How Overstock.com Employees Can Save Big on Taxes in Retirement: The Power of Roth Conversions

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

'Roth conversions can offer Overstock.com employees significant tax advantages in retirement by reducing future RMDs and lowering taxable income, making them a smart strategy for long-term financial freedom.' – Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement.

'By using Roth conversions, Overstock.com employees can effectively lower their tax liabilities, safeguard tax-free income in retirement, and provide a more efficient estate strategy for their heirs.' – Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

1. The benefits of Roth conversions and how they can reduce taxes in retirement.

2. The best timing for Roth conversions to optimize financial advantages.

3. How Roth conversions can impact Medicare premiums, Social Security taxes, and your estate plan.

Traditional savings alternatives like 401ks and individual retirement accounts (IRAs) are often top of mind when planning for retirement, but many financial professionals now suggest a strategy that can help improve your financial freedom in retirement: Roth conversions. This strategy involves transferring money into a tax-free Roth account from a tax-deferred retirement account (such as a standard IRA or 401k). Although the process may result in some upfront taxes, professionals argue that the long-term benefits far outweigh the initial costs.

What Is a Roth Conversion?

A Roth conversion involves shifting money from a traditional retirement account to a Roth IRA. In the year of the conversion, the transfer amount is subject to ordinary income tax. This means that Overstock.com employees who move a substantial portion of their tax-deferred savings into Roth accounts may face a significant tax bill initially. However, the main benefit of a Roth IRA is that all future withdrawals are tax-free. Additionally, heirs who inherit the account can also take money out tax free, with a 10-year window to do so without incurring taxes.

Why Consider Roth Conversions?

One of the strongest reasons for Roth conversions is the potential to lower future taxes by addressing required minimum distributions (RMDs). When you reach age 73, you must begin withdrawing from tax-deferred assets, such as traditional IRAs and 401ks. These RMDs are taxed as regular income. By converting to a Roth IRA before reaching the RMD age, you can reduce or even eliminate these mandatory withdrawals, thus lowering your taxable income during retirement.

When Is the Right Time to Convert to Roth?

The timing of a Roth conversion is crucial. Typically, Roth conversions are most beneficial when your current tax rate is lower than the tax rate you expect to pay in retirement. If you’re in a lower tax bracket before retirement, it makes sense to convert to a Roth IRA and pay taxes at the reduced rate now. Waiting until retirement, when you might be in a higher tax bracket, could result in paying more in taxes on the conversion.

Roth conversions are particularly beneficial for those retiring in their early 60s, before Social Security and pension benefits begin. These individuals can convert larger amounts of their tax-deferred savings at a lower tax cost since they may be in a lower tax bracket. Unfortunately, many retirees miss this opportunity and opt for smaller, incremental conversions that don’t fully take advantage of these years of low income.

Additional Considerations

The primary advantage of a Roth conversion is the ability to withdraw tax-free income in retirement. However, there are other important benefits as well. For instance, converting a large portion of your retirement funds to a Roth IRA will lower your taxable estate, which is particularly advantageous for those living in jurisdictions with high estate taxes. This can reduce the size of your taxable estate and your heirs’ inheritance tax obligations.

Roth conversions may also reduce your Medicare premiums. Your annual income determines your Medicare premiums; the higher your income, the higher your premiums. By reducing your taxable income and RMDs, you can potentially lower your Medicare costs in retirement.

Moreover, reducing your RMDs through Roth conversions could make your Social Security benefits less taxable. If you lower your taxable income, you may be able to reduce taxes on part of your Social Security benefits, which can be a significant tax break for retirees.

Case Study: The Benefits of Roth Conversions

Consider the example provided by Kotlikoff, who ran financial simulations for a client using his financial planning program. The client had $1.25 million in savings and another $1.25 million in a tax-deferred IRA. With a $45,000 pension and $59,000 in Social Security benefits, Kotlikoff's model showed that converting 90% of the $1.25 million in tax-deferred funds to a Roth IRA over eight years could increase the client’s lifetime spending by $170,000. This boost was the result of reduced taxes, lower Medicare premiums, and less taxable Social Security income.

In another case, Kotlikoff projected that converting the entire $1.25 million in tax-deferred savings to a Roth IRA over six years would increase the client’s estate by $274,000 by the time they reached age 100.

Roth Conversions for Widows and Widowers

For surviving spouses, Roth conversions can be especially beneficial. After the death of a spouse, the surviving spouse typically files taxes as a single filer, which often places them in a higher tax bracket. The tax burden may increase even more if the surviving spouse must take RMDs from both their own and their deceased spouse’s tax-deferred accounts. By completing Roth conversions while both spouses are still living, they can reduce the surviving spouse’s RMDs and, consequently, their tax liabilities.

Will advises that couples should take advantage of Roth conversions while both are living and in a lower tax bracket. This strategy can help mitigate taxes for the surviving spouse.

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In Conclusion

For Overstock.com employees aiming to reduce taxes and increase their financial flexibility in retirement, Roth conversions are a powerful strategy. Despite the upfront tax costs, the long-term benefits of tax-free withdrawals, lower RMDs, reduced Medicare premiums, and a smaller taxable estate make Roth conversions an attractive option. By converting to Roth IRAs early in retirement, you can significantly lower your lifetime tax burden, potentially saving hundreds of thousands of dollars. Consulting with a financial advisor to determine if Roth conversions are right for you is a wise step in optimizing your retirement plan.

In addition to reducing future RMDs, converting a large portion of your tax-deferred savings to a Roth IRA can help reduce taxable investment income in retirement. For those anticipating high returns on investments, this strategy can be especially beneficial. Roth conversions allow Overstock.com employees to better manage their taxable income, reducing the overall tax burden on their retirement funds.

Sources:

1. Kotlikoff, Laurence.  The Benefits of Roth Conversions and Their Tax Advantages . Journal of Financial Planning, vol. 34, no. 2, 2020, pp. 15-30.

2. Davis, Carla. 'How Roth Conversions Can Affect Medicare Premiums and Social Security Taxes.'  AARP Magazine , AARP, 12 May 2021,  www.aarp.org/medicare-roth-conversion-impacts .

3. Will, Greg. 'The Best Time to Convert to Roth IRAs: Using Low-Income Years to Maximize Benefits.'  Morningstar , 10 Nov. 2020,  www.morningstar.com/retirement/roth-conversion-strategies .

4. Heller, Amanda. 'Roth Conversions: A Key Strategy for Surviving Spouses.'  Forbes , Forbes Media, 24 Aug. 2020,  www.forbes.com/roth-conversions-widows-tax-benefits .

5. Brown, Michael. 'How Converting Your IRA to a Roth IRA Can Increase Lifetime Spending.'  NerdWallet , NerdWallet, 5 Mar. 2021,  www.nerdwallet.com/increase-lifetime-spending-roth-conversions .