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Essential Year-End Tax Strategies for Overstock.com Employees: What You Need to Know Before 2023

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

Here are some things for Overstock.com employees and retirees to consider as they weigh potential tax moves between now and the end of the year.

1. Defer income to next year
Overstock.com employees must consider opportunities to defer income to 2023, particularly if you think you may be in a lower tax bracket then. For example, you may be able to defer a year-end bonus or delay the collection of business debts, rent, and payments for services. As a Overstock.com employee, doing so may enable you to postpone payment of tax on the income until next year.

2. Accelerate deductions
Overstock.com employees and retirees should also look for opportunities to accelerate deductions into the current tax year. If you itemize deductions, making payments for deductible expenses such as medical expenses, qualifying interest, and state taxes before the end of the year (instead of paying them in early 2023) could make a difference on your 2022 return.

3. Make deductible charitable contributions
As a Overstock.com employee, if you itemize deductions on your federal income tax return, you can generally deduct charitable contributions, but the deduction is limited to 50% (currently increased to 60% for cash contributions to public charities), 30%, or 20% of your adjusted gross income (AGI), depending on the type of property you give and the type of organization to which you contribute. (Excess amounts can be carried over for up to five years.)

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4. Bump up withholding to cover a tax shortfall
As a Overstock.com employee, if it looks as though you will owe federal income tax for the year, consider increasing your withholding on Form W-4 for the remainder of the year to cover the shortfall. Time may be limited for Overstock.com employees to request a Form W-4 change and for their employers from Overstock.com to implement it in time for 2022. The biggest advantage in doing so is that withholding is considered as having been paid evenly throughout the year instead of when the dollars are actually taken from your paycheck. This strategy can be implemented by Overstock.com employees to make up for low or missing quarterly estimated tax payments.

5. Save more for retirement
Deductible contributions to a traditional IRA and pre-tax contributions to a Overstock.com-sponsored retirement plan such as a 401(k) can reduce your 2022 taxable income. As a fortune 500 employee, if you haven't already contributed up to the maximum amount allowed, consider doing so. For 2022, Overstock.com employees can contribute up to $20,500 to a 401(k) plan ($27,000 if you're age 50 or older) and up to $6,000 to traditional and Roth IRAs combined ($7,000 if you're age 50 or older).* The window to make 2022 contributions to a Overstock.com-sponsored plan generally closes at the end of the year, while you have until April 18, 2023, to make 2022 IRA contributions.

*Roth contributions are not deductible, but Roth-qualified distributions are not taxable.

6. Take the required minimum distributions
If you are a Overstock.com employee age 72 or older, you generally must take required minimum distributions (RMDs) from traditional IRAs and Overstock.com-sponsored retirement plans (special rules apply if you're still working and participating in Overstock.com's retirement plan). You have to make the withdrawals by the date required — the end of the year for most individuals. The penalty for failing to do so is substantial: 50% of the amount that wasn't distributed on time. As a fortune 500 employee, making these distributions in a timely manner is essential as to avoid the late penalty.

7. Weigh year-end investment moves
Overstock.com employees and retirees shouldn't let tax considerations drive investment decisions. However, it's worth considering the tax implications of any year-end investment moves that you make. For example, if you have realized net capital gains from selling securities at a profit, you might avoid being taxed on some or all of those gains by selling losing positions. As a Overstock.com employee, any losses over and above the number of your gains can be used to offset up to $3,000 of ordinary income ($1,500 if your filing status is married filing separately) or carried forward to reduce your taxes in future years.

Tags: Financial Planning , Tax , Retirement , 2022

What type of retirement savings plan does Overstock.com offer to its employees?

Overstock.com offers a 401(k) retirement savings plan to its employees.

Does Overstock.com match employee contributions to the 401(k) plan?

Yes, Overstock.com provides a matching contribution to employee 401(k) plans, subject to certain limits.

How can employees at Overstock.com enroll in the 401(k) plan?

Employees at Overstock.com can enroll in the 401(k) plan through the company’s human resources portal or by contacting the HR department for assistance.

What is the eligibility requirement for Overstock.com employees to participate in the 401(k) plan?

Most employees at Overstock.com are eligible to participate in the 401(k) plan after completing a specified period of service, typically within the first year of employment.

Can employees at Overstock.com take loans against their 401(k) savings?

Yes, Overstock.com allows employees to take loans against their 401(k) savings, subject to the plan’s terms and conditions.

What investment options are available in the Overstock.com 401(k) plan?

The Overstock.com 401(k) plan offers a variety of investment options, including mutual funds, target-date funds, and company stock, among others.

How often can Overstock.com employees change their 401(k) contribution amounts?

Employees at Overstock.com can change their 401(k) contribution amounts at any time, subject to the plan’s guidelines.

Is there a vesting schedule for employer contributions to the 401(k) plan at Overstock.com?

Yes, Overstock.com has a vesting schedule for employer contributions, which means that employees must work for a certain number of years before they fully own the employer match.

What happens to my 401(k) account if I leave Overstock.com?

If you leave Overstock.com, you have several options for your 401(k) account, including rolling it over to another retirement account, cashing it out, or leaving it with Overstock.com, depending on the plan rules.

How can Overstock.com employees access their 401(k) account information?

Employees can access their 401(k) account information through the plan’s online portal or by contacting the plan administrator.