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The Rise of Semi-Retirement for Sears Holdings Employees: A Flexible Transition to Retirement

Healthcare Provider Update: Healthcare Provider for Sears Holdings Sears Holdings typically provides healthcare benefits to its employees through various insurance plans, often with national insurers such as Aetna, UnitedHealthcare, or Anthem Blue Cross Blue Shield being among the health carriers they have partnered with. The specific providers can vary by location and employee selection during open enrollment periods. Potential Healthcare Cost Increases in 2026 As we progress into 2026, the healthcare landscape is expected to face significant challenges, particularly for employees of Sears Holdings. Forecasts indicate steep premium hikes, with some states imposing increases of over 60%, largely influenced by rising medical costs and the potential expiration of enhanced ACA premium subsidies. The Kaiser Family Foundation highlights that without congressional intervention, millions of marketplace enrollees could see their out-of-pocket costs surge by more than 75%. This convergence of factors threatens to impose a substantial financial burden on both individuals and employers, necessitating proactive strategies to mitigate rising expenses. Click here to learn more

'Sears Holdings employees considering semi-retirement can benefit from not only a flexible work schedule but also the financial advantages of continuing to contribute to retirement savings while maintaining a sense of purpose and social engagement.' – Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement.

'Transitioning to semi-retirement can be a smart strategy for Sears Holdings employees to balance continued financial growth with personal well-being, offering both income opportunities and a healthier work-life balance.' – Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

The benefits of semi-retirement for Sears Holdings employees, including financial and psychological advantages.
The economic opportunities, such as contributing to retirement accounts and delaying Social Security benefits.
Important considerations when transitioning to semi-retirement, including taxes, health care, and the impact on Social Security benefits.

As retirement approaches, many Sears Holdings employees are rethinking what it means to 'retire.' Traditionally, retirement has meant leaving the workforce entirely, but this notion is shifting, with semi-retirement becoming an increasingly popular and viable option. Semi-retirement offers a flexible way to transition into retirement while maintaining professional involvement, whether driven by a desire to stay active or by financial needs.

Semi-Retirement: What Is It?

Semi-retirement is when employees reduce their work hours, while still engaging in part-time or freelance opportunities. For Sears Holdings employees, this could involve cutting back hours at a full-time position, taking on part-time roles, or venturing into self-employment through consulting or freelance work.

Some may need to be in semi-retirement due to insufficient savings or unexpected financial circumstances, even after reaching the typical retirement age. Others may feel motivated to continue working due to personal fulfillment, a sense of purpose, or the social connections that work provides. Semi-retirement offers a balance between leisure and activity, benefiting many by enhancing their overall well-being.

Important Takeaways:

Sears Holdings employees who transition into semi-retirement can still earn an income while enjoying more free time.
Semi-retirement provides psychological as well as financial benefits, helping individuals maintain relationships and stay engaged.
It's important to understand the tax implications, and the effects on Social Security benefits and health care coverage, before entering semi-retirement.

The Economic Advantages of Semi-Retirement

One of the most direct financial benefits of semi-retirement is the ability to supplement retirement funds. Even though part-time jobs may not offer the same salary as full-time positions, they can still contribute to a financial cushion for retirement.

Sears Holdings employees in semi-retirement may still be eligible to make contributions to retirement accounts such as IRAs. Individuals over 50 can take advantage of catch-up contributions, allowing them to save even more for retirement. In 2025, the IRA contribution limit is $8,000, including a $1,000 catch-up contribution. Sears Holdings employees who participate in a 401k can benefit from a $7,500 catch-up contribution, increasing the maximum contribution to $30,000 for those over 50, and up to $35,500 for employees aged 60 to 63.

Additionally, continuing to work part-time can delay the start of Social Security benefits, which can increase the monthly payout when benefits are eventually claimed. For Sears Holdings employees who expect to live longer and wish to increase their retirement income, delaying Social Security can result in an approximately 8% increase in benefits for each year they wait after reaching full retirement age (FRA).

Semi-retirement can provide a cushion against unexpected financial setbacks, such as market downturns or unforeseen expenses. With a second income and the ability to delay drawing from retirement accounts, employees can strengthen their financial future.

The Psychological Benefits of Semi-Retirement

While the financial incentives are clear, semi-retirement also offers important psychological benefits. The transition from a full-time career to retirement can be overwhelming, especially for those who have worked for decades. The loss of a job-related identity and the potential for social isolation can take a toll on mental health, leading to increased risks of loneliness, anxiety, or depression.

Semi-retirement provides a solution by maintaining social connections and a sense of purpose. It offers structure while allowing for greater freedom, which can help employees stay engaged and emotionally fulfilled. Kevin Won, a financial advisor with The Retirement Group, suggests that reducing work hours rather than quitting altogether can contribute to a more successful retirement.

Not all Sears Holdings employees are suited for semi-retirement, however. Teresa Ghilarducci, a labor economist, warns that those in high-stress, low-control jobs might find that continuing to work, even part-time, could exacerbate stress and health issues. It's important for each employee to evaluate their own situation and whether part-time work will improve or hinder their quality of life.

How to Determine If Semi-Retirement Is Right for You

For Sears Holdings employees, deciding if semi-retirement is the right path involves considering both financial and personal factors. Financially, it's important to assess how much more needs to be saved and how long one must work in semi-retirement to cover retirement expenses. Thoughtful questions such as 'How much more do I need to save?' and 'How long will I need to work to support my retirement?' can guide the decision-making process.

Employees with adequate savings who still want to build their nest egg can use semi-retirement as an opportunity to work more flexibly and add to their retirement funds. This additional income could provide a cushion against economic uncertainties.

For those seeking purpose or a new challenge, semi-retirement may involve consulting, freelancing, or taking on projects that align with personal interests. Sears Holdings employees who are motivated by a desire to remain engaged in meaningful work will find semi-retirement an ideal option.

Things to Consider Before Moving Into Semi-Retirement

Before transitioning to semi-retirement, Sears Holdings employees should carefully consider the potential impact on their health care, taxes, and Social Security benefits.

Taxes:

Working part-time during semi-retirement can impact tax brackets. Additional income from part-time work or retirement account withdrawals may push employees into a higher tax bracket, increasing their tax liability. It's important to stay informed about tax changes and plan accordingly.

Social Security:

If an employee is under full retirement age (FRA), working part-time while receiving Social Security benefits may reduce the monthly income. For example, in 2025, employees under FRA who earn more than $23,400 may see a reduction of $1 in Social Security benefits for every $2 they earn above this threshold. Once FRA is reached, any withheld benefits will be reinstated.

Health Care:

Retirees under 65 must purchase health insurance through the marketplace until they are eligible for Medicare at age 65. Employees staying in their jobs may continue to access employer-sponsored insurance. Understanding how health care costs will be managed during the transition to retirement is crucial, especially for employees who will continue to rely on company health benefits.

The Bottom Line

Semi-retirement offers Sears Holdings employees a flexible, fulfilling way to ease into retirement without losing the financial and social benefits of work. With the potential to supplement retirement savings, delay Social Security claims, and maintain social connections, semi-retirement may provide a balanced approach to transitioning into full retirement.

By weighing the financial and personal factors, employees can make an informed decision that aligns with their long-term goals, leading to a smooth and sustainable retirement journey.

This growing trend reflects a shift toward a more gradual, controlled approach to retirement, with nearly 30% of Americans over 60 considering semi-retirement ¹ as a way to preserve both financial stability and personal fulfillment.

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Articles you may find interesting:

Sources:

1. ' 4 Key Reasons Retirement Is Out of Reach for Many Older Americans ,' by Cynthia Meason. Yahoo!finance, 17 June 2025.

Other resources:

1. 'The Rise of the Semi-Retired Life.' Investopedia, 25 Oct. 2016, www.investopedia.com/articles/retirement/102216/the-rise-semi-retired-life.asp .

2. 'The Amazing Tax Benefits of Semi-Retirement.' Can I Retire Yet?, 25 May 2020, www.caniretireyet.com/tax-benefits-of-semi-retirement/ .

3. 'Delayed Retirement Credits.' Social Security Administration, www.ssa.gov/benefits/retirement/delayed-retirement-credits/ .

4. 'How Working in Later Years Can Improve Your Health.' Investopedia, 28 May 2025, www.investopedia.com/articles/retirement/052816/how-working-later-years-can-improve-your-health.asp .

5. '5 Advantages of Semi-Retirement.' Minster Bank, 15 Sept. 2024, www.minsterbank.com/5-advantages-of-semi-retirement/

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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