Many people consider April 15th the date to remember. We have to be on our toes at tax time because a late return could result in a penalty. As the first of the baby boomers turn 65 next year, Medicare will present them with new dates to remember and another set of penalties if they’re not on their toes. At a recent presentation of Medicare coverage choices, I watched the audience sit openmouthed in disbelief as they were told that not signing up for Medicare within the appropriate window could result in penalties for the lifetime of their coverage.So in the spirit of spreading the news to boomers nearing 65 who are overloaded with news and information, here are the simple facts about Medicare penalties. There are two main choices for coverage: Medicare Part A (hospital insurance) and Medicare Part B (medical insurance). Medicare Part A is free for most enrollees, so everyone is encouraged to sign up. There is a seven-month window for enrolling: three months before your...

Are you looking for a career that combines income and purpose? Many folks on the other side of 50 have been thrust into exploring options outside their primary profession due to unemployment or a down economy; others, still in a job, are looking toward the day they can bid their boss a hearty goodbye and head off to their dream job. Whatever the motivation, a good dose of reality can lead to greater success in your encore career. This advice is from your author, who “found her calling” in her late 40s and today works a couple of dream jobs.Rule No. 1: Build a nest egg or learn to live on a lot less than you do now. This may seem obvious, but following your passion will most likely pay far less than your previous salary did. If you really want to be happy in your new career, create a financial plan that reflects this reality, or you can take the advice of my old accounting teacher, who said “Two can live as cheaply as one, if one doesn’t eat.” Rule No. 2: Test it out. There’s no...