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Sears Holdings Legacy Planning: 16 Essential Estate Tasks Before You Pass

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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

'Estate planning is essential for Sears Holdings employees nearing retirement to make sure their assets are properly allocated and their legacy is preserved, reducing future complications and optimizing the smooth transfer of benefits like retirement accounts and life insurance policies.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'By prioritizing estate planning, Sears Holdings employees can safeguard their retirement benefits, streamline the management of their assets, and confirm their loved ones are well cared for, ultimately providing peace of mind during the retirement transition.' – Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

  1. The importance of estate planning for Sears Holdings employees nearing retirement

  2. Key steps for organizing and managing your assets, including retirement accounts and insurance

  3. Common mistakes to avoid in estate planning and the benefits of starting early

The process of making arrangements for the administration and allocation of a person's assets upon their passing or in the case of incapacitation is known as estate planning. You can make sure your affairs are handled appropriately, your loved ones are cared for, and your wishes are respected by taking a few preparatory actions. From drafting a will to using key legal instruments to manage your financial and medical decisions, estate preparation entails a number of steps. For Sears Holdings employees nearing retirement, making these steps a priority is particularly important given the scope of benefits and accounts involved. To make sure your estate plan is in order, here is a checklist of 16 things to consider as part of  your estate planning process.

Important Takeaways:

  • Make sure your estate plan is carried out smoothly by keeping track of all your assets and wishes. It may help to keep thorough written lists and let your estate administrator know where they are.

  • To facilitate a smooth transfer of assets, designate named beneficiaries on insurance policies, retirement funds, and other accounts.

1. Inventory Your Assets

Sears Holdings employees should begin by listing all tangible assets. This includes items such as your house, vehicles, tools, jewelry, and personal collections. Don’t forget items of sentimental value like family heirlooms and photo albums.

2. Keep Records of Your Intangible Assets

Beyond physical possessions, Sears Holdings retirees should gather documentation for 401k accounts, IRAs, life insurance, and Sears Holdings benefit accounts. Include institution names, account numbers, and storage locations for any paper documents.

3. Compile a Debt List

List your outstanding debts such as mortgages, credit cards, HELOCs, and personal loans. Include all necessary details so your estate administrator can quickly identify and resolve any liabilities.

4. Create a Membership List

Whether you’re part of Sears Holdings alumni associations or other organizations, list all affiliations that could provide life insurance, survivor benefits, or charitable giving connections.

5. Make Copies of the Lists You Have

Keep at least three copies: one for yourself, one for your estate administrator, and one in a secure location such as a fireproof safe or safe deposit box. Sears Holdings’s employee resource centers may offer guidance on document storage.

6. Examine Your Retirement Funds

Sears Holdings offers a variety of retirement plans. Confirm that your 401k, pension plans, and life insurance policies have updated and correct beneficiaries, especially after life events like marriage or divorce.

7. Revisit Your Policy

Review annuity and insurance policies to make sure your heirs receive benefits without delays. Sears Holdings life insurance plans may be a key part of your legacy, so keeping this documentation up to date is critical.

8. Permit Designations for “Transfer on Death”

For Sears Holdings employees with brokerage or savings accounts, designating a TOD beneficiary can reduce the burden of probate. This applies to certain accounts depending on your state’s laws.

9. Select a Trustworthy Estate Administrator

Choose a dependable person who can handle the complexity of your estate. For Sears Holdings employees, this might be someone familiar with handling corporate benefits and related tax forms.

10.  Write Your Will

Draft a will that covers distribution of your assets, guardianship of minor children, and care of pets. A clearly written will is essential in avoiding confusion, especially when Sears Holdings retirement benefits are involved.

11. Examine Your Documents Frequently

Revisit your estate documents at least every two years or after major life changes to make sure they align with your current financial and family situation.

12. Make a Copy for Your Administrator

Make sure your estate administrator has access to the original will and is informed of its location. Only the original can be submitted to probate court.

13. Speak with a Financial Planner or Estate Attorney

In addition to speaking with any retirement advisor provided by Sears Holdings, take time to consult with an independent estate attorney to assess your unique family, financial, and tax planning needs.

14. Simplify Your Finances

Sears Holdings retirees often accumulate multiple retirement accounts from past employers. Consolidating them into one IRA can make future management more efficient.

15. Complete Any Other Vital Records

Documents like a durable power of attorney and a health care proxy allow decisions to be made on your behalf by someone you trust. Sears Holdings resources may help guide employees to legal support services for drafting these forms.

16. Make Use of College Funding Accounts

If you wish to help your grandchildren, setting up a 529 plan can benefit them while also helping reduce your taxable estate. Many Sears Holdings employees use these tools to support the next generation.

Typical Errors in Estate Planning

Failing to plan altogether is a major error. Not naming contingent beneficiaries or neglecting to update documents after major life events can create confusion and delay. Sears Holdings employees should take care to communicate their wishes clearly and review documentation often.

The Dangers of Living Without an Estate Plan

Without a clear estate plan, your assets could be tied up in probate. This process may delay access to Sears Holdings retirement benefits and increase legal costs for your heirs.

The Bottom Line

Though estate planning can seem overwhelming, especially for long-tenured Sears Holdings employees with layered benefits, starting now offers peace of mind. Early planning helps reduce future complications, allows for thoughtful giving, and helps preserve your legacy.

According to a 2020 study from the  National Institute on Aging , nearly 70% of Americans over age 65 will require long-term care. These costs can significantly reduce a retirement estate. Including long-term care insurance in your planning helps manage these risks and preserve your lifestyle and legacy.

Conclusion

Use this checklist to build a solid estate plan. From naming beneficiaries and cataloging your assets to preparing legal documents and discussing end-of-life preferences, every detail matters. Estate planning is like preparing for a major expedition—you want the right gear, a clear path, and a well-considered map. Thoughtful preparation today means fewer detours for your loved ones tomorrow.

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Sources:

1. Segal, Troy. 'Estate Planning: 16 Things to Do Before You Die.'  Investopedia , 16 Jan. 2025,  https://www.investopedia.com/articles/retirement/10/estate-planning-checklist.asp .

2. 'Estate Planning Checklist.'  Charles Schwab https://www.schwab.com/estate-planning/estate-planning-checklist .

3. 'Estate Planning Checklist: Five Tasks to Prioritize.'  Kiplinger https://www.kiplinger.com/retirement/estate-planning/602219/estate-planning-checklist-5-tasks-to-do-now-while-youre-still .

4. 'Estate Planning Mistakes to Avoid for Retirees and Pre-Retirees.'  Goldstone Financial Group https://www.goldstonefinancialgroup.com/essential-estate-planning-mistakes-to-avoid-for-retirees .

5. 'Estate Planning Checklist: 7 Key Steps To Making A Successful Plan.'  Bankrate https://www.bankrate.com/retirement/estate-planning-checklist .

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.

https://www.pbgc.gov/sites/default/files/documents/sears-holdings-summary-plan-description.pdf - Page 5, https://88sears.com/documents/pension-plan-2022.pdf - Page 12, https://88sears.com/documents/pension-plan-2023.pdf - Page 15, https://88sears.com/documents/pension-plan-2024.pdf - Page 8, https://www.consultrms.com/documents/sep-2022.pdf - Page 22, https://www.revenue.alabama.gov/documents/defined-benefit-plan.pdf - Page 28, https://www.mayoclinic.org/documents/mayo-pension-plan-2023.pdf - Page 20, https://mycentralstatespension.org/documents/annual-funding-notice-2023.pdf - Page 14, https://frs.fl.gov/documents/frs-pension-plan-2023.pdf - Page 17, https://fppta.org/documents/florida-pension-issues-2024.pdf - Page 23

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