A Dynamic Diva

Todays FutureName: Chamara Hollingsworth.

Age: 32


Women Innovators Network in the Caribbean (WINC)

Small Business Association

Technical Vocational Education and Training (TVET) Council

Samuel Jackman Prescod Polytechnic

University of the West Indies (Cave Hill)

Barbados Community College (BCC)

Christ Church Foundation School


Bachelor of Science in Management Studies

Associate Degree in Business Studies


Women’s Empowerment Coach, Personal and Professional Consultant and Coach, Entrepreneur, Event Planner, Speaker, Trainer.

You are sitting backstage getting ready to speak to a conference of women and the master of ceremonies is about to introduce you. What would that person say?

Chamara D. Hollingsworth is a Barbadian mother, entrepreneur, writer and speaker. As an avid believer in the power of self love. Chamara found her calling to facilitate the personal and professional alignment of women’s lives by encouraging them to empower themselves to build a foundation based on self love. After finding her passion for business at the Barbados Community College, Chamara fuelled her rapidly expanding knowledge of the business world with a more innate calling; her need to help people.

In 2010, Ms. Hollingsworth coupled her passion for self empowerment and entrepreneurship in Barbados and the rest of the region with her drive and opened her third business, Expressions Management Consultancy. She utilized this platform to develop workshops to bring clarity to aspiring and existing entrepreneurs and business owners and training sessions to enhance customer service. Expanding on the success of her previous years, Chamara used 2013 to launch a new business, Vision 2 Reality International. Its events are achieving increasing popularity, most notably the Dynamic Diva Hour of Power.

Chamara Hollingsworth.
Chamara Hollingsworth.

What are you passionate about?

My children, helping others to succeed, music, dance, writing and people seeing value in themselves.

What four words best describe you?

Passionate, creative, crazy, stubborn.

Do you have a philosophy that you live by?

Everything flows from inside out.

After leaving secondary school, you chose to attend the BCC. Why BCC and not a sixth form school and why did you choose to study Business Studies?

Actually, business studies was not even on my radar. I went into BCC to do Building and Civil Engineering but I was not focused at the time and I was failing and was given the option to leave or choose Maths and Economics or Business Studies. I chose Business Studies because it had a range of subjects to learn.

From an Associate Degree in Business Studies to a Bachelor’s in Management Studies. Was it your initial plan that after BCC, this area would be next?

My initial plan was to go and get a job after BCC. But after having the opportunity to intern and observing how the business I was in functioned, I realized that I actually had a love for business and decided to apply for the Management Studies degree.

Between 2007 and 2010, you worked in administrative roles at Project Coordinators Inc. and SDC Inc. What can you tell us about these companies and your experience there?

Even though I switched over to Business Studies, I was still at the time very interested in the technical fields and project management. So I worked for the two companies mentioned. PCI was responsible for managing the construction of the British American Building and SDC Inc. does building plans, residential and commercial construction as well as project management. I had the opportunity to learn more about managing human and material resources, project management, building drawings and construction.

In 2007, you completed two courses with the Small Business Association:  Managing Your Own Business and Business Plans and Project Proposals. Was this your preparation to enter into the world of entrepreneurship and why these two areas to start with?

To be honest, I had just come from 20+ years in the educational system and I felt as though I was going crazy outside of the school setting. I had just started a small printing and craft business at that time and thought that these two courses would have been ideal for me. They were very helpful at the time.

From employee to entrepreneur. Was the transition an easy one and what was the defining moment that confirmed for you that now was the time to take that leap?

No. The transition was not easy. Sometimes I feel as though I am still transitioning. When most of the people around you can show you all of the reasons why you should get a job at a time when you are about to step out into a place that scares you, it can be difficult. You start to doubt yourself and your decisions. I was thinking about starting a consultancy and I had just come out from maternity leave and a very short while after the jobsite I was working with was halted and everyone was sent home. I decided that this was my opportunity to go into business full time.

If you had an opportunity to live over your life from the time you entered secondary school, what is one thing you would do differently?

I would be less shy. More outgoing.

If you had to choose an animal to best represent you, which would you choose and why?

I would have to say a cat. Firstly, it has always been my favourite animal and evidently my first word. But cats are playful and agile and yet they can be pretty no-nonsense and they go after what they want.

Dynamic Diva is a brand that is growing in Barbados. Tell us about the brand and the Business Basics Workshop Series and the Design your Dynamic Goal Workshop.

Dynamic Diva originally started out as a one-off Hour of Power event focused on the topic of fear and turned into an ongoing seminar event and eventually a brand which seeks to create economical experiences to enlighten, educate and empower women.

The ‘Business Basics Workshop Series’ is a collection of workshops to help start-up and developing entrepreneurs through the different phases of their business by simplifying and explaining some of the areas in business. It includes workshops on Business Start-up, Marketing, Book-keeping, Communication and more.

The ‘Design Your Dynamic Goal Workshop’ is a workshop that helps the participants to get clear on what they want and to develop clear and concise goals and to start working on how they plan to reach the goal set.

Dynamic Diva Hour of Power
Dynamic Diva Hour of Power
The presentation to the speakers of the 2015 Divas that Dazzle Seminar.
The presentation to the speakers of the 2015 Divas that Dazzle Seminar.

Over the years, you became a personal and professional development trainer. Given that your mum was a teacher for many years, did you ever think you too would become a teacher and were you natural in this new role?

I never saw myself as a teacher. Everyone in my family, including myself, saw me following in my father’s footsteps and going into construction. When I think of it, though, teaching has always come naturally to me, although I never saw it as teaching.

“Business in a Nutshell” is a free seminar you conducted targeting relevant entrepreneurs and potential entrepreneurs covering some of the challenges and relevant solutions that entrepreneurs face. As an entrepreneur yourself, what are three challenges you and other entrepreneurs have faced?

Three challenges that I have faced over time are not getting the support in the way that I would like, facing and moving past my own doubts and fears, and balancing all of the tasks that come with the business.

Over the last three years, you have been a personal and professional development consultant and coach with Vision 2 Reality International. What services does this organization offer and what led to its creation?

Vision 2 Reality International offers public and private workshops and seminars, coaching packages and programmes which deal with goals, fears, self-love and more, corporate training, speaking engagements and business event coordination. It came about through observations and experiences that led me to realize that many women do not see themselves as important. We have a tendency to work extra hard to ensure that the people and things around us are in tip-top shape and then we forget to nurture ourselves. So Vision 2 Reality International was conceptualized to address that by offering our services to women in order to help them to see the value in themselves and work towards achieving their dreams and desires.

Tell us about your involvement with Micro Macro Internship Programme.

I am currently the Programme Manager for the Micro Macro Internship Programme. It is a programme created by the charity Small Enterprises for Education and Development to change the internship culture in Barbados. We are currently in Week 3 of this year’s programme and we have successfully placed 14 interns with businesses across Barbados and provide them with training two days each week from a variety of experts who have volunteered their time and wisdom to help to develop this group of 15-23-year-olds.

You successfully created and collaborated on a project with Dazzle Magazine. Tell us about Divas that Dazzle.

In 2015, Vision 2 Reality International was invited to participate in the Global Entrepreneurship Week of Activities which were hosted by the Barbados Youth Business Trust under the Dynamic Diva Brand. In summary, I had the opportunity to speak with Mr. Ryan Wills of Dazzle Magazine at another BYBT event and we decided to focus on an event that highlights the achievements of multiple female entrepreneurs in a relaxed setting and hence, Divas that Dazzle was born. The event was hosted at Artsplash Centre free of cost for participants and it was a night of positive and inspirational lessons for us all. We will be hosting this event again for this year’s Global Entrepreneurship Week.

You are the author of two books. What motivated you to write them and what are they about?

I have written two books which are very different. The first book “In the Words of Coco” is a collection of poems that I wrote between 2007 and 2009. The second book “Be You. Do You. Love You: A 30 Day Self-Love Challenge” was created as a result of a yearly seven day self-love challenge that I host on Facebook. This time, I decided to challenge myself to come up with 21 self-love activities and as I completed the challenge, I realized that it was something that I could share with others who want to make positive changes in their lives.

Would you say studying Business and Management prepared you with the knowledge needed to be a business owner?

They gave me a host of theoretical knowledge. I quickly came to realize that theoretical and practical are two completely different kettles of fish. In all fairness, though, some of the information that I would have learned still helps me to this day.

As a mother of two beautiful girls, do you find it difficult at times to balance your work as a professional and your responsibility as a mom?

I would be lying if I said it was easy. As time goes, I have realized that it is much easier to let go of the need to control every little detail. There are things that you cannot possibly plan for that just change the direction of any given day, sickness, injuries etc. It also helps to know that that there are people around who are willing to pitch in in some way or another. I remember two weeks after I had my second daughter, I turned up for the set-up of one of the Dynamic Diva Hour of Power Sessions, only to be sent home by my friends and boyfriend who had already finished setting up by the time I got there. I also can think of countless occasions where my daughters’ grandparents have pitched in by keeping/collecting/dropping off the girls at short notice so that I can take on opportunities that have come my way. The hardest part to me, as an entrepreneur, is knowing when to switch off the brain and separate the personal and the professional.

What’s next for Chamara and Dynamic Diva?

Wow! There are so many things to come. But in the immediate future, we will be celebrating three years in August (and I will be 33!) and we will be offering some birthday bonuses, dynamic discounts and awesome activities throughout the month of August.  We have our next Dynamic Diva Hour of Power coming up on August 31 and another round of the Make It Happen! Group Coaching Programme ready to go and more!

Who has contributed to your development and success that you would like to say thanks to?

There are quite a few people that have contributed in some way, shape, form or fashion (either as negative or positive reinforcement) to where I am now and my growth over the years. I can’t possibly name all: my parents for sure – Charles Reid and Marcia Hollingsworth, my boyfriend – Marlon Waithe and my daughters – Sierra and Nairobi – are the few that I would dare give mention to although I do very much appreciate every single person that has offered a hand, a word, shared and supported and more.

(If you are a young Barbadian professional, or know of any worthy of being highlighted for their amazing contribution, please contact us at corey@c2jfoundation.org)

2 Responses to A Dynamic Diva

  1. Rosalind Eastmond
    Rosalind Eastmond July 27, 2016 at 6:51 pm

    Congrats Msss.

  2. Nicole Cumberbatch
    Nicole Cumberbatch July 27, 2016 at 7:08 pm

    Congrats Chamara!


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