In the financial world, the only thing that stays the same is that everything changes. As we move through 2026, the strategies that worked five years ago—like the traditional “60/40” stock-to-bond split—are being re-evaluated in the face of persistent inflation and major legislative shifts. For seniors, the stakes are particularly high because there is less time to “bounce back” from a strategic error.
Whether you manage your own money or work with a professional, your annual review needs to go deeper than just checking your account balance. You need to be asking specific, “future-proof” financial planning questions that address the realities of 2026, from new “super catch-up” contribution limits to the sunsetting of major tax provisions. Here are the eight most critical queries to put on your checklist this month.
1. “Is My Portfolio Aligned with 2026 Market Volatility?”
With market swings becoming more frequent, you need to know if your asset allocation still matches your actual risk tolerance. It’s easy to find yourself “too concentrated” in a single sector that performed well last year, but that success can be a double-edged sword. According to Citizens Bank, an annual rebalance is essential to realign your risk with your objectives. Ask your advisor: “If the market took a 15% dive tomorrow, exactly how much of my liquid cash is protected?”
2. “Am I Maximizing the New 2026 ‘Super Catch-Up’ Limits?”
If you are still working part-time or haven’t fully retired, 2026 brings a unique opportunity. For workers aged 60 to 63, the IRS has implemented a ‘Super Catch-Up’ provision. You can now contribute up to $11,250 on top of the standard $24,500 limit for 401(k) and 403(b) plans. Ask: “Am I taking full advantage of this window to aggressively pad my nest egg before I stop working entirely?”
3. “How Does the 2026 Roth ‘Catch-Up’ Mandate Affect Me?”
There is a new “technicality” for high earners that could complicate your retirement tax planning. Starting in 2026, if you earned more than $145,000 in the previous year, your catch-up contributions must be made on a Roth (after-tax) basis. This means you won’t get an immediate tax break on that extra money. Ask: “Does my employer’s plan even allow for Roth contributions, and how will this shift change my tax liability this April?”
4. “Is My Estate Plan Shielded from the 2026 Sunset?”
The federal estate tax exemption is currently at historic highs, but it is scheduled to “sunset” or drop significantly at the end of next year. Many seniors are acting now to move assets out of their taxable estate. According to Timber Ridge, having an up-to-date estate plan is the most essential tip for 2026. Ask: “Should I be utilizing the $19,000 annual gift tax exclusion now to reduce my future estate tax burden?”
5. “Do My Beneficiary Designations Override My Will?”
This is one of the most vital financial planning questions because it’s a mistake that can’t be fixed after you’re gone. A beneficiary form on an IRA or life insurance policy overrides whatever is written in your will. If you haven’t checked these since a divorce, a birth, or a death in the family, your money could go to the wrong person. Ask: “Can we pull the ‘Transfer on Death’ (TOD) forms for every single one of my accounts today?”
6. “What Is My ‘Sequence of Returns’ Risk Strategy?”
If you are just starting your retirement in 2026, the market’s performance in these first few years matters more than any other time. A market crash early in retirement can permanently deplete your accounts because you are withdrawing money while values are low. Ask: “Do I have at least two years of living expenses in a ‘Cash Bucket’ so I don’t have to sell stocks during a market downturn?”
7. “Am I Accountable for the New RMD Age Rules?”
The age for Required Minimum Distributions (RMDs) has shifted to 73, and it will eventually move to 75. If you are in that “middle zone,” you might have an extra year or two of tax-deferred growth. However, Charles Schwab warns that if you miss a deadline, the penalty is a staggering 25% of the amount you failed to withdraw. Ask: “Exactly which date is my first RMD due, and have we calculated the amount based on my 12/31/2025 balance?”
8. “How Will a ‘Serious Health Event’ Impact the Surviving Spouse?”
Financial planning isn’t just about the couple; it’s about the survivor. If one spouse requires a $10,000-a-month memory care facility, will the other spouse have enough to live on? As noted by Empower Wealth, you must stress-test your income for a “one-spouse-remaining” scenario. Ask: “Is our plan built for two, and what happens to our Social Security and pension income when one of us passes?”
The “Checklist” for Peace of Mind
The best financial planning questions aren’t meant to cause stress; they are meant to eliminate it. Retirement in 2026 is a marathon, not a sprint, and your “gear” needs to be in top shape. By getting clear, written answers to these eight questions, you can stop worrying about the “what-ifs” and start focusing on the “what’s next.” Whether it’s adjusting your Roth contributions or finally updating those beneficiary forms, a little bit of maintenance today ensures your legacy remains secure for decades to come.
Have you had a “money talk” with your advisor or family this month? Which of these questions felt the most urgent for your situation? Let us know in the comments below!
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