A Conversation with Author Heather Monahan

My movement and mission is to share the message that confidence is created and not given and I believe this can change the world. Teaching people how they can become their own confidence creators can change the mindset of jealousy, scarcity and bullying. When a person is truly confident they don’t need to tear others down or treat others badly they simply move on and stay focused on their goals while lifting others up along the way. If we can teach the world how to build their own confidence we can change it for the better.

I had the pleasure of interviewing Heather Monahan, 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 twenty years in media, Ms. Monahan is one of the few women to break the glass ceiling and claim her spot in the C-suite in Corporate America. Ms. Monahan is also a member of Florida International University’s Advisory Council to further serve as a mentor and leader in the South Florida community.

Thank you so much for joining us! What is your “backstory”?

Mybackstory is I “started from the bottom”! For years my mother was on her own working three jobs trying to make ends meet for her four children. Those days were tough but they instilled a drive in me to succeed that can’t be dismissed.

I began with a paper route, then waiting tables, bartending and eventually I graduated school and became a sales person in the wine business. After being harassed in my job, I moved into the radio business as a seller.

After a phenomenal first year in radio sales, I was offered an equity partnership that moved me to Michigan to run our new acquisition. There I led a $25M company through growth and further acquisition ultimately delivering a $55M property in under 3 years for my partners and myself. After closing the sale, I moved to Florida to begin working for a publicly traded radio company where I pitched myself for a position that was not created yet and was awarded VP of Sales for the company. From there I pitched and was awarded the Executive Vice President position and ultimately the Chief Revenue Officer role. During that time I married, gave birth to my son Dylan and divorced. After Dylan was born, I got involved with charity work and launched my personal brand Boss In Heels. Boss In Heels was my way of showing others what it takes to get ahead at work and in life. Boss In Heels is what I wish I had access to when I was younger.

While Boss In Heels was received fabulously by so many, the company that I worked for did not feel the same way. It was made clear to me in no uncertain terms that I should shut down my personal initiative to empower others. In that moment, I needed to make a choice and I chose to follow my heart and do what was right even though it was not popular with my supervisor. Eventually, I was told that my position was being eliminated. That is when I jumped in full time to Boss In Heels and began writing my first book, Confidence Creator.


Can you share the funniest or most interesting story that occurred to you in the course of your career?

The most interesting story is that it took me years to realize that I needed to stop chasing money and instead start creating something meaningful, which is why I launched Boss In Heels. If that isn’t interesting in and of itself it was shocking to see the response I received from another woman that was completely opposed to my initiative and mandated that I shut it down.

I put disclaimers everywhere on my site and my social handles. I hired people to manage my initiative so that she couldn’t say I was being taken away from my job as CRO. I did everything I could to appease this woman and in the end it became clear that she was threatened by me shining my light. At that point, my life became very difficult because of that situation and the tension and angst around it. I received countless calls from those that loved me at work begging me to shut down my initiative and just as many calls from her telling me why I better stop what I was doing.

The pressure intensified until her father stepped down and she was given the CEO position. That time was tumultuous and difficult for me but through it I built my confidence by not backing down and standing up for what I believed in.

In the end, she was happy to fire me but that pivotal moment is what set me down this new path, which has been the most rewarding in my professional life.

What are some of the most interesting or exciting projects you are working on now?

Everything is so exciting! After a lifetime in one career as an expert, I started out as a beginner at 43 years old. The fact that when you Google me now, I show up as an Author simply blows me away. It’s so interesting that we allow ourselves to be put in lanes and having remained in my lane for so long that I was petrified to leap out of it and into a new one. Now, I have demolished all lanes around me. Every day, I meet with different people and consider new opportunities from e-learning products to my next book to consumer packaged goods opportunities to innovation around traditional products and models.

Which people in history inspire you the most? Why?

The game changers, the people that take risks and overcome adversity to move their mission and passion forward. There are so many!

Steve Jobs comes to mind as a true business inspiration to me. His vision and commitment to take a chance on personal computing before there was a known market for it and co-found Apple is inspiring and challenges me to try to see what is ahead before it is tangible. Knowing that he was inevitably forced out of Apple and realizing that he didn’t let that keep him down instead he simply got back and up and started another company. Eventually watching him come back as CEO of Apple after he was pushed out and then seeing him revive Apple and change the world as we know it is beyond inspiring.

Which literature do you draw inspiration from? Why?

I love to learn! For me, reading business biographies or self-help books that allow me to learn from others personal experiences is truly inspiring and educational.

How do you think your writing makes an impact in the world?

I typically get similar feedback from readers after they finish my book. I hear from most that they can’t believe I spoke directly to them. What I take from those comments is that we are all so much more alike than we are different. Realizing this helps people to know that they are not alone. So often we judge others based upon what they look like or what we “believe” their lives are like, Confidence Creator obliterates that notion. Through my struggles, I am able to inspire others to overcome theirs and continue to move forward.

What advice would you give to someone considering becoming an author like you?

Be your authentic self and it will come through on the paper. Being an author is definitely a journey and not a destination. Just start writing. At first you just want to try to write. Then you make the commitment to yourself and others that you ARE writing a book. Then you put the time in everyday and you write. Then you finish writing. Then you begin the editing process. Then you finish the editing process. Then you begin the self-publishing process. Then you create the name of your book. Then you create the cover. Then you finish those things and then you begin marketing. Then you begin launch strategy. Then you begin social strategy and influencer strategy and pricing strategy. Then you start your sales and promotion strategy and before that is ever finished everyone is asking what your second book is about.

Bottom line is you better be ready to work!

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

My movement and mission is to share the message that confidence is created and not given and I believe this can change the world. Teaching people how they can become their own confidence creators can change the mindset of jealousy, scarcity and bullying. When a person is truly confident they don’t need to tear others down or treat others badly they simply move on and stay focused on their goals while lifting others up along the way. If we can teach the world how to build their own confidence we can change it for the better.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

1. Life will not turn out the way you expect it to and that is great news!

When I was younger I believed there was a very clear path for me and that path was to become a CEO of a publicly traded company in the business that I had been in forever. Because I was so sure that my path was clear, I ignored all of the signs that were surrounding me. By picking my head up and looking around at the world, my passions and the opportunities in front of me, I have been able to create something so much better than I ever could have ever imagined.

2. You already have all of the answers inside of you.

At different times in my life, I focused so much on getting validation from others that I nearly silenced my inner voice. I would ask this person what I should do with this situation and rely on that person to tell me what to do over there. Over time, I learned that I was the only one that actually had the right answer for me. Making time to listen to your inner voice and act on it changed everything for me and it will for you too.

3. If success was easy everyone would have it.

I am often asked how I find the inner drive and commitment to keep going when I get knocked down so often and I find that question funny. It is clear that if you get knocked down and you stay down, you will not achieve your goal. Conversely, if you decide to get back up and go after it again you have a shot of getting there. Then I think of all of the people in the world that just kept getting back up regardless of adversity and I know that staying down is not in the cards for me. Getting back up is simply a choice, no need to over complicate it. The odds favor you when you get back up.

4. Others will project their fears and limitations onto you, it is up to you to take them on or dismiss them.

So many times over the past few years, I have had people that genuinely love me rise up and tell me to back off of my personal brand for fear I would be fired. I’ve had others scream and yell that I shouldn’t publish my book because it would never work and I’d fail and be mortified. Those people may mean well, however, what they are really doing is projecting their fears and self-imposed limitations onto you. I struggled with this a few times. I would take their fears on and sit with them for a day or two and in those moments I learned to reach out to others in my life that are like minded and have the capacity to stretch me instead of holding me back. When I would tap those people, they would remind me that just because the nay-sayers can’t do it, doesn’t mean that I can’t. Then I would re-focus on my goal and I would move forward one step at a time. I stand here today ecstatic that I listened to me and did not take on others limitations.

5. In every moment you are either creating your confidence or chipping away at it.

I used to believe that the world was just happening to me and I didn’t have a say in it. That was before I realized I had a say in every single moment. Owning that responsibility and deciding to take each moment and create confidence for myself has empowered me to live a life I didn’t know was possible. By asking yourself in each moment, will this decision build confidence for me or set me back? I have trained myself to do this and now it is second nature. If a decision is going to take me backwards, I can tell you this, I am not going that way. I am so committed to myself and doing what is right for me, decisions are no longer difficult or confusing.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

Yes!! Reese Witherspoon!

I have been told countless times by my readers that my book is a movie. Simultaneously, I have been bombarded by images of Reese Witherspoon on social media and one video of her speaking in particular, compelled me to research her. Finding her production company Hello Sunshine and her interest in books created by female authors got my attention immediately. Recently, Hello Sunshine’s video on demand was announced to spotlight female creators and their personal stories. This announcement tells me my meeting with Reese is destined to happen! When the universe gives you so many signs, I have learned you cannot ignore them, instead you need to keep putting it out there.