11 Crucial Questions To Ask Yourself — And Your Employer — During Open Enrollment

Photographed by Megan Madden.
It might be helpful to think of open enrollment in the United States — the time of year when workers can sign up for or adjust existing healthcare plans — as Christmas for grownups. You go shopping for things that ideally make life better.
Workers who aren't covered by an employer-sponsored plan can shop for plans on the Affordable Care Act exchanges starting on November 1, through December 15. Those who want to change their current plans from an employer must do so by a date specified by their company or organization.
Before you make any choices, consider how your life has changed over the last year, and how you might expect it to change in the coming year, advises Edukate CEO Chris Whitlow.
"If you're planning on growing your family, going back to school, taking a big vacation, or know you'll have a large medical expense, you'll want to factor those things in when choosing your benefits," he says.
You'll likely want to speak with the human resources point person (or team) at your job who oversees employee benefits, but don't expect them — or anyone else — to tell you what to choose. They're there to outline your options, not decide what you should do with your life.
"Asking your employer for specific advice is a touchy subject. While your HR team may want to help you with selecting the right benefits, there are potential legal ramifications for them if they provide you with specific advice. When it comes to selecting your benefits, knowledge is power and no one knows your situation better than you," Whitlow explains. "This is also true when asking your coworkers what they selected; their needs may not be the same as your needs."
Don't want to play an endless game of 20 Questions with your health and retirement savings? Look through these 11 questions you should ask yourself or your job to find the plan that's best for you.