Beyond the 401k Cap: Advanced Retirement Tactics for Landstar System Employees

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

'By leveraging health savings accounts, Roth conversion pathways, annuities, and intentional asset location, Landstar System employees can reduce their lifetime tax burden and establish a diversified suite of retirement income sources.' – Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

'By thoughtfully combining health savings accounts, Roth conversion strategies, and strategic asset placement, Landstar System employees can optimize tax efficiency and bolster their retirement income flexibility.' – Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

1. Leveraging Health Savings Accounts and tax-advantaged rollovers to extend retirement savings.

2. Advanced Roth strategies (backdoor and mega backdoor) for high-income earners.

3. Using annuities and tax-efficient brokerage techniques to diversify and preserve assets.

High-Income Earners’ Advanced Retirement Savings Strategies

Retirement planning presents unique opportunities and challenges for Landstar System employees who have reached the IRS limit on 401k contributions or whose income prevents direct Roth IRA funding. To build on strong saving habits and substantial assets, it help to understand alternative techniques that extend tax-advantaged growth beyond traditional workplace plans.

1. Health Savings Accounts (HSAs) as a Long-Term Investment Vehicle

Health Savings Accounts offer a remarkable “triple tax advantage”: contributions reduce taxable income, investment growth is tax-free, and qualified medical withdrawals remain untaxed, making HSAs one of the most efficient savings tools available. Landstar System employees enrolled in a high-deductible health plan can contribute up to the 2025 IRS caps—$4,300 for self-only coverage and $8,550 for family coverage, plus a $1,000 catch-up for those 55 and older. ¹  Non-medical withdrawals after age 65 incur ordinary income tax (but no penalty), enhancing flexibility, while premature non-qualified distributions face a 20% penalty, underscoring the need for disciplined planning.

2. The Backdoor Roth IRA: Unlocking Tax-Free Growth

Although direct Roth IRA contributions phase out at higher incomes, Landstar System employees can still tap a backdoor Roth IRA by making a non-deductible contribution to a traditional IRA and immediately converting to a Roth. ²  The IRS’s pro-rata aggregation rules require careful calculation when you hold other traditional IRAs, as conversions consider the aggregate pre- and after-tax balances, potentially triggering tax liabilities. Given the IRA contribution limit of $7,000 ($8,000 for those age 50 and above), working with a financial advisor can help facilitate smooth execution and manage potential tax on conversions.

3. The Mega Backdoor Roth: Supercharging Roth Savings

For those with eligible employer plans, the “mega backdoor Roth” ³  can significantly boost Roth balances by contributing after-tax dollars above standard 401k limits and then rolling them into a Roth IRA or Roth 401k via in-service distributions. With 2025 combined employee/employer contribution caps of $70,000 (or $77,500 including catch-ups), ⁴  this strategy can create substantial additional tax-free retirement income. Because only about 20% of plans offer the necessary features, confirm with HR whether your Landstar System plan supports after-tax contributions and in-service rollovers, and coordinate with advisors to optimize timing and tax efficiency.

4. Tax-Deferred Annuities to Extend Tax-Advantaged Savings

When you’ve exhausted IRAs and employer plans, tax-deferred annuities provide another avenue to shelter earnings from current taxation. Fixed annuities offer a stable interest rate, while variable annuities invest in market-linked subaccounts—allowing reallocation without immediate tax events. ⁵  Although earnings and withdrawals are taxed as ordinary income and early withdrawals before age 59½ may incur a 10% penalty, annuities can include income commitments or death benefits. Before adding an annuity, Landstar System employees should evaluate fees, investment options, and the insurer’s strength to confirm alignment with overall retirement goals.

5. Tax-Efficient Techniques in Brokerage Accounts

In addition to having no contribution limits, taxable accounts offer considerable flexibility and asset choice. Landstar System employees can enhance after-tax returns by favoring low-turnover ETFs for tax efficiency, selecting tax-managed mutual funds, and using separately managed accounts (SMAs) for bespoke strategies like tax-loss harvesting. Strategic asset location—placing tax-inefficient bonds in IRAs/401ks and tax-efficient equities or municipal bonds in brokerage—can further reduce annual tax drag. ⁶  According to Vanguard, disciplined asset placement can boost after-tax wealth by up to 0.30% per year, ⁷  demonstrating the value of meticulous tax management.

Conclusion

After reaching the contribution limit on your Landstar System 401k, advanced tactics such as HSAs, backdoor and mega backdoor Roth IRAs, tax-deferred annuities, and tax-efficient brokerage strategies allow high-income earners to diversify retirement income sources and mitigate lifetime taxes. Staying informed on IRS rules—like the SECURE 2.0 Act’s changes—and using tools such as Qualified Charitable Distributions can further help manage required distributions and Medicare implications. Proactive planning and professional guidance help make every dollar saved work harder for your retirement goals.

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Sources:

1. Internal Revenue Service. ' Revenue Proclamation 2024-25 .' Accessed 31 July 2025.

2. Fidelity Investments. “ Backdoor Roth IRA: Is It Right for You? ” Fidelity Viewpoints, 19 Dec. 2024. Accessed 13 July 2025.

3. MarketWatch. “ This Roth Strategy Lets Elite Savers Stash $70,000 in Their 401(k) in 2025 ,” by Vanessa Wong, 20 Nov. 2024. Accessed 13 July 2025.

4. IRS. ' 401(k) limit increases to $#23,500 for 2025, IRA limit remains $7,000 ,' 1 Nov. 2024. Accessed 31 July 2025.

5. Investopedia. “ Annuities Taxation Explained: What You Need to Know Before Investing ,” by The Investopedia Team, 15 June 2024. Accessed 13 July 2025.

6. Charles Schwab. “ How Asset Location Can Help Save on Taxes ,” by Hayden Adams, 11 Oct. 2024. Accessed 13 July 2025.

7. Vaguard. ' Asset location can lead to lower taxes. Here's how to get more value, ' 16 Aug. 2024. Accessed 31 July 2025.