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Sears Holdings Employees: 10 Estate Planning Mistakes That Can Derail Your Legacy

'For Sears Holdings employees, reviewing your estate plan every few years is essential to keep pace with evolving family needs, tax law changes, and shifting financial priorities.' — Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

'Sears Holdings employees who revisit their estate plans regularly are better positioned to adapt to tax law changes and life transitions that could otherwise disrupt long-term goals.' — Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

How changing life circumstances and tax laws may impact the effectiveness of your current estate plan.
Key estate planning components—such as trustees, health care directives, and trust structures—that may need to be updated.
Practical steps for Sears Holdings employees to keep their estate plans aligned with long-term financial and family goals.

Many individuals draft an estate plan—including health care directives, powers of attorney, trusts, and wills—and then set it aside for years. However, life circumstances, tax laws, and legal frameworks often shift over time. For Sears Holdings employees managing long-term financial objectives, revisiting an estate plan every three to five years—or after major changes—helps keep the plan aligned with current needs.

Ten Signs Your Estate Plan May Be Outdated

1. Executors and Trustees: Are They Still Suited for the Role?

Executors and trustees carry major legal responsibilities, such as handling assets, filing tax returns, distributing funds, and acting on behalf of beneficiaries. These appointments may have been made under circumstances that no longer apply.

- An executor may now be unable to serve due to health, relocation, or passing.
- Professionals named in the plan may have retired or exited the industry.
- Corporate fiduciaries may have undergone mergers or changes in structure.
- Adult children listed as successors may now have other obligations or limitations.

Sears Holdings employees may benefit from re-evaluating each fiduciary’s availability, financial awareness, and overall relationship with the family.

2. Trusts for Children: Have They Aged Well?

Trusts are often structured for minor children, outlining distribution ages and guardianship roles. But over time:

- Guardianship provisions may be unnecessary if children are now financially independent.
- Distributions set for age 25, 30, or 35 may have occurred or require adjustment.
- Direct distributions might expose funds to potential claims in divorce or lawsuits.
- Children’s maturity, spending patterns, or marital status may differ from earlier expectations.
- Beneficiary designations on insurance or retirement plans may now conflict with trust goals.

- It’s worth assessing whether trust terms and retirement designations continue to reflect intended outcomes.

3. Health Care Proxies and HIPAA Authorizations

- If HIPAA authorizations are outdated, health care agents may be blocked from accessing vital medical information.

- Without authorization, hospitals may limit updates or exclude family from treatment discussions.
- Delays can affect treatment decisions and family coordination.

Sears Holdings employees should verify that HIPAA documents are up to date—and that adult children, particularly those living independently, have health care directives of their own.

4. Growing Wealth and the Estate Tax Landscape

As of 2025, the federal estate and gift tax exemption is $13.99 million per individual and $27.98 million for couples. The annual gift tax exclusion is $19,000 per recipient.

However:

- These elevated exemptions are temporary and expected to sunset in 2026.
- Trust formulas created under prior laws may no longer be suitable.

Sears Holdings executives nearing the exemption limit may want to speak with advisors about reviewing their gift strategies and trust funding formulas.

5. State Residency and Legal Nuances

Estate laws differ significantly by state:

- Some states assess estate or inheritance taxes at lower thresholds than federal law.
- Community property vs. common law distinctions can change how assets are divided.

If a Sears Holdings employee has changed residency since creating their plan, a legal review may be warranted to enhance compliance with current state laws, particularly in states with unique estate tax structures like Massachusetts, Oregon, Washington, or Minnesota.

6. Portability and Credit Shelter Trusts

A surviving spouse may use any unused federal exemption from the deceased spouse through portability, but:

- A federal estate tax return is required within nine months of death (15 months with extension).
- Before portability, credit shelter trusts (CSTs) were common to preserve exemptions.

- Although no longer needed for federal purposes in some cases, CSTs may still be helpful for managing state or generation-skipping transfer (GST) taxes. Disclaimers and updates to trust structures may provide additional flexibility.

7. Charitable Giving: Aligning Purpose with Planning

Charitable giving is often a priority—but sometimes not reflected in estate documents. Potential planning tools include:

- Specific gifts to charities listed in a will or trust.
- Use of charitable lead or remainder trusts.
- Donor-advised funds or private family foundations.

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Sears Holdings retirees who value philanthropy should evaluate how well their estate plans incorporate these goals, and whether doing so could lead to tax advantages.

8. Estate Taxes vs. Income Tax Implications

Earlier estate plans emphasized reducing estate taxes, but income tax considerations are now equally important.

- The federal estate tax rate is 40%.
- Federal income tax rates can reach 37%, capital gains up to 20%, plus a 3.8% surtax.
- Trusts reach the highest tax brackets with just $15,650 in income.

- It may be beneficial to shift income-producing assets out of trusts or re-evaluate distributions to individuals in lower tax brackets.

9. Life Insurance: Still a Strong Fit?

Life insurance policies created years ago may no longer align with your estate or cost objectives.

Consider:

- Does the policy still perform competitively under current conditions?
- Are premium costs sustainable?
- Is it worth transferring ownership to an irrevocable life insurance trust (ILIT)?

It’s recommended that insurance policies be reviewed periodically to determine their ongoing relevance and financial impact.

10. Communication and Digital Organization

Many estate plans lack practical execution details. Family may not know where documents are stored. Fiduciaries might not have contact details or asset lists. Digital accounts and passwords may be inaccessible.

A comprehensive letter of instruction should include:

- Contacts for attorneys, advisors, and fiduciaries.
- An inventory of assets and their locations.
- Login details for important digital accounts.

Clear planning and information access can simplify responsibilities and reduce confusion during transitions.

Bottom Line: Estate Planning Is a Process, Not a Product

As your circumstances and regulations evolve, estate documents should evolve as well. Sears Holdings employees may consider:

- Revisiting documents every 3–5 years or after major changes.

- Involving attorneys, tax professionals, and financial advisors in reviews.

- Reassessing roles, ownership structures, and beneficiary choices.
- Including charitable goals and multi-generational intentions.

An estate plan should reflect your values and help facilitate your legacy.

Checklist: Key Areas to Review

Focus Area	Action Point
Fiduciaries	Confirm that trustees and executors are still appropriate.
Trusts and beneficiaries	Reassess terms, ages, and children's evolving needs.
Health care and HIPAA	Confirm that documents and authorizations are up to date.
Tax exposure	Compare current asset values with federal and state limits.
State of residence	Ensure estate documents align with state-specific rules.
Trust structures	Evaluate GST, CST, and disclaimer trusts for relevance.
Charitable giving	Review charitable gifts or plans embedded in documents.
Income vs. estate taxes	Assess tax impact by ownership type and beneficiary structure.
Life insurance	Re-evaluate life insurance policies for ongoing usefulness.
Communication plan	Share critical info with fiduciaries and heirs.

Legacy Planning in a Changing World

A plan drafted years ago may no longer reflect your current priorities. Keeping it updated allows for better alignment with family dynamics, tax laws, and economic trends.

Recent data indicates many individuals in their 60s fall into the 'senior sandwich generation,' simultaneously supporting aging parents and adult children. This multi-generational responsibility may require adjustments in estate planning such as modifying liquidity goals, rethinking timelines for inheritance, or creating structures that serve multiple generations.

Final Thought

An estate plan left unchanged is like using an outdated map—it may miss important updates such as new fiduciary considerations, revised tax laws, or shifts in your family’s structure. For Sears Holdings employees focused on long-term planning, periodic updates can help your legacy reflect today’s realities.

With consistent reviews and collaboration with qualified professionals, your estate documents can remain an effective and adaptable guide for your family and financial future.

Sources:

1. Doc & Law. The Connection Between Estate Planning and Retirement Planning. Doc & Law LLP, May 2025, pp. 1–3.

2. JustVanilla: Why You Need to Periodically Update Your Estate Plan (and the Consequences If You Don’t). JustVanilla, Mar. 2025, pp. 2–4.

3. Lanza, John R., and John E. Lanza. Why Revisiting Your Estate Plan Upon Retirement Is Crucial. Lanza & Lanza LLP, 25 July 2024, pp. 1–5.

4. Allegro, Alex. “Estate Planning Steps to Protect Your Loved Ones and Legacy.” Kiplinger , 9 June 2025, pp. 2–4.

5. Kiplinger Staff. “Think a Repeal of the Estate Tax Wouldn’t Affect You? Wrong.” Kiplinger , May 2025, pp. 1–3.

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.

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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.