New Update: Healthcare Costs Increasing by Over 60% in Some States. Will you be impacted?

How Southwest Airlines Retirees Are Using AI to Simplify Everyday Life

Healthcare Provider Update: Healthcare Provider for Southwest Airlines: Southwest Airlines collaborates with multiple health insurance providers, primarily utilizing Aetna and UnitedHealthcare for its employee health plans. These partnerships enable Southwest Airlines to offer its workforce a range of options for health coverage. Potential Healthcare Cost Increases in 2026: As we look ahead to 2026, Southwest Airlines employees are preparing for significant healthcare cost increases, which may greatly impact their out-of-pocket expenses. With projected ACA premium hikes exceeding 60% in certain states, the burden of rising healthcare costs is likely to be felt by employees more than ever. A recent industry survey indicates that over half of large employers are considering raising deductibles and out-of-pocket maximums, as they navigate growing medical costs driven by inflation and high drug prices. This financial landscape underscores the importance of proactive planning and informed health plan choices for employees aiming to mitigate these anticipated increases in healthcare expenses. Click here to learn more

'Artificial intelligence is helping many Southwest Airlines 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.

'Southwest Airlines 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:

How artificial intelligence (AI) is helping Southwest Airlines retirees simplify daily life and handle complex tasks.
The ways AI can enhance health, home, and financial organization in retirement.
Why retirees are increasingly confident using AI to boost efficiency and reclaim valuable time.

Many Southwest Airlines 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 Southwest Airlines’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 Southwest Airlines 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 Southwest Airlines 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 Southwest Airlines, 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 Southwest Airlines 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.

Featured Video

Articles you may find interesting:

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.

What type of retirement savings plan does Southwest Airlines offer to its employees?

Southwest Airlines offers a 401(k) retirement savings plan to help employees save for their future.

Does Southwest Airlines match employee contributions to the 401(k) plan?

Yes, Southwest Airlines provides a matching contribution to employees who participate in the 401(k) plan, subject to certain limits.

How can employees enroll in the 401(k) plan at Southwest Airlines?

Employees can enroll in the 401(k) plan through the Southwest Airlines benefits portal during the enrollment period or after they become eligible.

What is the eligibility requirement for Southwest Airlines employees to participate in the 401(k) plan?

Most employees at Southwest Airlines are eligible to participate in the 401(k) plan after completing a specified period of service.

Are there any fees associated with the 401(k) plan at Southwest Airlines?

Yes, there may be administrative fees associated with the 401(k) plan at Southwest Airlines, which are disclosed in the plan documents.

What investment options are available in the Southwest Airlines 401(k) plan?

The Southwest Airlines 401(k) plan typically offers a range of investment options, including mutual funds, target-date funds, and company stock.

Can Southwest Airlines employees take loans against their 401(k) savings?

Yes, Southwest Airlines allows employees to take loans against their 401(k) savings, subject to specific terms and conditions.

What happens to my 401(k) savings if I leave Southwest Airlines?

If you leave Southwest Airlines, you can choose to roll over your 401(k) savings into another retirement account, cash out, or leave it in the plan, depending on the plan's rules.

How often can Southwest Airlines employees change their 401(k) contribution amounts?

Employees at Southwest Airlines can change their 401(k) contribution amounts at any time, subject to the plan's guidelines.

Is there a vesting schedule for the matching contributions at Southwest Airlines?

Yes, Southwest Airlines has a vesting schedule for matching contributions, which means employees must work for a certain period to fully own those contributions.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.

Southwest Airlines provides a defined contribution 401(k) plan with company matching contributions. Employees can contribute pre-tax or Roth (after-tax) dollars, and Southwest matches up to 9.3% of eligible compensation. The plan includes various investment options, such as target-date funds, mutual funds, and a self-directed brokerage account. Southwest also offers an Employee Stock Purchase Plan (ESPP) with a discount on company stock. Financial planning resources and tools are available to help employees manage their retirement savings.

Southwest Airlines provides both RSUs and stock options to employees. RSUs vest over time, providing shares, while stock options allow employees to buy shares at a set price.