There’s a timely new book out called I Am Not a Robot: My Year Using AI to Do (Almost) Everything, written by Joanna Stern, a longtime personal technology columnist for the Wall Street Journal. Over the course of a year she used artificial intelligence tools for almost every part of daily life—work, parenting, household tasks and even writing the book itself. Her experiment raises useful questions for people planning retirement and for retirees wondering how AI can enrich their free time.
Stern’s book, which her site describes as an “instant NYT bestseller,” prompted me to explore how retirees might adopt AI both to accelerate their path to retirement and to enhance life afterward. I know retirees and semi-retirees who are already using AI for creative projects—writing books, generating music and art, and experimenting with tools such as ChatGPT, Grok and Claude.
While I haven’t fully immersed myself in these tools, I follow AI as an investment theme and pay attention to household examples of how it’s changing daily life. For many readers, AI will not only be a productive assistant but also a source of new hobbies and creative outlets.
Stern’s experiment gained wider attention after an interview on Jim Cramer’s Mad Money podcast, where Cramer discussed his own use of AI tools. Stern admits to being optimistic about technology’s potential, but her year-long test also convinced her that many AI tools still fall short. She candidly notes that a surprising number of them “suck” and that costs can add up quickly once free trials end and monthly subscriptions begin.
Putting chatbots, robots, wearables and self-driving cars to the test
Stern tried more than 100 AI tools—from chatbots and large language models to wearables, home robots and self-driving car experiments. She adopted a simple rule: keep using anything that proved genuinely useful; otherwise, drop it. In the process she tracked both usefulness and cost, and weighed whether each tool delivered enough value to justify ongoing expense.
Her testing surfaced several recurring themes. First, AI can amplify professional and consumer services, but it can also be used aggressively to upsell. Stern points to dentistry as an example where some providers use AI-driven marketing to push unnecessary treatments. On the other hand, she sees real potential for AI in healthcare: within a few years, she argues, medical consultations will commonly include large language models as “a second opinion,” improving diagnostic thoroughness and helping physicians and patients alike.
Beyond general-purpose models like ChatGPT and Claude, Stern evaluated niche tools for personal finance and wealth management—AI-driven planners and assistants designed to help people manage budgets, plan portfolios and interpret financial documents.
Retirees actually have the time to play around with AI
Retirement creates a unique opportunity: time. Many respondents I contacted for this topic noted that retirees have a distinct advantage over busy workers—the luxury of time to learn and iterate with AI tools. That time makes it possible to explore creative projects, deepen hobbies and learn how to use AI meaningfully instead of just tacking it onto an already crowded schedule.
Stern experimented with AI creative tools as well. She tried generative music platforms such as Suno and Udio, but concluded that AI music works best when it complements human creativity rather than replacing it. She also tested transcription and meeting-assistant services like Otter.ai and video tools like Sora for short clips and “cameo” deepfakes. Her experience supports a practical approach: use AI to handle tedious tasks—transcription, summarization, itinerary building—so people can focus on the parts of work or play that require human judgment and taste.
Her book ends with six practical rules for living with AI, beginning with the idea of working with AI rather than for it: use AI to move faster, spark ideas and automate the boring parts, but keep human judgment at the center.
I invited readers on Featured.com to share how AI might help retirees, and received more than 50 responses. Seventeen thoughtful replies were selected and published in full at Findependence Hub. Common themes emerged: health and finances are priority areas, while travel planning, creative hobbies and social uses (including senior dating) are frequent secondary use cases.
Wayne Lowry, CEO of Scale By SEO, summarized the advantage succinctly: “Retirees finally have something working folks don’t: time to actually learn the tool instead of just bolting it onto a busy day. That’s the unlock. AI rewards curiosity and iteration, and retirement is the perfect runway for both.”
Neill David Watson, founder of APMZEE, noted that later-life interests often stall on friction—research, logistics and learning curves. “AI dissolves that friction,” he said. “Whether it’s learning an instrument, sketching a small business plan, or starting a novel, AI can compress the setup into a first step you’ll actually take.”
Retirement is the ultimate unlock for AI
Runbo Li, CEO of Magic Hour AI, put it plainly: for many over 60 the biggest benefit of AI is that it removes the long learning curve—AI lowers the barrier between wanting to try something new and actually doing it. Given that, many experts recommend starting with the highest-impact areas: health and finances.
Marketing coordinator Melissa Basmayor suggests beginning with finances because the stakes are highest. Tools like ChatGPT or Claude won’t replace trusted advisors, but they can help retirees stress-test their understanding of investments and prepare better questions for financial advisors. Paste a fund prospectus into an AI assistant and ask for an explanation in plain English, she advises, or ask for questions you should raise with your advisor—prompts like these can pay for themselves.
Wayne Lowry recommends starting by asking a specific question you want answered rather than picking a tool first. For creative projects, use AI as a “curious co-pilot”: ask it to draft a memoir chapter outline, suggest chord progressions, or critique a poem. The value is getting unstuck and making progress when motivation wavers.
Dane Maxwell of Paperless Pipeline stresses practical adoption: pick tools that remove friction retirees already feel—voice transcription, calendar management, photo organization and travel itineraries. “AI for retirees works when it amplifies what they already want to do,” he says. “It fails when it demands they learn a new identity as a ‘tech user.’”
Personally, I expect to explore creative AI projects more deeply after I’m fully retired. For now I’ll keep following AI developments, maintain diversified investments tied to the sector where appropriate, and dip into creative experiments when they fit. If I decide to write another book, AI will surely be part of the process. For anyone curious about the intersection of retirement and AI, the key takeaway is simple: treat AI like a capable, fast intern—helpful, imperfect and best used when you verify its output. As Wayne Lowry puts it, retirees already have the checking and judgment skills that make AI safe and useful.
Read more Retired Money columns:
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