Sears Holdings Families Facing a New Challenge: Supporting Children While Preparing for 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 facing the dual pressures of supporting adult children while preparing for retirement should focus on setting clear financial boundaries and prioritizing long-term stability, balancing generosity with retirement readiness to help preserve both family well-being and future independence.' — Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'Sears Holdings employees navigating extended parenting responsibilities alongside retirement planning should view this as a call to reassess household budgets and timelines, since proactive adjustments today can help maintain balance between family support and long-term financial stability.' — Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

1. The rising financial challenges associated with parenting later in life and their impact on retirement.

2. Demographic and societal shifts contributing to extended parental responsibilities.

3. Practical strategies for Sears Holdings families balancing child support with retirement planning.

The Growing Expenses of Parenting Later in Life: Economic Factors and Retirement Consequences

Although being a parent has always been a big responsibility, its demands have altered in recent years. For Sears Holdings households, juggling retirement planning, demographic changes, postponed family planning, and the growing demands of adult children are posing new difficulties. Families’ perspectives on long-term planning are shifting because these priorities are overlapping with traditional retirement timeframes.

Parenting Beyond Traditional Timelines

“Parenting is happening later, longer, more intensively, and more expensively,” says Carlos Hernandez, a Wealth Enhancement financial advisor. In fact, many parents continue to support their children well beyond their college years. For many Sears Holdings families, this means finding ways to navigate ongoing financial assistance at a time when they are trying to optimize retirement resources.

Continuing to support adult children into one’s 50s, 60s, and beyond often strains household finances, which may prompt Sears Holdings employees to postpone retirement or adjust expectations for their long-term savings.

The extent to which this issue has grown is revealed by a recent AARP study: 75% of parents age 45+ with at least one adult child provide monetary support that averages roughly $7,000 per year. ¹

This raises a question for many Sears Holdings households: does continued assistance promote independence or dependency?

The Broader Context of Demographics

This trend reflects broader societal shifts rather than occurring in isolation. In 2023, 18% of adults aged 25–34 were living with their parents, ²  a statistic that underscores a trend for adult children to stay home longer due to job market realities, housing costs, and student debt pressures. 

Meanwhile, more people are having children later in life. According to the CDC, in 2023 more babies were born to women over 40 (4.1%) than to teens (4%). ³  For many parents, including those at Sears Holdings, this means that the years when retirement focus should be strongest often overlap with the financial responsibilities of raising children.

Important Considerations for Families Supporting Adult Children

• Given the pressures associated with these competing financial priorities, parents supporting adult children while also planning for retirement should consider the following strategies to stay on track:

• 1. Build a Detailed Financial Plan

• 'A common mistake many parents make is assuming their children will reach financial independence faster than they do,' explains Carlos Hernandez. For Sears Holdings parents, having clear goals and defined financial boundaries can help balance retirement needs with ongoing family obligations.

• 2. Have Honest Conversations About Money

• Although money conversations can be uncomfortable, open dialogue helps prevent misunderstandings. Sears Holdings families that talk about expectations for support with adult children often experience less stress and clearer roles.

• 3. Define Your Expectations Clearly

• Unspoken or unacknowledged support can create tension. For Sears Holdings parents, explicitly stating what they expect in return—such as household help or accountability for spending—can reduce resentment and improve family cooperation.

• 4. Encourage Accountability Through Practice

• If adult children live at home, Wealth Enhancement advisor Brent Wolf suggests charging rent but saving it on their behalf. For Sears Holdings families, this approach can help children learn discipline with money while accumulating reserves for eventual independence.

• 5. Consider the Limits of Longevity in Employment

• Wolf also cautions against assuming work will continue indefinitely. For Sears Holdings households, unexpected health changes or shifts in employment may make continued adult-child dependence more burdensome.

• 6. Be Transparent About Retirement Timing

• Conversations about retirement plans create clarity across generations. Sears Holdings employees who share their planning horizons often motivate children to begin participating in retirement-type accounts earlier.

• 7. Prioritize Stability in Later Years

• Brent Wolf reminds families that, while loans may be possible for education, retirement doesn’t typically offer borrowing options. For Sears Holdings households, this may mean giving priority to long-term consistency of retirement resources rather than helping to fund their children's education.

The Broader Economic Environment

Extended parenting pressures coexist with wider economic realities. Rising health care costs, increasing life spans, and market uncertainties complicate retirement for many families.

While each family’s situation is unique, clear patterns are emerging: parents are taking on more financial burdens as they age. For Sears Holdings households, disciplined planning, open communication, and firm boundaries are key to balancing generosity with personal stability.

Conclusion

Later and longer parenting has lasting financial implications. For Sears Holdings employees, adapting strategies to manage child support while preserving retirement-readiness may spell the difference between comfort and strain. Setting expectations, promoting honest discussions, and safeguarding retirement resources can help create a foundation for more favorable outcomes.

According to a report by Savings.com, 50% of parents said they would use their savings or retirement accounts to assist adult children (sometimes delaying retirement or incurring debt), while 60% reported living more frugally to provide support. ⁴

To reconcile this generosity with their personal needs, Sears Holdings families may benefit from professional advice around managing family expenses, medical costs, and income during retirement. 

Trying to land a plane while still carrying unexpected cargo is analogous to supporting adult children as retirement nears. For Sears Holdings families, extra weight strains carefully devised plans built over years of pension contributions, 401(k) accumulation, and retirement scheduling. Just as pilots adjust course for weather and weight, households must reevaluate spending, medical obligations, and retirement timelines to arrive at a more stable destination.

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Sources:

1. AARP Research. ' Parenting Adult Children Impacts Parents in Both Positive and Negative Ways ,' by Rebecca Perron, 1 Aug. 2025.

2. Pew Research Center. “ The shares of young adults living with parents vary widely across the U.S. ,” by Richard Fry, April 17, 2025.

3. Centers for Disease Control and Prevention, National Vital Statistics Reports, Volume 74, Number 3. ' Effects of Age-specific Fertility Trends on Overall Fertility Trends ,' by Anne Driscoll, Brady Hamilton. March 6, 2025.

4. Savings.com.' Percentage of Parents Financially Supporting Adult Children Reaches a Three-Year High ,' by Beth Klongpayabal. March 21, 2025.