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Like a lot of people, I’ve eased my way into retirement. Since I left my role as a senior editor at Kiplinger Personal Finance about a year ago, I’ve continued to write freelance articles and columns for the magazine, and I’ve contributed to Kiplinger Retirement Report along with other publications, too.
When I’m not writing about personal finance, I’m busy managing my own retirement finances, which sometimes feels like a full-time job. Some lessons I’ve learned:
Taxes are complicated. While I was working for an employer, I had taxes withheld from my paycheck, so I didn’t pay much attention to taxes until it was time for my husband and me to file our return. Now, we have income from multiple sources, including my self-employment earnings and withdrawals from tax-deferred savings plans.
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To avoid underpayment penalties, I’ve had to make quarterly estimated tax payments and keep track of deductible expenses to claim when I file our 2025 tax return. If you’re newly retired, you may want to enlist an experienced tax preparer to help you.
Health care is even more complicated. I wasn’t fully prepared for the complexities — and costs — that come with Medicare, or for the need for vigilance to make sure my records are accurate. Not long after I retired, I spent a day in the emergency room for a minor mishap. I handed over my Medicare and medigap cards and assumed everything would be covered.
But a few weeks later, I began to receive bills for thousands of dollars from various providers, stating that Medicare had declined to cover their services. After a few phone calls, I discovered that Medicare’s records stated, incorrectly, that my former employer’s health insurance plan was my primary insurer.
A helpful Medicare representative eventually straightened it out, but I had to ask the providers to resubmit their bills to Medicare. A friend who enrolled in Medicare around the same time had a similar experience. My advice: Once you make Medicare your primary insurer, call Medicare (800-633-4227) to make sure your records reflect that.
Like many retirees, I’m also facing higher costs for my premiums. For example, I recently learned that the insurance company that provided my Part D prescription-drug plan in 2025 sold its coverage to another insurer, which informed me that premiums for my Part D coverage would rise by more than 600%. I found a different plan with no monthly premium but a deductible of $615 — the maximum Part D plans can impose in 2026.
I take only one drug, which is generic, so switching to this plan should be affordable. But if I eventually need additional prescription drugs, I could face significant out-of-pocket costs. With premiums for supplemental coverage, Medicare Advantage and Part D increasing, researching your options during open enrollment has never been more important.
Lessons from readers. After I wrote about the challenges of paying for dental care in retirement in my November 2025 column, several readers wrote to say that they’ve saved a lot of money, without sacrificing quality, by getting dental implants and other treatments in Mexico. It’s certainly worth considering.
When I wrote about budgeting in my July 2025 column, another reader admonished me for switching to the lower-cost version of Netflix, arguing that life is too short to sit through ads. Maybe he has a point.
I’m extremely grateful I was able to retire on my own terms, giving me time to prepare for the financial and emotional minefields that can make retirement a challenge. If you retired recently, either by choice or necessity, I’d love to hear about your experiences and the lessons you’ve learned.
Note: This item first appeared in Kiplinger Personal Finance Magazine, a monthly, trustworthy source of advice and guidance. Subscribe to help you make more money and keep more of the money you make here.
