Taking Flight in a New Way: Sheyi Oyelowo’s Winning Transition to Business

His story is another vivid example of how the skills and experiences gained in one arena translate to another, paving the way for a fulfilling second career.

Taking the Shot: Early Passion for Basketball

Sheyi’s love for basketball began age nine, when he would gather with friends every Saturday to watch the sport. One day, a friend's mother gifted a basketball for the group, a gesture that instantly ignited a passion for it. Enrolling in a sports camp soon after, Sheyi recalls the thrill of scoring his first basket, a moment that solidified his desire to pursue basketball with fervour. 

"Sports became a home, a safe haven," Sheyi reflects. Beyond the physical activity, basketball provided him with mentorship through his coach, close friendships, and a sense of routine and discipline. The structure of sports taught him attention to detail and accountability—traits that would later become invaluable in his corporate career. The joy of his first school tournament and the cheers of the crowd cemented his professional ambitions.

Scoring Success on the Court

Sheyi’s basketball career flourished, playing professionally for over a decade with Spanish teams such as Club Gijón and Baloncesto de Leon. However, after completing his university course in Business, he had to reassess his future; Sheyi returned to London and decided to retire from basketball. "It was painful," he admits. "Basketball had been the last 18 years of my life." The transition was tough, as the security provided by a professional sports team—housing, transport, and sometimes even food—was suddenly gone.

The Transition: Stepping into the Corporate World  

Initially, navigating the corporate world was quite daunting, everything was unfamiliar: "As an athlete, LinkedIn was foreign," he recalls, laughing. But a friend's suggestion to update his LinkedIn profile proved to be a turning point. This simple action led to an outreach from add-victor. We connected Sheyi with Steve Rowbotham, Managing Director at Ink, a travel media agency, which led to an interview with him. Sheyi recalls the instant bond created with Steve White-Cooper, CEO of add-victor, former rugby professional who understood the challenges of transitioning from a professional career. It offered Sheyi a lifeline.

Despite having no prior experience in media, Sheyi's eagerness to learn shone through. "I'm a fast learner, all I needed was an opportunity," he asserts. That opportunity came through marketing Ethiopian Airlines via media solutions, leveraging his communication skills and work ethic honed from sports. Within a year, Sheyi ascended to a leadership position, managing teams across multiple countries and shaping Africa’s travel media landscape.

He collaborates with some of Africa’s largest organisations and serves as a liaison between Ethiopian Airlines and Ink. His contributions are shaping the travel media sector in Africa, still an emerging field. Ink produces 33 in-flight magazines for 24 airlines worldwide. "Travel media is very new in the African continent, so it’s a very thrilling opportunity," he says.

Sheyi attributes much of his corporate success to traits developed as an athlete: "As an athlete, you progress to be better for your team," he explains. "That resilience is beautiful when transferred to the corporate world." His guiding principle, "to stay liquid," underscores the importance of flexibility and a solution-oriented mindset.

Beyond the Buzzer: Looking Forward & Ahead

Sheyi’s story is a powerful reminder of what’s possible with the right attitude and support system. His seamless pivot from one passion to another, finding success in unexpected places, highlights his adaptability. By transferring the skills and discipline honed during his sports career to a new and challenging industry, he exemplifies the power of staying open to new opportunities.

Holly Errington