102-Year-Old Retiree Teaches Tech Skills to Younger Seniors

It is the kind of story that makes you rethink every assumption about aging and technology. In Sydney, Australia, a 102-year-old man named Dean Simes is proving that the “digital divide” isn’t a wall, but a hurdle that can be cleared at any age. Simes, who has been described by ABC Radio Sydney as perhaps the world’s oldest tech enthusiast, isn’t just using a tablet to keep up with the grandkids—he’s running the show. By leading a non-profit association called “Computer Pals,” Simes is teaching seniors, some of whom are significantly younger than himself, how to navigate the complexities of Windows 11, WhatsApp, and the emerging world of AI-driven search engines.

While this is happening in the Southern Hemisphere, the implications resonate deeply here in Chicago. In a city where the gap between the tech-savvy youth in the Loop and the older generations in neighborhoods like Bridgeport or Edgebrook can feel vast, the Simes model offers a blueprint for community-led digital literacy. The idea that a centenarian can transition from having no computer experience until after age 80 to becoming a mentor is a powerful reminder that curiosity is a more potent tool than youth.

The Simes Method: From Late Adopter to Digital Mentor

The trajectory of Dean Simes is an anomaly that challenges the stereotypical image of the “struggling senior” with a smartphone. Simes didn’t grow up with a keyboard; in fact, his direct contact with computers didn’t begin until he was in his 80s. This late start is precisely what makes his current role so impactful. He understands the friction points as he lived through them. After committing to a three-year course to master hardware, systems, and user interfaces, he didn’t just keep the knowledge for himself. In 2000, at the age of 75, he founded “Computer Pals” to ensure other seniors wouldn’t be left behind.

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The curriculum at Computer Pals isn’t just about “turning the device on.” It targets the specific vulnerabilities and needs of the elderly in a digital-first economy. Simes and his team focus on critical survival skills for the internet, such as:

Operating System Mastery: Navigating the specificities of Windows 11.
Cybersecurity Basics: Learning how to distinguish between legitimate links and malicious ones to avoid phishing scams.
Software Utility: Creating tables in Excel and managing communications via WhatsApp.
AI Integration: Adapting to the latest shift toward AI-based search engines.

This approach mirrors the needs we see across the Midwest. Whether it’s a senior trying to access telehealth portals or a retiree managing their portfolio online, the fear of “breaking something” is the primary barrier. Simes’ mantra—”practice, practice, practice”—is the only real cure for that anxiety. By framing technology as a skill to be practiced rather than an innate talent, he removes the shame associated with digital illiteracy.

Bridging the Generational Gap in the Digital Age

There is a poignant irony in the fact that Simes is teaching students who are “twice as young” as he is. In the current social landscape, we often expect Millennials or Gen Z to be the sole providers of tech support for their parents and grandparents. However, the Simes model suggests that peer-to-peer learning—or in this case, “elder-to-elder” learning—can be more effective. There is a shared pace and a mutual understanding of the cognitive shifts required to move from analog to digital thinking.

This movement toward digital inclusion is not just about convenience; it is about autonomy. When a senior learns to protect themselves from malware or use a search engine, they regain a level of independence that is often stripped away when they become dependent on family members for basic digital tasks. This is the same spirit of independence that drives Simes to maintain a rigorous daily routine of sports, bridge, and driving around Sydney to avoid becoming what he calls a “couch potato.”

For those of us looking to implement similar structures locally, the success of “Computer Pals” highlights the importance of non-profit, community-driven education. When the goal is empowerment rather than profit, the learning environment becomes a social hub, reducing the isolation that often accompanies both aging and the struggle to adapt to new technology. You can find more about these types of community initiatives by exploring our community support services guide.

Navigating Digital Literacy Resources in Chicago

Given my background in analyzing regional socio-economic trends, it’s clear that the “Simes Effect” could be replicated across Chicago’s diverse wards. If you or a loved one are struggling to bridge the digital gap in the Windy City, you don’t necessarily need a 102-year-old mentor, but you do need the right kind of specialized help. To avoid the pitfalls of overpriced “tech support” that doesn’t actually teach the user, I recommend looking for these three specific archetypes of local professionals.

Non-Profit Digital Literacy Instructors: Gaze for educators affiliated with public libraries or community centers. The key criterion here is a “pedagogy of patience.” You want instructors who focus on how to find the answer (teaching the logic of the OS) rather than just doing the task for you. Ensure they have experience with senior-specific learning speeds.
Patient-Centric Cybersecurity Consultants: Instead of high-level corporate security, seek out consultants who specialize in “end-user protection.” These professionals should be able to set up intuitive security layers—like password managers and two-factor authentication—while explaining the why in plain English, without using intimidating jargon.
Adaptive Technology Specialists: For those with physical limitations (such as arthritis or vision impairment), look for specialists who understand assistive technology. The criteria here should be their ability to customize hardware—such as larger keyboards, screen readers, or ergonomic mice—to build the digital interface physically accessible.

The goal is to move from being a passive consumer of technology to an active user. As Dean Simes has proven, the clock doesn’t dictate your ability to learn; only your willingness to keep practicing does. Whether you are navigating the streets of Sydney or the sidewalks of Chicago, the digital world is open to anyone brave enough to ask “how does this work?”

Ready to find trusted professionals? Browse our complete directory of top-rated digital literacy experts in the chicago area today.