Four Financial Questions to Ask Right Now

Key Financial Questions to Consider This Tax Season

Tax season is one of the few times a year when your entire financial picture is sitting right in front of you. Your income, your accounts, your distributions, your trajectory. It’s a uniquely clear moment—and it can be one of the most underused opportunities in financial planning.

Many clients understandably focus on gathering documents and getting through the filing process. That makes sense—tax prep is stressful enough. But there are a handful of questions that, if they are discussed during this window, can make a real difference over time. Not complicated strategies. Just the right conversations at the right moment.

Here are four key questions worth your attention this spring.

1. Am I Drawing Down My Accounts in the Right Order?

This one surprises a lot of people. If you’re retired and pulling from your savings, it turns out that which account you draw from first matters almost as much as how much you take.

Without a coordinated strategy, it’s easy to pull from whichever account feels easiest. But done thoughtfully, the sequence can keep you in a lower tax bracket, reduce what you pay in taxes over your lifetime, and help you avoid some nasty Medicare surcharges we’ll talk about in a moment.

The general idea: taxable accounts first, then traditional IRAs and 401(k)s, and let the Roth sit as long as possible. But there’s real strategy in how you apply that—and it should connect directly to what’s happening on your tax return each year. Tax season can be a good time to reevaluate your distribution strategy.

2. Is This a Good Year for a Roth Conversion?

A Roth conversion is simple in concept: you move money from a traditional IRA into a Roth, pay the tax now, and everything that grows from there comes out tax-free. The question is always when to do it.

The years that make the most sense are often the quieter ones—a year where income dipped because of a career change, the early years of retirement before Social Security kicks in, or a year where business was slower than usual. Those are windows where you’re paying a lower rate than you likely will later, especially once Required Minimum Distributions start pushing your taxable income up.

If your income looks lower than usual this year, it may be worth evaluating whether a Roth conversion makes sense before you file your return.

3. Could a Higher-Income Year Come Back to Affect My Medicare?

This is the one that catches people off guard the most. Medicare premiums aren’t a flat rate—they’re based on your income. And if you cross certain thresholds, your Part B and Part D premiums can increase meaningfully. We’re talking thousands of dollars a year in some cases.

Here’s the part most people don’t know: Medicare uses your income from two years ago. So a large Roth conversion, a property sale, or a big RMD this year could quietly raise your Medicare premiums in 2028. For clients who are retired and sitting on large IRA balances, this is something we think about carefully before making any major moves.

It’s not a reason to avoid these strategies—it’s just a reason to plan them thoughtfully.

4. When Should I Take Social Security?

If you’re anywhere in your 60s, this question is probably in the back of your mind. Social Security is one of the biggest financial decisions you’ll make in retirement—and most people make it based on when they become eligible, not based on an actual analysis.

The gap between claiming at 62 versus waiting until 70 can be over $100,000 in lifetime income. The right answer is different for everyone—it depends on your health, your other income, your spouse’s situation, and how your retirement is structured.

Taking a closer look at the numbers can help clarify when it may make the most sense to start Social Security.