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Embracing Change: My Journey from Law to AI in Retirement

One day in the early nineties, I stumbled upon a Time Magazine article about something called the internet. Intrigued, I purchased a book on the subject—a ritual in those days for anyone eager to learn. Before long, I found myself connected via dial-up, interacting with people across the globe. My career didn’t start in tech; it was in law, where I embraced every technological wave that came my way.

I spent 30 years in the legal field, retiring in 2020, just as the world started buzzing about generative AI, particularly with the rollout of ChatGPT in 2022. While some expressed fears of an impending robot uprising, I was more excited than apprehensive, eager to experiment with this new technology. Now, I rely on AI daily, using it as my assistant and advisor, without the pressures of integrating it into a workplace.

A Reluctant Transformation

When I entered law in 1982, typewriters were on their way out. As part of a younger generation of attorneys, I was adept at using a keyboard while many senior partners struggled to adapt. Over the years, I witnessed an accelerating wave of change—from word processors to document assembly systems, and the diminishing relevance of law libraries. Each technology brought its own challenges, leading many older attorneys to retire.

Rather than resist change, I strived to embrace it. I remember teaching myself database creation, a skill that eventually helped streamline various aspects of my practice. By the time I left the workforce, I had automated everything from timekeeping to document creation. I could often prepare estate plans faster than clients could reach the parking lot—a testament to the efficiency technology brought.

The Joys of AI in Retirement

My affinity for technology didn’t wane with retirement. When I discovered ChatGPT, it felt like having a new, exciting gadget to explore. Initially, I had no practical use for it, but soon realized how much easier it was than traditional search engines. AI provided swift, seamless access to information—I swapped Google and Wikipedia for Claude, an AI assistant built by Anthropic.

In conversations with friends at the park, I often turn to Claude for facts. Just the other day, I was taking a buddy to the Veterans Affairs hospital and needed to know if they had guest WiFi. Instead of sifting through search results, I asked Claude. Its ability to cite sources, while not flawless, has lightened my load significantly. If accuracy is critical, I double-check the information before acting on it.

I even find myself consulting Claude on health-related questions. While I acknowledge the risks of seeking medical advice online, Claude serves as a valuable first stop for managing my health in an aging body. The AI’s approachable demeanor and 24/7 availability make it a pleasant alternative to traditional consultations, and my primary care physicians have learned to appreciate my unique approach when I tell them what Claude suggested.

Observing the AI Revolution

There’s a palpable division among my retired friends regarding AI; some are curious, others indifferent. Discussions often veer toward concerns about future job losses for younger generations. Having spent years drafting briefs that AI can now generate, I understand the apprehension but believe it’s not the end of the world. AI may streamline research and writing, but the emotional nuances required in client interaction and court appearances remain irreplaceable.

I admit, there’s a part of me that envies practicing attorneys today. They get to integrate innovative tools into their work, tackling challenges I once faced. Yet, as a retiree, AI enhances my lifestyle rather than threatening it. For those still in the workforce, I encourage embracing this change; I believe the professionals who adapt will thrive.

Final Thoughts

Technological change isn’t new. Each wave—be it the internet, word processors, or now, AI—brings challenges and opportunities. For me, embracing these advancements has enriched my life, making retirement a rewarding chapter filled with discovery.

I’d love to hear from fellow retirees or anyone navigating AI in their careers. How has the evolution of technology impacted you? Share your stories and let’s connect!


If you’re interested in sharing your experience with AI in retirement, please reach out to Editor Charissa Cheong at ccheong@businessinsider.com!

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