The first thing you notice about Rasheed is his laugh. It rings through the phone, bright and infectious—the kind that instantly makes you smile along. He even laughs while describing the amusing contrasts within his life. With a sense of humor sharp enough for stand-up comedy and a self-proclaimed love of thrill-seeking, somehow, Rasheed found himself in… insurance, moonlighting as a poet. His outlook makes the world seem lighter, like things will work out simply because of his steadfast faith that they will.
So, when Rasheed landed his dream job at HUB International nearly a year ago, it seemed like destiny—though if you had asked him six months earlier, he might have sounded skeptical. As a recent graduate and fledgling Chicagoan, his initial job hunt was filled with uncertainty and waiting with no clear end in sight. But Rasheed, ever the optimist, treated it like any other challenge: something to push through, not avoid.
A promising job offer in sales yanked him from his familiar Florida hometown to the wild west known as the Windy City. Unfortunately, that opportunity was short-lived, and he soon found himself scrambling to find not only a new job but one that would stick. His research quickly led him to Skills for Chicagoland’s Future, where he recounts religiously checking the job board for something that would fit. After seeing the success other Skills alumni had achieved, he knew he’d found the right team, but it would take patience to find the right opportunity. “I saw that Skills was definitely a program that was going to provide me with the support needed as a new grad,” he shared. So, he checked daily for new apprenticeships and other entry-level opportunities.
After what felt like the umpteenth refresh, he finally saw it: HUB International was hiring an Insurance Program Representative. It ticked every box. The only catch? They were looking for someone already licensed in insurance. Undeterred, he applied anyway.
That’s when Skills’ Talent Acquisition team stepped in, realigning him with a supporting role at the same company—one that turned out to be even better than he imagined. Looking back, Rasheed calls it a perfect match. His current role as a Program Coordinator plays to his strengths of connection and breaking down complex ideas for the people he serves. Now, he’s not only on track to earn his license at his own pace with HUB’s training, but he’s also setting his sights on his next big leap: law school.
“There are plans for me to pursue law school and then… come back and work for HUB on their HR legal side. That’s the big picture, honestly. I don’t think that would have been a path for me had I not worked at HUB,” he shared.
“My manager wrote my recommendation letter! She provided me with the support. I couldn’t have asked for a better team and a better work environment, truly.”
He laughs, remembering how his mom responded to his recent success. “Well, I always did find you to be an insurance person,” she joked. There is truth to it, but beyond his professional aspirations, he also enjoys the newfound creative freedom that job stability has brought him. He recently published his own book of poems called ‘The Boy Who Comes From The Sun’, which he insists is his favorite personal achievement since joining HUB.
As he nears his one-year work anniversary, Rasheed hasn’t forgotten what it was like to be on the other side of employment. His advice to job seekers, especially recent graduates, is simple but powerful: keep going. “Waiting is an obstacle in itself,” he says. “But pushing through it builds grit and strength. You’ll come out better on the other side.”
Now that he’s joined the club of proud Skills alumni, he’s urging others to take advantage of Skills’ network, support, and vast range of opportunities.
Whether it’s in his work, his writing, or chasing his next adrenaline rush, Rasheed moves through life with an enthusiasm that embodies endless possibilities. And as he celebrates this milestone, one thing is clear: the best is yet to come.
