Essential Considerations for Overstock.com Employees Contemplating Retirement: What You Need to Know Before Making the Leap

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

With all of the changes at Overstock.com employees need to know what steps to take before leaving. Retiring, or worse, losing your job, is a monumental (for better or for worse) moment in your life. Your mind is racing, your palms are sweating, and you simply just doesn't know how to operate. The loss of a job, especially for those with over 20 years of service, affects the same receptors in the brain as the loss of a loved one. You have been connected with Overstock.comfor 20 years, and now the relationship is over. Remember to reach out to Overstock.com HR & Benefits departments for all Overstock.com summary plan descriptions.

The same five stages of grief apply for a person going through retirement, job loss, or the loss of a loved one. Denial, anger, bargaining, depression, and acceptance are a part of the framework that makes up our learning to get through the lack of employment.

As the reality of the situation settles, your emotions will be a mess. You might feel upset one minute, and annoyed the next, and it can be tempting to vent your frustrations. Remember, acting upon impulse almost never turns out well, and can make a difficult situation even worse.

Here are a few items to check off as you consider leaving Overstock.com:

1. Sit down and carefully analyze your finances. If you have a spouse or signifigant other, involve them in this process. Avoid doing financial business with friends or family. Money and friendships do not mix.

2. Call your Credit Union or Bank, and consider opening a line of credit against your home equity. Consider opening additional credit cards to create an emergency credit line. As many of you have been employed your whole life, you probably won't think to do this - once you are unemployed, it becomes exceedingly difficult to get credit, making it very important you take this line of action.

3. Go over your 401(k) contributions, if you were making them. Decide whether or not you should increase your contributions for your remaining time on payroll, or cease them entirely to build up more immediate cash. How you proceed may have big tax implications. Depending on when you stop contributing, you may end up in a much higher tax bracket due to your severance payment, unemployment, etc.

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4. It's not always wise to file for unemployment immediately after the loss of a job. Depending on the time of year you are laid off, paired with your financial situation, it could be beneficial to wait to file your claim so that your unemployment payments fall in the next tax year, when your overall income is lower due to the fact that you're unemployed. There are an overwhelming number of situations that you want to consider before making a move on this. We recommend speaking with a Overstock.com-focused retirement advisor to go over your options.

5. Unless you believe your layoff was deserved, speak to a trusted lawyer to go over your options. Venting your anger at managers and colleagues may feel amazing temporarily, but it will damage your career in the long run. You spent all this time building up your relationships at Overstock.com why burn them now? Avoid going online even anonymously to berate past Overstock.com staff & management.

6. Have a plan for how to fill the void on your LinkedIn profile and your resume. If you are pursuing a new job, having a job makes it much easier when finding your next adventure. In the mean time, you might consider becoming a consultant until you find a permanent position. You may also find the ability go go back to Overstock.com as a contractor working on your terms.

7. Figure out what you will tell your Overstock.com wcoworkers - create your go-to statement and practice it, so you can say it without becoming too emotional. It will be normal for friends and acquaintances to ask, and we assume you won't want to burst into tears or lash out every time the question is popped. However horrible you feel, it's crucial to remain calm and act professional, and try to avoid doing anything that might hinder your reputation or integrity. Remember to stay professional on social media when discussing Overstock.com.