Marriage and Money After 50: Key Planning Steps for Overstock.com Employees

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 navigating remarriage must recognize that pensions, 401(k)s, and estate plans often shift automatically without updated documentation, making proactive planning essential to preserve both retirement goals and family legacies.' – Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement Group.

'Overstock.com employees entering later-life marriages should carefully review pensions, 401(k)s, and beneficiary designations, as failing to update these arrangements can unintentionally redirect assets and disrupt long-term family plans.' – Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement Group.

In this article we will discuss:

1. How pensions, 401(k)s, and IRAs are affected by remarriage.

2. The role of property, investments, and trust structures in balancing family needs.

3. Healthcare and long-term care costs that may impact retirement planning.

Getting married later in life can be incredibly rewarding, providing companionship and renewed purpose. But for Overstock.com employees, it also brings unique financial complexities. Younger couples often focus on building assets, while those entering second or third marriages must evaluate how existing arrangements—such as investment portfolios, 401(k)s, IRAs, and pensions—will be impacted. Assets may already be structured to support retirement income or earmarked for children, and remarriage can unintentionally shift inheritance outcomes without careful planning.

Benefits for Survivors and Pensions

One of the most important financial considerations in later-life marriages is the pension. Unless specifically waived, surviving spouses are often entitled to pension survivor payments under federal law. This means a new spouse may legally receive benefits intended for children or other heirs, regardless of prior intentions. Overstock.com employees weighing joint-and-survivor versus single-life annuity options face critical choices that are often permanent. While the joint option provides income to a surviving spouse, it usually lowers monthly benefits and cannot be changed once selected.

IRAs, Beneficiary Designations, and 401(k)s

Defined contribution plans like 401(k)s and IRAs present similar challenges. Under ERISA rules, a spouse is the default beneficiary, overriding wills or trusts unless a notarized waiver is signed. For a Overstock.com employee with a large 401(k) balance, failing to update documentation after remarriage could result in the entire account going to a new spouse, leaving children without access. Regularly reviewing and updating beneficiary forms is important to align accounts with long-term legacy goals.

Real Estate and Investment Portfolios

Properties, taxable brokerage accounts, and even business interests must also be reviewed carefully. In some states, community property laws may convert individual holdings into joint ownership, creating unintended consequences. For Overstock.com retirees with real estate or long-held investments, these assets may become a source of conflict between children and stepchildren if expectations are not clearly documented. Prenuptial or postnuptial agreements can clarify which accounts fund household expenses and which remain separate.

Costs of Long-Term Care and Healthcare

Later-life marriages also increase exposure to healthcare and long-term care costs. With both spouses at higher risk of illness, shared assets may be depleted if one spouse requires extended medical treatment. Overstock.com employees can explore Medicaid planning strategies, long-term care insurance, or hybrid annuities to help manage these risks. Without planning, healthcare costs could significantly reduce retirement portfolios and alter intended inheritances.

Openness with Family Members

Family communication is a vital component of financial planning. If children discover after a parent’s death that pensions or retirement accounts automatically transferred to a new spouse, feelings of exclusion or betrayal may arise. Overstock.com families can lower the risk of disputes by openly discussing beneficiary waivers, trusts, or prenuptial agreements. Transparent conversations often prevent resentment and costly legal challenges later.

Trust Structures for Balance

Trusts provide a structured way to balance the needs of children and a new spouse. A Qualified Terminable Interest Property (QTIP) trust, for instance, allows the surviving spouse to receive income while preserving the principal for heirs. For Overstock.com retirees, this approach allows the surviving spouse to receive support while maintaining assets for the next generation.

Timing and Legal Performance

The timing of agreements also matters. Contracts signed immediately before a wedding may be challenged in court as coerced, weakening enforceability. Overstock.com employees should complete prenuptial agreements well before marriage, with full disclosure of pensions, stock options, and real estate holdings. Careful preparation strengthens legal standing and provides clarity for both partners.

Other Options Besides Marriage

For some couples, cohabitation agreements may be preferable to formal marriage, allowing them to maintain separate estates while living together. However, states that recognize “committed intimate relationships” may still impose property-sharing rules, creating complications. Just as with marriage, Overstock.com employees should seek legal guidance to reduce the chance of unexpected outcomes.

Final Thoughts

Managing wealth, retirement income, and family legacies in later-life marriages requires proactive planning. For Overstock.com employees, medical costs can erode retirement savings, 401(k)s are bound by federal spousal rules, pensions default to spouses, and investment accounts may be subject to state property laws. These issues can be addressed through strategies such as prenuptial agreements, trust planning, spousal waivers, and long-term care arrangements.

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Sources:

1. Employee Benefits Security Administration.  What You Should Know About Your Retirement Plan . U.S. Department of Labor, Sept. 2021, pp. 17–18.

2. Internal Revenue Service.  Publication 590-B: Distributions from Individual Retirement Arrangements (IRAs) . U.S. Dept. of the Treasury, 19 Mar. 2025, pp. 5–6, 10, 24.

3. CareScout Research.  2024 Cost of Care Survey . Genworth, 28 Feb. 2025, pp. 1–2.

4. Washington State Administrative Office of the Courts.  Family Law Handbook: Understanding the Legal Implications of Marriage and Divorce in Washington State . July 2019, pp. 17–19.

5. Uniform Law Commission.  Uniform Premarital and Marital Agreements Act (UPMAA) . National Conference of Commissioners on Uniform State Laws, 2012, pp. 11–14.