Dee-Ann Kentish-Rogers has featured as a guest on the Female Empowerment podcast, which explores women’s journeys in politics, diplomacy, business and activism.
During the 40 minute episode, which aired on Spotify and YouTube this July, she spoke with co-founder and host Simone Kehler Funk about ambition, identity and leadership.
The interview traced her journey from international athlete and Miss Universe finalist to lawyer and government minister, highlighting the challenges and turning points that shaped her path.
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Kentish-Rogers opened the talk by sharing reflections on her formative years growing up in Anguilla, explaining how the island’s close-knit community shaped her identity and sense of accountability.
She said her mother instilled a powerful message from an early age: “There’s always room at the top… if you practice excellence, there will always be room for you.”
Kentish-Rogers said this belief gave her the unquestioned confidence to “take up space” regardless of others’ attempts to pigeonhole her.
A diverse career
Discussing the diversity of her career – as an athlete, lawyer, beauty queen and politician – she attributed her ability to adapt and excel to an ingrained “curiosity” and a willingness to “reinvent yourself”.
After a career-threatening injury ended her athletic aspirations, she embraced change as an “inherent part of myself and adaptability”.
Despite varied roles, Kentish-Rogers said a unifying theme has been service which is inspired by her grandmother’s dedication to family.
Whether representing clients, constituents or her country, Kentish-Rogers said her work is always grounded in authentic representation and mentorship.
She recounted a pivotal moment when she stepped away from her ministerial role amid a politically charged environment.
“It was about doing what was right in that moment, over doing what was popular,” she said.
This act of principled independence demonstrated what she called “resilience of adaptive leadership”, embracing identity as fluid rather than fixed.
A future vision
Reflecting on her vision for Anguilla, she expressed optimism despite global uncertainties.
“We have the opportunity to become a shining star in the global geopolitical scene… in economic, social, sports and health development,” she said.
Kentish-Rogers continued by reflecting candidly on the challenge of self-doubt, which she described as something everyone faces at some point.
She explained how unsolicited feedback, often coming from multiple directions, can cloud a person’s focus, yet she found strength in perseverance.
Looking ahead, Kentish-Rogers revealed an exciting personal project – writing a memoir: “It’s taking its time. It’s very time consuming, but I thought it’s important.”
She noted the scarcity of such personal narratives from young Caribbean women and expressed hope that her story would highlight the region’s unique resourcefulness.
The memoir, she said, is a deliberate effort to document her journey for a wider audience.
An empathetic approach
Dee-Ann’s approach to leadership crystallises in a single word: empathy.
“Leadership means empathy, but not sympathy. The ability to be empathetic means that you can understand, but you still leave space for holding persons accountable and taking action,” she said.
She emphasised that true leadership requires authentic connection combined with decisiveness.
Finally, Kentish-Rogers expressed her aspiration to leave behind a legacy of authenticity in leadership.
“We need leaders who are living authentically, who don’t pretend or put on airs, but who are considerate of the impact that they have on others.”
Paraguay-based Kehler Funk told Anguilla Focus that speaking with Dee-Ann Kentish-Rogers was especially meaningful.
“Her path – from athlete and Miss Universe finalist to lawyer and becoming minister – reflects the kind of courageous and multidimensional leadership we love to highlight,” she said.
“One quote she shared has stayed with me: ‘There is always room at the top, if you practice excellence and you are good at what you’re doing.’
“That kind of insight is exactly what makes these conversations so powerful.”
Watch the podcast in full below:
