Heather Monahan, founder of Boss In Heels and author of “Confidence Creator,” lives every day with the mission to empower women to take control of their own lives by showing them their unique strengths.

But the decision to dedicate your life to supporting other women doesn’t come from an easy path.

After years of working hard to move up the ladder in sales while earning prestigious awards and titles, the end of her sales career didn’t go the way most people plan.


When she launched her personal brand, her boss wasn’t too satisfied with her decision. Ultimately, this led to her termination. So, Monahan realized she had to come to a conclusion. She could either chase her passion or do what her previous employer wanted her to do.

Monahan was used to taking the tough road, so this was an easy decision.

“Once I was fired, I had the opportunity to sit and think about what it was that I really wanted to do with my life which is what led me to write Confidence Creator and deciding that going all in and working for myself to elevate others was the right plan and future for me,” Monahan said.

Monahan is proof that when life isn’t going the way you want it to, sometimes you don’t have a choice but to follow your dreams.

But how did she rise up and find the confidence to take a massive risk and know it was all going to work out in the end?

Luckily, ENTITY had the chance to talk to Monahan about how she gained all the tools she needed to succeed.

ENTITY: What is the greatest challenge you faced and how did you overcome?

HM: The greatest challenge I have faced was creating my own confidence and ending a lifetime of self-doubt and mediocrity. I used to feel that life was happening to me and I was not in control of the ups and downs.

Through learning how to create my own confidence, I was able to take control of life and empower myself to direct it where I wanted it to go. This happened through a series of steps that I detail in my book. One of the key steps was deciding to answer my own questions and listen to my voice over everything else.

ENTITY: How did you gain the confidence you need to pitch yourself?

HM: I have been in sales since I graduated from college, so pitching myself has always been a way of life for me. Like anything the more you do it, the better you get at it. When I need to fire myself up before a pitch, I play my “Win, Win, Win” playlist which is a compilation of songs that get me so fired up!

I reference times in my life when I was scared to do something and it ended up working out pretty well. I use those experiences to shift my thinking at the moment to one of positivity. I envision myself making the pitch and seeing it go phenomenally.

I practice and practice more. The more I practice the more confident I feel. Anytime I am pitching myself for something I do my homework so I can see what the other person is looking for and how I can fill that need.

Ultimately, knowing that if I don’t ask I will not get always drives me to make the pitch. I would rather have a shot at it than not know what could have happened.

ENTITY: What is your advice to women who don’t know how to pitch themselves in any scenario, to a boss, an investor etc?

HM: Do your homework. If you spend time researching the opportunity, you can discover the need. Once you find the need it is on you to see how you can fill that void. Answer the question, “what is unique about me?” Discovering what your unique value proposition is and how your unique talents and skills can fill the other person’s need is what you need to do.

Once you figure that out you go to pitch and go for the close. In every pitch someone is sold. It is either you selling them on why they need you or them selling you on why they don’t. Going for the close doesn’t have to be difficult.

Offering up a choice is an easy way to close someone. “would you like me to start tomorrow or Monday?”

heather monahan on Confidence Building

ENTITY: What is the best piece of advice you ever received from someone else?

HM: There will always be another deal, another guy or another opportunity. Desperate is so unattractive.

ENTITY: What are some challenges that come with running your own business?

HM: Doing everything on your own is such a challenge! I laugh when people tell me that I am killing it. The reality is that the busier I get the crazier things get for me because I am a one-woman show. The more speaking engagements I have the more prep is needed, the more travel is needed, the more invoices need to be generated etc. The short-term goal is to get revenues to the next level so I can hire a full-time assistant. Once that happens, I really will be killing it!

ENTITY: What is your secret to work-life balance? Is there one?

HM: If there is a secret I wish someone would give it to me! I don’t believe there is such a thing as balance. I believe in doing my best in any moment and being present where I am. If I am working, I am all in and when I am at my son’s basketball game I am focused on him.

By giving my attention to what is in front of me, I am able to see things that are meaningful in the moment. Sometimes my son goes through hard times and he needs me more so I shift my time to be available for him. Then there are times where I am spending more time at work because there is a time crunch and I need to deliver.

Throughout it all, I focus on working out and taking care of myself which allows me to feel my best.

No woman ever has everything figured out, and that’s okay. But Monahan figured out how to turn what she’s passionate about into a career, which is what makes her a part of the #WomenThatDo.

Because to her, being a woman that does means “being a woman that takes action, stands up for herself and her beliefs while elevating others.”