Set these reminders, recurring. Every January: download my records and results from each patient portal, and update my one-page health file. Every month: check the explanations of benefits against any bills, and don't pay a bill until its explanation of benefits has arrived. Before each open enrollment: check that my doctors and hospital are in next year's network, price my prescriptions three ways, and look up the financial-assistance policy of the hospital I'd use. Every year on my birthday: confirm my health-care proxy and authorization forms are current, and that my proxy knows where they are. Each time you set one, add a one-line note saying why it matters.