retirement

When I’m 64

As you near your 65th birthday, you’ll face a slew of important decisions—and a deluge of mail.

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.”

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.

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.

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.

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.

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.

Most Popular

Retirement Income Shouldn’t Depend on the Market; It Should Depend on Math
retirement planning

Retirement Income Shouldn’t Depend on the Market; It Should Depend on Math

The math isn’t as tough as you might think. It all starts with dividing your assets into three different buckets.
May 23, 2022
Your Guide to Roth Conversions
Special Report
Tax Breaks

Your Guide to Roth Conversions

A Kiplinger Special Report
February 25, 2021
Why Are Gas Prices Still Going Up?
spending

Why Are Gas Prices Still Going Up?

The cost of a gallon of gas is heading back toward its March highs. What’s driving the resurgence, and will gas prices go down anytime soon?
May 23, 2022

Recommended

How to Find the Perfect Balance Between Spending and Saving
retirement

How to Find the Perfect Balance Between Spending and Saving

It's the key to being able to enjoy life now AND in the future. It's also the basis for a successful retirement plan, and it all starts with setting y…
May 24, 2022
Education is Key: 3 Financial Lessons for Retirees Nearing Retirement
retirement planning

Education is Key: 3 Financial Lessons for Retirees Nearing Retirement

When it comes to retirement planning, educating yourself can keep you from making big mistakes. Here are three key lessons that everyone preparing for…
May 24, 2022
Retirement Income Shouldn’t Depend on the Market; It Should Depend on Math
retirement planning

Retirement Income Shouldn’t Depend on the Market; It Should Depend on Math

The math isn’t as tough as you might think. It all starts with dividing your assets into three different buckets.
May 23, 2022
Don’t Move to Another State Just to Reduce Your Taxes
retirement

Don’t Move to Another State Just to Reduce Your Taxes

If you’re retired or near retirement, maybe a smarter plan for retirement income will allow you to stay put. Yes, your state income tax rate may be hi…
May 21, 2022