Overcoming Mid-Career Retirement Savings Hurdles

April 15, 2024

Practical tips for Gen X and Millennial workers to save for retirement

Life in the middle can be a pickle—just ask any mid-career employee. They're often caught between a rock and a hard place, or, more accurately, a kid's college fund and an aging parent's medical bills. Add to that the rising cost of living, and you've got a perfect storm for financial stress. 


Money and Happiness


Did you know that 59% of Americans think money can buy happiness? With the magic number being $1.2 million. Interesting though, for a significant portion of your workforce, financial happiness is tied to timely bill payments (67%), being debt-free (65%), and maintaining a healthy work-life balance (44%), thus highlighting the connection between financial security and happiness.[1] 


Of note, 73% agreed that a solid financial plan leads to greater happiness.1 Here are some ways you can help your mid-career employees through life challenges and assist them in pursuing their retirement savings goals.


Confirm Retirement Savings are on Track


Mid-career employees still have time on their side. By encouraging them to review their retirement contributions and plugging their information into a financial calculator, it could make the difference between retirement stress or retirement success. 

  • 1 - 5% deferral | Potentially insufficient to replace future income needs
  • 6 - 8% deferral | Better but below recommendations 
  • 10 - 15% deferral | Recommended by industry experts 


Leverage Financial Wellness Platforms


We live in a digital age where there's an app for everything, even financial wellness. By offering access to these platforms, you can empower your employees to take control of their finances. These platforms often include features like budgeting tools, financial health scores, and savings goal trackers. Adding these financial wellness apps to your employee benefits may greatly improve job satisfaction, retain employees longer, and increase workplace productivity.


Consider Family Caregiver Support Programs


Research shows that 56% of employees consider themselves caregivers.[2] Many mid-career employees are part of this “sandwich generation,” simultaneously raising children and caring for aging parents. Offering family caregiver support programs can help reduce this burden. This could be as simple as flexible work hours to accommodate morning drop-offs and afternoon pick-ups for children. It could also include more comprehensive support like resources for affordable care, aging-in-place, legal advice, and/or help with financial planning.


Because Education Isn’t Cheap


For employees who have children, one of the significant financial burdens for mid-career employees is saving for education. By offering information and access to 529 plans—tax-advantaged savings plans designed to encourage saving for future education costs—you can help reduce this stress. 


However, a word of caution: as much as parents value their children's education, it's important to remember that while loans are available for college, the same cannot be said for retirement. So, encourage your employees to save for themselves first.


Emergency Savings, Withdrawals, and Loans


The SECURE Act 2.0 has introduced two new employee options aimed at enhancing financial flexibility: 


  1. Payroll deducted emergency savings or “sidecar” emergency savings accounts: Non-highly compensated employees can contribute up to 3% of wages into a capped $2,500 Roth-like account. Excess contributions spill over into their Roth 401(k). Notably, the first four yearly withdrawals from this emergency savings account are free.
  2. Penalty-free emergency withdrawals: Another provision allows any participant to make a one-time, non-loan withdrawal of up to $1,000 from their retirement savings for emergencies, without the usual 10% tax penalty. The process requires minimal paperwork and can optionally be repaid within three years. Because this is not a loan and requires minimal paperwork, it could save busy HR professionals and 401(k) administrators time and streamline the distribution processes.


While it's advisable to leave retirement savings untouched, life happens. Providing options for loans or hardship withdrawals from retirement accounts can be a lifeline for employees facing financial difficulties. However, it's crucial to educate employees about the potential impact on their retirement savings to help them make informed decisions.


Leveraging Empathy 


Empathy is key when helping your mid-career employees overcome these hurdles. Establish a relationship with a specialized retirement plan advisor to help understand their unique challenges. Listen to their concerns and provide them with the tools and resources needed to achieve their retirement savings goals. Remember, a financially secure employee is likely to be more engaged, productive, and loyal—factors that can significantly contribute to your company's success.


[1] Empower. “Financial Happiness.” Jan 2024. 

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