Things that can trip you up when planning your retirement

Kiplinger's Personal Finance

When I was planning my retirement as editor this year, I thought I had everything under control. Prepared as I was, I didn’t reckon on some curveballs along the way or how labor intensive it would be to iron out all the devilish details.

I’d like to share a few nuggets of wisdom to smooth the way for future retirees.

Nugget No. 1: Check your employer’s rules

I knew that I was covered by my employer’s health insurance until the end of July, the month in which I retired. So I figured I also had until the end of July to use money in my flexible spending account. I found out just in time that I had to spend the money by my actual retirement date, July 7.

So on July 6, I made a beeline for my optometrist to buy a pair of prescription sunglasses and empty my account.

Nugget No. 2: Start early

For me, signing up for Medicare Part B turned out to be unexpectedly time-consuming. I knew I had eight months after leaving my job to sign up for Part B without paying a penalty. What I didn’t realize, and found out almost by chance, was that I should sign up six weeks to two months in advance of the month in which I wanted coverage to begin — in my case, Aug. 1 — to get the paperwork through the system.

I was already at the six-week mark, so I hotfooted it to the Social Security office to submit my application. I was handed a receipt dated June 21 and assured that my coverage would take effect on Aug. 1.

In the meantime, I was told, I’d receive a letter of enrollment in the mail so I could begin looking for a supplemental plan to fill the gaps in Medicare. And then I waited. No letter of eligibility.

Finally, on Aug. 2, a confirmation notice appeared in my online account at The physical letter, dated Aug. 7, arrived the following week. Bottom line: To avoid feeling adrift in the bureaucratic void, start the process at least two months in advance.

Nugget No. 3: It’s complicated

While I was waiting for my Part B confirmation, I began researching coverage to supplement Medicare and pay for prescription drugs. The links at and other sites were helpful but not conclusive. I spent hours poring over plan details to decide whether to sign up for a Medigap plan (and which one) or go with Medicare Advantage.

Give yourself time to research and find out what you need to know.

Your experience may be easier, of course, but don’t count on it.

Janet Bodnar is editor at large of Kiplinger’s Personal Finance magazine. Send your questions and comments to

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