Independent Thinking®
Aging with AI: Keeping Up with Alexa and Alex
November 21, 2025
Getting old is not for the faint of heart. But neither is staying young at heart. Technological advances are now coming so thick and fast that they can feel like personal challenges, even to digital natives. “Do I try to wrap my head around the latest, or can I let this one pass?” I’d like to encourage my fellow Baby Boomers to keep up, at work and at play.
I watched my father face that choice in the 1960s, in his factoring business. He relied on IBM electromechanical accounting machines, programmed with plugboards and punch cards. Noisy but efficient, they were a leap forward from handwritten ledgers. But by the 1970s, IBM was phasing them out in favor of electronic computers, disk storage and standardized programming languages — and he had to adapt, to his eventual business and personal benefit.
When I joined U.S. Trust in 1970, we worked with IBM mainframes, though a few handwritten ledgers lingered. By the 1980s, the pace of change quickened, and I was managing teams using IBM PCs running MS-DOS, and later, Windows. Lotus 1-2-3 revolutionized spreadsheets, soon replaced by Excel. Internal networks enabled file sharing and email, which in turn gave way to the internet. The 2010s layered on Office 365, Zoom, and advanced data analytics, and the 2020s has truly brought Artificial Intelligence, a term first coined in the 1950s, into our workplaces and our homes.
I’ve enjoyed every minute of it, logging onto AOL to hear “You’ve got mail,” chatting to Siri and Alexa, and embracing cloud services, digital photography, mobile devices, and global connectivity. Today, both of my homes are fully wired with high-speed internet, matched PCs, and cloud-based security. I bank online, use multifactor authentication, rely on GPS, manage health records digitally, wear health and fitness trackers. Indeed, I would argue that technology advancements are easing the challenges of aging, far more than they add to them. If you would like to view my interview with Andy Miller, Head of AARP’s Innovation Labs and Age Tech Collaborative on recent tech advances, please let us know.
I was also an early adopter of AI, although I still prefer to order my own thoughts (and, for now, to drive my own car). Large Language Models, or LLMs, are reshaping knowledge work, automating tasks, enabling predictive insights, and lowering transaction costs. And they continue to progress. LLMs are turning into agents and assistants, offering capabilities across text, images, audio, and code. Applications can write novels, generate movies, design art, draft business plans, and even refine their own performance. ChatGPT users are developing Alex, an AI browser that in agent mode can perform many of the tasks of an administrative assistant.
Yet this extraordinary potential comes with challenges, notably for those who resist change. Knowledge workers, artists, and authors must learn to work with AI; educators must grapple with how to integrate AI into learning; and health workers must identify the potential efficiencies while maintaining privacy and human connection. And we all have to be on high alert for deepfakes and other forms of misinformation. At Evercore, we are embracing a proprietary version of ChatGPT-5. AI will never replace the very human nature of our work. But I am confident that it can enhance our abilities, allowing our advisors to spend more time with our clients.
From punch cards to AI, technology continues to excite me, to keep me feeling young — at least at heart. If you too are an enthusiast, consider encouraging family and friends to engage, to make the choice to keep up. If you’re still on the fence, try downloading ChatGPT or any one of its competitors for yourself and entering a few prompts — and let me know what you discover.
Jeff Maurer is the Chairman of Evercore Wealth Management and Evercore Trust Company. He can be contacted at [email protected].
