own my best self?’ and then watch the amazing responses you get back from people. That in and of itself is a confidence building moment, and it will teach you that something that you thought was just normal isn’t that normal. It’s really special.

Joseph: I’d love to wrap up, Heather, with what you’re doing right now, speaking about speaking. I was wondering if you could tell more about your work that you do for the Harry Walker Agency and what your life is like now as a professional speaker.

Heather: I had reached out to Harry Walker Speaker Agency prior to writing my book. They told me that there wasn’t space for me on the team. Once my book came out number one on Amazon Business Biographies, they contacted me back and said they wanted to have me. The book was really the catalyst for me for so many different things to really take that next step.

The Harry Walker Agency sets a value on their speakers. Before, where I might feel fine going in to speak at a business for free, they don’t allow that, because they determine the value. Like anything, once you decide your value and you really own that, everybody else will own that and respect that as well. It’s really changed something that I enjoyed doing that I used to do for free, but now there’s a value associated with it in exchange, which makes it that much better for me.

It’s such a rewarding experience. I’ve been meeting a lot of new people, dealing with professional athletes and different companies I never thought I’d work with. I’m going to speak at a law firm to the partners, and I don’t have a background on law. It’s so interesting to see that everyone struggles with confidence. Everyone struggles with adversity, and no matter what your arena or what you do for a living, we’re all in this together.

Getting the chance to work with these different diverse groups and help everyone really own their confidence and embrace these challenges has been such a rewarding experience for me.

Joseph: Do you have any quick tips on how someone who is interested in doing more public speaking or wants to get up in front of audiences more, do you have any tips on how you can gain more confidence as a speaker?

Heather: Practice is everything. I practice in my house in front of a mirror. I make my poor child listen to my random speeches all of the time.

Also, speaking is interesting. People, they want to connect with you, and you need to get their attention, so the first thing I suggest doing is tell a personal story. Even if you’re speech is about something boring and statistics, still open with an engaging personal message, personal story, so that you get people listening to you. That’s half the battle.

Then throughout your speech, ask questions, open-ended questions, ‘Has anybody else in this room struggled with confidence? Do you guys understand what I’m saying, or is this off phase?’ Ask question of the audience so that they’re on their toes listening to you, and then you can see in their eyes what is resonating or what’s not resonating.

Really try to practice enough so that you don’t have to read the script. I really believe that people would rather listen to you talk, share stories, and make some key points versus reading a script and looking at a slide on the wall. It’s really about bring your personality to life, and the best way you can do that is by working on your confidence, taking baby steps and putting the time into practice.

I also believe in any time I am nervous, I have a win, win, win playlist that I fire up right before I’m going to go on stage and speak at anything. I also remind myself of different times I felt nervous before I got on a stage, and it actually went okay or it went well. I remind myself that if that one went well, this one’s got just as good a chance, if not better, to go great.

Joseph: That’s great advice there, Heather. Thanks so much for sharing that with us.

Speaking of confidence and being able to speak confidently in this topic of confidence, if people want to learn more about you or your story or your book, Confidence Creator, where can they go?

Heather: You can go to Amazon to get my book, Confidence Creator. It’s at Kindle, paperback, hardcover, and audible. If you want to learn or follow me on social media, I’m @heathermonahan, and my website is HeatherMonahan.com.

Joseph: Thank you so much, Heather, for telling us more about your life as an author and your own career transitions, your experience as a writer, and also your book, Confidence Creator, which I would highly recommend to people out there who are interested in this topic of confidence.

Best of luck with the ongoing book publicity and all of your speaking engagements. Thanks for joining us on the show today.

Heather: Thanks so much, Joseph.