How H&R Block Retirees Are Using AI to Simplify Everyday Life

Healthcare Provider Update: H&R Block's Healthcare Provider and Cost Increase Overview Healthcare Provider: H&R Block employees typically rely on major insurance carriers for their health benefits, though specific providers may vary by location. Generally, the company integrates offerings from national insurers such as UnitedHealthcare, Anthem Blue Cross Blue Shield, and others to provide comprehensive medical, dental, and vision coverage. Healthcare Cost Increases in 2026: As 2026 approaches, H&R Block employees may face significant increases in healthcare costs, primarily driven by anticipated record hikes in ACA marketplace premiums. With reports indicating potential rate increases exceeding 60% in some states and an overall expected rise of 18%, many employees could see out-of-pocket expenses swell substantially-by as much as 75% for those losing enhanced federal subsidies. This surge in healthcare expenses underscores the pressing need for H&R Block workers to review their benefits and explore strategic options, such as optimizing Health Savings Accounts (HSAs), to mitigate personal financial impacts. Click here to learn more

'Artificial intelligence is helping many H&R Block employees simplify their transition into retirement by organizing finances and daily routines, but the key is to use these tools as support—not substitution—for thoughtful planning and professional guidance.' — Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

'H&R Block employees are finding that AI can streamline everything from budgeting to wellness, but lasting success in retirement comes from combining technology’s efficiency with informed financial decision-making.' — Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

1. How artificial intelligence (AI) is helping H&R Block retirees simplify daily life and handle complex tasks.

2. The ways AI can enhance health, home, and financial organization in retirement.

3. Why retirees are increasingly confident using AI to boost efficiency and reclaim valuable time.

Many H&R Block retirees are discovering that slowing down isn’t always easy, despite looking for respite from decades of early mornings, complex undertakings, and global operations. Handling investments, planning vacations, and staying organized can still feel demanding during retirement.

That’s where artificial intelligence (AI) has stepped in. What once seemed futuristic is now a practical tool for H&R Block’s retired professionals who want to streamline routines and reclaim valuable time.

According to Wealth Enhancement financial planner Kevin Won, CFP®, AWMA®, CRPC®, “we’re seeing older adults experimenting with AI tools for efficiency. They understand that these tools can help them reclaim time, which is one of life’s most precious resources.”

Simplifying Complex Tasks

While still in the workforce, AI is helping H&R Block employees transform their daily workflow. Tasks that once took hours—such as reviewing financial reports or tracking industry or market data—now take minutes with the help of AI assistants that can summarize data, highlight key performance trends, and draft personal reports.

Others are using AI to enhance their personal lives. For instance, with an AI-powered trip planner, it's possible to enter your preferred travel destinations, dates, and hobbies, and have the chatbot design an itinerary for you complete with dining, sightseeing, and activity suggestions.

The same is true after retirement. “The retirees I work with value how AI brings order and clarity,” Won adds. “Whether it’s comparing health care options or managing monthly expenses, these tools can handle the heavy lifting so retirees can focus on other areas of their lives.”

Improving Health and Home Management

Many former H&R Block professionals are also turning to AI for personal wellness and home organization. Some use chatbots for home maintenance guidance, while others leverage AI to build custom workout plans that adapt to travel schedules or physical limitations. These tools help retirees maintain consistency without needing advanced tech skills or expensive memberships.

According to Won, “AI can give older adults autonomy. They don’t need to wait for instruction or assistance. Technology enables them to take the lead in their daily lives, including finances and health care choices.”

A Modern Assistant for Financial Confidence

Retirees can also use AI to help arrange their financial information before meetings with advisors. From summarizing financial articles to preparing questions, AI helps retirees save time while staying informed. Some even use it as a digital filing assistant, categorizing tax documents, receipts, and travel logs for the upcoming year.

Won cautions, however, that “AI should be viewed as guidance, not a promise. It’s a powerful assistant, but it can still make errors—especially on topics like health or finance—so always double-check important information.”

From Skepticism to Confidence

While some retirees were initially hesitant to adopt AI, many have now incorporated it into their routines. Surveys show that, while older generations are slower to adopt new technologies, comfort and usage are steadily rising.¹

Won explains, “Retirees who’ve spent decades adapting to innovation in corporate environments, like H&R Block, already have the resilience and mindset needed to learn new tools. Now, AI works for them—reducing complexity, not adding to it.”

A Smart Way to Simplify Retirement

For many retirees, using AI is about boosting productivity, not just curiosity. Automating travel planning, organizing budgets, and reducing decision fatigue can make retirement more manageable and less stressful.

According to Won, “you’re really adding peace of mind when you integrate smart tools into daily life. The goal isn’t to master the technology. It’s to let it operate behind the scenes so you can focus on what matters most.”

If you’re a H&R Block retiree looking to organize your finances, streamline health care costs, or enjoy your retirement with fewer hassles, The Retirement Group can help. Call (800) 900-5867 to speak with a knowledgeable representative today.

For more information, visit WealthEnhancement.com or call Wealth Enhancement Group at (800) 492-1222 to speak with a Certified Financial Planner.

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Sources:

• 1. Kakulla, Brittne, Laura Skufca, Patty David, Jessica Boothe, and Kristen Garrett. ' Empowering Independence With Technology Among Adults Age 50-Plus .'  Washington, DC: AARP Research, Jan. 2025.

• 2. “Young Adults Are Leading the Way in AI Adoption.” AP-NORC Center for Public Affairs Research, 29 July 2025.

• 3. Chui, Michael, et al.  The Economic Potential of Generative AI: The Next Productivity Frontier.  McKinsey Global Institute, June 2023.

• 4. Chatbots in Consumer Finance. Consumer Financial Protection Bureau, June 2023.

• 5. “Older Adults Express Mixed Views on Artificial Intelligence.” NORC at the University of Chicago, Oct. 2023.