Landstar System Retirement Roadmap: Creating Income Confidence Beyond the Paycheck

Healthcare Provider Update: Healthcare Provider for Landstar System Landstar System, Inc. partners with various healthcare providers to offer health insurance benefits to its employees. While the specific healthcare provider can vary depending on the insurance plan chosen by employees, Landstar commonly collaborates with major national insurers such as Aetna, Blue Cross Blue Shield, and UnitedHealthcare to provide comprehensive health coverage. Healthcare Cost Increases in 2026 As employers brace for steep healthcare cost increases in 2026, the outlook looks particularly daunting due to multiple economic pressures. With projections of medical costs rising by 8.5% and insurers requesting average premium increases of over 20%, workers can expect to see their out-of-pocket expenses soar as enhanced federal premium subsidies expire. The confluence of increased treatment costs, an aging workforce, and overall inflation is exacerbating these challenges, leaving many employees concerned about their ability to afford necessary healthcare services. Without proactive measures, more individuals could find themselves priced out of adequate coverage, emphasizing the urgent need for strategic planning ahead of these changes. Click here to learn more

'For Landstar System employees navigating retirement without the cushion of traditional pensions, income annuities may offer a practical way to structure consistent monthly income, helping to reduce stress around spending and reinforce confidence in long-term planning.'  – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'For Landstar System employees transitioning from a savings mindset to spending in retirement, establishing predictable income through annuities can help create a sense of control and clarity, empowering retirees to use their resources with greater confidence.'  – Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

1. How income annuities can help Landstar System retirees create a consistent retirement income stream.

2. Why behavioral finance research shows retirees may spend more confidently with steady income.

3. The role annuities play in supplementing Social Security and addressing the decline of traditional pensions.

Creating a reliable income stream to support decades of life without a paycheck is a central focus of retirement planning for Landstar System employees—not simply accumulating assets. Many retirees face the challenge of balancing lifestyle spending with the risk of running out of resources due to longer lifespans, market fluctuations, and inflation. One popular option is using annuities to help generate regular income. Income annuities, in particular, have been shown to reduce anxiety tied to portfolio withdrawals and support more confident retirement spending.

Studies on Retirement Spending Patterns

For Landstar System retirees, shifting from saving to spending can be emotionally difficult. Research from the Retirement Income Institute (RII), ¹  a nonprofit in Washington, D.C., finds that uncertainty about portfolio longevity often leads to overly cautious spending. About one-third of retirees surveyed said they prefer to live off investment earnings alone, without touching principal—even when they have room in their budget for additional expenses like travel or dining.

This cautious mindset is frequently tied to concerns about longevity risk. Even Landstar System retirees with large portfolios may feel uneasy without consistent income. According to RII, 60% of respondents said they would feel more comfortable spending if they received an extra $10,000 in annual income, compared to only 40% who favored a $140,000 increase in net worth. This illustrates the emotional and practical impact of consistent cash flow over portfolio size.

Traditional Retirement Income Sources Present Difficulties

In past generations, pensions and Social Security played a larger role in retirement income planning. However, fewer Landstar System employees now retire with traditional defined benefit pensions. According to U.S. Bureau of Labor Statistics data, only 15% of private sector workers have access to such plans. ²

Meanwhile, the average Social Security benefit—$2,005 per month as of June 2025 ³ —often does not cover core expenses such as housing and health care.

Delaying Social Security benefits can help raise monthly income. Benefits increase by about 8% for each year postponed after full retirement age (67 for most), with those who wait until age 70 receiving monthly payments more than 24% higher than at 67.

Annuities as an Alternative to Private Pensions

With traditional pensions less common, annuities are gaining attention as a way for Landstar System employees to establish consistent retirement income. Michael Finke, co-author of the RII study and professor at The American College of Financial Services, notes that annuities shift longevity and market risks to insurance providers. Fixed income annuities convert a lump sum into scheduled payments for life or a fixed term.

This consistent payment structure can help build confidence. Finke’s findings show retirees with annuities are about twice as likely to use their savings for enjoyment compared to those relying solely on investment accounts.

How Income Annuities Work

An income annuity involves an agreement with an insurance provider to deliver fixed payments in exchange for an upfront premium. Depending on the terms, payments may last for life or a specific period. Landstar System retirees often appreciate that this income is unaffected by market performance.

Some common features that add value to income annuities include:

• Cost-of-Living Adjustments (COLAs):  Designed to align payments with inflation

• Cash-Refund Options:  Allow a payout to beneficiaries if the annuitant passes before the full value is paid

These features can offer greater peace of mind for retirees who are planning for inflation or family legacies.

Using Income Annuities Wisely in Retirement Planning

For those seeking stable cash flow, income annuities can help fund basic living expenses. Start by identifying which needs—housing, utilities, groceries—are covered by Social Security or other sources. Any gap may be addressed by annuity income.

With core costs accounted for, retirees may use remaining funds more freely for lifestyle choices such as travel, home improvements, or philanthropy—potentially enabling them to enjoy retirement more fully.

Limitations and Considerations

Although annuities offer predictable income, they come with trade-offs. After the “free-look” period, the lump sum invested is generally no longer accessible. This could be a concern for retirees who expect significant one-time expenses.

Additionally, annuity payments depend on the claims-paying ability of the issuing insurer. It’s important to review the strength of the insurer through independent agencies such as AM Best, Moody’s, or S&P Global.

Because annuities can be complex and may involve tax consequences, Landstar System employees are encouraged to consult financial professionals who can help structure a retirement plan that integrates annuities, Social Security, and other sources of income.

More General: Spending Confidence and Behavioral Finance

Annuities may offer more than just income. They can act as psychological anchors. Behavioral finance research suggests that predictable income can reduce hesitation around spending. ⁴  For retirees, even those with strong portfolios, the presence of steady payments may reduce worry about depleting their assets.

This predictability may help retirees focus more on enjoying their time—whether it’s with family, traveling, or pursuing goals—rather than closely monitoring their investments.

In Conclusion

Annuities are attracting renewed attention among retirees looking for consistent income and emotional reassurance. In an environment where traditional pensions are rare and markets are volatile, income annuities may help fill essential budget needs.

For Landstar System employees, converting a portion of their savings into annuity income may help support consistent lifestyle spending and reduce financial stress in retirement.

Takeaway:

Learn how annuities may reduce the risk of running out of retirement savings, offer predictable payments, and support more confident spending. This article draws from research by the Retirement Income Institute and The American College, comparing annuities to pensions and exploring ways to handle market and longevity risks effectively.

Analogy:

Planning for retirement is like embarking on a cross-country road trip without a precise weather forecast or final destination. Your retirement savings are the fuel, but without a reliable guide, each turn may feel uncertain. For Landstar System employees, annuities can serve as the GPS—offering structure, regular updates, and peace of mind. With consistent income to cover the basics, retirees are free to explore life’s scenic routes—whether that means traveling, pursuing passions, or simply relaxing—without constantly checking the fuel gauge.

Featured Video

Articles you may find interesting:

Sources:

1. Retirement Income Institute. ' Guaranteed Income: A License To Spend ,' by David Blanchett and Michael Finke, June 2024.

2. U.S. Bureau of Labor Statistics. ' 15% of private industry workers had access to a defined benefit plan ,' 19 Apr. 2024. 

3. Kiplinger. ' The Average Monthly Social Security Check: June 2025 ,' by Donna LeValley, July 2025. 

4. TIAA. “ Want a longer, happier life? ' 2023.