Massachusetts native Heather Monahan used a Clark University degree in psychology, 20 years of sales and marketing experience, and a ton of hard-won, firsthand knowledge to become a multimedia force. In April 2006, she launched, a site aimed at empowering women to use their unique attributes for achieving success in life.

Currently based in Miami, this business expert (aka Boss in Heels) has worked all corners of the corporate environment, giving her the creds to inform women on the best way to approach the working world with expectations of success.

Solo Mom to son Dylan (nine), Monahan’s life as a single parent only amplifies her understanding of the day-in, day-out demands we gals face in the workplace and in life. Her openness and honesty regarding her own struggles make her all the more accessible, inspiring women to embrace our power, celebrate our individuality, command respect . . . and run the planet.

Oh, and she’s gorgeous and looks like she’s 25.

Q: How did come about?

A: Years of knowing I was not living up to my fullest potential and feeling frustrated about it led me here. It wasn’t something that happened overnight. It’s been a lifetime in the works. I’ve always been happy when I help people and use my experiences to elevate others. But I realized I was so focused on my job and everyday tasks that I’d let go of this.

Over the years, I’ve had successes and allowed amazing people into my life. They helped me develop real confidence. As my confidence grew, I was able to look at how I spend my time, what I am doing, and how I can change it all in an instant if I want to. That is what I am now doing.

Q: What is Boss in Heels (#bossinheels)?

A: Boss in Heels means a few things to me. When people hear the term boss, often they think of a stoic male figure. To me, Boss in Heels is representative of being you. For me, it’s celebrating that I am a woman while still commanding respect and delivering results in the workplace. Boss in Heels is about treating employees, partners, and clients well, and having a vested interest in their success. It’s a more modern way of leading.

Q: When and how did you become a Solo Mom?

A: I found myself very unhappy in my marriage, and after trying to change things, I realized the only thing I could change was myself. My son was one when I filed for divorce; that was eight years ago. My ex and I share custody.

Q: Did being a single mom impact your career?

A: Definitely. When my son was one and I was traveling so much, I realized I was not in a position to take much risk and that I needed stability. The situation really changed the way I looked at things. Before that time, I was consumed with how to innovate and change and grow. After we divorced, for the first few years of my son’s life, I was singularly focused on stability. It was the right choice.

Q: How do you manage?

A: First of all, life is not easy when you are a single mom. I have a nanny, as I travel for work and am gone a lot, but she doesn’t live with us. I’m still alone. When I get home from work, it’s 9:00 p.m., and we have no milk, there’s no one else to run out and grab it. It’s the little things that make you realize you are alone.

I feel a lot of pressure to race home knowing my son is with a nanny. It’s stressful. At the same time I am lucky to be able to afford a nanny so I can make my work trips and forge ahead in business. You constantly struggle with feeling like a failure at home or at work. The beauty is the longer you do it on your own, the more you realize you can do both and it will work out. That is a pretty powerful realization.

Q: When your status shifted from married to single mom, did you feel a shift in your community?

A: People definitely looked at me differently. Some people felt bad for me and talked about how hard it is to be a single mother. Then there were those who didn’t want to be around me and gave me the evil eye. There’s this weird idea that a newly divorced mom is going to covet someone’s husband. That was never an interest to me, and it didn’t feel good when some women distanced themselves. Divorce and being a single mom is tough enough. Thank goodness for the supportive friends I have to offset the others.

Q: Was there a defining moment that drove home you were raising a child alone?

A: Many. One was the first time my son got very sick. He was one year old. It was midnight. He was throwing up and spiked a fever, and I realized I didn’t have anyone to go out and get Pedialyte. At that moment, I knew it was me and my son moving forward, and we were doing this together.

Q: Of what are you the most proud as a Solo Mom—about yourself?

A: I am proud that I launched my personal brand in the face of so much adversity while working a full-time job and raising my son. The example I am able to provide for my son—that you do not give up or back down when you believe in something, regardless of what others say—makes me feel extremely proud. Instead of just telling my son to pursue his dreams regardless of obstacles, I am actually doing it for him to see. This is really powerful!

Second to this is my pride in how I handled my divorce. Since the beginning, I decided my goal was to have a good and friendly relationship with my ex-husband regardless of challenges. It hasn’t been easy, but I’ve made this work. Today we can all be together and get along, and it is much more positive than it would have been had I decided to dig in and fight. Peace and kindness are where it’s at for the long haul.

Q: What is your favorite single-parenting tip?

A: Find people whom you can rely on and trust. No one can do this alone. I have so many friends who jump in and help when I’m in a pinch. I notify my son’s teachers every year that I am divorced and travel for work, and that I need help. They rise to the occasion. By communicating with others and asking for help, I’ve created friendships and connections that have benefited our lives immensely.

Q: Do you have a favorite Solo Mom shortcut?

A: Getting my son ready for school while I’m getting ready for work is a nightmare, so I let him stay up 30 minutes later the night before with the requirement that he has to get ready for school on his own—no problems, no issues, or the deal is off. It pretty much guarantees the mornings go smoothly.

Q: Which brings me to my final, and favorite, question: Do you date?

A: Yes, I date. It is really hard, as you know. I travel for work, so I try to coordinate my work trips with my ex when I am out of town. Therefore, in order to date it’s choosing to leave my son with a babysitter. Leaving him isn’t easy. Dating as a single mom is never easy!