Tips From The Top: One On One With Heather Monahan

I spoke to Heather Monahan, social media influencer, women’s empowerment expert and founder of Boss In Heels, about her unique journey and best advice

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Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. What is something about you that would surprise people?

Heather: People might be surprised to know that my childhood was a very tough one. My mother left a bad marriage with 4 small children and no money. She worked three jobs to make ends meet and there were times where my childhood was very dark. So often today we see people’s social media feeds and create our own back story for that person. I think it is so important for others to know that my life is not perfect and never was.

Adam: How did you get here? What failures, setbacks or challenges have been most instrumental to your growth?

Heather: How I got to where I am today is a combination of hard work, an ability to learn from my failures and ultimately figuring out how to build sustainable confidence. Some of the biggest setbacks and challenges that were instrumental in my growth range from being harassed and bullied at work to being fired once I had reached the C-suite at a publicly traded company.

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Heather: The defining qualities of an exceptional leader are authenticity, vulnerability, communication and commitment to innovation. One of the ways aspiring leaders can take their leadership skills to the next level is by asking for help. When you ask for help from the people around you, you will identify where your shortcomings are and get assistance in improving. Everyone has a blind spot; the key is identifying what it is and taking action to improve it. Another way aspiring leaders can grow is by surrounding themselves with people more talented than they are and growing as a result.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?


1. Don’t chase the paycheck, chase the dream and passion you have inside of you. If you chase the paycheck you will inevitably find yourself one day wondering why you did.

2. If you don’t believe in your vision whole-heartedly why would anyone else? Stay committed to your vision and goal and let nothing deter you and nothing will.

3. Be prepared for adversity and change and instead of responding to it become a master at identifying it before it strikes. By remaining alert and open to what is coming, you will be able to connect the dots and leapfrog the challenges others will trip over.

Adam: What is the single best piece of advice you have ever received?

Heather: If it was that easy, everyone would be doing it. This has been fantastic advice. Success isn’t easy and that is exactly why the majority of people don’t have it. When you really want something, it is not going to be a lay-up. There are going to be roadblocks. You are going to be faced with challenges and you just need to accept that this is the way it is in life. So realize that you are better than accepting easy and forge ahead no matter what. There is always a solution you just need to work hard enough to find it.

Adam: What is one thing everyone should be doing to pay it forward?

Heather: Mentoring is the single thing I can point to that has changed my life and those around me the most. Whether you do it through a charity like Big Brothers Big Sisters or you choose to do it at work with new hires, the experience of giving insight to others and helping them sidestep landmines is so rewarding. If we aren’t extending a hand to help those around us, how does our world improve?

Adam: What are your hobbies and how have they shaped you?

Heather: My favorite hobby has always been working out. At one point in my life, I wasn’t putting myself first and I stopped working out. This time ended up being disastrous for me physically and mentally. What I have learned is that when I put myself first and take care of myself, I am able to take care of everyone else around me. Doing what I love and making it a priority daily makes me a better person. The airlines have taught me this same lesson each time I fly when I hear that the oxygen mask goes on you first. 

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