Most career advice assumes people change jobs once, carefully, after years of planning. Real careers rarely work that way. They bend around opportunities, setbacks, and the slow discovery of what a person is actually good at. Few New York entrepreneurs illustrate that better than Islam Elfiky, whose working life has followed a path across several industries, from elite squash in Cairo and Washington, D.C., to building a sports facility, co-founding a healthcare technology company, and now developing a new hospitality venture.
Each move looked like a leap at the time. In hindsight, they look more like a sequence, with every chapter preparing him for what came next. Looking back at his career since graduating from The George Washington University with an economics degree in 2014 at age 22, a handful of lessons stand out. They apply to anyone at a career crossroads, whether they’re leaving a sport, leaving a stable job, or simply wondering whether it’s too late to start over.
Your First Career Is Training, Not a Trap
For years, Elfiky’s identity was built around squash. He grew up in Cairo, in one of the world’s most competitive squash cultures, made the Egyptian national junior team, and reached a world ranking of 165 before moving to the United States. At George Washington, he held the No. 1 position on the men’s ladder for two seasons, went 21-3 in 2011-12, and was named the university’s Male Athlete of the Year.
When a career is so closely tied to who you are, leaving it can feel like losing part of yourself. The first piece of advice is to see it differently. Years of competition aren’t wasted time once you stop competing. They teach you how to prepare, handle pressure, lose on Saturday, and show up again on Monday. Former athletes often underestimate how rare those habits are in the working world and how directly they transfer to sales meetings, investor pitches, and long product cycles.
Put that advice into practice by writing those habits down. Before changing careers, list what the old career actually taught you beyond its technical skills. That list becomes the bridge.
Build the Bridge Before You Cross It
The move out of sports didn’t happen in a single jump. From 2014 to 2016, Elfiky co-founded Squash on Fire, a project to bring Washington, D.C., a high-end squash facility open to the public rather than tucked away in a private club. The facility opened in 2017.
That venture sat halfway between the world he knew and the world he was entering. It drew on his credibility in the sport while requiring him to learn about real estate, fundraising, partnerships, and operations. For Islam Elfiky, it was a chance to build a company on familiar ground.
The lesson he could offer his younger self is that career changes go better when the first step overlaps with what you already know. Look for a project that builds on your existing reputation while teaching you the skills of the field you want to enter. That kind of venture lowers the risk and helps you explain the move to your next employer, partner, or investor.
Find the Skill That Travels
On paper, squash facilities and pharmacy software share nothing. In practice, Elfiky took on the same role at both: business development. Since 2020, he has served as Co-Founder and Head of Business Development at MedsNow, a New York company focused on bringing independent pharmacies online by giving them the credentials and technology to sell digitally while meeting compliance and regulatory requirements.
For anyone planning a career change, it helps to recognize that industries can change while the core skill you bring to them stays the same. For some people, it’s selling. For others, it’s building teams, managing operations, or helping technical experts and customers understand each other. Identify the one skill that has made you useful in every setting so far, and then choose the next industry based on where it’s most needed.
Learn the New Language Fast, and Ask for Help
Healthcare technology came with its own vocabulary, regulations, and gatekeepers. Moving into it meant learning quickly and accepting help. MedsNow was selected for XRC Labs’ Cohort 14, the retail and consumer-health accelerator’s largest class at the time. The program connected the founders with a network of more than 330 mentors and gave them access to major retail partners. The company later presented at XRC Ventures’ 2023 Demo Day.
The advice here is simple and often ignored. Newcomers to an industry should seek structured programs, mentors, and peers instead of trying to learn everything on their own. Accelerators, professional associations, and experienced operators can help them learn in months what might otherwise take years of trial and error. During a career change, asking questions can spare you costly mistakes.
Let Curiosity Choose the Next Chapter
Elfiky’s most recent shift is toward hospitality, an industry tied to his longstanding interest in restaurants, Egyptian food, and memorable guest experiences. He’s currently developing a new venture with Yalla Hospitality, and his own writing has explored the turn from patient care to guest care, connecting serving patients well with serving diners well.
That move reflects a lesson a younger Islam Elfiky might not have believed: the subjects you return to in your spare time often point to your next career. Interests that seem like hobbies at 22 can become businesses at 35. Pay attention to what you read about, talk about, and notice when you walk into a room. Those patterns can help you recognize where your interests might lead.
Don’t Wait for Perfect Certainty
Every career change includes a period when the old path is closed, and the new one isn’t yet proven. Many people stay stuck because they want guarantees before they move. The advice he could give his younger self is to accept that certainty never comes. You can, however, gather enough evidence to justify the next step.
A useful rule is to get your finances, skills, and support system as ready as you can, then set a deadline to decide. Preparation reduces risk. Endless preparation just delays the same decision.
Keep the Values, Change the Work
Through every change, one thread has stayed constant. His family runs a hospital business in Egypt with a strong focus on social work and community care, and he remains involved. That connection explains why so much of his professional life has stayed close to health and service, even as he moved between industries.
The final piece of advice is to separate what you do from why you do it. Titles, industries, and job descriptions can change many times over a working life. The values behind them are what make each new chapter feel like part of the same story rather than starting from zero.
The Takeaway for Anyone Considering a Change
Career changes are rarely clean breaks. Often, they’re a way to use the same strengths in new settings. Looking back, Islam Elfiky would tell his younger self to treat sports as training, build bridges before crossing them, identify the skill that travels, ask for help early, follow curiosity, act without perfect certainty, and keep the same values throughout. Changing careers doesn’t have to mean starting over; you can carry what you’ve learned into whatever comes next.
About Islam Elfiky
Islam Elfiky is a New York-based entrepreneur and former Division I squash player from Cairo, Egypt. A graduate of The George Washington University with a degree in economics, he co-founded Squash on Fire in Washington, D.C., and has served as Co-Founder and Head of Business Development at MedsNow since 2020. He’s now developing a new hospitality venture with Yalla Hospitality while staying involved in his family’s hospital business in Egypt. More about his work across technology, healthcare, and hospitality is available online.
