Anika Conolly knows a thing or two about perseverance. The 27-year-old aspiring singer and West Bay native entered her first pageant when she was 9 only to place second alternate. Later, after returning from Canada, where she attended boarding school and university, Conolly entered the Islands’ most prestigious pageant, Miss Cayman Islands, in 2015. She came away empty-handed and heartbroken, but as a sister to three younger siblings, she wanted to set a good example of working hard towards a goal.
This year, she took home the Miss Cayman Islands crown as the oldest contestant and champions a message of never giving up on your dreams. When she’s not working as a talent acquisitions specialist for Caribbean Utilities Company, she is working hard on her next dream of writing and recording music. According to Conolly, she’s recorded one track so far but is hoping to have a handful more done before 2017 is over.
You left the Cayman Islands to study abroad. Other than the weather, what brought you back to the Island?
A lot of things. I love the ocean. I love swimming. I love being able to be near the beach. I love my family and friends. The way we interact with each other — we take care of each other, we’re there for each other, we look out for each other — that’s the Caymankind that you hear a lot about.
Also, the food is amazing here. I loved eating in Toronto, but I don’t think anything beats a good Cayman-style fish dinner.
You’re an aspiring singer. Have you been singing all your life?
Not my whole life, and not well either. When I entered Cayman’s Our Little Miss pageant at the age of 13, it was the first time I decided to sing as my talent. I did horrible, but I didn’t let it deter me. When I went away to boarding school, I actually had voice lessons and joined a choir at the school. I quickly learned that I had a pretty wide range.
What style of music do you sing?
I do a mixture. I like a lot of jazz, so Ella Fitzgerald and Billie Holiday are some of my favourite inspirations. I also like Whitney Houston. I sing a lot of Broadway songs [and show tunes] as well — Chicago, Singin’ in the Rain, Disney. My style of singing has a mixture of all of those genres within it.
What made you want to get into pageants as a young girl?
Pageants were not on my radar at 9 years old. I didn’t want to dress up in frilly dresses, go out on stage and put myself out there for the whole world to see. I preferred to stay at home and read Nancy Drew books. But my mom saw the opportunities and understood the positive impact and skills that you develop by being a part of pageants.
When I was 16 years old, I wanted to do the Miss Teen pageant, but because I was going away to school, I had to forfeit that opportunity. I told myself, “When I come back from school, I want to do Miss Cayman,” because at that point, all of the things that I’d learned through the pageants I had been in, those skills were able to help me succeed in other areas in my life. You’re taught how to conduct yourself in an interview; you learn confidence by being able to stand on stage. I didn’t win the first year I entered in 2015. But I didn’t want to give up, so I went again this year and it paid off.
How hard was it for you not achieving your goal of winning Miss Cayman Islands in 2015?
It was a little heartbreaking that I didn’t win. But I have three younger sisters, and for me, being the oldest, I wanted to give them a really great role model to look up to. As a role model, it’s important to show the skills of resilience, perseverance and determination when it comes to achieving your dreams. I didn’t want them to think that giving up was okay.
Were you scared of entering the pageant again?
I was totally afraid. First of all, I was the oldest of all of the contestants by two years. And all of the girls that I competed with had their own special, unique talents that they brought to the table. They worked hard to try to win the title, just as hard as I did. I didn’t take it for granted that I’d been in the pageant before, because everyone has their own personal drive. Everyone has a skill and a talent to bring to the table.
When they called your name, what was going through your head?
When they were announcing the winners, I was preparing to congratulate whoever won, because you never know what the decision will be. In my head, I was thinking, ”Okay, I’ve got to keep my smile on and not show any disappointment.” When they actually called my name, it took me a second for it to register. The whole moment was just surreal. It took me about a whole month for it to sink in that I had won.
What are your responsibilities as Miss Cayman Islands?
My responsibility is to represent my country as an ambassador. I work alongside the Department of Tourism to promote Caymankind and the Cayman Islands as our tourism product. I will also be representing Cayman at the Miss Universe pageant in November. I also believe that as Miss Cayman Islands, my responsibility is to be a positive role model for those that look up to me.
Do you have a philanthropy that you champion?
I just want to help everyone, but children and youth are one of my biggest passions. Any sort of after-school programme or any initiative that’s geared towards helping kids to either get out of at-risk situations or to excel in the future is a passion of mine. The Cayman Islands Cancer Society is also another organisation that is close to my heart because my grandmother died from lung cancer. I’d like to be able to raise awareness of ways we can prevent cancer and ways we can help those who struggle or have been affected by cancer.
How do you celebrate the holidays on the Cayman Islands?
It’s sort of a Cayman tradition that at Christmastime we sweep our yard with sand. We don’t really do it anymore, and instead we gather all of our family together to eat and bond. So every year, someone in our family will have a cookout at their house and we’ll all go over to eat. Cousins, uncles, aunts, grandparents, long-lost relatives — we’ll all come together and celebrate.
Is there one dish you really look forward to during Christmas?
One thing I must have at Christmas is Cayman-style beef with custard-topped cornbread, mashed potatoes and cranberry sauce.
Are you the cook, or is your mom the cook?
We cook different dishes. She will cook the meats, and I’ll make the sides like the cornbread, mashed potatoes, stuffing and coleslaw. There was one year I decided to try making a turkey, and it did not end well.
Author: Daniel Guzman
Photographer: Jim Gates