As you near your 65th birthday, you’ll face a slew of important decisions—and a deluge of mail. Getty Images By Bob Niedt, Online Editor April 3, 2020From Kiplinger’s Personal Finance A few months ago, just before my 64th birthday, I received a piece of snail mail from Anthem HealthKeepers, a blast from the future, taunting and prodding. “It’s your 64th birthday!” the pitch began. “Just 9 months until you can enroll in Medicare.” Among the enclosures were a Medicare pre-enrollment checklist and a phone number just in case I wanted to speak with a “health benefits adviser.”SEE ALSO: Retirees, Avoid These 11 Costly Medicare Mistakes Great. I hadn’t even started celebrating my 64th birthday when I was forced to do math about my looming 65th. Nine months? That means I should begin enrolling in Medicare three months before next February, which is, if I calculated it correctly, November. Sponsored Content I began to think seriously about my retirement when I started seeing friends and family retiring, taking Social Security at 62 and tapping their pensions. For them, it made sense to start taking benefits when they were first eligible, for myriad reasons (including the oft echoed “because it might not be there when I reach full retirement age”). I plan to keep working for a few more years, putting off Social Security as long as I can so my benefits can grow. But my plan to stay in the full-time workforce beyond age 65 has somehow eluded the insurance companies; they’re trolling me with Medicare pitches via snail mail as well as social media. Sure, the seven-month window to sign up for Medicare begins three months before the month of my 65th birthday and extends until three months after. However, because I have medical coverage through my employer, I don’t have to apply for Medicare until I’m no longer working—or ideally, three months before I stop working (see Signing Up for Medicare When You’re Still Covered by an Employer’s Health Plan, or go to medicare.gov). Even with that option, most experts say, it doesn’t hurt to apply for Medicare Part A when you turn 65 even if you’re still working full-time because it’s free. Advertisement Lots of homework. Probably the biggest hurdle as retirement approaches is all the homework you have to do, and the harsh hits you take in terms of penalties and coverage gaps if you don’t play by the rules and meet the deadlines. “There’s a lot involved in turning 65,” says Bob Ziff, whose Morrisville, Pa.-based insurance brokerage business, Avanti Benefits Corp., walks clients through the Medicare application (and annual updating) process. “Should I enroll in Medicare? Do I have to? What we do is help people with the best approach.” And things have changed big time in the 35 years Ziff has operated Avanti. In the early years, most employers were paying full premiums for employees, says Ziff. Now, you might save money switching to Medicare Part B. (See If You’re 65 and Still Working, Avoid Pitfalls and Maximize Benefits.) At least I know I won’t be alone as I keep working past 65. In 2024, approximately 36% of those of us between age 65 and 69 will be working, according to the Bureau of Labor Statistics. That’s up from 22% in 1994. Advertisement Beyond that, bigger decisions are going to come into play, including one that has forced me to truly rethink retirement: Where to land? It’s something my wife and I have been exploring the past few years since we realized we wouldn’t be able to retire comfortably where we currently live, in northern Virginia. The cost of living so close to Washington, D.C., is prohibitive to us as retirees. Plus, the frantic pace, rapid growth and the relentless traffic make this region less than ideal. We’ve been exploring other parts of Virginia, as well as the Carolinas. But that’s the subject of another column. SEE ALSO: Does Medicare Cover That? Some of those communities are following the game plan of Anthem HealthKeepers: trolling me on Facebook and e-mail and via the U.S. mail with pitches for housing developments and retirement communities. Maybe the hardest part of preparing for retirement is dealing with all the mail and messages.