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Flying High: Rexy Rolle Changing the Game in the Airline Industry

NNPA NEWSWIRE — She’s climbed the corporate ladder, but nothing was handed to her – Rolle clearly has earned her wings. “My family instilled a very strong work ethic in me as a child. We strongly believe in the principle of big faith and hard work,” Rolle said.

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By Stacy M. Brown, NNPA Newswire Correspondent
@StacyBrownMedia

Although she acknowledges setting “big goals,” Sherrexcia “Rexy” Rolle said the magic really happens in the small steps it takes to reach those ambitions.

“That’s where the victories are won, in your daily to do list,” said Rolle, whose boardroom and classroom accomplishments likely turn as many heads as her modelesque looks.

At 30, Rolle serves as vice president of operations and general counsel of Western Air Limited, her family’s company and the largest privately-owned airline in the Bahamas.

She’s climbed the corporate ladder, but nothing was handed to her – Rolle clearly has earned her wings. “My family instilled a very strong work ethic in me as a child. We strongly believe in the principle of big faith and hard work,” Rolle said.

Western Air, a commercial airline that operates daily scheduled and on-demand flights to major destinations throughout the Bahamas, including Nassau, Grand Bahama, Exuma, Bimini, Abaco, and San Andros, also provides charter services to the Caribbean, Central and South America.

In business since 2000, Western Air was founded by Rolle’s parents, Rex and Shandrice. The airline conducts an average of 42 flights per day, 365 days a year and has a team of 165 employees.

“My dad was a private pilot at the time and my mom was an international business major, just graduating college,” Rolle said.

“My Mom and I went to Andros for my great grandmother’s funeral and on our return, we were stuck at the airport for almost the entire day. I remember her and I saying, that there must be a better way to travel from one island to the next,” she said.

“It wasn’t difficult to convince my Dad who is an aviation enthusiast. We sought financing for one aircraft and the aircraft financier believed so much in the idea and offered to finance three aircrafts, zero down as a package,” Rolle continued.

Rolle’s family wasn’t rich, as her dad was one of 13 children who came from very humble means. “My parents’ journeys, the good and the bad, inspire me and are what makes me believe that I can do anything with God, hard work and dedication,” she said.

Rolle, who is originally from Mastic Point, Andros in the Bahamas, grew up in Fort Lauderdale, Fla. After attending eighth and ninth grade in Andros, she attended Montverde Academy, an international boarding school.

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Rolle completed her undergraduate studies at the University of Ottawa in Canada where she excelled in a joint honors program in Political Science and Communications. Later, Rolle earned a Masters in Mass Media and Communications at Lynn University in Boca Raton, Fla. After graduating from Thomas Jefferson Law School in San Diego, Rolle was admitted to the State Bar of California.

Rolle, who also has done some modeling, enjoys a passion for music and entertainment.

She enjoys acting, singing, songwriting and dance and promises to soon “unveil her growth artistically, and put [her] long-standing love for all things music and entertainment to good use.”

She’s working on new music she believes will be a hit. “Music enhances our consciousness. Depending on what I’m listening too, it makes me think about where I am in life, and what I’m doing.

“I’ve listened to songs that have made me feel fearless, songs that have inspired my thoughts on love and relationships, songs that have strengthened my daily hustle, or encouraged me not to take life so seriously and of course, songs that make me dance instantly. Music inspires me in more ways than one,” Rolle said.

Still, her beginnings at Western Air proved quite humbling.

She started as a baggage handler and worked her way up to vice president of operations, eventually orchestrating several strategic acquisitions for the airline – the first of which were two Saab 340A and a multi-aircraft deal with Embraer for the acquisition of three ERJ 145 LR 50-seater jets.

Rolle also is training to become a pilot, having logged more than 44 flight hours.

“When I realize what an impact Western Air plays in people’s lives on the daily, it certainly motivates me to keep pushing and progressing to better their experience,” Rolle said.

While her family counts as role models, Rolle said she’s also inspired by Oprah Winfrey, who is the “Aunty in my head.”

“She inspires me because she seems to have mastered the art of balance and remaining in a state of gratitude, all while being courageous in various business and creative pursuits,” Rolle said of the Talk Show queen and magnate.

Life and her achievements haven’t been without obstacles, Rolle said. However, she noted that obstacles only serve to propel one forward because “once you’ve survived it, it sets the precedent to similar challenges.”

“I’ve faced the most obstacles when we sought to do things that were never done before. For example, when I was spearheading the opening of Western Air’s Grand Bahama Passenger terminal we got major push back on a number of levels because it was the first of its kind in the Bahamas,” she said.

“A passenger terminal with its own security screening, acting independently from the airport itself. Our ability to conduct such operations was challenged by major players in the industry.

“To say the least I had to cut our way through a number of legal red tapes, take the risk and seek approval from the authorities in the position to validate our right to operate.

“Opening the passenger terminal was a pivotal point for our company and was instrumental in securing market share on that route. I was a fairly new attorney at that time. While it was a bit intimidating, it was a rewarding experience.”

Rolle said she refuses to allow negative stereotypes to affect the way she does business or carries herself.

As a successful black woman attorney and executive in the airline industry, Rolle isn’t easily intimidated.

“For some, a lawyer or a VP of an airline should look and act a certain way, perhaps more conservative, perhaps older, white and male. But I thrive on being unapologetic about who I am,” Role said.

“My hair is big, my heels are high, but my opinion and work ethic is strong. I also understand there is a misconception that working in a family business is easy or that things are handed it to you. But we believe in demonstrating your individual value and earning your stripes,” she said.

Rolle continued:

“It’s an uncommon opportunity that I feel blessed to be a part of, but responsibilities are great. As long as I am producing results for the betterment of our passengers and our staff, I’m not moved by any pushback or resentment.”

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Oakland Post: Week of April 1 – 7, 2026

The printed Weekly Edition of the Oakland Post: Week of April 1 – 7, 2026

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Oakland Post: Week of March 18 – 24, 2026

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Financial Wellness and Mental Health: Managing Money Stress in College 

While everyone’s financial situation is unique, several common sources of stress have the potential to strain your financial health. These include financial and economic uncertainty, existing debts, unexpected expenses, and mental or physical health changes. Financial stress may differ from situation to situation, but understanding the factors contributing to yours may help you begin to craft a plan for your unique circumstances. 

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As a college student, managing financial responsibilities can be stressful.

If you’ve found yourself staying up late thinking about your finances or just feeling anxious overall about your financial future, you’re not alone. In one survey, 78% of college students who reported financial stress had negative impacts on their mental health, and 59% considered dropping out. While finances can impact overall stress, taking steps to manage your finances can support your mental, emotional and physical well-being.

When it comes to money, the sources of stress may look different for each student, but identifying the underlying causes and setting goals accordingly may help you feel more confident about your financial future.

Consider these strategies to help improve your financial wellness and reduce stress.

Understand what causes financial stress

While everyone’s financial situation is unique, several common sources of stress have the potential to strain your financial health. These include financial and economic uncertainty, existing debts, unexpected expenses, and mental or physical health changes. Financial stress may differ from situation to situation, but understanding the factors contributing to yours may help you begin to craft a plan for your unique circumstances.

2. Determine your financial priorities

Start by reflecting on your financial priorities. For students this often includes paying for school or paying off student loans, studying abroad, saving for spring break, building an emergency fund, paying down credit card debt or buying a car. Name the milestones that are most important to you, and plan accordingly.

3. Create a plan and stick to it

While setting actionable goals starts you on the journey to better financial health, it’s essential to craft a plan to follow through. Identifying and committing to a savings plan may give you a greater sense of control over your finances, which may help reduce your stress. Creating and sticking to a budget allows you to better track where your money is going so you may spend less and save more.

4. Pay down debt

Many students have some form of debt and want to make progress toward reducing their debt obligations. One option is the debt avalanche method, which focuses on paying off your debt with the highest interest rate first, then moving on to the debt with the next-highest interest rate. Another is the debt snowball method, which builds momentum by paying off your smallest debt balance, and then working your way up to the largest amounts.

5. Build your financial resilience

Some financial stress may be inevitable, but building financial resilience may allow you to overcome obstacles more easily. The more you learn about managing your money, for instance, the more prepared you’ll feel if the unexpected happens. Growing your emergency savings also may increase resilience since you’ll be more financially prepared to cover unexpected expenses or pay your living expenses.

6. Seek help and support 

Many colleges have resources to help students experiencing financial stress, like financial literacy courses or funds that provide some assistance for students in need. Talk to your admissions counselor or advisor about your concerns, and they can direct you to sources of support. Your school’s counseling center can also be a great resource for mental health assistance if you’re struggling with financial stress.

The bottom line

Financial stress can affect college students’ health and wellbeing, but it doesn’t have to derail your dreams. Setting smart financial goals and developing simple plans to achieve them may help ease your stress. Revisit and adjust your plan as needed to ensure it continues to work for you, and seek additional support on campus as needed to help keep you on track.

 JPMorgan Chase Bank, N.A. Member FDIC

© 2026 JPMorgan Chase & Co.

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