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October is pumpkin season. Walk into almost any grocery store and you’ll see them stacked outside—small pumpkins, giant pumpkins, oddly shaped pumpkins and the occasional perfect pumpkin waiting to become a jack-o’-lantern. It got me thinking: How do you know when your retirement is ripe? Unlike a pumpkin, retirement doesn’t come with a convenient sticker…

Fall is here and the holidays are almost 2 months away. There is something special about the holidays in retirement. You may have more time to travel. You may be able to host the family meal instead of rushing home from work. You may want to spoil the grandchildren a little—or simply enjoy traditions that…

When people begin planning for retirement, one concern tends to rise to the top of the list: “How can I make sure my money lasts?” It is an understandable question. Retirement may last 20, 30, or even more years, and unlike a paycheck from an employer, retirement income must often be created from a combination…

September brings the official start of the Fall season and the familiar rhythm of backpacks, school schedules, college applications, and new beginnings. For parents and grandparents, it can also bring a more complicated question: How can I help my children or grandchildren with education costs while still protecting my own financial future? That question becomes especially…

A million dollars sounds like the finish line. But when you retire, it can actually be the beginning of some of your most important financial decisions. Reaching $1 million in a 401(k) is a significant retirement milestone. But here’s the part many people don’t think about: Having $1 million saved and knowing how to turn…

The storm passes. The next morning, you find water coming through the ceiling. A roofer comes out, and the news is worse than expected: part of the roof needs to be replaced. The estimate is $12,000. You didn’t plan for that. You weren’t expecting to pull money from your retirement savings for a roof. But…

The year before retirement is not the time to wait for your last paycheck. It’s the time to look closely at the decisions that could shape your financial life after work. One thing that’s easy to overlook: the years around retirement can create a tax window that may not be available later. And that’s the…

You may be planning to work for several more years. But what happens if you don’t get that choice? A layoff, health issue, caregiving responsibility, or unexpected change at work can force retirement sooner than planned—and suddenly, decisions about Social Security, healthcare, savings, and income become urgent. Retiring earlier than expected can create a financial…

If you and your spouse each have a traditional IRA, you might assume a Roth conversion decision is straightforward. Pick an amount, pay the taxes, move the money to a Roth, and move on. But there can be more to the decision when you’re married. The question isn’t always simply how much you should convert.…

Some Medicare beneficiaries could pay more for prescription drug coverage in 2027. While not every plan is expected to increase its premiums, a temporary program that’s been helping keep Medicare Part D costs from rising too quickly is set to wind down after 2026. If you’re the type who renews your prescription drug plan automatically…