Growing up near the airport in Montego Bay, Jamaica, Tasha Richardson was accustomed to seeing planes take off and land. Yet, despite having a front-row seat to the world of aviation, she never imagined that one day she would be the person flying them.
“I grew up close to the airport and saw planes take off and land all the time, but it never clicked that I could be the one flying,” she recalled. “I didn’t know any pilots growing up.”
Today, Richardson is a licensed commercial pilot in the United States, an achievement that began not with a childhood dream, but with an unexpected encounter in the cockpit of an aircraft.
Her journey from flight attendant to pilot has required significant financial investment, personal sacrifice and the confidence to find her place in an industry where women remain underrepresented. And while earning her commercial pilot qualification marks a major milestone, Richardson has even bigger ambitions.
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An Unexpected Path to the Cockpit
A former student of Corinaldi Avenue Primary School and Montego Bay High School, Richardson credits her upbringing in Montego Bay with instilling the determination that would eventually guide her aviation career.
She migrated to the United States at 17, adapting to life in different cities and gaining experiences that would later prove valuable in the unpredictable world of aviation.
Following the COVID-19 pandemic, she began working as a flight attendant with Breeze Airways. She enjoyed travelling and the opportunities that came with the job, but becoming a pilot was not initially part of her plans.
That changed approximately three years ago when, during a layover, a pilot invited her into the cockpit.
Listening to him communicate with air traffic control sparked a fascination she had never experienced before. On subsequent flights, pilots began teaching her about aircraft operations and explaining what it would take to become a pilot herself.
Rather than treating her interest as an unrealistic ambition, they encouraged her to pursue it, beginning with obtaining the required aviation medical certificate.
“They made it feel within reach,” she recalled.
With their guidance, Richardson began taking the steps towards flight training, setting herself on a career path she had never previously considered.
The Realities of Learning to Fly
Turning that newfound interest into a professional qualification proved considerably more demanding than Richardson initially imagined.
Flight training required not only learning complex technical skills but also managing the financial burden, demanding schedules and personal sacrifices that came with pursuing her ambition.
“Every time you turn that engine on, you’re burning cash,” she explained, acknowledging the substantial cost of building the knowledge and flying experience required to progress.
Beyond the financial investment, Richardson struggled with what she describes as imposter syndrome. Some training flights left her feeling confident in her abilities, while others caused her to question whether she was making sufficient progress.
Learning to separate an unsuccessful lesson from her overall capabilities became an important part of her development. She gradually came to understand that difficult flights were opportunities to improve rather than reasons to abandon her goal.
The demands of training also affected her personal life. Between studying, flying and managing fatigue, she frequently missed birthdays, weddings and opportunities to spend time with family and friends.
For Richardson, those sacrifices were particularly difficult because pursuing her career sometimes meant being absent for important moments in the lives of people she loved.
Still, she remained committed to completing her training, drawing encouragement from family and friends who supported her even when they did not fully understand the technical challenges she faced.
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Finding Her Voice in a Male-Dominated Industry
“Being in a male-dominated field has been hard at times,” Richardson admitted, recalling occasions when she felt she was treated differently.
Her experience echoes those of pioneering Jamaican aviators Captain Maria Ziadie-Haddad and Captain Marlene Smith, who also had to advocate for themselves. Ziadie-Haddad overcame barriers to financing her training, securing assistance through Jamaica’s Women’s Bureau before becoming the Caribbean’s first female commercial jet airline pilot in 1979 and later Air Jamaica’s first female captain. Smith challenged an initial rejection over her height, eventually becoming an Air Jamaica pilot and later a captain with Spirit Airlines.
For Richardson, self-advocacy meant challenging teaching approaches that did not accommodate her cultural background.
“I came to accept that my training would look different, because I learn differently and I don’t share the same background as most people in the room,” she explained. “I had to make the learning relatable to me.”
When instructors used unfamiliar references, she requested alternatives, sometimes drawing on her Jamaican upbringing. She also learnt to change instructors when necessary, recognising the importance of speaking up for herself in an industry where representation remains limited.
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The Moment She Became a Commercial Pilot
One of Richardson’s greatest moments of doubt came just before her commercial pilot checkride, the practical examination required to earn her qualification. Feeling unprepared, she confided in her instructor, who reminded her that being a pilot meant making decisions and trusting her training, whether she chose to proceed or postpone.
Reassured, Richardson did a few push-ups to release her nervous energy and went ahead with the examination. After completing the flight, however, she was left wondering whether she had passed. Her examiner remained silent even after they landed and shut down the aircraft.
It was only when they stepped out of the plane that he finally broke the silence.
“Let me be the first to congratulate you on being a commercial pilot,” he told her.
Overwhelmed with excitement and relief, Richardson asked the examiner for a hug before they went inside to complete the paperwork. After the financial sacrifices, demanding lessons and moments of self-doubt, she had earned her commercial pilot qualification.
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Flying With Jamaican Pride and Bigger Ambitions
Although earning her commercial pilot qualification represents a significant achievement, Richardson sees it as another step towards her ultimate career goal.
Her immediate priority is to continue accumulating flight hours and advancing towards Part 135 charter operations in the United States. Longer term, she hopes to become captain of a large-cabin business jet, such as a Gulfstream G650, flying corporate operations in Southwest Florida.
It is an ambitious goal, but one she is approaching through continued training, additional qualifications and experience.
For young Jamaicans interested in aviation, Richardson offers encouragement tempered by a practical understanding of the industry’s financial demands. She advises aspiring pilots to investigate funding opportunities, pursue scholarships and prepare for the significant investment that flight training requires.
She also encourages them to remain open to discovering new interests and changing career directions, just as she did.
Above all, her achievement carries a special significance because of where her journey began.
“I represent Jamaica on the ground and in the skies, because we Jamaicans, we love to represent,” she said.
Having grown up in a community where she knew no pilots, Richardson is proud to have entered a profession she once never imagined pursuing. She hopes her experience will encourage others from similar backgrounds to recognise opportunities that may initially seem beyond their reach.
And as she continues working towards the captain’s seat of a corporate jet, the Montego Bay native is determined to see just how far her aviation career can take her.