Southwest Airlines Employees: Is Timing the Market Worth the Risk?

Southwest Airlines employees navigating volatile markets should remember that staying disciplined with a long-term financial plan can often lead to more favorable outcomes than reacting emotionally to short-term headlines. – Kevin Landis, a representative of The Retirement Group, a division of Wealth Enhancement.

Southwest Airlines employees should remember that emotional decisions and market timing can derail years of disciplined planning—staying the course with a tailored strategy is often the most effective path to long-term success. – Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

1. Why market timing can carry significant risk—even when headlines seem clear.

2. How emotional decisions may influence long-term investment outcomes.

3. The value of sticking to a customized financial plan.

Unforeseen events can significantly influence investor outcomes, as recent market activity has demonstrated. Amid ongoing volatility, the markets have been experiencing unpredictable ups and downs. Southwest Airlines employees who exited the market before recent spikes may have missed out on potential returns. Similarly, selling into a down market may crystalize losses, impacting the long-term performance of a portfolio.

Tyson Mavar, a wealth manager and financial advisor at Wealth Enhancement, states, “This is precisely why we advise clients not to attempt to time the market.” Trying to forecast what happens next can often lead to subpar results, especially for Southwest Airlines employees focused on retirement goals.

Mavar highlighted that reacting to fear during market turbulence can throw long-term planning off track. Investors who follow a disciplined, strategic framework often experience more favorable results over time—particularly important for Southwest Airlines professionals preparing for retirement with significant pensions and savings.

At Wealth Enhancement, the emphasis is on consistent planning rather than reacting to daily headlines. Their methodology is designed to adapt through fluctuations, anchored in long-term objectives. “We help clients focus on what’s within their control—such as investment planning, portfolio structure, and saving behaviors,” Mavar noted—guidance that Southwest Airlines employees may find helpful when facing market ups and downs.

Historical data shows that maintaining investment positions during market disruptions tends to result in better outcomes. Trying to exit and reenter markets at precisely the right time rarely works—and can often lead to missed opportunities during major rebounds. For Southwest Airlines employees nearing retirement, staying consistent may yield better outcomes than trying to chase timing strategies.

The central message for anyone at Southwest Airlines rethinking their portfolio or hesitant about reentering the market: have a thoughtful financial plan in place before markets fluctuate. Results often stem from consistency and preparation, not from spur-of-the-moment decisions.

A recent DALBAR study (2023) found that the average equity fund investor earned just 6.81% annually over a 30-year period—substantially lower than the S&P 500’s 10.12% annualized return. This gap was largely attributed to emotional investment behavior, such as exiting during downturns and reentering too late. For Southwest Airlines employees, this data emphasizes the potential value of consistent investment strategies during job transitions and retirement planning.

Want to know how missing the right moment can impact your financial future? This article highlights the risks of reactive investing, offers time-tested strategies, and illustrates how aligning with a structured retirement-focused plan can help navigate unpredictable markets—particularly for Southwest Airlines employees in transition.

Trying to time the market is like attempting to hop onto a moving train in the dark. It might work occasionally, but more often, it leads to missteps. Markets can change course quickly based on unexpected developments. Long-term investors—like Southwest Airlines retirees with a structured approach—often benefit from staying the course, much like a traveler who follows a steady itinerary rather than chasing every departing train. According to DALBAR (2023), those who remain consistent tend to outperform those making frequent timing decisions.

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Sources:

1. DALBAR, Inc. 30th Annual Quantitative Analysis of Investor Behavior (QAIB) Report . 2024, pp. 1–3.

2. Benz, Christine. A Down-Market Survival Guide for Retirees. Morningstar , Sept. 2022.

3. Financial Strategies Group . Emotional Investing Part 2: The Costs of Investing Emotionally. 2024.

4. The Wall Street Journal Staff. How to Make Major Money Decisions Right Now: A WSJ Guide. The Wall Street Journal , Apr. 2025.

5. Morningstar Research Team . Does Tolerance for Risk Change in Retirement? Morningstar , Nov. 2024.