21 Questions with Boss Mom Michelle Dempsey, (Like the 50 Cent song, Only More Empowering)


Meet Michelle Dempsey, my new woman and mompreneur crush. She is the founder of Very-Well Written, where she helps businesses with content and brand marketing. You can also find her wisdom all over the Internet at top sites such as Mind Body Green, Elite Daily, Huffpost, Forbes and Scary Mommy. When she’s not hustling at work, she can be found doing mom things with her adorable two-and-a-half year old daughter, coffee in hand. And during those child-free moments, cardio, binge-watching Netflix, and more coffee keep her sane.

We connected over our shared desire to use our big voices to help women find theirs, to empower them to own their struggles and live their passions, our well-developed ability to say no to people and things that don’t serve us, and the mom struggle that is indeed, very real.

1. Describe yourself in five words.

Dynamic, creative, sincere, inspirational, no holds barred

2. The moment that changed my life was

The moment I learned that my intuition was really onto something, and that it was worth trusting. It was one of those moments where everything came into focus, and finally, everything that came before it made perfect sense.

3. I found my voice when

I realized my words had the power to inspire and influence others, and that sharing my truth meant helping others to heal from theirs.

4. I’m empowered because

I’ve learned to say no and mean it. I’ve learned to walk away from what doesn’t serve me without apologizing for it. I’ve learned the power of my intelligence, my kindness, and my womanhood. I’ve learned that you don’t get what you want in life, you get what you are, so if you want great, be better.

5. I empower others because

I am as authentic as I am transparent. I say what everyone else is thinking. I choose risk over comfort. I go after what I want like it’s the last train of the night. I don’t apologize for being who I am yet I always lead with kindness. 

6. Putting yourself first is

Not selfish. At all. Putting yourself first is the single best thing you can learn to do for yourself in this lifetime yet it’s every woman’s biggest challenge. We’re mothers, we’re daughters, we’re friends, we’re wives, hell, some of us are even ex-wives, and the expectation is that we do for everyone else first, right? And then what? We burn out, lose our sense of self and live with regret and resentment. We get divorced, we hate our jobs, we can’t believe we never told that friend how much she hurt us and now can’t stand the sight of her. It took me 30-plus people-pleasing years to learn that there is no shame in advocating for your own needs before anyone else’s. Even as a mom, a really devoted one at that, I know that I can’t pour from an empty cup, and when Mama’s taken care of, everyone else benefits. We’re not taught to put ourselves on a pedestal and I’m not sure why. But what I do know is, once you get to that place where you value, and I mean really and truly value who you are, putting yourself first becomes a ritual as natural, and necessary as breathing. 

7. I take care of myself by

Taking time for myself at some point, even if it’s just a few moments, every single day. Working out helps me focus and regroup, and in the interest of being authentic, it helps me deal with being a semi-anxious workaholic. I sleep when I need to sleep, and when shit hits the fan I shut off my phone and head for a massage. I surround myself only with people who bring happiness and joy to my life, do my best to keep outside drama to a minimum, and breathe deeply through the moments that aren’t so pretty.

8. Best mom win

When my daughter first started school, at a teeny 18-months old, she came home one day with a bite mark on her arm. Her teacher informed me that another little girl in class had bitten her during a typical toddler battle over some toys. When I asked how my daughter retaliated, thinking she likely resorted to hurting this little girl for biting her, I was told that she hugged and kissed her teeny attacker and gave her the toy she wanted to play with. Sounds simple, maybe, but knowing that my daughter reacted with kindness meant more than I could ever put into words. That was the moment I realized I was doing something right.

9. Worst mom fail

Happens every morning when I lose the battle over what’s for breakfast because someone is running late for work and another someone had to be in school five minutes ago.

10. Motherhood is

The single greatest thing that has ever happened to my life. Sound cliché? Then you must not be a mom.

 11. Moms should

Reread question #6. And then stop what they’re doing, look in the mirror, and repeat after me, “Hello, you gorgeous goddess, you’re slaying this whole mom game. I’m so proud of you and damn that ass looks great.” Then try to be easier on yourself. And maybe have a glass of wine.

12. Before I became a mom, I wish someone told me

All of those little things my Mom did that annoyed and drove me crazy would become exactly my way of mothering. And that your child can and will survive even if they drink formula, and that all the things you swore you wouldn’t do as a mom would become exactly the things you do the most as a mom.

13. Women need each other because

No one knows a woman like a woman. Our needs, our struggles, our emotions and feelings. The support of other women, the powerful feeling of knowing that a group of trusted ladies have your back no matter what – that’s a big part of what I live for. As the co-founder of a professional networking group for women, I am always so intent on opening the doors to amazing women who truly understand what it means to help another woman rise. It’s vital. 

14. My last meal would be

At Il Mulino in Miami and would include calamari with extra lemon, spaghetti carbonara, and a Caesar salad. And a gin and tonic, or two. Oh and dessert, but I don’t discriminate. 

15. Three things I can’t live without are

Love, my laptop, and coffee.

 16. My perfect day is

Spent in the company of those I love, with my laptop, and some coffee.

17. The books I swear by are

Daring Greatly by Brené Brown. “Loving ourselves through the process of owning our story is the bravest thing we’ll ever do.” If that doesn’t describe the turn my life has taken, then nothing ever could.

18. When life gives you lemons

Order more calamari.

19. I don’t wait for doors to open, I

Kick them the f*ck down.

20. I want my daughter to know

It is who she is at her core, how she treats others, what her passions are and what drives her, that will truly define her as a woman. Not what she looks like, who she chooses to love, whether or not she’s the most popular girl in her high school class, or if she avoids broccoli in the same way some of us avoid dental visits for the rest of her life.

21. You can find me at

Target, screaming toddler in cart, grande latte in hand, hoping for a BOGO on the Lysol wipes and veggie sticks.

BIO: Michelle Dempsey MS, CPRW is an entrepreneur, internationally published writer and marketing guru, girl gang leader, radio host, and above all things, a mother. Michelle Dempsey turned a passionate hobby into a thriving career. Internationally published and known for her ability to connect with readers on a deeper level, Michelle launched her own business, Michelle Dempsey: Very Well-Written, offering content marketing and consulting services to businesses of all kinds. Michelle partners with all clients in a collaborative process that allows her to write from the point of view of her client, a winning strategy for success. She speaks to female audiences regularly on topics including empowerment, personal development, and business success, and last year, co-founded one of South Florida's fastest growing networking groups for professional women, ProFemmes.

This article originally appeared at Mogul.

Get Your Mompreneur On With Expert Dawn Andrews (Part 2)


I'm back with Dawn Andrews--mom, business strategist, life coach, and successful entrepreneur. Today she talks about women getting into business, what holds them back, and how to juggle being your own boss and the boss of your family at the same time. What Holds Women Back

Permission is the biggest thing. I find that for many women, it’s almost as if they are waiting for someone outside to tap them and say “Yeah, you can do this. Go for it!” Thankfully, because of growing up in an entrepreneurial family, and I’m not saying I don’t experience permission issues in other areas in my life, but when it came to that “go make your own thing,” that has never been an issue for me in terms of getting something started.

Pretty, Polished, and Perfect

The phenomenon is that men, because they don’t generally have that permission issue, just go out and do stuff, ask for stuff and forge forward with an initiative without much concern until they bump into something. They they figure out how to get around the rock that got in their way. Women want to have everything laid out. They want to know they have a clear path ahead of them before they even begin. And no path is every going to be clear. So we will spend time spinning, making sure everything is pretty, polished, perfect, and organized, so we know all the steps. But that isn’t how life works. What kills their possibility of going into business is that they’re looking for a sure thing and anything that is worth pursuing, as everyone who is a mother will know, is a dam hot mess.

Parenting is a hot mess. Some days it’s great and you’re crushing it and you’re the paragon of motherhood and other days you couldn’t be more ashamed of yourself. The same is true with business. My business exploded when I became a mother. I think it’s because it started to crack off that shell of trying to have things organized and a linear path to follow, knowing that one step was going to lead to the next step. Because everything was like a rodeo once my kids came out. Parenting is a great place to practice. With your kids, you need to ask and be clear about what you want. I’ve also found that has helped me in my business. I have no compunction about asking whoever I need for whatever I need. Maybe they will say yes and maybe they will say no, but I have my toddlers to thank for giving me that skill set. 

 On Being a Mom and a Successful Entrepreneur

There’s no balance. It’s just what wins the day or what I hope will win the day. Early on, I made a list of the things that were important to me to be connected to and involved with for my kids at their various stages and ages. They are about to turn seven and nine right now. It’s important to me to be able to take them to school, pick them up from school, go to award ceremonies, special activities, or any special event or field trip at school.

It’s also important for me to get sleep, take care of myself, and have a sense of joy in my life—and not have it just be either work or kids. So what that looks like now is there are certain days I take the kids to school and certain days I pick them up. We definitely are all about having a team. I don’t have a full time nanny, but I have a team of people. I definitely have somebody help clean the house once a week because I would lose my mind. We have somebody to help do the gardening. Recently I’ve added in an assistant and some other team members to my business because it’s growing again in a big way. Whenever I start to feel overwhelmed, I look at how I can add some team. What would it do if you added one more day of babysitting or added one more day of preschool camp? Start to think incrementally, especially if financially you’re not in a place where you can go to all the way towards what your dream scenario would be. Start piecemeal adding in team members to live the life your looking to live. We totally move in a pack.

You Have an Idea for a New Business--Now What?

You need to get a community. The challenge is finding people who are as action-oriented and dedicated as you want to be. Often times, the first place we’re looking to is the other moms in our moms group or our closest friends and they or may not share the passion or enthusiasm for starting a new business. So you do need to find preferably other women and other moms that are interested in getting businesses off the ground and get a community together so you have others to help hold you accountable. Use that group of women and other people in your life to start testing if that idea is interesting or not. Sometimes you have to just engage in the mess and giving the idea a try. Get really clear on who you want to serve. What’s your really specific niche of people you want to work with? The more specific you can get, the better—age range, location, etc. Start to narrow down the demographics of your audience and once you have that, you have the seeds of something you can really start growing.

Growing Your Big Idea

Grow Your Big Idea is a small business incubator and it’s for inception of idea to making your first money for what you’re doing. It’s going to be offered two times a year. The next time I’m going to offer it will be in October or November of this year. It’s a five-week program to move you from that idea piece to making money with your business and you will do it with other women.  I’m giving you all the behind the scene details of of how to develop your idea, how to protect it, how to raise money for it, and how to package it up and get that first version out into the world and get paid. It takes care of that community piece because you can use the other women as your focus group to help and hold you accountable.  he next round is going to be $997 for five weeks. That’s includes the training and to be part of the community ongoing.  What I’m looking to build is a community of women who go through this process and are looking to play the game of business together.

You can find Part One here.


BIO: Dawn Andrews is the trusted advisor to more than 250 individuals and businesses in the world of entertainment. Her company, Free Range Thinking, is credited with cultivating extraordinary leaders, and she is committed to transforming leaders from the inside out. She’s an intuition based thinker who teaches you to Grow Your Big Idea (tm), reclaim your time without sacrificing results, improve communication skills and leadership performance through organizational effectiveness, and, most soulfully, to find your passion, work less and make more.

Get Your Mompreneur On With Expert Dawn Andrews (Part 1)


Meet my good friend and expert Dawn Andrews, business strategist and life coach in the world of entertainment. I immediately connected with Dawn this past spring at Campowerment and recently participated in her new small business incubator, Grow Your Big Idea. Read on to find out how you too can join the Grow Your Big Idea community, why Dawn thinks more women need to get involved in business, and how she doesn’t find balance between being the entrepreneur boss of her own company and being the mom boss of her house and two boys, ages 7 and 9. A Business Strategist and Life Coach

The main reason people come to a business strategist is because they own a company of some sort and have reached a plateau in their development or growth. What’s unique about the business strategy that we do is that we help business owners take their businesses from personable to sellable.  A lot of people start their companies and grow organically and they’re growing on their own energy, ideas, and enthusiasm, but they don’t have the wherewithal to create a business plan and put together something that actually has value beyond just the monthly revenue they make. As a business strategist, I look at people’s businesses, predominantly service and creatively-oriented or businesses in entertainment and help them strategize growth and what their exit strategy would be. The life coaching part comes in handy because usually any time any of us are growing, we come up against our past history and psychology. The life coach part helps businesses deal with their own personal roadblocks.

Becoming a Coach

I was a director of marketing for an entertainment company and I grew up in an entrepreneurial family. The best way I can put it is that I always grew up in an environment where making your own thing was more desirable to being employed by somebody else. I don’t think I consciously knew that at the time, but as I got into my late twenties and thirties, there was a time when a lot of traction was happening in business—lots of lay offs and smaller companies were being bought by larger companies.  I just looked around and thought, “This just seems silly.” Why am I sweating it that I’m going to be in the next round of layoffs when I can just do something myself.

It didn’t occur to me at the time that’s not how most people think. Most people are scrambling to find another job, networking with friends, or polishing up their resume. I just didn’t want to take that ride at someone else’s mercy anymore. I called and hired a career coach at the time to just pull something out of me that I could turn into something that made money and I realized it was her job that I wanted. So I went to coaching school because there are schools specifically for that skill set. Thankfully, I wasn’t in the first round of layoffs, but I was in the third or fourth and by the time that round came I was already in training, I had a few clients and the basis for what the business is now.

Going to Coaching School

Coaching school is awesome and it’s for real. It’s not an easy let’s just go and talk and have nice classes about self-development and have fun. It’s a very rigorous training program. You’re dealing with people’s psychology and how they relate to their lives. Most coaching programs are anywhere from 18 months to three years, depending on the level of certification you want to get. You can physically go somewhere as part of your local college or you can go to a coaching school. The top coaching schools are CTI, International Coaching Academy, and CoachVille. For busy moms, many programs have classes that work around that and offer classes at 6 in the morning or 10 at night.  

What I will tell you, for those of you who want to be a coach, is that getting your business started and learning the skills of a coach or transferring your life skills into coaching is one level of the difficulty, but running a business or starting a practice that includes coaching takes a lot of energy and effort. You can do it, but don’t be surprised or put off by that.

Starting Out

The year before I graduated from coaching school, I sent a letter out to everyone I knew announcing the launch of the business. And this is rolodex days when people actually sent letters. I said, “I started this, this is what I’m doing, and I’m looking for anyone who wants coaching about anything.” It was a free for all. There was no focus, no niche, no nothing. And at rock-bottom prices. It was just so I could start using the skills and tools that I had and the method that I had learned to get some practice. It probably took about a month of the letters out and then calling and cajoling people just to get them interested in giving it a try. It wasn’t that long before I was being paid for it—very little but I was being paid for it.

We Need More Women in Business

As women, we have a unique perspective. And I feel like because of the way we’re wired, physiologically, we can see a larger picture of what’s going on in the world. We can see how we feel; we can check on how others are feeling. We can see how people are being affected by our environment, our politics, and what’s going on in the world. Having more women in business is going to create a more holistic rise in the way that our culture works. Most men, are designed to get on a track, focus on one goal, and go get that thing. That’s also necessary, but it’s missing the larger picture view. When women get into business and express themselves, they’re more likely to team up in terms of businesses working together for a greater good. They’re more likely to be charitable or to connect their business to some larger cause. I think it just gets better when women are in business.

On Wednesday, Dawn will be talking about women getting into business, what holds them back, and how to juggle being your own boss and the boss of your family at the same time. Subscribe below and never miss a post!



BIO: Dawn Andrews is the trusted advisor to more than 250 individuals and businesses in the world of entertainment. Her company, Free Range Thinking, is credited with cultivating extraordinary leaders, and she is committed to transforming leaders from the inside out. She’s an intuition based thinker who teaches you to Grow Your Big Idea (tm), reclaim your time without sacrificing results, improve communication skills and leadership performance through organizational effectiveness, and, most soulfully, to find your passion, work less and make more.