Why Sears Holdings Employees Are Embracing Retirement Jobs – It’s Not Just About Money

'Increasingly, Sears Holdings retirees are recognizing that their retirement plans need to evolve with rising costs and changing expectations—side gigs provide not only additional financial security but also a sense of purpose and fulfillment, crucial for a well-rounded retirement experience.' – Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement Group.

'Many Sears Holdings retirees are finding that returning to work in some capacity offers more than just extra income; it enhances their mental and social well-being, providing both financial and personal fulfillment during their post-career years.' – Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement Group.

In this article, we will discuss:

The financial challenges retirees are facing, including inflation and rising healthcare costs.
The growing trend of retirees pursuing side jobs or gigs for additional income and personal fulfillment.
The broader benefits of working in retirement, such as maintaining mental health, purpose, and social engagement.

Many Sears Holdings retirees are discovering that their ideal retirement scenario is not as financially stable as they had imagined, especially as the financial landscape continues to shift. The reality of living on a fixed income has brought unexpected challenges for many. A record 11.2 million Americans over 65 are employed today, with this number expected to rise to 14.8 million, or 8.6% of the workforce, by 2033, according to the U.S. Bureau of Labor Statistics. Once thought to be uncommon, this trend is becoming more widespread as retirees look for additional income to cover rising living costs and maintain their desired lifestyles.

While many factors contribute to this shift, money concerns are at the core of the challenges retirees face today. A recent D.A. Davidson survey reveals that 60% of retired Americans wish they had a side career or gig, compared to just 8% who already do. A startling two out of five retirees say they can’t afford their dream retirement, emphasizing the growing financial strain on this group, including those who retired from Sears Holdings.

Undoubtedly, inflation has played a significant role in this shift. In recent years, the cost of living, including essentials like groceries and gas, has seen a sharp increase. Many retirees, including those who spent years at Sears Holdings, are finding that their money doesn’t go as far as they had hoped, especially after entering retirement with expectations about their lifestyle. The uncertainty surrounding Social Security only adds to the problem. While the Social Security trust fund is not expected to run out of funds until 2035, many retirees are concerned about the future of this vital financial support, particularly as life expectancies rise and the fund’s long-term viability is questioned.

Retirement planning is also affected by personal factors beyond inflation and Social Security concerns. Many retirees, even those from companies like Sears Holdings, don’t have enough saved for retirement, and some even carry significant debt into retirement. Additional financial pressures, such as supporting aging parents or adult children, can also strain retirement funds. Medical costs only make matters more challenging; according to Fidelity Investments, a 65-year-old retiring in 2024 can expect to spend an average of $165,000 on healthcare throughout retirement. These costs can create a significant gap between expectations and reality, highlighting the need for additional income.

A side job can provide more than just financial stability, even for retirees who aren’t facing immediate financial challenges. Many find that working in retirement helps them stay engaged and gives them a sense of purpose. According to the D.A. Davidson poll, 55% of seniors with retirement gigs cite maintaining social or mental engagement as their primary motivator, and 93% of retirees with side jobs report that they love their work. This highlights the broader reality that employment, even in retirement, provides a framework that supports mental and physical well-being for retirees, including those who worked at Sears Holdings.

Take Andy Roy, a 74-year-old retiree from Saratoga Springs, New York. After a long career working for himself, Roy began mowing the grass at the Albany Rural Cemetery a few days a week four years ago. Roy admits that while the job pays well, the true benefit is the sense of purpose it provides. “It’s beneficial. I feel like I’m helping. It serves as a small anchor during the day and gives me a sense of purpose,” he says. Beyond the work, Roy has formed close friendships with his coworkers and developed an interest in the rural cemetery movement. While the pay is appreciated, he acknowledges that the sense of fulfillment is the true reward, something Sears Holdings retirees may also discover after leaving their careers.

Similarly, 72-year-old Merry Farnum, a retiree from Falmouth, Maine, has taken on a new challenge as a launch driver at Handy Boat, a local boatyard. After working as an Associated Press news photographer, Farnum now spends her days transporting people between land and their boats, a job that keeps her active and outdoors. “The biggest payoff is the challenge and the structure it gives my life,” she says, noting that the money is useful, but the real motivation is the sense of accomplishment. Farnum’s experience demonstrates that working in retirement can offer financial stability while enriching one’s life, just like retirees from Sears Holdings who take on new challenges in their post-career years.

In recent years, the demand for such opportunities has surged. With the growth of the gig economy, retirees, including those who spent years with Sears Holdings, can now pursue work that aligns with their interests and abilities, free from the constraints of the 9–5 schedule. Thanks to platforms that facilitate side jobs—like tutoring, freelancing, pet sitting, and driving for ride-sharing services—retirees can find work that is both financially rewarding and personally fulfilling. This flexibility allows retirees to decide how much they want to work, balancing their financial needs with the desire for leisure and personal time.

It’s important to consider the potential benefits of side gigs beyond just the financial stability they provide. Many retirees, including former Sears Holdings employees, seek a sense of purpose and belonging after leaving the workforce, which can be found through freelance or part-time employment. Maintaining an active lifestyle can also boost cognitive function and lower the risk of depression, issues that are common among retirees who may feel isolated or disconnected.

However, retirees considering whether to pursue a side job should also be aware of potential impacts on taxes, health benefits, and Social Security. Income from a side job may affect Social Security benefits depending on when an individual starts receiving them and how much they earn. It is also crucial to consult a financial advisor to fully understand the tax implications of extra income and how it fits into the broader retirement strategy, especially for Sears Holdings retirees looking to get the most out of their post-career years.

In conclusion, more and more retirees are incorporating side gigs or retirement jobs into their retirement plans. While financial strains, like inflation and rising healthcare costs, are pushing many to seek additional income, the benefits of working in retirement go beyond just financial gain. Retirement jobs help retirees maintain an active and rewarding lifestyle, offering social interaction, mental stimulation, and a renewed sense of purpose. Whether it’s for debt repayment, growing retirement savings, or simply staying involved, retirement work is an essential component of a fulfilling post-career life for former Sears Holdings employees, as well as other retirees.

A recent AARP study reveals that many seniors over 65 are working not only for extra income but for mental and social engagement as well. According to the report, nearly 60% of part-time working retirees cite the opportunity to stay active and connected with their communities as a primary motivator. Work provides an organized way to maintain mental sharpness and social connections, crucial elements for well-being as individuals live longer. AARP’s December 2024 article, 'The Benefits of Working in Retirement,' discusses these findings, which also resonate with Sears Holdings retirees.

Examine how more and more retirees are seeking side employment for mental stimulation, purpose, and social interaction in addition to extra income. With inflation, healthcare costs, and concerns about Social Security, many retirees—including those who worked for Sears Holdings—are turning to flexible work options to stay active and enhance their retirement experience. Discover how part-time jobs, such as driving a boatyard launch or working at a local cemetery, are helping retirees reach financial stability while maintaining fulfilling, structured lives. The growing trend of working in retirement offers advantages that go far beyond financial gain.

Retirement is like a car that’s been sitting idle in the driveway for years. It runs fine, but without regular maintenance and direction, it may start to feel uninspired. Just like a car needs fuel, upkeep, and a destination, retirees are finding that side gigs provide more than just extra income—they give a sense of purpose, a chance to connect with others, and an opportunity to maintain both physical and mental health. Rediscovering purpose is more important than simply reentering the workforce, something many Sears Holdings retirees are discovering as they explore new roles after their careers.

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Articles you may find interesting:

Source:

Riquier, Andrea. 'Why a Record Number of Adults Over 65 Are Working – And It’s Not Just About Money.' MarketWatch , 30 Apr. 2025, pp. 1-2. marketwatch.com .
'Financial Impact of Side Jobs on Retirement Savings.' AARP Research , 2018, pp. 3-4. aarp.org .
'How Side Gigs Can Improve Mental Health for Retirees.' RL Communities Blog , 2023, pp. 1-2. rlcommunities.com .
'The Benefits of Social Engagement for Seniors.' Baptist Retirement Community Blog , 2024, pp. 2-3. baptistretirement.org .
Barron's Staff. 'Retirees Face Sticker Shock on Healthcare Costs If They Don’t Prepare.' Barron's , 8 Aug. 2024, pp. 1-2. barrons.com .

How does the Sears Holdings Pension Plan differentiate between normal retirement, early retirement, and late retirement options for Kmart participants? In what ways do these options influence the retirement planning process for employees of Sears Holdings, and what specific considerations should Kmart employees be aware of when choosing one of these retirement paths, particularly in relation to their vested status?

Differentiation of Retirement Options: The Sears Holdings Pension Plan offers distinct options for normal, early, and late retirement. Normal retirement is available at age 65 or after five years of plan participation, whichever is later. Early retirement can be taken from age 55 but before 65, provided the employee is vested, with benefits subject to actuarial reduction unless certain conditions are met (like having at least 90 points, which is a sum of age and years of credited service). Late retirement pertains to any retirement after the normal retirement age, with pensions recalculated to reflect the delay in benefit commencement.

Considering the frozen status of the Sears Holdings Pension Plan, how does this impact the benefits eligibility for Kmart employees, and what implications does it have for their retirement savings strategies? In what ways should current employees factor in this frozen status when evaluating their overall retirement readiness and potential alternatives outside of the company plan?

Impact of Frozen Status: The freezing of the Sears Holdings Pension Plan on January 31, 1996, means that there have been no new accruals of benefits or participants since that date. For Kmart employees, this impacts their benefits eligibility by capping the pension benefits at levels earned up to the freeze date. Employees need to consider this stagnation in benefits when planning for retirement, potentially seeking additional retirement savings avenues to bridge any shortfall.

What are the essential calculations involved in determining the retirement benefits under the Sears Holdings Pension Plan for Kmart employees? Specifically, how do the Career Average Pay and Final Average Pay formulas come into play, and what factors should employees consider when estimating their future retirement payouts?

Essential Calculations for Retirement Benefits: Pension benefits for Kmart employees under the Sears Holdings Pension Plan are calculated using either the Career Average Pay or the Final Average Pay formulas. These calculations take into account an employee's years of credited service and compensation up to the freeze date. Factors like estimated Social Security benefits and specific formulas (such as a deduction based on Social Security benefits under the Final Average Pay formula) play crucial roles in determining the final pension payout.

How can Sears Holdings employees best navigate the process of applying for benefits under the Pension Plan? What specific steps should participants take to ensure their applications are processed correctly, and what important deadlines should they be aware of to avoid any negative consequences on their retirement benefits?

Navigating the Benefits Application Process: To apply for pension benefits, employees must submit a formal application, ideally 30 to 90 days before the intended commencement date. It is crucial to ensure all personal information, including marital status and spouse details, is up-to-date to avoid delays or inaccuracies in benefit processing. Missing application deadlines can lead to postponed benefit payments or unwanted default options.

In what situations can Kmart employees expect to receive a Deferred Vested Pension, and how is the calculation for this pension affected by their previous employment and vesting service? Employees should be aware of the important factors influencing their eligibility and the steps necessary to maintain their retirement benefits after leaving the company.

Eligibility and Calculation for Deferred Vested Pension: A Deferred Vested Pension is available to employees who leave the company after becoming vested but prior to qualifying for retirement. The calculation mirrors that of a normal retirement pension, with possible early commencement reductions. Understanding the timing of benefit commencement and the potential reductions for early start is vital for planning.

How does the Sears Holdings Pension Plan address tax considerations for employees receiving both monthly payments and lump sum payments upon retirement? What tax implications should Kmart participants be aware of, particularly in relation to IRS rules for distributions and potential penalties for early withdrawal?

Tax Implications of Pension Receipt: Pension payments, whether monthly or lump sum, are subject to federal taxes. Monthly benefits are taxed as ordinary income, while lump sums might be eligible for special tax treatments or rollover options to defer taxes. It’s important for Kmart employees to consider these implications and possibly consult with a tax advisor to optimize tax liability.

What are the rights and protections afforded to Kmart participants under the Employee Retirement Income Security Act (ERISA) as they navigate their retirement benefits with the Sears Holdings Pension Plan? How can employees leverage these rights to ensure they are receiving all the benefits to which they are entitled?

ERISA Rights and Protections: Under ERISA, Kmart employees are entitled to certain rights including the ability to appeal denied benefits, access to plan information, and assurances of fair and equitable treatment of their benefits. Leveraging these protections ensures that employees receive all due benefits.

What steps should Kmart employees take to update their personal information to ensure they continue receiving their benefits without interruption, especially in the context of missing participants or uncashed checks? What resources and contacts at Sears Holdings are available to assist with these updates?

Updating Personal Information: Maintaining accurate personal information with the pension plan is crucial for uninterrupted benefit payments. Employees should promptly update changes such as address, marital status, or beneficiaries to prevent issues with benefit distributions or lost checks.

How does the process of transferring between affiliated employers impact pension benefits for Kmart employees under the Sears Holdings Pension Plan? What considerations should be taken into account concerning Credited Service and Vesting Service during such transfers, and how can employees ensure they do not lose any entitled benefits?

Impact of Transfers Between Affiliated Employers: Transferring between Sears Holdings’ affiliated employers can affect pension benefits differently depending on whether the employer participates in the pension plan. It's essential to understand how such transfers impact credited and vesting service accruals.

For Kmart employees seeking more information about their benefits under the Sears Holdings Pension Plan, what is the best way to contact company representatives? How can they effectively communicate their questions or concerns to ensure they receive accurate and timely information regarding their retirement benefits?

Contacting Plan Representatives: Kmart employees seeking clarity on their pension benefits should contact the Sears Holdings Pension Service Center. Effective communication, including prepared questions and necessary documentation, will aid in obtaining accurate and comprehensive information.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.

Sears Holdings Corporation's pension plans were taken over by the Pension Benefit Guaranty Corporation (PBGC) following the company's bankruptcy. The two defined benefit pension plans have been frozen since 2005, meaning no new benefit accruals are added. The plans are underfunded by approximately $1.4 billion, with PBGC assuming responsibility to ensure pension payments continue. These plans cover about 90,000 participants who worked for Sears, Roebuck and Co., and Kmart Corporation. Despite the underfunding, PBGC is expected to cover the vast majority of pension benefits owed under these plans. Participants can manage their benefits and verify information through PBGC's online platform or service center.

Bankruptcy and Store Closures: Sears Holdings emerged from bankruptcy with significant store closures, reducing from nearly 700 stores to less than 25. The company has been liquidating its remaining assets and recently announced more store closures in 2024. The focus is on resolving bankruptcy-related issues and managing the liquidation process effectively (Sources: The Layoff, Yahoo Finance).

Sears Holdings offered both RSUs and stock options before its bankruptcy. RSUs vested over time, providing shares, while stock options allowed employees to buy shares at a fixed price.

Sears Holdings, now part of Transformco, has faced numerous challenges in recent years, impacting its ability to provide comprehensive employee healthcare benefits. The strategic transformations initiated since 2017 aimed to improve operational performance and liquidity, which included measures such as obtaining additional loan proceeds and real estate sales. However, the company's financial struggles and store closures have also led to significant changes in employee benefits, including healthcare. As part of its efforts to stabilize and restructure, Sears has focused on reducing outstanding debt and pension obligations, contributing almost $4 billion to its pension plan since 2005 due to prolonged low interest rates. In 2023, Transformco continued to navigate its financial challenges, which have influenced its healthcare benefits offerings. The company has aimed to maintain basic healthcare coverage for its employees despite ongoing restructuring efforts. This includes providing access to medical, dental, and vision plans, although the specifics of these benefits and any enhancements over the past years have been less prominently highlighted compared to the broader financial strategies and operational changes. The focus on financial stability and cost reduction remains critical for Transformco as it seeks to ensure the viability of its employee benefits programs amid economic uncertainties.

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For more information you can reach the plan administrator for Sears Holdings at 3333 beverly road Hoffman Estates, IL 60179; or by calling them at 1-800-697-3277.

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