Power Women: Kelisha Mills of The Ultimate Mompreneur On How To Successfully Navigate Work, Love and Life As A Powerful Woman

An Interview With Candice Georgiadis

Patience — Success doesn’t happen overnight. I am sure we have heard the many stories about the number of years it takes to turn a profit or to truly see lasting success. Patience and strategy are important. You cannot be patient for something that you do not have a plan for. Create the plan, be patient and reap the success!

How does a successful, strong, and powerful woman navigate work, employee relationships, love, and life in a world that still feels uncomfortable with strong women? In this interview series, called “Power Women” we are talking to accomplished women leaders who share their stories and experiences navigating work, love and life as a powerful woman.

As a part of this series I had the distinct pleasure of interviewing Kelisha Mills.

Kelisha Mills is a wife, mom of 4 and an entrepreneur for over 15 years. She represents a community of Caribbean Women making a global impact through their business and their lifestyle. Her message is spread through curated luxury events, retreats and experiences and the many stages upon which she speaks.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your childhood “backstory”?

I grew up in a country town in south Trinidad. I am the oldest of 4 children. My childhood life was as country as it could get: animals, fruit trees, lots of land and lots of family members living in the same household. I always knew that there was something different about me. I had an entrepreneurial spirit from a young age. I would sell handmade hair accessories for $2 each to persons in my village. Coming to think of it now, I don’t recall what I did with my earnings. I was so young.

I also learned from a young age that I could sing. I got involved in all school and church choirs. My dream was to go to Berkeley College of Music in NY and to become a star; a dream that died because of many factors; lack of money being one of them.

I did very well in school and started my first job at age 19.

Can you tell us the story about what led you to this particular career path?

In 2005, after the death of my mom, I moved to Tobago with my son to be closer to my partner. I was not working and my partner was holding down two jobs at a hotel and at a school. We talked about starting a business. We both had procurement backgrounds, so it was natural to start there. We began providing stationery and general items to Government offices. An opportunity came along to buy a franchise the next year, and it was there that we started our real entrepreneurship journey. Everything happened so fast. It showed me how quickly life can change when you make strategic moves.

Can you share the most interesting story that happened to you since you began your career?

We invested everything we owned into this new business. Two years later, the recession of 2009 hit and placed us in a cash flow nightmare. The lifestyle we created became out of reach as our income was not covering our expenses. I learned that proper financial planning and forecasting is so important. Creating a business on a wish and a dream is very juvenile. Saying that your business will be successful does not get you away from the fact that you actually have to do the work and have proper structures and goals in place. The experience has forever changed the way I do business. I am a stickler for processes and having them mapped out. That way I have a lot more control of my outcomes.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Endurance — My entrepreneurship experience has spanned 15 years. During that time, I have had many ups and downs. In the beginning, I had many down moments. To be honest, the down times were more than 7 of those years. There were times when I thought that there was no way out, no silver lining to the endless financial and emotional struggles. However, I stuck it out. I can remember on my 35th birthday. I was in such a low place. I could not even buy an ice cream for myself. From that day I promised myself that I would never find myself in that situation ever again. By the next year, I would be in control of my financial wellbeing. It didn’t happen overnight, but I gradually changed my business and my life for the better. I believe those that know me can appreciate what I have been through, and have seen my life blossom from who I was then to who I am now.

Decisiveness — The longer you take to make decisions, the longer you take to get the solution. If I had made the decision to change my life a year or two earlier, then I would have been in a better position much sooner. Decisions will always have to be made. It takes a great leader to make quick decisions without fear of knowing how the solution would come. I was never good at making decisions. Being a female entrepreneur and a mom, I let emotions and empathy cloud my judgements at times. Decisiveness really grew on me over the years because there were some situations that were do or die. I remember when we had to close our business. I wanted to hold on to it because I had an emotional attachment to it. However, each day that we remained open cost us dearly, and we did not have the finances to sustain it. The day I let go, I felt such a relief, even though I did not know how we were going to bounce back from this having so many expenses and young children. Eventually we figured it out. We now have three successful businesses.

Integrity — I definitely was not the best at this in the beginning of my journey. I was young and new to business. I thought that writing post dated cheques and deflecting calls would buy me time to get the funds I needed to pay my bills. When our business closed, I knew within myself that I had to come clean with all of our suppliers and customers on our real situation. I had meetings with all of them and made plans on how we would repay. I followed through over the years and was able to settle almost all of the outstanding debt. I have had many conversations with those customers and suppliers that were impressed with our resilience and for doing what we promised them. Integrity goes a long way. I always think twice about any decision to make sure that my integrity will remain intact. I was a very shy and timid business owner. Now I can stand confidently and talk about any challenge followed by how it will be solved with integrity.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. The premise of this series assumes that our society still feels uncomfortable with strong women. Why do you think this is so?

I believe that society is slowly but surely becoming more comfortable with strong women. Times are constantly changing. Platforms are becoming even more social, that means that there are now more voices than ever sharing their opinions worldwide, especially since the pandemic.

I even think that the term “strong woman” has changed since 2020. Words like “soft life”, “peace” and “ease” have replaced “hustle”, “grind” and “strong woman”. Femininity is regaining its place for women, because they have seen how much “strength” is related to anxiety, stress, imposter syndrome, overwhelm and too much responsibility.

In my opinion, women are realizing that they do not have to compete with men. Being uncomfortable with strong women is seen more as a mindset that men and women have to change. A woman can be strong and feminine. In my sold out Ultimate Mompreneur Brunch, our panelist, Mrs Liz “Lady” Montano spoke about this. Being vocal as a woman entrepreneur can imply that she is aggressive and too “strong”.

Being strong can also be termed as being strong willed.

In Taming of the Shrew, men pine after Bianca for her beauty and her dowry. She is soft spoken and sweet. Katherine is just the opposite. She is forward and loud; strong willed. Men do not want Katherine. They are frightened of her. I don’t think that anyone would consider Bianca as a strong woman. Not all strong women speak loudly and with assertiveness. If you are familiar with the story, you would know that Bianca had many suitors because of her beauty. I would consider Bianca as strong because she stood her ground and insisted she would not marry until she found her true love, no matter how much her sister beat her or how much her father arranged suitors for her.

Without saying any names, can you share a story from your own experience that illustrates this idea?

Definitely! I remember going to Europe for a retreat. I was so timid and shy. Though I dressed the part and paid lots of money to be at the retreat, I looked for every opportunity to be invisible. I sat in the furthest seat. When asked a question, I would be the last to answer. During the retreat, there were some agendas that were shared that did not align with me. Since I was so shy, it would have seemed that I gave in to the agendas. I stood up for my spirituality and beliefs. I became so aware of what goes on in certain high level circles. I believe that I am strong because I have consistently spoken about my belief and faith, and have never tried to conform to trends.

What should a powerful woman do in a context where she feels that people are uneasy around her?

I believe that eye contact is a powerful tool that either intimidates people or makes them comfortable. For those who are easily intimidated, when you make direct eye contact with a powerful woman, you tend to look away. A strong woman should make the person comfortable by speaking to them in a warm tone and by referencing their name. Oftentimes, that person may feel insignificant and unworthy to be in the presence of the powerful woman. It is all about comfort and feeling seen.

What do we need to do as a society to change the unease around powerful women?

Society can accept that strong women are human. If unease comes because the strong woman speaks her mind and is loud, then society should accept that the woman is speaking her truth. I believe that unease comes from insecurity. If you are confident in yourself, then there is no need to feel intimidated or uneasy with someone else’s strength.

In my own experience, I have observed that often women have to endure ridiculous or uncomfortable situations to achieve success that men don’t have to endure. Do you have a story like this from your own experience? Can you share it with us?

I mentioned earlier that I loved to sing as a young girl. An older man approached me after hearing me sing at a concert. He told me that I had a beautiful voice and that I should come to his studio to lay my voice on a track. Being young and naive, I jumped at the opportunity. My mom was totally against it. She told me that I was being used, and that the gentleman had no business inviting a minor to his studio without an adult present. Being defiant, I decided to still go by myself. When I got there, there was not one, but two men at the studio. The men made uncomfortable gestures and alluded that I can reach far with my looks, size and voice. I felt so betrayed. I have been to music studios throughout my life. I have never seen men uncomfortable in the studio unless their track was “wack”. Females who have a timid demeanor always get raw deals and are made to feel like they have to give up their morals to get ahead in their craft. From my research, the musical greats like Beyonce, Whitney Houston and Mariah Carey all have stories of situations like this. That goes to show that these instances truly do happen.

In your opinion, what are the biggest challenges faced by women leaders that aren’t typically faced by their male counterparts?

I think that one of the biggest challenges women leaders face that aren’t typically faced by their male counterparts is the limit on how much income they can make. In leadership roles, Corporate America and in business, women are always offered the lower (dare I even say the lowest) offers. According to Forbes, the number of female CEOs has been slowly increasing over the last decade, but only 6% of the CEOs of the largest 500 companies in the U.S. are women. Now, I also read, “If a female top manager has a female CEO, her compensation is roughly 16% lower than it would have been if she had a male CEO.” This is alarming. It is difficult enough that women earn less than their male counterparts, it is even more disturbing that their peers make it even more difficult. I believe this is an entirely different topic that needs exploring.

Let’s now shift our discussion to a slightly different direction. This is a question that nearly everyone with a job has to contend with. Was it difficult to fit your personal and family life into your business and career? For the benefit of our readers, can you articulate precisely what the struggle was?

It is indeed difficult to fit your personal and family life into your business and career. The struggle is lack of boundaries. When I had no boundaries, I would allow everyone into my space. I was not strong enough to tell my children that I needed space or time alone to complete critical tasks. I would allow my boss to contact me on weekends to answer questions that were on his to do list. I would check emails all hours of the night.

It was when I started having boundaries that I became calmer and had more structure around my family life and business. The Book “Set Boundaries, Find Peace by Nedra Glover Tawwab also helped a great deal.

What was a tipping point that helped you achieve a greater balance or greater equilibrium between your work life and personal life? What did you do to reach this equilibrium?

My tipping point was when I got an eye infection from being in front of my computer for an extensive period of time without a break. I literally could not see for a few hours. I was in immense pain. I was ordered off screens for two weeks by my doctor. I knew that I needed a break, but the demands of deadlines that were imposed on me by myself and my employers was high. I wanted to complete all the tasks, but it was at the expense of my health. Besides the pandemic, this was one event that sit me right down. I had two weeks to reflect on my life and I knew that I never wanted to be in that position again. So I introduced boundaries. It was hard at first for those around me to adjust. But as long as I stuck to my position, they began to conform.

I work in the beauty tech industry, so I am very interested to hear your philosophy or perspective about beauty. In your role as a powerful woman and leader, how much of an emphasis do you place on your appearance? Do you see beauty as something that is superficial, or is it something that has inherent value for a leader in a public context? Can you explain what you mean?

I see physical beauty as an accessory. It is not necessary. If you have it, I would call it a bonus. If you don’t have it, I believe there are many other traits that bring forth beauty. I would not say that I am the most attractive person in the world, however, the way I carry myself, I am told by many that it is one thing about me that they admire, and they call it beauty.

For many years I was lost and did not take care of my health and my physical appearance. I did not buy clothes. I did not wear makeup. My face always looked stressed. Since the pandemic, I felt within myself that I could do more to give others encouragement to make it through. By the way I was looking, no one would believe that I could speak to anything regarding leadership or business. I started working on being a reflection of who I wanted to become. I gradually started buying new pieces for my wardrobe. I changed my hairstyle. I bought lipstick for the first time in 12 years. I visited a dermatologist to start correcting hyperpigmentation and my uneven skin tone. As simple and as insignificant as that may sound, it made a huge difference in how I saw myself and how others viewed me.

I said earlier that physical beauty is an accessory. Even without makeup or fancy clothing, I still carry myself with a certain level of class, because you never know who you may meet when you leave your home.

How is this similar or different for men?

I believe for men it is the same. You are taken seriously when you carry yourself in a classy way. A study was done that asked participants to rate how friendly, trustworthy or strong the person in a photo appeared. The photos with a happy outlook were deemed more friendly and trustworthy. However, men with broader faces were assumed to be stronger in stature and will. So, people make assumptions based on your physical appearance.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Powerful Woman?” (Please share a story or example for each.)

The five things you need to Thrive and Succeed as a Powerful Woman are:

1. Boundaries — If you give people the chance, they will always try to cross the line. They will go as far as you let them. Clients have a way of trying to get the most out of their investment, so they call, email text and show up to your office whenever they feel like it. I had a client leave lots of messages after their calls went unanswered. It bordered harassment. The best thing to do is to clearly state your boundaries in your contracts and email footers. My email footer currently reads, “**I don’t read emails or accept work-related calls after 5:00pm on weekdays and on weekends. If you’re reaching out at these times, it is very likely you may not get a response. I’ll be sure to reply at my earliest opportunity the next business day.”
2. A Strong Network — Different doors can open because of your network. A strong network is an invaluable tool because their recommendation can cause you to be in rooms that you are not qualified to be in. I was called to be a part of an exclusive discussion because of a close colleague in my network. It pays to strengthen your network. I am always researching and reaching out to leaders to start a conversation. Who knows where your connection may lead mutually.
3. Confidence — As I mentioned before, I was very shy, and for no reason. I am sure that I missed out on many opportunities because I failed to shoot my shot. Not anymore! Now, I speak more confidently when in public, and I also dress the part. I believe they go hand in hand
4. Persistence — In life and business, there are periods of success and failure. For both periods, persistence is key. When you are in times of success, persistence has to be ever abound because you have to continue with what works. In times of failure, you have to remain focused on the goal and continue to work through whatever challenge is facing you. If I was not persistent in completing my life plan back in 2015, I would not be where I am today. I did not stop in spite of delays and setbacks. I was able to complete my Bachelors Degree after 5 years because of persistence. Many times I wanted to give up. But I kept focused on the goal. Which brings me to my next point.
5. Patience — Success doesn’t happen overnight. I am sure we have heard the many stories about the number of years it takes to turn a profit or to truly see lasting success. Patience and strategy are important. You cannot be patient for something that you do not have a plan for. Create the plan, be patient and reap the success!

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I would like to have a private breakfast or lunch with Tabitha Brown. I believe she displays all of the five traits I listed above. I know they all were a work in progress. I would like to understand what it was like for her to go through her process of discovering her true authentic self and her secrets to thriving and succeeding as a powerful woman.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.