Want to avoid stress in retirement? Don’t overlook these time sensitive decisions — they could cost thousands if ignored

Turning 65 brings a lot of new milestones, but it also brings time-sensitive decisions and deadlines you might not know about.

Linda recently retired after a 40-year career and assumed she could sign up for supplemental health coverage whenever she wanted. She didn’t know about the one-time, six-month Medigap enrollment window tied to Medicare.

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By the time she started looking into plans, her guaranteed enrollment period was nearly over — and she almost lost the chance to get affordable coverage without medical underwriting.

As you approach retirement, several decisions can cost you thousands if you don’t plan ahead.

Missing your Medigap window can be costly

When you first enroll in Medicare Part B, you enter a six-month Medigap open enrollment period [1].

During this time, insurers cannot deny you coverage or charge you higher premiums. It’s your best chance to get affordable, guaranteed protection. If you miss this window, it could result in higher costs, fewer options, or even denials.

Roth IRA conversions and Medicare premiums

Converting pre-tax retirement accounts to a Roth IRA can be a smart move for tax planning, but timing is crucial. Large conversions can trigger IRMAA (Income-Related Monthly Adjustment Amount), which increases your Medicare Part B and Part D premiums [2].

Because IRMAA uses your income from two years prior, a big conversion at 63 could unexpectedly spike your Medicare costs at 65.

Dental work and planned surgeries

Medicare generally doesn’t cover dental work, and many standalone dental plans have waiting periods — up to six months for fillings and up to a year for crowns and other more work. If you need major dental work, it may be cheaper to get it done before you leave employer coverage [3].

The same is true for planned surgeries like joint replacements. Handling these procedures earlier can save thousands out of pocket.

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Employer payouts and PTO cash-outs

Lump-sum payouts from unused vacation or sick time can unintentionally push your income over IRMAA thresholds, raising your Medicare costs [4]. If you have a large paid time off (PTO) balance, consider spreading payouts across multiple tax years.

Social Security and HSA contributions

If you plan to delay Social Security to maximize your benefit, remember to apply for Medicare benefits within three months of your 65th birthday [5].

Once you enroll in Medicare, you can’t contribute to a Health Savings Account (HSA) anymore. Part A coverage can be retroactive up to six months. Plan your final HSA contributions carefully to avoid penalties.

How to stay ahead of retirement decisions

Managing all these moving pieces can feel overwhelming, but you don’t have to go it alone. If you need help, consider using the following resources:

• Talk to a Medicare-savvy financial advisor: They can help with Medigap enrollment, IRMAA strategies and Roth conversion planning.

• Use free resources like SHIP: State Health Insurance Assistance Programs offer unbiased Medicare counselling to help you understand your options.

• Create a retirement calendar: Mark key dates for Medicare enrollment, Social Security, Roth conversions and tax deadlines so nothing slips through the cracks [6].

Retirement planning isn’t just about saving enough — it’s about making the right steps at the right time.

Missing your Medigap enrollment window or mistiming Roth conversions can cost thousands and reduce flexibility. With careful planning and expert guidance, you can protect your finances and your peace of mind in retirement.

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Article sources

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[1]. Vanguard. “What are the key dates for my retirement?”

[2]. Kiplinger. “Want to Avoid the IRMAA? Consider a Roth Conversion”

[3]. Medicare. “Dental Services”

[4]. Patriot Software. “How to Handle Taxes on Vacation Payout”

[5]. Social Security. “Starting Your Retirement Benefits Early”

[6]. United Healthcare. “Understand how Medicare will affect your HSA”

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.