DEAR BRUCE >> My goal is to retire by age 55 (two years away). I'm single with no children and have a well-paying job. I have always been a saver, and my brokers tell me I can retire whenever I want to. My mortgage has long been paid off, and my only monthly expenses are utilities.

My biggest concern is health care. Where's the best place to start to get options for buying it on my own?

— Lynn

DEAR LYNN >> It seems to me that you have very little to concern yourself with. You plan to retire at age 55, which I am not necessarily going to agree with, but nonetheless, go for it! You have two years to go out and search the health care markets.

There are several good companies that will look for the best possible plan for your specific circumstance. If you make a mistake, you may have to correct it, but that's not the most difficult thing in the world.

I am really wondering why you're trying to retire at 55. You're just starting to hit your stride. Retirement is not all it's cracked up to be, trust me. I would try taking some time off before making a big decision.

DEAR BRUCE >> On some of the blogs I read regularly, there are ads for publications claiming to help maximize your monthly Social Security payments by taking advantage of several soon-to-be-closed loopholes in the Social Security program. From what I can see, these loopholes address the issue of when to file and, for a married couple, who should file.


What about those of us in our late 70s? My husband (78) and I (76) live almost entirely on his Social Security checks as I was a stay-at-home mom and did not earn any Social Security awards. Our monthly income is $2,777 a month, including my spousal award. This generally covers the basic bills, but we both have health issues that require many prescriptions, and there is a fair amount of deferred maintenance on our home.

In a nutshell, is there anything in these loopholes that will help us?

— Reader

DEAR READER >> I really don't know if there are any loopholes, but I am told that a significant number of people on Social Security could collect more if they knew all of the ins and outs of the system. If that is the case, it may pay to take a look and see what these publications have to say.

For example, because you need a lot of prescription drugs, there may be some additional benefits. Unless you have to put up a ton of money in advance, it might certainly pay for you to invest a few bucks and see what the "loopholes" are. If they seem to be in your favor, you will want to contact someone directly involved in the company you are buying the information from or a consultant in terms of getting the most from Social Security.

Send questions to