Open Enrollment For Employee Benefits, Health Insurance and Medicare

Goal: To review individual and group (employer) health insurance during open enrollment (including Medicare). Also review all other group employee benefits for open enrollment. 

What is open enrollment for insurance?

Open enrollment for insurance is the period during which you can purchase health insurance, make changes to health insurance along with enrolling in or making changes to your individual and group (employer) insurance plans. There are special enrollment periods for health insurance, medicare and group/employer insurance where you can enroll or make changes if you have  a major qualifying event such as marriage, birth, adoption, divorce, death, starting or leaving a job.

Health Insurance Open Enrollment: 

Medicare open enrollment is October 15 to December 7, 2019 (here). 

Individual health care coverage open enrollment on is November 1 to December 15, 2019 for the Federal Health Care Insurance Exchange at is used by residents of Alabama, Alaska, Arizona, Arkansas, Delaware, Florida, Georgia, Hawaii, Iowa, Illinois, Indiana, Kansas, Kentucky, Louisiana, Maine, Michigan, Mississippi, Missouri, Montana, North Carolina, North Dakota, Nebraska, New Jersey, New Hampshire, Nevada, Ohio, Oklahoma, Oregon, Pennsylvania, South Carolina, South Dakota, Tennessee, Texas, Utah, Virginia, Wisconsin, West Virginia and Wyoming. 

States that maintain their own health care exchange will have open enrollment starting on October 15th (typically) and will usually have longer open enrollment periods. Following are the states with their own exchange: California, Colorado, Connecticut, District of Columbia, Idaho, Maryland, Massachusetts, Minnesota, Nevada, New York, Rhode Island, Vermont, Washington. Be sure to check with your State’s Exchange website to confirm the open enrollment dates. 

Group (Employer) Insurance

What should I consider during group (employer) open enrollment?

  • Insurance that you and your dependents have outside of your employer such as individual insurance or coverage through a spouse/domestic partner’s/parents group insurance plan.
  • If you are planning to leave your employer in the next year, consider whether your group insurance is portable and if an individual policy is needed. Most group insurance coverage is not portable.
  • Understand what each benefit is and what your options are. Use all available resources to learn about your options including your human resources/benefits department, the insurance company and trusted websites such as and
  • Do you have a need for a particular benefit?  For example, accidental death and dismemberment coverage is not a great buy, so unless your employer pays for it, you should skip it.  
  • Is your employer offering any new benefits? Employers are offering a wider range of benefits such as long term care insurance, legal plans, identity theft protection, pet insurance and student loan refinancing programs.
  • Wellness plans are becoming more common. Be sure to inderstand the terms and options. These plans can include financial incentives for participation and meeting certain benchmarks.
  • Carefully review any changes to your employers plans.

Note: Employers usually now provide a set credit which is applied towards your cumulative employee benefits premiums and contributions rather than directly covering the premiums for each benefit..  

Next step: 

Access the Get Ready Toolkit and download the Health Care costs worksheet, group (employee) benefits and deductions worksheet along  along with insurance worksheets for all types of insurance (here).

The Get Ready Toolkit also includes a subscription to the Get Ready Newsletter which follows the Get Ready Financial Calendar to help you stay financially prepared.

Pick up a copy of Get Ready: A Step-By-Step Planner for Maintaining Your Financial First Aid kit to guide you through organizing your financial documents and creating your cash flow statement and net worth statement. Pick up a copy on Amazon (here), purchase a digital copy (here) or learn more (here).

Learn More: 

The Optimal Insurance Deductible Calculator