Savvy Senior: Do I need to sign up for Medicare if I'm still working? Jim Miller, FacebookTwitterEmail Dear Savvy Senior, I will turn 65 in a few months and plan to keep working for several more years. I have good health insurance from my employer now. Do I have to sign up for Medicare when I reach 65? Looking Ahead Dear Looking, Whether you need to enroll in Medicare at 65 if you continue to work and have health insurance through your job depends on how large your employer is. The same rules apply if your health insurance comes from your spouse’s job.