Guide to Managing Medical Benefits When You Leave or Start a Job

Leaving a job typically means saying goodbye to workplace benefits such as health insurance and medical spending accounts. No matter if you quit, get fired, or get furloughed, it's essential to know your options so you can make the most of those perks.

If you're starting a new job with benefits or becoming self-employed, you'll have critical decisions to make about what's best for you and your family. I recently received a couple of questions about how to handle benefits during work transitions, and I'll answer them throughout this post. We'll review the best options for managing medical benefits when you leave or start a new job.

What happens to health insurance when you leave a job?

When it's time to leave a job with benefits, it's essential to let your employer know so you can evaluate your options for managing or replacing them right away. The sooner you understand your choices, the more time you'll have to do your homework and consider what's best. 

Any insurance perks you have typically end on the last day of the month you get terminated. So, be strategic about choosing your last day, when possible.

If you leave an employer on good terms or get a severance package, ask for an extra month or two of medical coverage if you need it.

For instance, if you work through November 30, your health insurance may end on that day. But if you work through December 1, your insurance may last until December 31. Also, remember that most things in business are negotiable. If you leave an employer on good terms or get a severance package, ask for an extra month or two of medical coverage if you need it.

Here are four work transitions you may need to manage:

1. You leave a job for a new employer with benefits

Congrats! Benefits at your new job may start on your first day, or you may be subject to a waiting period, such as 30 or 90 days. Don't roll the dice with a gap in critical coverages such as health and life insurance. Something unexpected—a car accident, illness, or death—could be financially devastating for you or your surviving family.

If you have a spouse or partner who also has workplace insurance benefits, you may be wondering which plan to choose or whether you can double up on benefits. Keep reading for tips to handle this situation wisely. 

2. You leave a job for a new employer with no benefits

If your new job is with a small company, it may not offer expensive perks such as health insurance. But that doesn't mean you can...

Keep reading on Quick and Dirty Tips