Boosting Retirement Confidence for Near-Retirees

May 16, 2024

Employees late in their careers need information that helps smooth the transition into retirement.

We are entering the “Great Retirement” era, where tens of thousands are hitting retirement age daily. By 2030, the entire baby boomer generation will be 65 or older. These hard working and resilient employees were the first to experience the shift from guaranteed pension plans to defined contribution plans such as 401(k)s. With retirement in sight, near-retirees are a key target audience for financial wellness programs. 


Older employees are likely to experience heightened financial stress and anxiety as they transition from work into retirement. The bad news is that financial stress can have a corrosive effect in the workplace. The good news is that near-retirees are likely to be open to, and may actively seek, information that helps transform retirement uncertainty into retirement confidence. 


The information can be delivered in a variety of ways, including through education programs and communications strategies. Having a professional offer individual financial advice or coaching can make it easier for employees to apply what they’ve learned. As you consider how best to convey the value of your workplace benefits, here are four topics that should resonate with near-retirees.


Saving in the Home Stretch 

It’s good to start with the basics, reminding employees that they have opportunities to set aside tax-advantaged savings in traditional and/or Roth workplace retirement plan accounts. If your plan permits them, discuss the value of catch-up contributions. 

  • Plan participants who are 50 or older can save more with catch-up contributions. The IRS adjusts this each year; but for 2024, the limit is $7,500. 
  • The SECURE Act allows a new level of catch-up contribution in 2025. Participants aged 60 to 63 can make catch-up contributions equal to the greater of $10,000, adjusted annually for inflation or 150% of the 2024 catch-up contribution amount (indexed for inflation). 
  • In 2026, catch-up contributions made by participants earning $145,000 or more annually must be Roth contributions.


The Incredible Versatility of HSAs 

Healthcare costs can be a big financial burden for older workers. However, relatively few employees have confidently saved for healthcare expenses, even those who participate in qualifying high-deductible healthcare plans (HDHP) paired with health savings accounts (HSAs). It’s a missed opportunity. 


HSAs give employees another tax-advantaged way to save and invest for retirement. HSAs offer a triple-tax advantage. 


  • Eligible employees contribute pre-tax dollars 
  • Any investment earnings grow tax deferred
  • Withdrawals used for qualified medical expenses are tax-free


Of note, after age 65, HSA savings can be withdrawn for any purpose without a penalty (although distributions used for non-medical purposes may be taxable). The funds can be used to reimburse premiums for some Medicare costs, as well as healthcare costs not covered by Medicare. Typically, eligible employees can continue to make HSA contributions until they apply for Medicare or Social Security.


A Primer on Social Security and Medicare Benefits 

Almost half of employees want employers to educate them about Social Security and Medicare benefits.[1] Employers can provide programs that offer insights on how to optimize Social Security benefits and make Medicare decisions, or they can hire a knowledgeable professional to provide individual counseling. 


Either way, it’s important to manage expectations of Social Security. The most recent Trustees Report estimated that Social Security Trust Fund reserves will be depleted in 2034. Unless Congress acts, benefits may be reduced by 20% in the future.[2] Since Social Security benefits are one of the few guaranteed income options available, it may be beneficial to discuss other guaranteed income options as well.


The Advantages of Account Consolidation 

It is not uncommon for adults to have held 12 or more jobs throughout the course of their careers. If they left assets behind in former employers’ workplace retirement plans, account consolidation could help clarify how much they’ve saved and how their savings are invested. In addition, if your workplace retirement plan allows roll-ins, account consolidation could potentially lift average plan balances and lower plan expenses.


The Future is Bright 

Near-retirees are receptive to education and communications about saving for the future. Employers who offer programs that help smooth the transition from work to retirement often realize benefits, including greater employee loyalty and improved productivity. If you would like more information, please get in touch.


[1] Bank of America. “2023 Workplace Benefits Report.” Aug 2023.

[2] Social Security Administration. “Status of the Social Security and Medicare Programs.” 2023.

September 15, 2026
The Challenge Sometimes the most expensive retirement plan mistakes aren't dramatic. They're quiet. A former client of ours changed retirement plan providers following an acquisition several years prior. On the surface, everything appeared to be operating normally after moving to the new provider: employees continued making contributions to the plan, the plan’s investments remained in place, and the business continued its normal operations. Then another merger opportunity came along. As part of their due diligence process, the buyers reviewed the retirement plan. What they found immediately raised concerns. The annual Form 5500 filings required by ERISA law had not been submitted for several years. That also meant that none of the required compliance testing had been completed, and routine administrative responsibilities had also gone undone. What had started as a routine review quickly became a significant obstacle to completing the business sale. The Hidden Risk Many employers assume that once a retirement plan provider is hired, responsibility for the plan’s ongoing administration has effectively been transferred to that provider. But a plan sponsor is never completely relieved of its responsibility to oversee the plan. Even when outside providers are hired to handle filings, testing, recordkeeping, or other administrative functions, the employer still needs to make sure those responsibilities are being fulfilled. At the same time, there is an important difference between a provider that simply waits for the employer to supply information and one that actively works with the employer to make sure the plan stays on track. In this case, some of the missing work may have resulted from information requested by the provider that was never supplied by the employer. Technically, the employer still had a responsibility to provide that information and ensure the work was completed. But years of required administration should not quietly disappear into a communication gap. A proactive administrator follows up. If the usual contact isn’t responding, they escalate the issue. They make sure the appropriate people understand what is outstanding, why it matters, and what could happen if it isn’t addressed. Retirement plans require ongoing attention every year, including government filings, compliance testing, participant administration, documentation, and, when necessary, operational corrections. When those responsibilities are neglected, the consequences may not become obvious immediately. Instead, problems can accumulate quietly in the background until an IRS inquiry, Department of Labor investigation, audit, or—as in this case—a business transaction suddenly exposes years of unresolved issues. The prospective buyer made it clear that the retirement plan issues needed to be addressed before the transaction could move forward. The Rescue Knowing we had previously administered their plan, the current company leadership contacted us. Our first step was to determine the full scope of the problem. The timing made the situation particularly challenging. This wasn’t simply a retirement plan cleanup project. A business transaction was underway, and the company needed answers quickly. We assembled a team to determine the full scope of the problem and begin developing a path forward. Because we have deep experience with taking over neglected plans, we were able to separate perceived problems from actual compliance issues and reconstruct the plan's history. In reviewing the prior documentation, we identified exactly which administrative functions had been completed and which had been missed. We gathered historical payroll and participant data and developed a comprehensive correction strategy. Having access to historical plan records was especially important. Retirement plan problems may not surface until years after the underlying event, making good record retention critical. If you’re curious about how long to hold onto plan documentation, please see our blog post here . The final correction effort proved to be far more manageable than originally feared. Instead of allowing uncertainty around the retirement plan to continue hanging over the transaction, the employer now understood what had actually gone wrong, what needed to be corrected, and what steps were required to move forward. The Outcome With the correction efforts clarified and a clear roadmap in place, the employer was able to begin correcting the plan and continue moving toward its business transaction. More importantly, the company avoided entering the acquisition process with unresolved retirement plan liabilities hanging over or ruining the deal. The experience also reinforced an important lesson: Changing retirement plan providers doesn't eliminate administrative responsibilities. But it also demonstrated why the quality of the administrator matters. A good retirement plan administrator doesn’t simply process the information that arrives. They help make sure the information arrives in the first place. The Lesson: Oversight Is a Shared Process Employers ultimately have a responsibility to oversee their retirement plans, even when they hire professionals to handle much of the day-to-day work. That doesn’t mean the employer should have to become a retirement plan expert or personally track every filing deadline and compliance requirement. That’s one of the reasons experienced administration matters. A proactive provider should help keep the employer informed, identify missing information, follow up when something is outstanding, and escalate issues before a missed request becomes a missed filing—or several years of missed filings. The cost of failing to do so can extend well beyond an annual administration fee: Missed filings and potential penalties Incomplete compliance testing Corrective work Additional professional fees Delayed business transactions Uncertainty during mergers and acquisitions  By the time those costs appear, they can far exceed whatever might have been saved by choosing a lower-cost service model. That’s why retirement plan administration shouldn’t simply be viewed as paperwork. It should be viewed as an ongoing partnership in managing risk.
August 18, 2026
The Challenge A business owner came to us after receiving confusing news from their retirement plan actuary. Their Defined Benefit (Cash Balance) Plan had performed exceptionally well over several years; strong investment returns seemed to have created what’s called an overfunded Plan. While it seems like a positive name, an overfunded plan can create excessive and unexpected tax liabilities. So, their actuary recommended terminating the Plan by transferring the excess assets into the company's other Plan, a 401(k)/Profit Sharing Plan, before eventually closing both Plans, a lengthy and complicated process.
July 15, 2026
As we wrap up the second quarter of 2026, one trend continues to stand out: retirement plans are becoming increasingly specialized. Whether driven by changing regulations, unique workforce structures, or evolving business goals, employers are finding that a one-size-fits-all approach simply doesn't work. This quarter, we explored the unique retirement plan challenges facing several industries—including medical and dental practices, construction companies, architecture and design firms, wineries, and California employers navigating CalSavers requirements. We also continued our series on the hidden risks of low-quality retirement plan services, highlighting how operational complexity, fragmented accountability, and misaligned incentives can create costs that extend far beyond administrative fees. For employers still evaluating their retirement plan options, we also discussed opportunities that many business owners overlook, including the ability to establish retirement plans after filing a tax extension and potentially generate meaningful tax savings. Below is a recap of the articles we published this quarter. We hope they provide practical insights to help you reduce risk, improve plan performance, and make more informed retirement plan decisions.
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