“You can’t just pick one moment”, says Mrs Francine Jackson, when asked what the proudest moment of her life was to date. Sat with her at her dining room table surrounded by walls adorned from top to bottom with pictures of loved ones and achievements that illustrate an incredibly full life – she might well be right.

Over the course of two days, Cayman Parent was offered the unique privilege of a seat at the table with four generations of Caymanian women, who took turns sharing their own defining moments. From these, arose relevant conversations on empowerment, ambition, faith, community, parenting – and insight into what it takes to maintain intentional, meaningful family relationships while juggling professional success and the pressures of everyday life.

This is what Mrs Francine, her daughter Jennifer, her granddaughter Rita, and her great-granddaughter Elizabeth had to say.

Mrs Francine Jackson

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After pause for thought, Mrs Francine eventually did settle on her proudest moment: “My proudest moments are through my family.” It is a humble answer from someone with a resume as remarkable as Mrs Francine’s: teacher, insurance agent, Cayman’s longest serving civil registrar, founding member of the United Church’s Women’s Fellowship, recipient of the Gold Medal of Merit, wife, matriarch and renowned hostess. Even in graciously offering you a seat at her table, you are struck by the realisation that, as an influential figure in the women’s suffrage movement in Cayman, Mrs Francine has enabled generations of women to occupy a seat at any table.

Born in Bodden Town, Mrs Francine was raised in West Bay by her adoptive parents, Caleb and Mabel Powell. There she met and married her late husband Vernon Jackson OBE JP who was trained as a schoolteacher. In 1956, the couple relocated to Bodden Town after Vernon was offered the position of headmaster at the Bodden Town All Age School. Vernon went on to carve out an impressive career in Government Service, mostly in Education.

During this time, Mrs Francine, by then a mother of three, and a group of notable women, including Evelyn Wood, Nettie McCoy, Marie Rankine, and Evangeline McLaughlin, reinvigorated the local push for women’s suffrage.

Prior to receiving the vote, Mrs Francine explains that women’s voices carried no real weight in Cayman society: “Men were the elders, the managers, the committee members…”. Through a concerted effort, these women lobbied to change that. Handwritten meeting minutes were carried from district to district, a petition was circulated, and women from across the Island made their way to George Town (a major logistical feat in those days!) to demonstrate in front of the Town Hall. With a total of 358 signatures, the petition was a success. Mrs Francine cast her first vote in 1959 and smashed through another glass ceiling as one of the first four women to stand for political office that same year.

Mrs Francine, the late Mr Vernon and their three children, Jennifer, Joy and Andre. Photo by Rebecca Davidson Photography

In short, Mrs Francine’s professional strides have been empowering. She leads by creating opportunities for others and her influence has spanned generations. She is a founding member of the Lighthouse School, which has enabled learning opportunities for thousands of children since its formation, she was a locally travelling insurance agent whose clients came to resemble something closer to friends, and together she and Vernon have given their blessing to over 8,000 unions since establishing their wedding planning and officiant business, Cayman Weddings, in 1984. Today, Mrs Francine still officiates one to two weddings a week, and the beautiful wedding ceremonies that she and her husband wrote continue to be used.

This trait of selflessness is present in how she operates personally too and is something Mrs Francine and Vernon both endeavoured to instil within their children. “Growing up, it wouldn’t be unusual for everyone to have to take a bit of food off their own plate to make up enough for a needy neighbour”, remembers her daughter, Jennifer.

Mrs Francine with 12 of her 13 great-grandchildren / Photo by: Maggie Jackson of Déjà vu Photos

It was this same table that Mrs Francine, Vernon, and their three children (daughters Jennifer and Joy, son Andre) sat around three times a day to share meals. The institution of communal mealtime has always been upheld in the Jackson household: “It is where you can sit and talk as a family,” explains Mrs Francine. “Nowadays it’s very different altogether. People are a lot busier. But I still feel good about the fact that we weren’t so busy in my day to sit and eat together.”

As her children have grown up and started families of their own, daily meals together are augmented by weekly gatherings at Mrs Francine’s house. On any given Sunday evening you can find the matriarch surrounded by many members of the extended Jackson clan, including some of her 13 great-grandchildren, and various friends, enjoying her famous High Tea. The takeaway from such a tradition is clear: spending time together is a priority. What this looks like may vary from family to family – but for the Jacksons, carving out time to congregate around a table, eat and catch-up on each other’s week, is a significant part of preserving their close relationships.

Perhaps belonging to the United Church’s caring community for over 90 years, during which she helped found the Women’s Fellowship and has consistently remained an active member, informed Mrs Francine’s values on relationships. “I thank God constantly for my Church family,” she says. She has had prayers answered alongside these people, celebrated life’s highs, and navigated life’s lows. She feels a deep sense of connectedness with the John Gray Memorial United Church community – and she reminds each member of it when she calls them each year on their birthday!

Jennifer Dilbert, MBE JP

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All families have a set of beliefs, values, and attitudes that are handed down from generation to generation. Jennifer Dilbert, daughter of Francine and Vernon Jackson, confirms this to be true with the inheritance of a strong set of guiding principles and a career as impactful and diverse as both her mother’s and father’s.

Growing up in Bodden Town, “life was good”, recalls Jennifer. “My siblings, Joy and Andre, and I spent a lot of time outdoors and in those days, you could safely walk the beach from one end of the district to the other even as a child. Everyone knew you and played a part in bringing you up.” After attending primary and secondary school in Cayman, Jennifer left the Island for Brock University in Canada, where she studied Economics. Shortly after completing her degree, she returned to Cayman where she began her civil service career in the statistics office (now ESO) and managed the 1979 Population Census. That same year she was crowned Miss Cayman, and after a busy year of travel and promoting Cayman, she married teenage sweetheart Leonard Dilbert, also a civil servant.

So began an over 30-year long career in the civil service, during which she headed the Financial Services Supervision Department (the precursor to the Cayman Islands Monetary Authority), remained a key figure in the development and drafting of the Cayman Islands legislation for financial regulation, served as the Cayman Islands Government Representative in the United Kingdom for eight years, established the Cayman Islands’ Freedom of Information Office, and held the post as Cayman’s first Information Commissioner. Leonard and Jennifer both rose up the ranks of the civil service to become Chief Officers, while raising their two daughters Rita and Juliette.

Jennifer and Leonard with their daughters Rita and Juliette.

Jennifer’s parents instilled in her a self-confidence and sense of self-worth, “without which I could not have progressed in my career or life in general”, she explains. However, she believes her long list of accolades would not have been possible without an incredible support system. Their nanny, the late Lorine Hylton, and their parents, always pitched in to help Leonard and Jennifer balance work and home life. “I’m really sorry for people who have to juggle it all without any support – because it’s hard even with a lot of help”, Jennifer says, “and I’m particularly blessed to have a husband who has always supported me both practically and emotionally“.

Prior to relocating to the UK for the Cayman Islands Government Representative position, the couple, with their daughters Rita and Juliette in tow, took a year-long sabbatical on Vancouver Island in Canada. Despite both Leonard and Jennifer’s rapidly advancing careers, the focus that year was on family. When asked about their parenting style, Jennifer echoes the same sentiments that were bestowed upon her by her parents: “Spending time together as a family is just so important. Sitting at the dining room table, chatting – that is how values get passed down.”

Jennifer describes her almost decade-long stint working in the UK Cayman Islands Government offices as busy but rewarding. She advocated for Cayman through the Houses of Parliament and the European Union, she was a founding member of what is now Cayman Connection, she set up the UK Friends of Cayman group, and she re-established the All-Party Parliamentary Group. A flip through her photo albums (of which she has one printed for every year!) illustrates fond memories of her many official events such as Buckingham Palace Garden Parties, Opening of Parliament, and her Annual Office Receptions. She recalls enjoying dozens of the famed summer classical music ‘Proms’, outings with her father, mother and Leonard as well as days at Ascot and Glyndebourne, and picnics in the park or back garden with friends when the weather was nice. It was this same circle of friends that Jennifer got to ‘clink’ her Champagne glass with when she heard the news she was to be appointed a Member of the Order of the British Empire (MBE). “On the morning it was supposed to be in The Times, I got up early to buy a copy. I remember sitting on a bench on the way home, flipping through the paper – just to check it was really there!”

Jennifer with her parents and husband, Leonard, after receiving her MBE.

With so much to be thankful for, Jennifer has always been interested in giving back to the community: “I had so much support – I want to pay it forward”. She is on several Boards and Committees, including the Board of the National Gallery, Board of Elders for the John Gray United Church, and the National Executive of the Women’s Fellowship. Along with her mother, she assists with the Church’s ministries such as Young Parents Programme, visitation of the elderly, support for bereaved families, food pantry, Christmas meals, soup kitchens and more.

Life has carried Jennifer many places and in moments of indecisiveness she has leant into her faith. Her favourite Bible verse, Proverbs (3:5-6), perhaps sums up her approach to life best, “Trust in the Lord with all your heart, and lean not on your own understanding. In all your ways acknowledge Him and He will direct your paths”.

Rita and Elizabeth Powell

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Sitting with Rita and Elizabeth Powell, we are reminded of two things. Firstly, that our values are most clearly demonstrated in how we choose to spend our time and energy. Secondly, of the power strong familial bonds hold for uplifting the next generation.

For Rita Powell, daughter to Jennifer Dilbert, granddaughter to Francine Jackson and mother to four children of her own – her interest has always been in service to the community. “I had many role models growing up in West Bay. My mum, dad, grandmother and grandfather were all in public service, so this is something that became a core value of our household.” Upon completing a degree in Art, Media and Design, Rita decided on a career in education and enrolled in teacher training, receiving a PGDE, a Post Graduate Diploma in Education. At the helm of her own classroom, she noticed that there were certain students who were having a harder time than others. Further study and completion of a dyslexic remediation course opened her eyes to a world of learning disorders, and she turned her focus to special needs education and transitioned into the role of Special Education Needs Coordinator. Rita presently works at John Gray High School as an on-site Inclusion Specialist where she implements interventions for children who may be experiencing social, emotional and/or learning difficulties so that they are able to cope in a general education setting. She is also studying for a Master’s in Mental Health Psychology. Reflecting on her professional achievements, Rita explains that anything she involves herself in “is to fill a need. Although we have made so much progress, there is still so much to be done to assist the vulnerable children in our community.”

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Alongside busy careers, Rita and her husband Dominique pour their time and energy into raising their children: Elizabeth (15), Alexander (12), Lionel (7) and Eli (3) and are proud of Dominique’s daughter Glory (19) who is studying abroad. Like the values passed down from her mother and grandmother, the couple firmly believes there is no substitution for spending quality time together as a family: “We have dinner every night at the table. We communicate, we swap jokes, we tell each other about our day. We have a wonderful time!”

It is, nonetheless, a huge mission to make sense of six schedules. Thankfully, Rita has many helping hands to keep things ticking along: “My parents and Dominique’s mother, who has the affectionate title ‘Mum-Mum’, all are willing to do everything they can to help out,” she shares. “And of course – a giant whiteboard is essential!” On the topic of Rita and Dominique’s approach to parenting, Rita explains there is no ‘one-size-fit-sall’ method, however she shares three things that work for their family: “We try to keep up-to-date on what is best practice. We recognise all four of our children as individuals with individual needs, so that we can respond accordingly. And finally, we try not to repeat mistakes.”

Rita has learned many lessons from her roles as educator and mother, but one which she wants to impress upon others is to remember to praise the process and keep positive. She explains that children ultimately just want to be loved and make others proud, “I see it in my students at school as they try every single day to do their best, and my own children are no exception. They are such kind and compassionate people, and I am very thankful for the efforts they make.”

It seems this gratitude is mutual. “I am lucky to be growing up surrounded by family members – there is always someone to keep me company and talk to”, shares Elizabeth, Rita’s eldest child who currently attends Cayman Prep and High School. These connections give way to a deeply rooted mutual respect and genuine care for each other, visible in Elizabeth’s easy relationship with her mother, the laughs she shares with her grandmother and the way she is sure to greet her great-grandmother first when she enters a room.

When asked what the best part is about growing up in Cayman, she answers “the sense of community”. Like the family members before her, Elizabeth is interested in preserving this community for future generations. She volunteers at the National Art Gallery, acts as Key Club Treasurer and volunteers with her mother and grandmother at the John Gray Memorial United Church.

Her future stretches out wide in front of her and she is excited for what is to come! She plans to travel abroad for university – supported by the family and community that has always encouraged her to chase her dreams.

Rita and Dominique with their children Elizabeth, Alexander, Lionel and Eli and Dominique's mother, Margaret Powell.

Sitting around the table with these four women, one thing is certain: there is power in people coming together. There is strength in having a common purpose and it flows easily through the branches of this family tree. At points, this common purpose has been lifting each other up to feel supported personally and professionally, raising a child, embracing the role of grandmother, mother, sister, and daughter, working to better the community and always being each other’s biggest cheerleaders.

Families come in many shapes and sizes, and they are never without their challenges. Mrs Francine, Jennifer, Rita, and Elizabeth have experienced their own share of hardships, disappointment, stress, and frustration – however in these moments they have found comfort in the arms of family and kept faith in God that it is all going according to His plan.

Article Credits

Photography: Rebecca Davidson

Shoot Location: The National Gallery of the Cayman Islands

Clothing & Accessories: Funky Monkey

Make Up: Kadian Edie from Luxury Couture Beauty

Hair: Amanda Darcy & Francis Campos from Rock Gorgeous Hair