Heneka Watkis-Porter redefining leadership at sea

Six years ago, Heneka Watkis-Porter made a decision that would redirect the trajectory of her life. The shift did not come all at once, but through a series of jolting experiences that forced her to confront whether she was living with intention.

From that reckoning emerged Grace to Grow Mentorship and Training, a vow she made to God – and to herself – to help women step boldly into their purpose.

“Life-threatening experiences in 2020, coupled with the pandemic, delayed our start. But by 2022, we opened our virtual doors to women who needed clarity about what it means to walk in purpose”, Watkis-Porter said.

What began as a mentorship and leadership programme has since evolved into something more immersive: a leadership experience at sea called LeadHerShip.

Each time she hears her biography read aloud, she admits she is amazed “I am still that little girl from St Mary. Everything I have accomplished has been through God’s help,” she said.

Her entrepreneurial path started with Patwa Apparel and a sauce line – ventures that taught her how to build from the ground up and how to hear ‘no’ without quitting. Her podcast, The Entrepreneurial You, later widened her reach from local radio to a global audience, bringing interviews with figures such as Richard Branson, Lisa Nichols, Les Brown and Seth Godin.

From hosting the Caribbean’s first Virtual SME Conference and Expo to facilitating Leadercast events and partnering with the Jamaica Stock Exchange for She Leads, her work expanded steadily from individual coaching to convening communities of leaders keen to grow.

LeadHerShip, she said, is the natural convergence of her lessons in leadership, faith, storytelling and community-building.

The idea first surfaced in 2018, while she was facilitating Leadercast Women. Over time, a mix of prayer, prophecy and unsolicited affirmation pointed her back to the sea. A church leader spoke of events aboard a ship. Women at a retreat sensed the experience belonged offshore before she had even mentioned it.

“At some point, you stop waiting for more confirmations and start doing the work,” she said.

The work culminated in November 2025, when the inaugural LeadHerShip cruise launched – just a week after Hurricane Melissa. The timing would have discouraged many. Airports were closed. Forecasts were uncertain.

“Outside, the forecasts were chaotic. Inside, I felt an unexplainable peace, with just a little ‘tups’ of nerves,” she said.

For Watkis-Porter, cancelling the voyage was never on the table. “I didn’t need to see the whole picture. I just needed to get through that moment, and then the next would be worked out.”

The journey confirmed her belief that storms – literal or figurative – come to pass, not to stay. It also underscored the resilience of Jamaican women. “I saw determination. I saw adaptability. I saw women who refused to let circumstances stop them from walking in purpose.”

LEAVING FAMILAR SPACES

As participants processed what they had left behind after the hurricane, the programme shifted. A virtual session offered space for reflection and healing. From those conversations emerged a partnership between Grace to Grow and Young Women and Men of Purpose (YWOP/YMOP), supporting recovery efforts in the fishing village of Parottee, St Elizabeth.

It was then that Watkis-Porter knew LeadHerShip had outgrown the confines of a conference.

“There was a moment at dinner on the first night when I thought, ‘It has happened.’ But I have learned not to depend on feelings. I depend on knowing I have done something purposeful,” she said.

The cruise, she insists, is not novelty but strategy. “There is something powerful about being removed from familiar spaces. When you step outside of routine, you create room to think differently.”

Days begin with journalling on deck against blue horizons. Structured leadership sessions sit alongside laughter, exploration and shared meals. Growth, rest and joy coexist in what she calls “a moving sanctuary.”

LeadHerShip 2027 will stretch from four nights to seven, sailing from Tampa to Belize, Mexico and Honduras. Participants can expect deeper content, stronger community and clearer pathways from inspiration to action.

Central to the experience is what she terms “purposeful disconnection.” “In a world where we are constantly connected, we have never been more distracted. Cruising gives you permission to put your phone down, tune into God’s voice and hear your own thoughts again,” she said.

Through her leadership community and years of convening entrepreneurs, Watkis-Porter has noticed a consistent gap: many are pushed into leadership roles without the emotional intelligence, boundaries or self-awareness needed to thrive.

She hopes that one day a young Caribbean woman will stand on a global stage and say she dared to believe because she saw someone from her island create something extraordinary.

“If God gives you a vision, you don’t wait forever to move,” she said. “LeadHerShip is my invitation to women to stop waiting and start sailing into their next chapter.”

Spaces for the 2027 voyage will be deliberately limited to preserve depth and intimacy. “If something in this story tugs at you,” she adds, “don’t just read about LeadHerShip. Come sail with us.”

keisha.hill@gleanerjm.com