Overstock.com Families Facing a New Challenge: Supporting Children While Preparing for Retirement

Healthcare Provider Update: Healthcare Provider for Overstock.com Overstock.com provides its employees with health insurance options through major insurers offering Affordable Care Act (ACA) plans, including well-known providers like UnitedHealthcare and Anthem. Potential Healthcare Cost Increases in 2026 In 2026, employees at Overstock.com are expected to face significant increases in healthcare costs, driven by anticipated premium hikes in the ACA marketplace. Projections indicate that some states might see premium increases exceeding 60%, exacerbated by the potential expiration of enhanced federal premium subsidies. As many employees may bear a larger share of healthcare expenses, it is crucial for Overstock.com workers to stay informed about their benefits and explore strategies to manage rising costs. The combination of inflated medical expenses and changing employer strategies could lead to a challenging healthcare landscape, stressing the importance of proactive financial planning. Click here to learn more

'Overstock.com 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.

'Overstock.com 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 Overstock.com 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 Overstock.com 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 Overstock.com 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 Overstock.com 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 Overstock.com 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 Overstock.com, 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 Overstock.com 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. Overstock.com 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 Overstock.com 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 Overstock.com 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 Overstock.com 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. Overstock.com 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 Overstock.com 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 Overstock.com 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 Overstock.com 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, Overstock.com 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 Overstock.com 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.

Featured Video

Articles you may find interesting:

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.