New Update: Healthcare Costs Increasing by Over 60% in Some States. Will you be impacted?

Creating Peace of Mind Through Family Planning Conversations at Sears Holdings

“Sears Holdings employees who foster open-ended family dialogues and co-create a shared vision around their estate plans can replace lingering uncertainty with genuine confidence—and for personalized guidance, consult a legal, financial, or tax advisor” – Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

“By inviting open, curiosity-driven discussions around estate planning, Sears Holdings employees can transform documents into a living blueprint for family unity. Yet, for tailored advice, it’s best to consult a legal, financial, or tax advisor” – Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

The role of meaningful, informed conversations in finding genuine peace of mind.
Three intentional steps to engage Sears Holdings families in collaborative estate planning.
Practical strategies for aligning legal documents with family values and long-term goals.

Arthur has made financial services his life’s work, thoughtfully preparing for every aspect of his family’s future. He's provided his wife Estelle and their three adult children with contact information for his lawyer, Sam, who works closely with Arthur’s financial advisor. Whenever the subject of estate planning arises, Arthur calmly reassures them, “You honestly have nothing to worry about—just call Sam.” While well-intentioned, this approach overlooks a key truth: real peace of mind comes not from handing over a name, but from meaningful, informed conversations—something that may resonate deeply with many Sears Holdings employees and their families.

Insights from the Generations Project's℠ Later-in-Life Conversations Study, conducted by the Fidelity Center for Family Engagement, reveal that peace of mind is among the top two goals in later-life planning discussions for baby boomers, Gen Xers, and millennials. ¹ Despite this, it remains one of the least addressed subjects. A surprising 66% of parents admit they are hesitant to discuss this with their children. ¹ When family members lack clarity, uncertainty—and anxiety—can quickly grow.

Notably, peace of mind appears to stem from open dialogue about long-term goals, setting clear expectations, and providing family members with easy access to trusted information. This includes decisions about beneficiary designations, executors, health care proxies, wills, trusts, and dependent care insurance. Without such clarity, family members may experience what Dr. Timothy Habbershon of the Fidelity Center for Family Engagement calls “wondering anxiety”—uncertainty about long-term financial needs, health incidents, or how estate plans may affect them.

Dr. Habbershon contrasts this with the clarity gained from openness and thoughtful conversation. Transparency is the remedy to the discomfort caused by unasked questions. By speaking candidly and exchanging ideas, families—Sears Holdings employees included—can replace lingering anxieties with productive dialogue rooted in trust and understanding.

Those who realize that documents alone are insufficient should take one step further: encouraging active participation. To foster true peace of mind and deeper family bonds, consider these three intentional steps:

1. Ask What Questions Family Members May Have

Effective planning begins with curiosity. Instead of explaining or defending existing plans, start by listening. Arthur could begin the conversation with Estelle and their children by asking:

- “What part of our planning feels unclear to you?”

- “How does our current approach impact your sense of comfort?”

- “What else would you want to know to feel more confident about our future?”

By resisting the urge to justify decisions, Arthur uncovers the uncertainties behind their concerns. Posing follow-up questions like “Can you expand on that?” or “What would make this clearer for you?” invites deeper dialogue and mutual respect.

2. Invite Input on the Planning Process

For Wealth Enhancement advisor Michael Corgiat, a guiding principle is to enroll adult children in the planning process now, when you can have informed discussions. Too often, even well-meaning planners take a “we know what’s best” approach. By clarifying your intentions in advance, and in your own words, you can help strengthen connections—something Sears Holdings families may find especially valuable.

Arthur might ask:

- “How does this process feel from your perspective?”

- “Do you feel you’ve had enough input?”

- “What changes might help you feel more included?”

These questions focus less on legal language and more on collaborative engagement. Giving family members a role in the process builds confidence and reduces anxiety around future changes.

3. Co-Create a Vision for Later Life

Planning is not just about future legal steps—it’s about present-day relationships. Encouraging family members to think together about how they want to spend time, support one another, and adapt to change brings emotional and practical priorities into alignment for Sears Holdings households.

Arthur might ask:

- “What shared experiences should we prioritize in the coming year?”

- “Which conversations or activities would feel most meaningful?”

- “How should we navigate shifts in care, housing, and health needs?”

These discussions allow families to align financial and legal tools with their personal values. By bringing everyone into the conversation, Arthur reinforces not only clarity, but also family unity.

Bringing It All Together

Estate planning documents are important, but they’re only part of the story. The conversations that surround them create the true emotional foundation for peace of mind. Families that engage in open, participatory planning are more likely to feel greater confidence and less uncertainty about the future. In contrast, the 66% of parents who shy away from these conversations risk leaving loved ones confused and concerned.

Sears Holdings employees can take three practical steps to shift from good intentions to meaningful family engagement:

1. Use curiosity-driven, open-ended questions to draw out concerns.

2. Seek feedback about the process, not just the outcomes.

3. Build a shared vision that blends daily life with legal planning.

This inclusive approach helps transform vague concerns into actionable clarity. Discussions about wills, trusts, proxies, and beneficiaries become shared efforts, illuminating financial, legal, and emotional priorities. The result is an environment of mutual trust, support, and understanding—a space where true peace of mind can grow.

According to Fidelity’s State of Wealth Mobility study, 56% of adults never had discussions about money management with their parents, yet among families that do, two-thirds actively engage in estate and retirement planning—with a significant boost in confidence as a result. ²

Just as an orchestra needs each musician to understand their role, estate plans resonate most when everyone involved hears the same tune, contributes their part, and works in harmony to carry forward a shared vision.

Featured Video

Articles you may find interesting:

Sources:

1. Fidelity Center for Family Engagement. ' The Generations Project ^SM : Findings from the Later-in-Life Conversations Study .' 2024.

2. Fidelity Investments. “ Americans Ready to Break the Cycle of Avoiding Family Discussions on Finances ,” 19 Nov. 2024.

Other Resources:

1. Barron's. “ Northern Trust Reveals ‘Secrets of Enterprising Families’ ,” by Abby Schultz. 9 April 2024.

2. Investopedia. “ How to Have 'The Talk' With Your Parents: The Financial Discussion You Can't Avoid Forever ,' by Lucy Lazarony. 7 July 2025.

3. Kiplinger. “ Six Ways to Make Talking With Family About Estate Planning Easier ,” by Jacob Wolinsky. 9 Apr. 2025.

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.

Additional Articles

Check Out Articles for Sears Holdings employees

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.